MiMeDB: Showing metabocard for Lithocholic acid glycine conjugate (MMDBc0000141)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:37:22 UTC

Update Date

2024-04-30 19:31:11 UTC

Metabolite ID

MMDBc0000141

Metabolite Identification

Common Name

Lithocholic acid glycine conjugate

Description

Lithocholic acid glycine conjugate is an acyl glycine and a bile acid-glycine conjugate. is an acyl glycine and a bile acid-glycine conjugate. It is a secondary bile acid produced by the action of enzymes existing in the microbial flora of the colonic environment. In hepatocytes, both primary and secondary bile acids undergo amino acid conjugation at the C-24 carboxylic acid on the side chain, and almost all bile acids in the bile duct therefore exist in a glycine conjugated form (PMID: 16949895 ). Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute, depending only on the presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g. membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues (PMID: 11316487 , 16037564 , 12576301 , 11907135 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652302052018532D          

 36 39  0  0  0  0            999 V2000
10000.021310001.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8836 9999.7851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.7435 9997.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8836 9997.3033    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5962 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3087 9999.7851    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.0213 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8823 9998.9568    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.8823 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.5968 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3113 9998.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.309310000.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.594810000.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5948 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.3093 9998.9659    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.1710 9999.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4565 9998.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4565 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.1710 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.023810000.2033    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.0238 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.8084 9999.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.2933 9999.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.808410000.4583    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.808410001.2833    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.524110001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.237710001.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.953410001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.667010001.2833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10004.382710001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.096310001.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.812010001.6958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10005.096310000.4583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.953410002.5208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.093710001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.524110000.8708    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
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 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
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 20 21  1  0  0  0  0
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 18  3  1  6  0  0  0
 19  9  1  0  0  0  0
  9  4  1  1  0  0  0
 16  8  1  0  0  0  0
  8  2  1  1  0  0  0
 14  8  1  0  0  0  0
 14  5  1  6  0  0  0
 11 15  1  0  0  0  0
 15  6  1  1  0  0  0
 24 25  1  0  0  0  0
 24 36  1  6  0  0  0
 25 26  1  0  0  0  0
 25 35  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 34  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 15 21  1  0  0  0  0
 21  7  1  6  0  0  0
 12 20  1  0  0  0  0
 20  1  1  1  0  0  0
 24 20  1  0  0  0  0
 24 23  1  0  0  0  0
M  END

HMDB0000698
     RDKit          3D
Lithocholic acid glycine conjugate
 74 77  0  0  0  0  0  0  0  0999 V2000
    3.2846    3.0246   -1.4917 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4824    2.1994   -0.4719 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3179    1.6215    0.5827 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4188    0.6959    0.1928 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1778    0.2184    1.4089 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8301    0.6204    2.5448 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2715   -0.6739    1.2785 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0183   -1.1527    2.3916 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0863   -2.0609    1.9242 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1965   -2.2830    0.6946 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9841   -2.6885    2.7811 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4692    1.4436   -1.1767 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8125    0.4639   -2.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4696   -0.2509   -2.4881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4902    0.3528   -1.5277 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6834   -0.4178   -1.1539 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6665   -0.3050   -2.3305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9822   -0.9487   -2.0158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5444   -0.5833   -0.6817 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3506    0.6996   -0.7172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2366    0.7173    0.5194 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2463    2.0306    1.0425 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7286   -0.2020    1.5864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2141   -0.0146    1.6658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5259   -0.5424    0.4247 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0568   -1.9699    0.6527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3815    0.3019   -0.0105 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4737    0.6735    1.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3288    1.5377    0.5878 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4495    0.6847   -0.3556 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9338   -0.5910    0.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7521    3.8972   -1.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5108    3.4297   -2.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9537    2.4004   -2.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8975    3.0564    0.0571 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8164    2.4339    1.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7296    1.0738    1.3787 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1056   -0.2424   -0.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1792    1.1568   -0.4677 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5259   -0.9827    0.3123 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5282   -0.3004    2.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3824   -1.6419    3.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7844   -3.5837    3.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8124    2.2221   -1.7198 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1352    1.0166   -3.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5710   -0.2757   -2.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1626    0.0104   -3.5211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839   -1.3353   -2.4112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8397    1.3302   -1.9665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5735   -1.4923   -0.9852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7658    0.7380   -2.6664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1970   -0.8766   -3.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7050   -0.6161   -2.7899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8952   -2.0522   -2.1437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2796   -1.3929   -0.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7344    1.6004   -0.8054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0269    0.6807   -1.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2827    0.4560    0.2906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9362    2.0967    1.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1171    0.1817    2.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0240   -1.2438    1.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8177   -0.5636    2.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0737    1.1011    1.7725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0460   -2.0163    1.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7974   -2.4213    1.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1626   -2.5615   -0.2822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7504    1.2695   -0.4629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0468    1.3253    1.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1090   -0.1737    1.7027 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2523    1.9147    1.4394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7925    2.3660    0.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0024   -0.5709    1.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8318   -0.9442   -0.2731 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1626   -1.3963    0.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  1
 25 27  1  0
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 29 30  1  0
 30 31  1  1
 30 12  1  0
 30 15  1  0
 27 16  1  0
 25 19  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  1
  3 36  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
 11 43  1  0
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 18 53  1  0
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 20 57  1  0
 21 58  1  6
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 23 60  1  0
 23 61  1  0
 24 62  1  0
 24 63  1  0
 26 64  1  0
 26 65  1  0
 26 66  1  0
 27 67  1  6
 28 68  1  0
 28 69  1  0
 29 70  1  0
 29 71  1  0
 31 72  1  0
 31 73  1  0
 31 74  1  0
M  END


  Mrv1652302052018532D          

 36 39  0  0  0  0            999 V2000
10000.021310001.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8836 9999.7851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.7435 9997.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8836 9997.3033    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5962 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3087 9999.7851    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.0213 9998.5503    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8823 9998.9568    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.8823 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.5968 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3113 9998.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.309310000.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.594810000.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5948 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.3093 9998.9659    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.1710 9999.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4565 9998.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4565 9998.1317    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.1710 9997.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.023810000.2033    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.0238 9999.3783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.8084 9999.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.2933 9999.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.808410000.4583    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.808410001.2833    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.524110001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.237710001.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.953410001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.667010001.2833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10004.382710001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.096310001.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.812010001.6958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10005.096310000.4583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.953410002.5208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.093710001.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.524110000.8708    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
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 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
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 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
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 18  3  1  6  0  0  0
 19  9  1  0  0  0  0
  9  4  1  1  0  0  0
 16  8  1  0  0  0  0
  8  2  1  1  0  0  0
 14  8  1  0  0  0  0
 14  5  1  6  0  0  0
 11 15  1  0  0  0  0
 15  6  1  1  0  0  0
 24 25  1  0  0  0  0
 24 36  1  6  0  0  0
 25 26  1  0  0  0  0
 25 35  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 34  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 15 21  1  0  0  0  0
 21  7  1  6  0  0  0
 12 20  1  0  0  0  0
 20  1  1  1  0  0  0
 24 20  1  0  0  0  0
 24 23  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000141

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(=O)NCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H43NO4/c1-16(4-9-23(29)27-15-24(30)31)20-7-8-21-19-6-5-17-14-18(28)10-12-25(17,2)22(19)11-13-26(20,21)3/h16-22,28H,4-15H2,1-3H3,(H,27,29)(H,30,31)/t16-,17-,18-,19+,20-,21+,22+,25+,26-/m1/s1

> <INCHI_KEY>
XBSQTYHEGZTYJE-OETIFKLTSA-N

> <FORMULA>
C26H43NO4

> <MOLECULAR_WEIGHT>
433.6239

> <EXACT_MASS>
433.319208869

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
51.31536464563915

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid

> <ALOGPS_LOGP>
3.71

> <JCHEM_LOGP>
3.9167870809999994

> <ALOGPS_LOGS>
-5.45

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.94682470220906

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7732726092807374

> <JCHEM_PKA_STRONGEST_BASIC>
-1.114714379730807

> <JCHEM_POLAR_SURFACE_AREA>
86.63000000000001

> <JCHEM_REFRACTIVITY>
120.48479999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.53e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000698
     RDKit          3D
Lithocholic acid glycine conjugate
 74 77  0  0  0  0  0  0  0  0999 V2000
    3.2846    3.0246   -1.4917 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4824    2.1994   -0.4719 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3179    1.6215    0.5827 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4188    0.6959    0.1928 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1778    0.2184    1.4089 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8301    0.6204    2.5448 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2715   -0.6739    1.2785 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0183   -1.1527    2.3916 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0863   -2.0609    1.9242 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1965   -2.2830    0.6946 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9841   -2.6885    2.7811 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4692    1.4436   -1.1767 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8125    0.4639   -2.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4696   -0.2509   -2.4881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4902    0.3528   -1.5277 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6834   -0.4178   -1.1539 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6665   -0.3050   -2.3305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9822   -0.9487   -2.0158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5444   -0.5833   -0.6817 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3506    0.6996   -0.7172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2366    0.7173    0.5194 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2463    2.0306    1.0425 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7286   -0.2020    1.5864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2141   -0.0146    1.6658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5259   -0.5424    0.4247 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0568   -1.9699    0.6527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3815    0.3019   -0.0105 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4737    0.6735    1.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3288    1.5377    0.5878 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4495    0.6847   -0.3556 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9338   -0.5910    0.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7521    3.8972   -1.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5108    3.4297   -2.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9537    2.4004   -2.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8975    3.0564    0.0571 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8164    2.4339    1.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7296    1.0738    1.3787 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1056   -0.2424   -0.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1792    1.1568   -0.4677 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5259   -0.9827    0.3123 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5282   -0.3004    2.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3824   -1.6419    3.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7844   -3.5837    3.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8124    2.2221   -1.7198 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1352    1.0166   -3.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5710   -0.2757   -2.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1626    0.0104   -3.5211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839   -1.3353   -2.4112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8397    1.3302   -1.9665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5735   -1.4923   -0.9852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7658    0.7380   -2.6664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1970   -0.8766   -3.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7050   -0.6161   -2.7899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8952   -2.0522   -2.1437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2796   -1.3929   -0.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7344    1.6004   -0.8054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0269    0.6807   -1.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2827    0.4560    0.2906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9362    2.0967    1.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1171    0.1817    2.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0240   -1.2438    1.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8177   -0.5636    2.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0737    1.1011    1.7725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0460   -2.0163    1.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7974   -2.4213    1.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1626   -2.5615   -0.2822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7504    1.2695   -0.4629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0468    1.3253    1.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1090   -0.1737    1.7027 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2523    1.9147    1.4394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7925    2.3660    0.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0024   -0.5709    1.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8318   -0.9442   -0.2731 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1626   -1.3963    0.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  1
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  1
 30 12  1  0
 30 15  1  0
 27 16  1  0
 25 19  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  1
  3 36  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
 11 43  1  0
 12 44  1  6
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  6
 16 50  1  1
 17 51  1  0
 17 52  1  0
 18 53  1  0
 18 54  1  0
 19 55  1  1
 20 56  1  0
 20 57  1  0
 21 58  1  6
 22 59  1  0
 23 60  1  0
 23 61  1  0
 24 62  1  0
 24 63  1  0
 26 64  1  0
 26 65  1  0
 26 66  1  0
 27 67  1  6
 28 68  1  0
 28 69  1  0
 29 70  1  0
 29 71  1  0
 31 72  1  0
 31 73  1  0
 31 74  1  0
M  END

HEADER    PROTEIN                                 05-FEB-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-FEB-20         0                                  
HETATM    1  C   UNK     0    8666.7068668.598   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8662.7168666.266   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8658.7218662.405   0.000  0.00  0.00           O+0
HETATM    4  H   UNK     0    8662.7168661.633   0.000  0.00  0.00           H+0
HETATM    5  H   UNK     0    8664.0468663.961   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8665.3768666.266   0.000  0.00  0.00           H+0
HETATM    7  H   UNK     0    8666.7068663.961   0.000  0.00  0.00           H+0
HETATM    8  C   UNK     0    8662.7148664.719   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8662.7148663.179   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8664.0478662.409   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8665.3818663.179   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8665.3778667.816   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8664.0448667.046   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8664.0448665.506   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8665.3778664.736   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8661.3868665.489   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8660.0528664.719   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8660.0528663.179   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8661.3868662.409   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8666.7118667.046   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8666.7118665.506   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8668.1768665.030   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8669.0818666.276   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8668.1768667.522   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8668.1768669.062   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8669.5128669.832   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8670.8448669.062   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8672.1808669.832   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0    8673.5128669.062   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0    8674.8488669.832   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8676.1808669.062   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0    8677.5168669.832   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0    8676.1808667.522   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0    8672.1808671.372   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0    8666.8428669.832   0.000  0.00  0.00           C+0
HETATM   36  H   UNK     0    8669.5128668.292   0.000  0.00  0.00           H+0
CONECT    1   20                                                            
CONECT    2    8                                                            
CONECT    3   18                                                            
CONECT    4    9                                                            
CONECT    5   14                                                            
CONECT    6   15                                                            
CONECT    7   21                                                            
CONECT    8    9   16    2   14                                             
CONECT    9    8   10   19    4                                             
CONECT   10    9   11                                                       
CONECT   11   10   15                                                       
CONECT   12   13   20                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15    8    5                                             
CONECT   15   14   11    6   21                                             
CONECT   16   17    8                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19    3                                                  
CONECT   19   18    9                                                       
CONECT   20   21   12    1   24                                             
CONECT   21   20   22   15    7                                             
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   25   36   20   23                                             
CONECT   25   24   26   35                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   34                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   28                                                            
CONECT   35   25                                                            
CONECT   36   24                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

COMPND    HMDB0000698
HETATM    1  C1  UNL     1       3.285   3.025  -1.492  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.482   2.199  -0.472  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.318   1.621   0.583  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.419   0.696   0.193  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.178   0.218   1.409  1.00  0.00           C  
HETATM    6  O1  UNL     1       4.830   0.620   2.545  1.00  0.00           O  
HETATM    7  N1  UNL     1       6.272  -0.674   1.279  1.00  0.00           N  
HETATM    8  C6  UNL     1       7.018  -1.153   2.392  1.00  0.00           C  
HETATM    9  C7  UNL     1       8.086  -2.061   1.924  1.00  0.00           C  
HETATM   10  O2  UNL     1       8.197  -2.283   0.695  1.00  0.00           O  
HETATM   11  O3  UNL     1       8.984  -2.688   2.781  1.00  0.00           O  
HETATM   12  C8  UNL     1       1.469   1.444  -1.177  1.00  0.00           C  
HETATM   13  C9  UNL     1       1.812   0.464  -2.224  1.00  0.00           C  
HETATM   14  C10 UNL     1       0.470  -0.251  -2.488  1.00  0.00           C  
HETATM   15  C11 UNL     1      -0.490   0.353  -1.528  1.00  0.00           C  
HETATM   16  C12 UNL     1      -1.683  -0.418  -1.154  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.666  -0.305  -2.330  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.982  -0.949  -2.016  1.00  0.00           C  
HETATM   19  C15 UNL     1      -4.544  -0.583  -0.682  1.00  0.00           C  
HETATM   20  C16 UNL     1      -5.351   0.700  -0.717  1.00  0.00           C  
HETATM   21  C17 UNL     1      -6.237   0.717   0.519  1.00  0.00           C  
HETATM   22  O4  UNL     1      -6.246   2.031   1.042  1.00  0.00           O  
HETATM   23  C18 UNL     1      -5.729  -0.202   1.586  1.00  0.00           C  
HETATM   24  C19 UNL     1      -4.214  -0.015   1.666  1.00  0.00           C  
HETATM   25  C20 UNL     1      -3.526  -0.542   0.425  1.00  0.00           C  
HETATM   26  C21 UNL     1      -3.057  -1.970   0.653  1.00  0.00           C  
HETATM   27  C22 UNL     1      -2.381   0.302  -0.010  1.00  0.00           C  
HETATM   28  C23 UNL     1      -1.474   0.673   1.110  1.00  0.00           C  
HETATM   29  C24 UNL     1      -0.329   1.538   0.588  1.00  0.00           C  
HETATM   30  C25 UNL     1       0.449   0.685  -0.356  1.00  0.00           C  
HETATM   31  C26 UNL     1       0.934  -0.591   0.228  1.00  0.00           C  
HETATM   32  H1  UNL     1       3.752   3.897  -1.020  1.00  0.00           H  
HETATM   33  H2  UNL     1       2.511   3.430  -2.195  1.00  0.00           H  
HETATM   34  H3  UNL     1       3.954   2.400  -2.085  1.00  0.00           H  
HETATM   35  H4  UNL     1       1.898   3.056   0.057  1.00  0.00           H  
HETATM   36  H5  UNL     1       3.816   2.434   1.203  1.00  0.00           H  
HETATM   37  H6  UNL     1       2.730   1.074   1.379  1.00  0.00           H  
HETATM   38  H7  UNL     1       4.106  -0.242  -0.300  1.00  0.00           H  
HETATM   39  H8  UNL     1       5.179   1.157  -0.468  1.00  0.00           H  
HETATM   40  H9  UNL     1       6.526  -0.983   0.312  1.00  0.00           H  
HETATM   41  H10 UNL     1       7.528  -0.300   2.922  1.00  0.00           H  
HETATM   42  H11 UNL     1       6.382  -1.642   3.164  1.00  0.00           H  
HETATM   43  H12 UNL     1       8.784  -3.584   3.220  1.00  0.00           H  
HETATM   44  H13 UNL     1       0.812   2.222  -1.720  1.00  0.00           H  
HETATM   45  H14 UNL     1       2.135   1.017  -3.153  1.00  0.00           H  
HETATM   46  H15 UNL     1       2.571  -0.276  -2.040  1.00  0.00           H  
HETATM   47  H16 UNL     1       0.163   0.010  -3.521  1.00  0.00           H  
HETATM   48  H17 UNL     1       0.584  -1.335  -2.411  1.00  0.00           H  
HETATM   49  H18 UNL     1      -0.840   1.330  -1.966  1.00  0.00           H  
HETATM   50  H19 UNL     1      -1.573  -1.492  -0.985  1.00  0.00           H  
HETATM   51  H20 UNL     1      -2.766   0.738  -2.666  1.00  0.00           H  
HETATM   52  H21 UNL     1      -2.197  -0.877  -3.158  1.00  0.00           H  
HETATM   53  H22 UNL     1      -4.705  -0.616  -2.790  1.00  0.00           H  
HETATM   54  H23 UNL     1      -3.895  -2.052  -2.144  1.00  0.00           H  
HETATM   55  H24 UNL     1      -5.280  -1.393  -0.410  1.00  0.00           H  
HETATM   56  H25 UNL     1      -4.734   1.600  -0.805  1.00  0.00           H  
HETATM   57  H26 UNL     1      -6.027   0.681  -1.594  1.00  0.00           H  
HETATM   58  H27 UNL     1      -7.283   0.456   0.291  1.00  0.00           H  
HETATM   59  H28 UNL     1      -6.936   2.097   1.744  1.00  0.00           H  
HETATM   60  H29 UNL     1      -6.117   0.182   2.567  1.00  0.00           H  
HETATM   61  H30 UNL     1      -6.024  -1.244   1.483  1.00  0.00           H  
HETATM   62  H31 UNL     1      -3.818  -0.564   2.539  1.00  0.00           H  
HETATM   63  H32 UNL     1      -4.074   1.101   1.772  1.00  0.00           H  
HETATM   64  H33 UNL     1      -2.046  -2.016   1.090  1.00  0.00           H  
HETATM   65  H34 UNL     1      -3.797  -2.421   1.376  1.00  0.00           H  
HETATM   66  H35 UNL     1      -3.163  -2.561  -0.282  1.00  0.00           H  
HETATM   67  H36 UNL     1      -2.750   1.269  -0.463  1.00  0.00           H  
HETATM   68  H37 UNL     1      -2.047   1.325   1.801  1.00  0.00           H  
HETATM   69  H38 UNL     1      -1.109  -0.174   1.703  1.00  0.00           H  
HETATM   70  H39 UNL     1       0.252   1.915   1.439  1.00  0.00           H  
HETATM   71  H40 UNL     1      -0.792   2.366   0.040  1.00  0.00           H  
HETATM   72  H41 UNL     1       1.002  -0.571   1.341  1.00  0.00           H  
HETATM   73  H42 UNL     1       1.832  -0.944  -0.273  1.00  0.00           H  
HETATM   74  H43 UNL     1       0.163  -1.396   0.037  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3   12   35
CONECT    3    4   36   37
CONECT    4    5   38   39
CONECT    5    6    6    7
CONECT    7    8   40
CONECT    8    9   41   42
CONECT    9   10   10   11
CONECT   11   43
CONECT   12   13   30   44
CONECT   13   14   45   46
CONECT   14   15   47   48
CONECT   15   16   30   49
CONECT   16   17   27   50
CONECT   17   18   51   52
CONECT   18   19   53   54
CONECT   19   20   25   55
CONECT   20   21   56   57
CONECT   21   22   23   58
CONECT   22   59
CONECT   23   24   60   61
CONECT   24   25   62   63
CONECT   25   26   27
CONECT   26   64   65   66
CONECT   27   28   67
CONECT   28   29   68   69
CONECT   29   30   70   71
CONECT   30   31
CONECT   31   72   73   74
END

HMDB0000698
     RDKit          3D
Lithocholic acid glycine conjugate
 74 77  0  0  0  0  0  0  0  0999 V2000
    3.2846    3.0246   -1.4917 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4824    2.1994   -0.4719 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3179    1.6215    0.5827 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4188    0.6959    0.1928 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1778    0.2184    1.4089 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8301    0.6204    2.5448 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2715   -0.6739    1.2785 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0183   -1.1527    2.3916 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0863   -2.0609    1.9242 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1965   -2.2830    0.6946 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9841   -2.6885    2.7811 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4692    1.4436   -1.1767 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8125    0.4639   -2.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4696   -0.2509   -2.4881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4902    0.3528   -1.5277 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6834   -0.4178   -1.1539 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6665   -0.3050   -2.3305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9822   -0.9487   -2.0158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5444   -0.5833   -0.6817 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3506    0.6996   -0.7172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2366    0.7173    0.5194 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2463    2.0306    1.0425 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7286   -0.2020    1.5864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2141   -0.0146    1.6658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5259   -0.5424    0.4247 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0568   -1.9699    0.6527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3815    0.3019   -0.0105 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4737    0.6735    1.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3288    1.5377    0.5878 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4495    0.6847   -0.3556 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9338   -0.5910    0.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7521    3.8972   -1.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5108    3.4297   -2.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9537    2.4004   -2.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8975    3.0564    0.0571 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8164    2.4339    1.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7296    1.0738    1.3787 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1056   -0.2424   -0.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1792    1.1568   -0.4677 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5259   -0.9827    0.3123 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5282   -0.3004    2.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3824   -1.6419    3.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7844   -3.5837    3.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8124    2.2221   -1.7198 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1352    1.0166   -3.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5710   -0.2757   -2.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1626    0.0104   -3.5211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839   -1.3353   -2.4112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8397    1.3302   -1.9665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5735   -1.4923   -0.9852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7658    0.7380   -2.6664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1970   -0.8766   -3.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7050   -0.6161   -2.7899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8952   -2.0522   -2.1437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2796   -1.3929   -0.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7344    1.6004   -0.8054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0269    0.6807   -1.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2827    0.4560    0.2906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9362    2.0967    1.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1171    0.1817    2.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0240   -1.2438    1.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8177   -0.5636    2.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0737    1.1011    1.7725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0460   -2.0163    1.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7974   -2.4213    1.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1626   -2.5615   -0.2822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7504    1.2695   -0.4629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0468    1.3253    1.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1090   -0.1737    1.7027 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2523    1.9147    1.4394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7925    2.3660    0.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0024   -0.5709    1.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8318   -0.9442   -0.2731 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1626   -1.3963    0.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  1
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  1
 30 12  1  0
 30 15  1  0
 27 16  1  0
 25 19  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  1
  3 36  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
 11 43  1  0
 12 44  1  6
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  6
 16 50  1  1
 17 51  1  0
 17 52  1  0
 18 53  1  0
 18 54  1  0
 19 55  1  1
 20 56  1  0
 20 57  1  0
 21 58  1  6
 22 59  1  0
 23 60  1  0
 23 61  1  0
 24 62  1  0
 24 63  1  0
 26 64  1  0
 26 65  1  0
 26 66  1  0
 27 67  1  6
 28 68  1  0
 28 69  1  0
 29 70  1  0
 29 71  1  0
 31 72  1  0
 31 73  1  0
 31 74  1  0
M  END

Synonyms

Value	Source
Glycolithocholate	ChEBI
Lithocholylglycine	ChEBI
N-((3-alpha,5-beta)-3-Hydroxy-24-oxocholan-24-yl)glycine	ChEBI
Glycolithocholic acid	Kegg
N-((3-a,5-b)-3-Hydroxy-24-oxocholan-24-yl)glycine	Generator
N-((3-Α,5-β)-3-hydroxy-24-oxocholan-24-yl)glycine	Generator
Lithocholate glycine conjugate	Generator
Lithocholic acid glycine conjugic acid	Generator
3a-Hydroxy-5b-cholanic acid glycine ester	HMDB
3a-Hydroxy-5b-cholanoylglycine	HMDB
3a-Hydroxy-N-(carboxymethyl)-5b-cholan-24-amide	HMDB
3alpha-Hydroxy-5beta-cholan-24-Oate	HMDB
3alpha-Hydroxy-5beta-cholan-24-Oic acid	HMDB
3alpha-Hydroxy-5beta-cholan-24-Oic acid N-(carboxymethyl)amide	HMDB
Lithocholoyglycine	HMDB
N-(3a-Hydroxy-5b-cholan-24-oyl)-glycine	HMDB
N-(3a-Hydroxy-5b-cholanoyl)glycine	HMDB
N-(Carboxymethyl)-3a-hydroxy-5b-cholan-24-amide	HMDB
Glycolithocholic acid, monosodium salt	HMDB
3alpha-Hydroxy-5beta-cholanoylglycine 3-sulfate	HMDB
3alpha-Hydroxy-5beta-cholanoylglycine 3-sulphate	HMDB
3α-Hydroxy-5β-cholanoylglycine 3-sulfate	HMDB
3α-Hydroxy-5β-cholanoylglycine 3-sulphate	HMDB
Glycolithocholic acid 3-sulfate	HMDB
Glycolithocholic acid 3-sulphate	HMDB
Glycolithocholic acid 3alpha-sulfate	HMDB
Glycolithocholic acid 3alpha-sulphate	HMDB
Glycolithocholic acid 3α-sulfate	HMDB
Glycolithocholic acid 3α-sulphate	HMDB
Glycolithocholic acid sulfate	HMDB
Glycolithocholic acid sulphate	HMDB
N-[(3alpha,5beta)-24-Oxo-3-(sulfooxy)cholan-24-yl]glycine	HMDB
N-[(3α,5β)-24-Oxo-3-(sulfooxy)cholan-24-yl]glycine	HMDB
Sulfoglycolithocholic acid	HMDB
Sulfolithocholylglycine	HMDB

Molecular Formula

C₂₆H₄₃NO₄

Average Mass

433.6239

Monoisotopic Mass

433.319208869

IUPAC Name

2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid

Traditional Name

[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid

CAS Registry Number

474-74-8

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(=O)NCC(O)=O

InChI Identifier

InChI=1S/C26H43NO4/c1-16(4-9-23(29)27-15-24(30)31)20-7-8-21-19-6-5-17-14-18(28)10-12-25(17,2)22(19)11-13-26(20,21)3/h16-22,28H,4-15H2,1-3H3,(H,27,29)(H,30,31)/t16-,17-,18-,19+,20-,21+,22+,25+,26-/m1/s1

InChI Key

XBSQTYHEGZTYJE-OETIFKLTSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glycinated bile acids and derivatives. Glycinated bile acids and derivatives are compounds with a structure characterized by the presence of a glycine linked to a bile acid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Glycinated bile acids and derivatives

Alternative Parents

Substituents

Glycinated bile acid
Hydroxy bile acid, alcohol, or derivatives
Monohydroxy bile acid, alcohol, or derivatives
3-hydroxysteroid
Hydroxysteroid
3-alpha-hydroxysteroid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Cyclic alcohol
Secondary alcohol
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid derivative
Carboxylic acid
Organic 1,3-dipolar compound
Monocarboxylic acid or derivatives
Propargyl-type 1,3-dipolar organic compound
Organopnictogen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Alcohol
Organooxygen compound
Organonitrogen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

N-acylglycine (CHEBI:37998 )
bile acid glycine conjugate (CHEBI:37998 )
Glycine conjugates (LMST05030009 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0015 g/L	ALOGPS
logP	3.71	ALOGPS
logP	3.92	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	3.77	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.63 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	120.48 m³·mol⁻¹	ChemAxon
Polarizability	51.32 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Bile
Blood
Feces
Gall Bladder
Intestine
Kidney
Liver
Urine

Tissue Locations

Gall Bladder
Intestine
Kidney
Liver

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192015	Bile salt sulfotransferase	Enzyme	Q06520	Homo sapiens
MMDBp0194143	Glycine N-acyltransferase	Enzyme	Q6IB77	Homo sapiens
MMDBp0194144	Glycine N-acyltransferase-like protein 1	Enzyme	Q969I3	Homo sapiens
MMDBp0194145	Glycine N-acyltransferase-like protein 2	Enzyme	Q8WU03	Homo sapiens
MMDBp0194146	Glycine N-acyltransferase-like protein 3	Enzyme	Q5SZD4	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Firmicutes	5	Human ; Human feces; Human saliva; Human mucosa; Human supragingival plaque; Human subgingival plaque	Microbial culture; Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria/Eubacteria	Actinobacteria	5	Human ; Human feces; Human saliva; Human mucosa; Human supragingival plaque; Human stool	Microbial culture; Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria/Eubacteria	Bacteroidetes	5	Human feces; Human stool; Human ; Human urine	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria/Eubacteria	Proteobacteria	1		Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected and Quantified	0.009		0.005	0.015	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	9518169
Human Blood	Detected and Quantified	0.009		0.005	0.015	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	15375183
Human Bile	Detected and Quantified	620		590	650	uM	Adult (>18 years old)	Both	Normal	HMDB	16548228
Human Blood	Detected and Quantified	0.009		0.005	0.015	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	16548228
Human Feces	Detected and Quantified	6.68	18.49			nmol/g dry feces	Not Specified	Not Specified	Normal	HMDB	22664055
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected and Quantified	0.009		0.005	0.015	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	9518169
Human Blood	Detected and Quantified	0.009		0.005	0.015	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	15375183
Human Blood	Detected and Quantified	0.009		0.005	0.015	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	16548228
Human Feces	Detected and Quantified	6.68	18.49			nmol/g dry feces	Not Specified	Not Specified	Normal	HMDB	22664055
Human Bile	Detected and Quantified	620		590	650	uM	Adult (>18 years old)	Both	Normal	HMDB	16548228
Human Gall bladder	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Kidney	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000698

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022187

KNApSAcK ID

Not Available

Chemspider ID

103116

KEGG Compound ID

C15557

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5666

PubChem Compound

115245

PDB ID

Not Available

ChEBI ID

37998

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Cowen AE, Korman MG, Hofmann AF, Cass OW, Coffin SB: Metabolism of lithocholate in healthy man. II. Enterohepatic circulation. Gastroenterology. 1975 Jul;69(1):67-76. [PubMed:1097294 ]
Cowen AE, Korman MG, Hofmann AF, Cass OW: Metabolism of lethocholate in healthy man. I. Biotransformation and biliary excretion of intravenously administered lithocholate, lithocholylglycine, and their sulfates. Gastroenterology. 1975 Jul;69(1):59-66. [PubMed:1150035 ]
Cowen AE, Korman MG, Hofmann AF, Thomas PJ: Metabolism of lithocholate in healthy man. III. Plasma disappearance of radioactivity after intravenous injection of labeled lithocholate and its derivatives. Gastroenterology. 1975 Jul;69(1):77-82. [PubMed:1150037 ]
Lee BL, New AL, Ong CN: Comparative analysis of conjugated bile acids in human serum using high-performance liquid chromatography and capillary electrophoresis. J Chromatogr B Biomed Sci Appl. 1997 Dec 19;704(1-2):35-42. doi: 10.1016/s0378-4347(97)00443-x. [PubMed:9518169 ]
St-Pierre MV, Kullak-Ublick GA, Hagenbuch B, Meier PJ: Transport of bile acids in hepatic and non-hepatic tissues. J Exp Biol. 2001 May;204(Pt 10):1673-86. doi: 10.1242/jeb.204.10.1673. [PubMed:11316487 ]
Davis RA, Miyake JH, Hui TY, Spann NJ: Regulation of cholesterol-7alpha-hydroxylase: BAREly missing a SHP. J Lipid Res. 2002 Apr;43(4):533-43. [PubMed:11907135 ]
Chiang JY: Bile acid regulation of hepatic physiology: III. Bile acids and nuclear receptors. Am J Physiol Gastrointest Liver Physiol. 2003 Mar;284(3):G349-56. doi: 10.1152/ajpgi.00417.2002. [PubMed:12576301 ]
Claudel T, Staels B, Kuipers F: The Farnesoid X receptor: a molecular link between bile acid and lipid and glucose metabolism. Arterioscler Thromb Vasc Biol. 2005 Oct;25(10):2020-30. doi: 10.1161/01.ATV.0000178994.21828.a7. Epub 2005 Jul 21. [PubMed:16037564 ]
Tadano T, Kanoh M, Matsumoto M, Sakamoto K, Kamano T: Studies of serum and feces bile acids determination by gas chromatography-mass spectrometry. Rinsho Byori. 2006 Feb;54(2):103-10. [PubMed:16548228 ]
Goto T, Myint KT, Sato K, Wada O, Kakiyama G, Iida T, Hishinuma T, Mano N, Goto J: LC/ESI-tandem mass spectrometric determination of bile acid 3-sulfates in human urine 3beta-Sulfooxy-12alpha-hydroxy-5beta-cholanoic acid is an abundant nonamidated sulfate. J Chromatogr B Analyt Technol Biomed Life Sci. 2007 Feb 1;846(1-2):69-77. doi: 10.1016/j.jchromb.2006.08.013. Epub 2006 Sep 1. [PubMed:16949895 ]
Lucas LN, Barrett K, Kerby RL, Zhang Q, Cattaneo LE, Stevenson D, Rey FE, Amador-Noguez D: Dominant Bacterial Phyla from the Human Gut Show Widespread Ability To Transform and Conjugate Bile Acids. mSystems. 2021 Aug 31:e0080521. doi: 10.1128/mSystems.00805-21. [PubMed:34463573 ]

Showing metabocard for Lithocholic acid glycine conjugate (MMDBc0000141)

MOL for #<Metabolite:0x00007f9251453978>

3D MOL for #<Metabolite:0x00007f9251453978>

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3D-SDF for #<Metabolite:0x00007f9251453978>

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3D PDB for #<Metabolite:0x00007f9251453978>

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INCHI for #<Metabolite:0x00007f9251453978>

Structure for #<Metabolite:0x00007f9251453978>

3D Structure for #<Metabolite:0x00007f9251453978>