MiMeDB: Showing metabocard for Glycoursodeoxycholic acid (MMDBc0000365)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:36:12 UTC

Update Date

2024-04-30 19:31:55 UTC

Metabolite ID

MMDBc0000365

Metabolite Identification

Common Name

Glycoursodeoxycholic acid

Description

Glycoursodeoxycholic acid 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


  Mrv1652302052016282D          

 37 40  0  0  0  0            999 V2000
 9998.0682 9999.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.9308 9998.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.0703 9996.5053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9993.7911 9996.5053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.9308 9996.0917    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9996.6432 9997.3385    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3557 9998.5732    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.0682 9997.3385    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9995.2183 9998.1574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.5038 9997.7450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.5038 9996.9200    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9995.2183 9996.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3563 9999.4039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.6419 9998.9914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.6419 9998.1664    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.3563 9997.7541    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9995.9295 9997.7450    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9995.9295 9996.9200    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.6439 9996.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3583 9996.9200    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.0707 9998.9913    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.0707 9998.1664    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.8553 9997.9114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3402 9998.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8553 9999.2464    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.855310000.0714    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.570010000.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.285510000.0714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.999310000.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.715010000.0714    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10002.428610000.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.144310000.0714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.857910000.4839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.1443 9999.2464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.999310001.3089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.140610000.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5700 9999.6589    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 11  4  1  6  0  0  0
 20  3  1  1  0  0  0
 12 18  1  0  0  0  0
 18  5  1  1  0  0  0
  9 17  1  0  0  0  0
 17  2  1  1  0  0  0
 15 17  1  0  0  0  0
 15  6  1  6  0  0  0
 20 16  1  0  0  0  0
 16  7  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 26  1  0  0  0  0
 25 37  1  6  0  0  0
 26 27  1  0  0  0  0
 26 36  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 35  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 25 21  1  0  0  0  0
 25 24  1  0  0  0  0
 16 22  1  0  0  0  0
 22  8  1  6  0  0  0
 13 21  1  0  0  0  0
 21  1  1  1  0  0  0
M  END

HMDB0000708
     RDKit          3D
Glycoursodeoxycholic acid
 75 78  0  0  0  0  0  0  0  0999 V2000
    3.3317    2.8194   -1.3272 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4965    1.9246   -0.3829 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4035    1.3018    0.5800 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5160    0.4572    0.0199 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3441   -0.0822    1.1540 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0343    0.2110    2.3272 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4484   -0.9063    0.8332 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2582   -1.4346    1.9311 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3407   -2.2558    1.3841 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4423   -2.4010    0.1414 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2575   -2.8768    2.2241 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4387    1.2457   -1.0793 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6795    0.3214   -2.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4127   -0.5574   -2.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5204    0.1216   -1.4114 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6762   -0.5654   -0.8602 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5880   -1.2413   -1.8484 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3299   -2.6309   -1.8934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0295   -0.9603   -1.6497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4906   -0.8490   -0.2313 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7352    0.0261   -0.2285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3969   -0.1270    1.1054 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.6075    0.5573    1.1812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4430    0.2915    2.1737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1321    0.8085    1.6215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4819   -0.1712    0.6775 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8613   -1.2618    1.5032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5382    0.5492   -0.2297 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7255    1.6161    0.3735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3177    1.2447    0.7523 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4357    0.4482   -0.2402 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0135   -0.7880    0.3535 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8325    2.1866   -2.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0205    3.3787   -0.6603 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6625    3.5932   -1.7798 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9673    2.7705    0.2392 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9481    2.1569    1.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8968    0.7988    1.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1919    1.1457   -0.5703 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2298   -0.3318   -0.6622 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6576   -1.1153   -0.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6382   -0.5577    2.4871 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5825   -2.0466    2.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1712   -2.5191    2.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7542    2.0698   -1.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5136   -0.3517   -2.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7370    0.8959   -3.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6444   -1.6072   -2.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0394   -0.5636   -3.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7674    1.1207   -1.8381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4402   -1.3280   -0.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2949   -0.8602   -2.8631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6372   -3.0127   -2.7387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4005   -0.0853   -2.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5971   -1.8335   -2.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8068   -1.8376    0.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4389    1.0840   -0.4246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4076   -0.3533   -1.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5971   -1.2277    1.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3291    0.0534    0.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9014    1.1264    2.7436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2701   -0.5194    2.9190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4494    0.9016    2.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2785    1.7617    1.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5136   -1.4232    2.4112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9142   -2.2527    0.9652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8625   -1.0678    1.8788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1599    0.9929   -1.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2148    1.9997    1.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6562    2.4922   -0.3056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3093    0.7449    1.7705 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2244    2.1911    0.9447 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4788   -1.7318    0.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0074   -0.6776    1.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0693   -0.9965    0.0894 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
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  1
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  1
 31 12  1  0
 31 15  1  0
 28 16  1  0
 26 20  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  1
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
 11 44  1  0
 12 45  1  6
 13 46  1  0
 13 47  1  0
 14 48  1  0
 14 49  1  0
 15 50  1  6
 16 51  1  1
 17 52  1  6
 18 53  1  0
 19 54  1  0
 19 55  1  0
 20 56  1  1
 21 57  1  0
 21 58  1  0
 22 59  1  1
 23 60  1  0
 24 61  1  0
 24 62  1  0
 25 63  1  0
 25 64  1  0
 27 65  1  0
 27 66  1  0
 27 67  1  0
 28 68  1  6
 29 69  1  0
 29 70  1  0
 30 71  1  0
 30 72  1  0
 32 73  1  0
 32 74  1  0
 32 75  1  0
M  END


  Mrv1652302052016282D          

 37 40  0  0  0  0            999 V2000
 9998.0682 9999.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.9308 9998.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.0703 9996.5053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9993.7911 9996.5053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.9308 9996.0917    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9996.6432 9997.3385    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3557 9998.5732    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.0682 9997.3385    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9995.2183 9998.1574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.5038 9997.7450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.5038 9996.9200    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9995.2183 9996.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3563 9999.4039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.6419 9998.9914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.6419 9998.1664    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.3563 9997.7541    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9995.9295 9997.7450    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9995.9295 9996.9200    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9996.6439 9996.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3583 9996.9200    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.0707 9998.9913    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.0707 9998.1664    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.8553 9997.9114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3402 9998.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8553 9999.2464    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.855310000.0714    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.570010000.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.285510000.0714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.999310000.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.715010000.0714    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10002.428610000.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.144310000.0714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.857910000.4839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.1443 9999.2464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.999310001.3089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.140610000.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5700 9999.6589    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 11  4  1  6  0  0  0
 20  3  1  1  0  0  0
 12 18  1  0  0  0  0
 18  5  1  1  0  0  0
  9 17  1  0  0  0  0
 17  2  1  1  0  0  0
 15 17  1  0  0  0  0
 15  6  1  6  0  0  0
 20 16  1  0  0  0  0
 16  7  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 26  1  0  0  0  0
 25 37  1  6  0  0  0
 26 27  1  0  0  0  0
 26 36  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 35  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 25 21  1  0  0  0  0
 25 24  1  0  0  0  0
 16 22  1  0  0  0  0
 22  8  1  6  0  0  0
 13 21  1  0  0  0  0
 21  1  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000365

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](O)C[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/C26H43NO5/c1-15(4-7-22(30)27-14-23(31)32)18-5-6-19-24-20(9-11-26(18,19)3)25(2)10-8-17(28)12-16(25)13-21(24)29/h15-21,24,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16+,17-,18-,19+,20+,21+,24+,25+,26-/m1/s1

> <INCHI_KEY>
GHCZAUBVMUEKKP-XROMFQGDSA-N

> <FORMULA>
C26H43NO5

> <MOLECULAR_WEIGHT>
449.6233

> <EXACT_MASS>
449.314123491

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
52.19389243425874

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid

> <ALOGPS_LOGP>
2.40

> <JCHEM_LOGP>
2.608022284

> <ALOGPS_LOGS>
-4.75

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.791653018199504

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7732907141500656

> <JCHEM_PKA_STRONGEST_BASIC>
-0.48930218820632587

> <JCHEM_POLAR_SURFACE_AREA>
106.86000000000001

> <JCHEM_REFRACTIVITY>
122.07729999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.93e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000708
     RDKit          3D
Glycoursodeoxycholic acid
 75 78  0  0  0  0  0  0  0  0999 V2000
    3.3317    2.8194   -1.3272 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4965    1.9246   -0.3829 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4035    1.3018    0.5800 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5160    0.4572    0.0199 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3441   -0.0822    1.1540 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0343    0.2110    2.3272 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4484   -0.9063    0.8332 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2582   -1.4346    1.9311 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3407   -2.2558    1.3841 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4423   -2.4010    0.1414 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2575   -2.8768    2.2241 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4387    1.2457   -1.0793 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6795    0.3214   -2.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4127   -0.5574   -2.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5204    0.1216   -1.4114 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6762   -0.5654   -0.8602 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5880   -1.2413   -1.8484 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3299   -2.6309   -1.8934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0295   -0.9603   -1.6497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4906   -0.8490   -0.2313 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7352    0.0261   -0.2285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3969   -0.1270    1.1054 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.6075    0.5573    1.1812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4430    0.2915    2.1737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1321    0.8085    1.6215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4819   -0.1712    0.6775 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8613   -1.2618    1.5032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5382    0.5492   -0.2297 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7255    1.6161    0.3735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3177    1.2447    0.7523 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4357    0.4482   -0.2402 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0135   -0.7880    0.3535 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8325    2.1866   -2.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0205    3.3787   -0.6603 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6625    3.5932   -1.7798 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9673    2.7705    0.2392 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9481    2.1569    1.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8968    0.7988    1.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1919    1.1457   -0.5703 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2298   -0.3318   -0.6622 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6576   -1.1153   -0.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6382   -0.5577    2.4871 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5825   -2.0466    2.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1712   -2.5191    2.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7542    2.0698   -1.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5136   -0.3517   -2.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7370    0.8959   -3.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6444   -1.6072   -2.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0394   -0.5636   -3.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7674    1.1207   -1.8381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4402   -1.3280   -0.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2949   -0.8602   -2.8631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6372   -3.0127   -2.7387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4005   -0.0853   -2.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5971   -1.8335   -2.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8068   -1.8376    0.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4389    1.0840   -0.4246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4076   -0.3533   -1.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5971   -1.2277    1.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3291    0.0534    0.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9014    1.1264    2.7436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2701   -0.5194    2.9190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4494    0.9016    2.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2785    1.7617    1.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5136   -1.4232    2.4112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9142   -2.2527    0.9652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8625   -1.0678    1.8788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1599    0.9929   -1.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2148    1.9997    1.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6562    2.4922   -0.3056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3093    0.7449    1.7705 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2244    2.1911    0.9447 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4788   -1.7318    0.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0074   -0.6776    1.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0693   -0.9965    0.0894 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
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  1
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  1
 31 12  1  0
 31 15  1  0
 28 16  1  0
 26 20  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  1
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
 11 44  1  0
 12 45  1  6
 13 46  1  0
 13 47  1  0
 14 48  1  0
 14 49  1  0
 15 50  1  6
 16 51  1  1
 17 52  1  6
 18 53  1  0
 19 54  1  0
 19 55  1  0
 20 56  1  1
 21 57  1  0
 21 58  1  0
 22 59  1  1
 23 60  1  0
 24 61  1  0
 24 62  1  0
 25 63  1  0
 25 64  1  0
 27 65  1  0
 27 66  1  0
 27 67  1  0
 28 68  1  6
 29 69  1  0
 29 70  1  0
 30 71  1  0
 30 72  1  0
 32 73  1  0
 32 74  1  0
 32 75  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    8663.0618666.335   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8659.0718664.003   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8663.0658660.143   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8655.0778660.143   0.000  0.00  0.00           O+0
HETATM    5  H   UNK     0    8659.0718659.371   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8660.4018661.699   0.000  0.00  0.00           H+0
HETATM    7  H   UNK     0    8661.7318664.003   0.000  0.00  0.00           H+0
HETATM    8  H   UNK     0    8663.0618661.699   0.000  0.00  0.00           H+0
HETATM    9  C   UNK     0    8657.7418663.227   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8656.4078662.457   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8656.4078660.917   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8657.7418660.148   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8661.7328665.554   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8660.3988664.784   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8660.3988663.244   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8661.7328662.474   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8659.0688662.457   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8659.0688660.917   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8660.4028660.148   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8661.7358660.917   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8663.0658664.784   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8663.0658663.244   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8664.5308662.768   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8665.4358664.014   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8664.5308665.260   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8664.5308666.800   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8665.8648667.570   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8667.2008666.800   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8668.5328667.570   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0    8669.8688666.800   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0    8671.2008667.570   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    8672.5368666.800   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0    8673.8688667.570   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0    8672.5368665.260   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0    8668.5328669.110   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0    8663.1968667.570   0.000  0.00  0.00           C+0
HETATM   37  H   UNK     0    8665.8648666.030   0.000  0.00  0.00           H+0
CONECT    1   21                                                            
CONECT    2   17                                                            
CONECT    3   20                                                            
CONECT    4   11                                                            
CONECT    5   18                                                            
CONECT    6   15                                                            
CONECT    7   16                                                            
CONECT    8   22                                                            
CONECT    9   10   17                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12    4                                                  
CONECT   12   11   18                                                       
CONECT   13   14   21                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17    6                                             
CONECT   16   15   20    7   22                                             
CONECT   17   18    9    2   15                                             
CONECT   18   17   19   12    5                                             
CONECT   19   18   20                                                       
CONECT   20   19    3   16                                                  
CONECT   21   22   25   13    1                                             
CONECT   22   21   23   16    8                                             
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   26   37   21   24                                             
CONECT   26   25   27   36                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   35                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   29                                                            
CONECT   36   26                                                            
CONECT   37   25                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

COMPND    HMDB0000708
HETATM    1  C1  UNL     1       3.332   2.819  -1.327  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.497   1.925  -0.383  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.403   1.302   0.580  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.516   0.457   0.020  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.344  -0.082   1.154  1.00  0.00           C  
HETATM    6  O1  UNL     1       5.034   0.211   2.327  1.00  0.00           O  
HETATM    7  N1  UNL     1       6.448  -0.906   0.833  1.00  0.00           N  
HETATM    8  C6  UNL     1       7.258  -1.435   1.931  1.00  0.00           C  
HETATM    9  C7  UNL     1       8.341  -2.256   1.384  1.00  0.00           C  
HETATM   10  O2  UNL     1       8.442  -2.401   0.141  1.00  0.00           O  
HETATM   11  O3  UNL     1       9.258  -2.877   2.224  1.00  0.00           O  
HETATM   12  C8  UNL     1       1.439   1.246  -1.079  1.00  0.00           C  
HETATM   13  C9  UNL     1       1.680   0.321  -2.199  1.00  0.00           C  
HETATM   14  C10 UNL     1       0.413  -0.557  -2.323  1.00  0.00           C  
HETATM   15  C11 UNL     1      -0.520   0.122  -1.411  1.00  0.00           C  
HETATM   16  C12 UNL     1      -1.676  -0.565  -0.860  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.588  -1.241  -1.848  1.00  0.00           C  
HETATM   18  O4  UNL     1      -2.330  -2.631  -1.893  1.00  0.00           O  
HETATM   19  C14 UNL     1      -4.029  -0.960  -1.650  1.00  0.00           C  
HETATM   20  C15 UNL     1      -4.491  -0.849  -0.231  1.00  0.00           C  
HETATM   21  C16 UNL     1      -5.735   0.026  -0.229  1.00  0.00           C  
HETATM   22  C17 UNL     1      -6.397  -0.127   1.105  1.00  0.00           C  
HETATM   23  O5  UNL     1      -7.608   0.557   1.181  1.00  0.00           O  
HETATM   24  C18 UNL     1      -5.443   0.291   2.174  1.00  0.00           C  
HETATM   25  C19 UNL     1      -4.132   0.809   1.621  1.00  0.00           C  
HETATM   26  C20 UNL     1      -3.482  -0.171   0.677  1.00  0.00           C  
HETATM   27  C21 UNL     1      -2.861  -1.262   1.503  1.00  0.00           C  
HETATM   28  C22 UNL     1      -2.538   0.549  -0.230  1.00  0.00           C  
HETATM   29  C23 UNL     1      -1.726   1.616   0.373  1.00  0.00           C  
HETATM   30  C24 UNL     1      -0.318   1.245   0.752  1.00  0.00           C  
HETATM   31  C25 UNL     1       0.436   0.448  -0.240  1.00  0.00           C  
HETATM   32  C26 UNL     1       1.013  -0.788   0.354  1.00  0.00           C  
HETATM   33  H1  UNL     1       3.833   2.187  -2.064  1.00  0.00           H  
HETATM   34  H2  UNL     1       4.020   3.379  -0.660  1.00  0.00           H  
HETATM   35  H3  UNL     1       2.662   3.593  -1.780  1.00  0.00           H  
HETATM   36  H4  UNL     1       1.967   2.770   0.239  1.00  0.00           H  
HETATM   37  H5  UNL     1       3.948   2.157   1.104  1.00  0.00           H  
HETATM   38  H6  UNL     1       2.897   0.799   1.442  1.00  0.00           H  
HETATM   39  H7  UNL     1       5.192   1.146  -0.570  1.00  0.00           H  
HETATM   40  H8  UNL     1       4.230  -0.332  -0.662  1.00  0.00           H  
HETATM   41  H9  UNL     1       6.658  -1.115  -0.152  1.00  0.00           H  
HETATM   42  H10 UNL     1       7.638  -0.558   2.487  1.00  0.00           H  
HETATM   43  H11 UNL     1       6.582  -2.047   2.560  1.00  0.00           H  
HETATM   44  H12 UNL     1      10.171  -2.519   2.424  1.00  0.00           H  
HETATM   45  H13 UNL     1       0.754   2.070  -1.522  1.00  0.00           H  
HETATM   46  H14 UNL     1       2.514  -0.352  -2.184  1.00  0.00           H  
HETATM   47  H15 UNL     1       1.737   0.896  -3.169  1.00  0.00           H  
HETATM   48  H16 UNL     1       0.644  -1.607  -2.071  1.00  0.00           H  
HETATM   49  H17 UNL     1       0.039  -0.564  -3.368  1.00  0.00           H  
HETATM   50  H18 UNL     1      -0.767   1.121  -1.838  1.00  0.00           H  
HETATM   51  H19 UNL     1      -1.440  -1.328  -0.099  1.00  0.00           H  
HETATM   52  H20 UNL     1      -2.295  -0.860  -2.863  1.00  0.00           H  
HETATM   53  H21 UNL     1      -2.637  -3.013  -2.739  1.00  0.00           H  
HETATM   54  H22 UNL     1      -4.401  -0.085  -2.244  1.00  0.00           H  
HETATM   55  H23 UNL     1      -4.597  -1.833  -2.094  1.00  0.00           H  
HETATM   56  H24 UNL     1      -4.807  -1.838   0.166  1.00  0.00           H  
HETATM   57  H25 UNL     1      -5.439   1.084  -0.425  1.00  0.00           H  
HETATM   58  H26 UNL     1      -6.408  -0.353  -1.025  1.00  0.00           H  
HETATM   59  H27 UNL     1      -6.597  -1.228   1.240  1.00  0.00           H  
HETATM   60  H28 UNL     1      -8.329   0.053   0.706  1.00  0.00           H  
HETATM   61  H29 UNL     1      -5.901   1.126   2.744  1.00  0.00           H  
HETATM   62  H30 UNL     1      -5.270  -0.519   2.919  1.00  0.00           H  
HETATM   63  H31 UNL     1      -3.449   0.902   2.505  1.00  0.00           H  
HETATM   64  H32 UNL     1      -4.279   1.762   1.110  1.00  0.00           H  
HETATM   65  H33 UNL     1      -3.514  -1.423   2.411  1.00  0.00           H  
HETATM   66  H34 UNL     1      -2.914  -2.253   0.965  1.00  0.00           H  
HETATM   67  H35 UNL     1      -1.863  -1.068   1.879  1.00  0.00           H  
HETATM   68  H36 UNL     1      -3.160   0.993  -1.045  1.00  0.00           H  
HETATM   69  H37 UNL     1      -2.215   2.000   1.302  1.00  0.00           H  
HETATM   70  H38 UNL     1      -1.656   2.492  -0.306  1.00  0.00           H  
HETATM   71  H39 UNL     1      -0.309   0.745   1.771  1.00  0.00           H  
HETATM   72  H40 UNL     1       0.224   2.191   0.945  1.00  0.00           H  
HETATM   73  H41 UNL     1       0.479  -1.732   0.123  1.00  0.00           H  
HETATM   74  H42 UNL     1       1.007  -0.678   1.478  1.00  0.00           H  
HETATM   75  H43 UNL     1       2.069  -0.996   0.089  1.00  0.00           H  
CONECT    1    2   33   34   35
CONECT    2    3   12   36
CONECT    3    4   37   38
CONECT    4    5   39   40
CONECT    5    6    6    7
CONECT    7    8   41
CONECT    8    9   42   43
CONECT    9   10   10   11
CONECT   11   44
CONECT   12   13   31   45
CONECT   13   14   46   47
CONECT   14   15   48   49
CONECT   15   16   31   50
CONECT   16   17   28   51
CONECT   17   18   19   52
CONECT   18   53
CONECT   19   20   54   55
CONECT   20   21   26   56
CONECT   21   22   57   58
CONECT   22   23   24   59
CONECT   23   60
CONECT   24   25   61   62
CONECT   25   26   63   64
CONECT   26   27   28
CONECT   27   65   66   67
CONECT   28   29   68
CONECT   29   30   69   70
CONECT   30   31   71   72
CONECT   31   32
CONECT   32   73   74   75
END

HMDB0000708
     RDKit          3D
Glycoursodeoxycholic acid
 75 78  0  0  0  0  0  0  0  0999 V2000
    3.3317    2.8194   -1.3272 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4965    1.9246   -0.3829 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4035    1.3018    0.5800 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5160    0.4572    0.0199 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3441   -0.0822    1.1540 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0343    0.2110    2.3272 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4484   -0.9063    0.8332 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2582   -1.4346    1.9311 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3407   -2.2558    1.3841 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4423   -2.4010    0.1414 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2575   -2.8768    2.2241 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4387    1.2457   -1.0793 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6795    0.3214   -2.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4127   -0.5574   -2.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5204    0.1216   -1.4114 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6762   -0.5654   -0.8602 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5880   -1.2413   -1.8484 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3299   -2.6309   -1.8934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0295   -0.9603   -1.6497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4906   -0.8490   -0.2313 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7352    0.0261   -0.2285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3969   -0.1270    1.1054 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.6075    0.5573    1.1812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4430    0.2915    2.1737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1321    0.8085    1.6215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4819   -0.1712    0.6775 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8613   -1.2618    1.5032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5382    0.5492   -0.2297 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7255    1.6161    0.3735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3177    1.2447    0.7523 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4357    0.4482   -0.2402 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0135   -0.7880    0.3535 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8325    2.1866   -2.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0205    3.3787   -0.6603 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6625    3.5932   -1.7798 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9673    2.7705    0.2392 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9481    2.1569    1.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8968    0.7988    1.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1919    1.1457   -0.5703 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2298   -0.3318   -0.6622 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6576   -1.1153   -0.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6382   -0.5577    2.4871 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5825   -2.0466    2.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1712   -2.5191    2.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7542    2.0698   -1.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5136   -0.3517   -2.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7370    0.8959   -3.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6444   -1.6072   -2.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0394   -0.5636   -3.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7674    1.1207   -1.8381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4402   -1.3280   -0.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2949   -0.8602   -2.8631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6372   -3.0127   -2.7387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4005   -0.0853   -2.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5971   -1.8335   -2.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8068   -1.8376    0.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4389    1.0840   -0.4246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4076   -0.3533   -1.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5971   -1.2277    1.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3291    0.0534    0.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9014    1.1264    2.7436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2701   -0.5194    2.9190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4494    0.9016    2.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2785    1.7617    1.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5136   -1.4232    2.4112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9142   -2.2527    0.9652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8625   -1.0678    1.8788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1599    0.9929   -1.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2148    1.9997    1.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6562    2.4922   -0.3056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3093    0.7449    1.7705 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2244    2.1911    0.9447 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4788   -1.7318    0.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0074   -0.6776    1.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0693   -0.9965    0.0894 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
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  1
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  1
 31 12  1  0
 31 15  1  0
 28 16  1  0
 26 20  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  1
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
 11 44  1  0
 12 45  1  6
 13 46  1  0
 13 47  1  0
 14 48  1  0
 14 49  1  0
 15 50  1  6
 16 51  1  1
 17 52  1  6
 18 53  1  0
 19 54  1  0
 19 55  1  0
 20 56  1  1
 21 57  1  0
 21 58  1  0
 22 59  1  1
 23 60  1  0
 24 61  1  0
 24 62  1  0
 25 63  1  0
 25 64  1  0
 27 65  1  0
 27 66  1  0
 27 67  1  0
 28 68  1  6
 29 69  1  0
 29 70  1  0
 30 71  1  0
 30 72  1  0
 32 73  1  0
 32 74  1  0
 32 75  1  0
M  END

Synonyms

Value	Source
3alpha,7beta-Dihydroxy-5beta-cholanoylglycine	ChEBI
Glycine ursodeoxycholic acid	ChEBI
Glycylursodeoxycholic acid	ChEBI
GUDCA	ChEBI
N-(3alpha,7beta-Dihydroxy-5beta-cholan-24-oyl)glycine	ChEBI
N-[(3alpha,5beta,7beta)-3,7-Dihydroxy-24-oxocholan-24-yl]glycine	ChEBI
Ursodeoxycholylglycine	ChEBI
3a,7b-Dihydroxy-5b-cholanoylglycine	Generator
3Α,7β-dihydroxy-5β-cholanoylglycine	Generator
Glycine ursodeoxycholate	Generator
Glycylursodeoxycholate	Generator
N-(3a,7b-Dihydroxy-5b-cholan-24-oyl)glycine	Generator
N-(3Α,7β-dihydroxy-5β-cholan-24-oyl)glycine	Generator
N-[(3a,5b,7b)-3,7-Dihydroxy-24-oxocholan-24-yl]glycine	Generator
N-[(3Α,5β,7β)-3,7-dihydroxy-24-oxocholan-24-yl]glycine	Generator
Glycoursodeoxycholate	Generator
(3beta,5beta,7beta)-3,7-Dihydroxycholan-24-oic acid	HMDB
(3β,5β,7β)-3,7-Dihydroxycholan-24-oic acid	HMDB
3beta,7beta-Dihydroxy-5beta-cholan-24-oic acid	HMDB
3beta,7beta-Dihydroxy-5beta-cholanic acid	HMDB
3beta,7beta-Dihydroxy-5beta-cholanoic acid	HMDB
3beta-Ursodeoxycholic acid	HMDB
3β,7β-Dihydroxy-5β-cholan-24-oic acid	HMDB
3β,7β-Dihydroxy-5β-cholanic acid	HMDB
3β,7β-Dihydroxy-5β-cholanoic acid	HMDB
3β-Ursodeoxycholic acid	HMDB
Isoursodeoxycholic acid	HMDB

Molecular Formula

C₂₆H₄₃NO₅

Average Mass

449.6233

Monoisotopic Mass

449.314123491

IUPAC Name

2-[(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-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,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](O)C[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/C26H43NO5/c1-15(4-7-22(30)27-14-23(31)32)18-5-6-19-24-20(9-11-26(18,19)3)25(2)10-8-17(28)12-16(25)13-21(24)29/h15-21,24,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16+,17-,18-,19+,20+,21+,24+,25+,26-/m1/s1

InChI Key

GHCZAUBVMUEKKP-XROMFQGDSA-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
Dihydroxy bile acid, alcohol, or derivatives
Hydroxy bile acid, alcohol, or derivatives
3-hydroxysteroid
Hydroxysteroid
7-hydroxysteroid
7-alpha-hydroxysteroid
3-alpha-hydroxysteroid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Fatty amide
Fatty acyl
N-acyl-amine
Cyclic alcohol
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Organooxygen compound
Organopnictogen compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxygen compound
Organonitrogen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

C24 bile acids, alcohols, and derivatives (LMST04010445 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0079 g/L	ALOGPS
logP	2.4	ALOGPS
logP	2.61	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	3.77	ChemAxon
pKa (Strongest Basic)	-0.49	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	106.86 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	122.08 m³·mol⁻¹	ChemAxon
Polarizability	52.19 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

Blood
Feces
Gall Bladder
Intestine
Liver
Urine

Tissue Locations

Gall Bladder
Intestine
Liver

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
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	2	Human feces; Human stool; Human ; Human urine	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 Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	22624806
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both		HMDB	22624806
Human Feces	Detected and Quantified	2.39	2.1			nmol/g dry feces	Not Specified	Not Specified	Normal	HMDB	22664055
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Colorectal cancer	HMDB	25037050
Human Blood	Detected and Quantified	0.1		0	0.5	uM	Infant (0-1 year old)	Both	Severe acute malnutrition	HMDB	27163928
Human Blood	Detected and Quantified	0.1		0	0.4	uM	Infant (0-1 year old)	Both	Normal	HMDB	27163928
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Blood	Detected and Quantified	0.19		0.1	0.7	uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 165-177. Edited by Cornelius Lentner., West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp., Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	0.1		0	0.4	uM	Infant (0-1 year old)	Both	Normal	HMDB	27163928
Human Feces	Detected and Quantified	2.39	2.1			nmol/g dry feces	Not Specified	Not Specified	Normal	HMDB	22664055
Human Blood	Detected and Quantified	0.19		0.10	0.70	uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
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 Liver	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	22624806
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	22624806
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0000708

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022194

KNApSAcK ID

Not Available

Chemspider ID

19973534

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5676

PubChem Compound

12310288

PDB ID

Not Available

ChEBI ID

89929

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Igimi H, Carey MC: pH-Solubility relations of chenodeoxycholic and ursodeoxycholic acids: physical-chemical basis for dissimilar solution and membrane phenomena. J Lipid Res. 1980 Jan;21(1):72-90. [PubMed:7354256 ]
Marschall HU, Griffiths WJ, Zhang J, Wietholtz H, Matern H, Matern S, Sjovall J: Positions of conjugation of bile acids with glucose and N-acetylglucosamine in vitro. J Lipid Res. 1994 Sep;35(9):1599-610. [PubMed:7806974 ]
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 ]
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 ]

Showing metabocard for Glycoursodeoxycholic acid (MMDBc0000365)

MOL for #<Metabolite:0x00005645c9f2cb40>

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Structure for #<Metabolite:0x00005645c9f2cb40>

3D Structure for #<Metabolite:0x00005645c9f2cb40>