MiMeDB: Showing metabocard for 2-(9Z-Octadecenoyl)-glycerol (MMDBc0054152)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 22:56:12 UTC

Update Date

2024-04-30 20:51:43 UTC

Metabolite ID

MMDBc0054152

Metabolite Identification

Common Name

2-(9Z-Octadecenoyl)-glycerol

Description

2-(9Z-octadecenoyl)-glycerol, also known as MG(0:0/18:1(9Z)/0:0), is a monoacylglyceride. A monoglyceride, more correctly known as a monoacylglycerol, is a glyceride consisting of one fatty acid chain covalently bonded to a glycerol molecule through an ester linkage. Monoacylglycerol can be broadly divided into two groups; 1-monoacylglycerols (or 3-monoacylglycerols) and 2-monoacylglycerols, depending on the position of the ester bond on the glycerol moiety. Normally the 1-/3-isomers are not distinguished from each other and are termed 'alpha-monoacylglycerols', while the 2-isomers are beta-monoacylglycerols. Monoacylglycerols are formed biochemically via release of a fatty acid from diacylglycerol by diacylglycerol lipase or hormone sensitive lipase. Monoacylglycerols are broken down by monoacylglycerol lipase. They tend to be minor components only of most plant and animal tissues, and indeed would not be expected to accumulate because their strong detergent properties would have a disruptive effect on membranes. 2-Monoacylglycerols are a major end product of the intestinal digestion of dietary fats in animals via the enzyme pancreatic lipase. They are taken up directly by the intestinal cells and converted to triacylglycerols via the monoacylglycerol pathway before being transported in lymph to the liver. Mono- and Diglycerides are commonly added to commercial food products in small quantities. They act as emulsifiers, helping to mix ingredients such as oil and water that would not otherwise blend well.

Structure

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


  Mrv1652303302019432D          

 26 25  0  0  1  0            999 V2000
   19.6035   -6.9471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9284   -7.3369    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.2532   -6.9471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2786   -7.3369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5781   -7.3369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4715   -7.9067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4462   -7.9364    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6109   -8.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3254   -7.9067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0399   -8.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7543   -7.9067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4688   -8.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1833   -7.9067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8978   -8.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6123   -7.9067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3267   -8.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0412   -8.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7557   -7.9067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4701   -8.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1847   -7.9067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8991   -8.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6136   -7.9067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3281   -8.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0425   -7.9067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7570   -8.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7570   -9.1442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  3  1  0  0  0  0
  2  6  1  6  0  0  0
  2  7  1  1  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  2  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
 25 24  1  0  0  0  0
 26 25  2  0  0  0  0
  6 25  1  0  0  0  0
M  END

HMDB0011537
     RDKit          3D
MG(0:0/18:1(9Z)/0:0)
 65 64  0  0  0  0  0  0  0  0999 V2000
   -8.2001    1.3569    0.4908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0539    0.6713   -0.2978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4889   -0.6878   -0.6697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6516   -1.5249   -1.5088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3010   -1.9010   -1.0735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2491   -0.8569   -0.9343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9761   -1.6151   -0.5153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8202   -0.6128   -0.3432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6633   -1.4077    0.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0293   -1.2335    1.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4073   -0.2304    2.1544 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8320    0.6864    2.2992 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1666    1.3172    0.9925 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3576    2.2415    1.0329 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5600    1.4528    1.4664 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8015    2.2946    1.5348 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1294    2.8877    0.2142 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3891    1.8559   -0.7981 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4702    2.1496   -2.0424 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5656    0.5186   -0.4981 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8156   -0.4493   -1.5011 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1520   -1.1165   -1.1512 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4397   -2.0853   -2.1184 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7720   -1.5385   -1.3555 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9267   -2.0727   -0.0797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7696    2.1866    1.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6156    0.6072    1.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9491    1.7675   -0.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2279    0.6201    0.4508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7930    1.2674   -1.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7344   -1.2980    0.2637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5139   -0.6045   -1.1803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2770   -2.4850   -1.7188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5690   -1.0259   -2.5432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3358   -2.5010   -0.1007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9494   -2.7210   -1.7939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9585   -0.4154   -1.9324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3946   -0.0634   -0.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6840   -2.3027   -1.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1530   -2.0599    0.4764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6253   -0.2839   -1.4184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1148    0.2257    0.2631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3379   -2.1824   -0.6675 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8590   -1.8683    1.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2104    0.4523    1.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5877   -0.7298    3.1587 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6762    0.0185    2.6121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6842    1.4501    3.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4245    0.5231    0.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3332    1.8863    0.5424 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1552    3.1068    1.7037 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5019    2.6759    0.0242 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7288    0.5827    0.8230 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4035    1.0130    2.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7137    3.0768    2.3322 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6193    1.6082    1.9061 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0107    3.5829    0.3324 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2972    3.5335   -0.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8479   -0.0214   -2.5185 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9304   -0.3436   -1.1909 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0352   -1.5904   -0.1543 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2109   -2.6127   -1.8459 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8915   -2.3229   -2.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7702   -1.1022   -1.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1703   -1.7504    0.4715 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 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  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 24 25  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  0
  6 38  1  0
  7 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  0
 10 44  1  0
 11 45  1  0
 11 46  1  0
 12 47  1  0
 12 48  1  0
 13 49  1  0
 13 50  1  0
 14 51  1  0
 14 52  1  0
 15 53  1  0
 15 54  1  0
 16 55  1  0
 16 56  1  0
 17 57  1  0
 17 58  1  0
 21 59  1  0
 22 60  1  0
 22 61  1  0
 23 62  1  0
 24 63  1  0
 24 64  1  0
 25 65  1  0
M  END


  Mrv1652303302019432D          

 26 25  0  0  1  0            999 V2000
   19.6035   -6.9471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9284   -7.3369    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.2532   -6.9471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2786   -7.3369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5781   -7.3369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4715   -7.9067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4462   -7.9364    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6109   -8.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3254   -7.9067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0399   -8.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7543   -7.9067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4688   -8.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1833   -7.9067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8978   -8.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6123   -7.9067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3267   -8.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0412   -8.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7557   -7.9067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4701   -8.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1847   -7.9067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8991   -8.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6136   -7.9067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3281   -8.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0425   -7.9067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7570   -8.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7570   -9.1442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  3  1  0  0  0  0
  2  6  1  6  0  0  0
  2  7  1  1  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  2  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
 25 24  1  0  0  0  0
 26 25  2  0  0  0  0
  6 25  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054152

> <DATABASE_NAME>
MIME

> <SMILES>
[H]C(CO)(CO)OC(=O)CCCCCCC\C=C/CCCCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C21H40O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(24)25-20(18-22)19-23/h9-10,20,22-23H,2-8,11-19H2,1H3/b10-9-

> <INCHI_KEY>
UPWGQKDVAURUGE-KTKRTIGZSA-N

> <FORMULA>
C21H40O4

> <MOLECULAR_WEIGHT>
356.5399

> <EXACT_MASS>
356.292659768

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
44.89247664847446

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,3-dihydroxypropan-2-yl (9Z)-octadec-9-enoate

> <ALOGPS_LOGP>
6.25

> <JCHEM_LOGP>
5.609255553000001

> <ALOGPS_LOGS>
-5.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.979619369539545

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.278372843553583

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9827691981262365

> <JCHEM_POLAR_SURFACE_AREA>
66.75999999999999

> <JCHEM_REFRACTIVITY>
104.42609999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
19

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.66e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-oleoylglycerol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0011537
     RDKit          3D
MG(0:0/18:1(9Z)/0:0)
 65 64  0  0  0  0  0  0  0  0999 V2000
   -8.2001    1.3569    0.4908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0539    0.6713   -0.2978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4889   -0.6878   -0.6697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6516   -1.5249   -1.5088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3010   -1.9010   -1.0735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2491   -0.8569   -0.9343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9761   -1.6151   -0.5153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8202   -0.6128   -0.3432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6633   -1.4077    0.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0293   -1.2335    1.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4073   -0.2304    2.1544 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8320    0.6864    2.2992 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1666    1.3172    0.9925 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3576    2.2415    1.0329 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5600    1.4528    1.4664 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8015    2.2946    1.5348 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1294    2.8877    0.2142 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3891    1.8559   -0.7981 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4702    2.1496   -2.0424 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5656    0.5186   -0.4981 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8156   -0.4493   -1.5011 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1520   -1.1165   -1.1512 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4397   -2.0853   -2.1184 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7720   -1.5385   -1.3555 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9267   -2.0727   -0.0797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7696    2.1866    1.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6156    0.6072    1.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9491    1.7675   -0.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2279    0.6201    0.4508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7930    1.2674   -1.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7344   -1.2980    0.2637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5139   -0.6045   -1.1803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2770   -2.4850   -1.7188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5690   -1.0259   -2.5432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3358   -2.5010   -0.1007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9494   -2.7210   -1.7939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9585   -0.4154   -1.9324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3946   -0.0634   -0.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6840   -2.3027   -1.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1530   -2.0599    0.4764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6253   -0.2839   -1.4184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1148    0.2257    0.2631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3379   -2.1824   -0.6675 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8590   -1.8683    1.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2104    0.4523    1.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5877   -0.7298    3.1587 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6762    0.0185    2.6121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6842    1.4501    3.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4245    0.5231    0.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3332    1.8863    0.5424 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1552    3.1068    1.7037 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5019    2.6759    0.0242 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7288    0.5827    0.8230 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4035    1.0130    2.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7137    3.0768    2.3322 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6193    1.6082    1.9061 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0107    3.5829    0.3324 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2972    3.5335   -0.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8479   -0.0214   -2.5185 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9304   -0.3436   -1.1909 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0352   -1.5904   -0.1543 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2109   -2.6127   -1.8459 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8915   -2.3229   -2.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7702   -1.1022   -1.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1703   -1.7504    0.4715 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 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  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 24 25  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  0
  6 38  1  0
  7 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  0
 10 44  1  0
 11 45  1  0
 11 46  1  0
 12 47  1  0
 12 48  1  0
 13 49  1  0
 13 50  1  0
 14 51  1  0
 14 52  1  0
 15 53  1  0
 15 54  1  0
 16 55  1  0
 16 56  1  0
 17 57  1  0
 17 58  1  0
 21 59  1  0
 22 60  1  0
 22 61  1  0
 23 62  1  0
 24 63  1  0
 24 64  1  0
 25 65  1  0
M  END

HEADER    PROTEIN                                 30-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-MAR-20         0                                  
HETATM    1  C   UNK     0      36.593 -12.968   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      35.333 -13.696   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      34.073 -12.968   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      37.853 -13.696   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      32.812 -13.696   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      34.480 -14.759   0.000  0.00  0.00           O+0
HETATM    7  H   UNK     0      36.300 -14.815   0.000  0.00  0.00           H+0
HETATM    8  C   UNK     0      10.474 -15.529   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.807 -14.759   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.141 -15.529   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.475 -14.759   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.808 -15.529   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      17.142 -14.759   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.476 -15.529   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      19.810 -14.759   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      21.143 -15.529   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.477 -15.529   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      23.811 -14.759   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      25.144 -15.529   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      26.478 -14.759   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      27.812 -15.529   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      29.145 -14.759   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      30.479 -15.529   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      31.813 -14.759   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      33.146 -15.529   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      33.146 -17.069   0.000  0.00  0.00           O+0
CONECT    1    2    4                                                       
CONECT    2    1    3    6    7                                             
CONECT    3    2    5                                                       
CONECT    4    1                                                            
CONECT    5    3                                                            
CONECT    6    2   25                                                       
CONECT    7    2                                                            
CONECT    8    9                                                            
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26    6                                                  
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   50    0
END

COMPND    HMDB0011537
HETATM    1  C1  UNL     1      -8.200   1.357   0.491  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.054   0.671  -0.298  1.00  0.00           C  
HETATM    3  C3  UNL     1      -7.489  -0.688  -0.670  1.00  0.00           C  
HETATM    4  C4  UNL     1      -6.652  -1.525  -1.509  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.301  -1.901  -1.074  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.249  -0.857  -0.934  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.976  -1.615  -0.515  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.820  -0.613  -0.343  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.663  -1.408   0.046  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.029  -1.234   1.171  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.407  -0.230   2.154  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.832   0.686   2.299  1.00  0.00           C  
HETATM   13  C13 UNL     1       1.167   1.317   0.992  1.00  0.00           C  
HETATM   14  C14 UNL     1       2.358   2.241   1.033  1.00  0.00           C  
HETATM   15  C15 UNL     1       3.560   1.453   1.466  1.00  0.00           C  
HETATM   16  C16 UNL     1       4.802   2.295   1.535  1.00  0.00           C  
HETATM   17  C17 UNL     1       5.129   2.888   0.214  1.00  0.00           C  
HETATM   18  C18 UNL     1       5.389   1.856  -0.798  1.00  0.00           C  
HETATM   19  O1  UNL     1       5.470   2.150  -2.042  1.00  0.00           O  
HETATM   20  O2  UNL     1       5.566   0.519  -0.498  1.00  0.00           O  
HETATM   21  C19 UNL     1       5.816  -0.449  -1.501  1.00  0.00           C  
HETATM   22  C20 UNL     1       7.152  -1.116  -1.151  1.00  0.00           C  
HETATM   23  O3  UNL     1       7.440  -2.085  -2.118  1.00  0.00           O  
HETATM   24  C21 UNL     1       4.772  -1.539  -1.355  1.00  0.00           C  
HETATM   25  O4  UNL     1       4.927  -2.073  -0.080  1.00  0.00           O  
HETATM   26  H1  UNL     1      -7.770   2.187   1.063  1.00  0.00           H  
HETATM   27  H2  UNL     1      -8.616   0.607   1.181  1.00  0.00           H  
HETATM   28  H3  UNL     1      -8.949   1.768  -0.220  1.00  0.00           H  
HETATM   29  H4  UNL     1      -6.228   0.620   0.451  1.00  0.00           H  
HETATM   30  H5  UNL     1      -6.793   1.267  -1.167  1.00  0.00           H  
HETATM   31  H6  UNL     1      -7.734  -1.298   0.264  1.00  0.00           H  
HETATM   32  H7  UNL     1      -8.514  -0.604  -1.180  1.00  0.00           H  
HETATM   33  H8  UNL     1      -7.277  -2.485  -1.719  1.00  0.00           H  
HETATM   34  H9  UNL     1      -6.569  -1.026  -2.543  1.00  0.00           H  
HETATM   35  H10 UNL     1      -5.336  -2.501  -0.101  1.00  0.00           H  
HETATM   36  H11 UNL     1      -4.949  -2.721  -1.794  1.00  0.00           H  
HETATM   37  H12 UNL     1      -3.959  -0.415  -1.932  1.00  0.00           H  
HETATM   38  H13 UNL     1      -4.395  -0.063  -0.227  1.00  0.00           H  
HETATM   39  H14 UNL     1      -2.684  -2.303  -1.312  1.00  0.00           H  
HETATM   40  H15 UNL     1      -3.153  -2.060   0.476  1.00  0.00           H  
HETATM   41  H16 UNL     1      -1.625  -0.284  -1.418  1.00  0.00           H  
HETATM   42  H17 UNL     1      -2.115   0.226   0.263  1.00  0.00           H  
HETATM   43  H18 UNL     1      -0.338  -2.182  -0.667  1.00  0.00           H  
HETATM   44  H19 UNL     1       0.859  -1.868   1.434  1.00  0.00           H  
HETATM   45  H20 UNL     1      -1.210   0.452   1.941  1.00  0.00           H  
HETATM   46  H21 UNL     1      -0.588  -0.730   3.159  1.00  0.00           H  
HETATM   47  H22 UNL     1       1.676   0.018   2.612  1.00  0.00           H  
HETATM   48  H23 UNL     1       0.684   1.450   3.071  1.00  0.00           H  
HETATM   49  H24 UNL     1       1.425   0.523   0.235  1.00  0.00           H  
HETATM   50  H25 UNL     1       0.333   1.886   0.542  1.00  0.00           H  
HETATM   51  H26 UNL     1       2.155   3.107   1.704  1.00  0.00           H  
HETATM   52  H27 UNL     1       2.502   2.676   0.024  1.00  0.00           H  
HETATM   53  H28 UNL     1       3.729   0.583   0.823  1.00  0.00           H  
HETATM   54  H29 UNL     1       3.403   1.013   2.497  1.00  0.00           H  
HETATM   55  H30 UNL     1       4.714   3.077   2.332  1.00  0.00           H  
HETATM   56  H31 UNL     1       5.619   1.608   1.906  1.00  0.00           H  
HETATM   57  H32 UNL     1       6.011   3.583   0.332  1.00  0.00           H  
HETATM   58  H33 UNL     1       4.297   3.534  -0.120  1.00  0.00           H  
HETATM   59  H34 UNL     1       5.848  -0.021  -2.518  1.00  0.00           H  
HETATM   60  H35 UNL     1       7.930  -0.344  -1.191  1.00  0.00           H  
HETATM   61  H36 UNL     1       7.035  -1.590  -0.154  1.00  0.00           H  
HETATM   62  H37 UNL     1       8.211  -2.613  -1.846  1.00  0.00           H  
HETATM   63  H38 UNL     1       4.891  -2.323  -2.140  1.00  0.00           H  
HETATM   64  H39 UNL     1       3.770  -1.102  -1.461  1.00  0.00           H  
HETATM   65  H40 UNL     1       4.170  -1.750   0.471  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29   30
CONECT    3    4   31   32
CONECT    4    5   33   34
CONECT    5    6   35   36
CONECT    6    7   37   38
CONECT    7    8   39   40
CONECT    8    9   41   42
CONECT    9   10   10   43
CONECT   10   11   44
CONECT   11   12   45   46
CONECT   12   13   47   48
CONECT   13   14   49   50
CONECT   14   15   51   52
CONECT   15   16   53   54
CONECT   16   17   55   56
CONECT   17   18   57   58
CONECT   18   19   19   20
CONECT   20   21
CONECT   21   22   24   59
CONECT   22   23   60   61
CONECT   23   62
CONECT   24   25   63   64
CONECT   25   65
END

HMDB0011537
     RDKit          3D
MG(0:0/18:1(9Z)/0:0)
 65 64  0  0  0  0  0  0  0  0999 V2000
   -8.2001    1.3569    0.4908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0539    0.6713   -0.2978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4889   -0.6878   -0.6697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6516   -1.5249   -1.5088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3010   -1.9010   -1.0735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2491   -0.8569   -0.9343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9761   -1.6151   -0.5153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8202   -0.6128   -0.3432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6633   -1.4077    0.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0293   -1.2335    1.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4073   -0.2304    2.1544 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8320    0.6864    2.2992 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1666    1.3172    0.9925 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3576    2.2415    1.0329 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5600    1.4528    1.4664 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Synonyms

Value	Source
1,3-Dihydroxypropan-2-yl oleate	ChEBI
2-(9Z-Octadecenoyl)-glycerol	ChEBI
2-Glyceryl monooleate	ChEBI
2-mono-C18:1	ChEBI
2-Monoolein	ChEBI
2-Monooleoylglycerol	ChEBI
2-Oleoyl-glycerol	ChEBI
UNII-9a2389K694	ChEBI
1,3-Dihydroxypropan-2-yl oleic acid	Generator
2-Glyceryl monooleic acid	Generator
1-Monoacylglyceride	HMDB
1-Monoacylglycerol	HMDB
2-(9Z-Octadecenoyl)-rac-glycerol	HMDB
2-OG	HMDB
b-Monoacylglycerol	HMDB
beta-Monoacylglycerol	HMDB
MAG(0:0/18:1)	HMDB
MAG(0:0/18:1n9)	HMDB
MAG(0:0/18:1W9)	HMDB
MAG(18:1)	HMDB
MG(0:0/18:1)	HMDB
MG(0:0/18:1n9)	HMDB
MG(0:0/18:1W9)	HMDB
MG(18:1)	HMDB
2-Oleoylglycerol	HMDB
2-OG lipid	HMDB
2-Oleyl glycerol ether	MeSH

Molecular Formula

C₂₁H₄₀O₄

Average Mass

356.5399

Monoisotopic Mass

356.292659768

IUPAC Name

1,3-dihydroxypropan-2-yl (9Z)-octadec-9-enoate

Traditional Name

2-oleoylglycerol

CAS Registry Number

Not Available

SMILES

[H]C(CO)(CO)OC(=O)CCCCCCC\C=C/CCCCCCCC

InChI Identifier

InChI=1S/C21H40O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(24)25-20(18-22)19-23/h9-10,20,22-23H,2-8,11-19H2,1H3/b10-9-

InChI Key

UPWGQKDVAURUGE-KTKRTIGZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-monoacylglycerols. These are monoacylglycerols containing a glycerol acylated at the 2-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerolipids

Sub Class

Monoradylglycerols

Direct Parent

2-monoacylglycerols

Alternative Parents

Substituents

2-acyl-sn-glycerol
Fatty acid ester
Fatty acyl
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-monoglyceride (CHEBI:73990 )
monooleoylglycerol (CHEBI:73990 )
Monoacylglycerols (LMGL01010024 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0017 g/L	ALOGPS
logP	6.25	ALOGPS
logP	5.61	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	14.28	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	104.43 m³·mol⁻¹	ChemAxon
Polarizability	44.89 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

All Tissues
Blood
Feces
Urine

Tissue Locations

All Tissues

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191984	Monoglyceride lipase	Enzyme	Q99685	Homo sapiens
MMDBp0192180	Hormone-sensitive lipase	Unknown	Q05469	Homo sapiens
MMDBp0193807	2-acylglycerol O-acyltransferase 2	Enzyme	Q3SYC2	Homo sapiens
MMDBp0193981	2-acylglycerol O-acyltransferase 1	Enzyme	Q96PD6	Homo sapiens
MMDBp0194080	2-acylglycerol O-acyltransferase 3	Enzyme	Q86VF5	Homo sapiens
MMDBp0194109	Lysophosphatidic acid phosphatase type 6	Enzyme	Q9NPH0	Homo sapiens
MMDBp0195471	Acylglycerol kinase, mitochondrial	Unknown	Q53H12	Homo sapiens
MMDBp0196461	Ectonucleotide pyrophosphatase/phosphodiesterase family member 6	Enzyme	Q6UWR7	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
Bacteria/Eubacteria	Actinobacteria	1	Human
Eukaryota/Fungi	Ascomycota	3
Eukaryota/Fungi	Basidiomycota	8	Human feces

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected and Quantified	166	130	uM	Adult (>18 years old)	Both	Normal	HMDB	21359215
Human All tissues	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
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	28587349
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

HMDB0011537

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB009514

KNApSAcK ID

Not Available

Chemspider ID

4478086

KEGG Compound ID

Not Available

BioCyc ID

CPD0-1812

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5319879

PDB ID

Not Available

ChEBI ID

73990

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Ghosh S, Strum JC, Bell RM: Lipid biochemistry: functions of glycerolipids and sphingolipids in cellular signaling. FASEB J. 1997 Jan;11(1):45-50. doi: 10.1096/fasebj.11.1.9034165. [PubMed:9034165 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. doi: 10.1194/jlr.R600022-JLR200. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. doi: 10.1194/jlr.R700005-JLR200. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 2-(9Z-Octadecenoyl)-glycerol (MMDBc0054152)

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Structure for #<Metabolite:0x00007f9204f9aa68>

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