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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (8) Show 8 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2009-01-08 17:24:47 UTC

Update Date

2022-03-07 02:51:11 UTC

HMDB ID

HMDB0011568

Secondary Accession Numbers

HMDB11568

Metabolite Identification

Common Name

MG(18:2(9Z,12Z)/0:0/0:0)

Description

MG(18:2(9Z,12Z)/0:0/0:0) 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


  Mrv0541 02241201452D          

 26 25  0  0  1  0            999 V2000
   23.4628   -4.9615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7878   -5.3513    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.1126   -4.9615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1380   -5.3513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4375   -5.3513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3308   -5.9211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3055   -5.9508    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5769   -5.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2914   -4.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0059   -5.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7203   -4.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4348   -5.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1493   -4.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8638   -4.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5783   -5.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2927   -4.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0072   -4.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7217   -5.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4361   -4.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1507   -5.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8651   -4.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5796   -5.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2941   -4.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0085   -5.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7230   -4.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7230   -4.1137    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  2  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
  5 25  1  0  0  0  0
M  END

HMDB0011568
     RDKit          3D
MG(18:2(9Z,12Z)/0:0/0:0)
 63 62  0  0  0  0  0  0  0  0999 V2000
    8.3960   -0.5435   -0.6625 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6480   -0.6488   -1.9525 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0752    0.6599   -2.4194 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1088    1.2685   -1.4576 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9160    0.3540   -1.1986 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0462    1.0484   -0.2520 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7184    0.6044    0.9356 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1384   -0.6340    1.5446 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1880   -1.6537    1.9215 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8912   -1.6649    1.7634 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0480   -0.6418    1.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0256   -0.0640    2.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8171    0.9860    1.4533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5855    0.4390    0.2751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5372   -0.6647    0.6802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5554   -0.2227    1.6680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4595    0.8829    1.2520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2939    0.5183    0.0777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2259   -0.6418   -0.3959 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1471    1.4074   -0.5185 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9947    1.2466   -1.5629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2572    0.5231   -1.3390 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.8637    0.4191   -2.6454 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2806   -0.8166   -0.7641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8788   -0.9685    0.5416 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5884    0.4931   -0.3396 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7897   -1.0801    0.1191 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3831   -1.0663   -0.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8853   -1.4474   -1.9718 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4029   -0.9525   -2.7366 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8437    1.3916   -2.6816 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5094    0.4450   -3.3602 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5553    1.6263   -0.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6812    2.1769   -1.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3174    0.2805   -2.1673 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1997   -0.6552   -0.9604 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6471    2.0301   -0.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0623    1.2936    1.5197 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8850   -1.1358    0.8540 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8433   -0.3833    2.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6355   -2.5543    2.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4034   -2.6004    2.1612 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3329   -1.2602    0.4695 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4557    0.0586    0.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5835   -0.8695    2.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5835    0.4974    2.9506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5016    1.3954    2.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1581    1.8044    1.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1972    1.2763   -0.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9486    0.0794   -0.5299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9448   -1.4747    1.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0222   -1.0225   -0.2387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2230   -1.1213    1.8546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1120   -0.0440    2.6910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9137    1.8401    1.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1381    1.0990    2.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2490    2.2519   -2.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4766    0.7158   -2.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9843    1.1819   -0.7696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2541   -0.2168   -3.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3068   -1.2466   -0.9238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6245   -1.4980   -1.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6696   -0.8187    1.1316 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  2  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
 22 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
  7 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 12 46  1  0
 13 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 15 52  1  0
 16 53  1  0
 16 54  1  0
 17 55  1  0
 17 56  1  0
 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
M  END


  Mrv0541 02241201452D          

 26 25  0  0  1  0            999 V2000
   23.4628   -4.9615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7878   -5.3513    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.1126   -4.9615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1380   -5.3513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4375   -5.3513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3308   -5.9211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3055   -5.9508    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5769   -5.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2914   -4.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0059   -5.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7203   -4.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4348   -5.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1493   -4.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8638   -4.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5783   -5.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2927   -4.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0072   -4.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7217   -5.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4361   -4.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1507   -5.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8651   -4.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5796   -5.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2941   -4.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0085   -5.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7230   -4.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7230   -4.1137    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  2  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
  5 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0011568

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@](O)(CO)COC(=O)CCCCCCC\C=C/C\C=C/CCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C21H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(24)25-19-20(23)18-22/h6-7,9-10,20,22-23H,2-5,8,11-19H2,1H3/b7-6-,10-9-/t20-/m0/s1

> <INCHI_KEY>
WECGLUPZRHILCT-GSNKCQISSA-N

> <FORMULA>
C21H38O4

> <MOLECULAR_WEIGHT>
354.524

> <EXACT_MASS>
354.277009704

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
43.42712570606009

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2,3-dihydroxypropyl (9Z,12Z)-octadeca-9,12-dienoate

> <ALOGPS_LOGP>
5.56

> <JCHEM_LOGP>
5.247333896333334

> <ALOGPS_LOGS>
-5.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.561713304317518

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.619245765321082

> <JCHEM_PKA_STRONGEST_BASIC>
-2.968684336972288

> <JCHEM_POLAR_SURFACE_AREA>
66.75999999999999

> <JCHEM_REFRACTIVITY>
105.54269999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.63e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2,3-dihydroxypropyl (9Z,12Z)-octadeca-9,12-dienoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0011568
     RDKit          3D
MG(18:2(9Z,12Z)/0:0/0:0)
 63 62  0  0  0  0  0  0  0  0999 V2000
    8.3960   -0.5435   -0.6625 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6480   -0.6488   -1.9525 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0752    0.6599   -2.4194 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1088    1.2685   -1.4576 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9160    0.3540   -1.1986 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0462    1.0484   -0.2520 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7184    0.6044    0.9356 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1384   -0.6340    1.5446 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1880   -1.6537    1.9215 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8912   -1.6649    1.7634 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0480   -0.6418    1.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0256   -0.0640    2.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8171    0.9860    1.4533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5855    0.4390    0.2751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5372   -0.6647    0.6802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5554   -0.2227    1.6680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4595    0.8829    1.2520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2939    0.5183    0.0777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2259   -0.6418   -0.3959 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1471    1.4074   -0.5185 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9947    1.2466   -1.5629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2572    0.5231   -1.3390 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.8637    0.4191   -2.6454 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2806   -0.8166   -0.7641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8788   -0.9685    0.5416 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5884    0.4931   -0.3396 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7897   -1.0801    0.1191 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3831   -1.0663   -0.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8853   -1.4474   -1.9718 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4029   -0.9525   -2.7366 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8437    1.3916   -2.6816 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5094    0.4450   -3.3602 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5553    1.6263   -0.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6812    2.1769   -1.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3174    0.2805   -2.1673 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1997   -0.6552   -0.9604 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6471    2.0301   -0.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0623    1.2936    1.5197 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8850   -1.1358    0.8540 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8433   -0.3833    2.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6355   -2.5543    2.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4034   -2.6004    2.1612 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3329   -1.2602    0.4695 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4557    0.0586    0.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5835   -0.8695    2.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5835    0.4974    2.9506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5016    1.3954    2.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1581    1.8044    1.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1972    1.2763   -0.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9486    0.0794   -0.5299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9448   -1.4747    1.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0222   -1.0225   -0.2387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2230   -1.1213    1.8546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1120   -0.0440    2.6910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9137    1.8401    1.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1381    1.0990    2.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2490    2.2519   -2.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4766    0.7158   -2.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9843    1.1819   -0.7696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2541   -0.2168   -3.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3068   -1.2466   -0.9238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6245   -1.4980   -1.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6696   -0.8187    1.1316 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  2  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
 22 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
  7 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 12 46  1  0
 13 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 15 52  1  0
 16 53  1  0
 16 54  1  0
 17 55  1  0
 17 56  1  0
 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
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      43.797  -9.261   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      42.537  -9.989   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      41.277  -9.261   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      45.058  -9.989   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      40.017  -9.989   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      41.684 -11.053   0.000  0.00  0.00           O+0
HETATM    7  H   UNK     0      43.504 -11.108   0.000  0.00  0.00           H+0
HETATM    8  C   UNK     0      16.010  -9.989   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.344  -9.219   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.678  -9.989   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      20.011  -9.219   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.345  -9.989   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.679  -9.219   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      24.012  -9.219   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      25.346  -9.989   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      26.680  -9.219   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      28.013  -9.219   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      29.347  -9.989   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      30.681  -9.219   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      32.015  -9.989   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      33.348  -9.219   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      34.682  -9.989   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      36.016  -9.219   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      37.349  -9.989   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      38.683  -9.219   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      38.683  -7.679   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   25                                                       
CONECT    6    2                                                            
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    5                                                  
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   50    0
END

COMPND    HMDB0011568
HETATM    1  C1  UNL     1       8.396  -0.544  -0.663  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.648  -0.649  -1.953  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.075   0.660  -2.419  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.109   1.268  -1.458  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.916   0.354  -1.199  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.046   1.048  -0.252  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.718   0.604   0.936  1.00  0.00           C  
HETATM    8  C8  UNL     1       4.138  -0.634   1.545  1.00  0.00           C  
HETATM    9  C9  UNL     1       3.188  -1.654   1.922  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.891  -1.665   1.763  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.048  -0.642   1.153  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.026  -0.064   2.144  1.00  0.00           C  
HETATM   13  C13 UNL     1      -0.817   0.986   1.453  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.585   0.439   0.275  1.00  0.00           C  
HETATM   15  C15 UNL     1      -2.537  -0.665   0.680  1.00  0.00           C  
HETATM   16  C16 UNL     1      -3.555  -0.223   1.668  1.00  0.00           C  
HETATM   17  C17 UNL     1      -4.459   0.883   1.252  1.00  0.00           C  
HETATM   18  C18 UNL     1      -5.294   0.518   0.078  1.00  0.00           C  
HETATM   19  O1  UNL     1      -5.226  -0.642  -0.396  1.00  0.00           O  
HETATM   20  O2  UNL     1      -6.147   1.407  -0.519  1.00  0.00           O  
HETATM   21  C19 UNL     1      -6.995   1.247  -1.563  1.00  0.00           C  
HETATM   22  C20 UNL     1      -8.257   0.523  -1.339  1.00  0.00           C  
HETATM   23  O3  UNL     1      -8.864   0.419  -2.645  1.00  0.00           O  
HETATM   24  C21 UNL     1      -8.281  -0.817  -0.764  1.00  0.00           C  
HETATM   25  O4  UNL     1      -7.879  -0.968   0.542  1.00  0.00           O  
HETATM   26  H1  UNL     1       8.588   0.493  -0.340  1.00  0.00           H  
HETATM   27  H2  UNL     1       7.790  -1.080   0.119  1.00  0.00           H  
HETATM   28  H3  UNL     1       9.383  -1.066  -0.682  1.00  0.00           H  
HETATM   29  H4  UNL     1       6.885  -1.447  -1.972  1.00  0.00           H  
HETATM   30  H5  UNL     1       8.403  -0.953  -2.737  1.00  0.00           H  
HETATM   31  H6  UNL     1       7.844   1.392  -2.682  1.00  0.00           H  
HETATM   32  H7  UNL     1       6.509   0.445  -3.360  1.00  0.00           H  
HETATM   33  H8  UNL     1       6.555   1.626  -0.517  1.00  0.00           H  
HETATM   34  H9  UNL     1       5.681   2.177  -1.956  1.00  0.00           H  
HETATM   35  H10 UNL     1       4.317   0.280  -2.167  1.00  0.00           H  
HETATM   36  H11 UNL     1       5.200  -0.655  -0.960  1.00  0.00           H  
HETATM   37  H12 UNL     1       3.647   2.030  -0.598  1.00  0.00           H  
HETATM   38  H13 UNL     1       3.062   1.294   1.520  1.00  0.00           H  
HETATM   39  H14 UNL     1       4.885  -1.136   0.854  1.00  0.00           H  
HETATM   40  H15 UNL     1       4.843  -0.383   2.424  1.00  0.00           H  
HETATM   41  H16 UNL     1       3.635  -2.554   2.417  1.00  0.00           H  
HETATM   42  H17 UNL     1       1.403  -2.600   2.161  1.00  0.00           H  
HETATM   43  H18 UNL     1       0.333  -1.260   0.469  1.00  0.00           H  
HETATM   44  H19 UNL     1       1.456   0.059   0.460  1.00  0.00           H  
HETATM   45  H20 UNL     1      -0.583  -0.869   2.550  1.00  0.00           H  
HETATM   46  H21 UNL     1       0.583   0.497   2.951  1.00  0.00           H  
HETATM   47  H22 UNL     1      -1.502   1.395   2.206  1.00  0.00           H  
HETATM   48  H23 UNL     1      -0.158   1.804   1.127  1.00  0.00           H  
HETATM   49  H24 UNL     1      -2.197   1.276  -0.119  1.00  0.00           H  
HETATM   50  H25 UNL     1      -0.949   0.079  -0.530  1.00  0.00           H  
HETATM   51  H26 UNL     1      -1.945  -1.475   1.164  1.00  0.00           H  
HETATM   52  H27 UNL     1      -3.022  -1.022  -0.239  1.00  0.00           H  
HETATM   53  H28 UNL     1      -4.223  -1.121   1.855  1.00  0.00           H  
HETATM   54  H29 UNL     1      -3.112  -0.044   2.691  1.00  0.00           H  
HETATM   55  H30 UNL     1      -3.914   1.840   1.075  1.00  0.00           H  
HETATM   56  H31 UNL     1      -5.138   1.099   2.109  1.00  0.00           H  
HETATM   57  H32 UNL     1      -7.249   2.252  -2.030  1.00  0.00           H  
HETATM   58  H33 UNL     1      -6.477   0.716  -2.447  1.00  0.00           H  
HETATM   59  H34 UNL     1      -8.984   1.182  -0.770  1.00  0.00           H  
HETATM   60  H35 UNL     1      -8.254  -0.217  -3.118  1.00  0.00           H  
HETATM   61  H36 UNL     1      -9.307  -1.247  -0.924  1.00  0.00           H  
HETATM   62  H37 UNL     1      -7.624  -1.498  -1.382  1.00  0.00           H  
HETATM   63  H38 UNL     1      -8.670  -0.819   1.132  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    7   37
CONECT    7    8   38
CONECT    8    9   39   40
CONECT    9   10   10   41
CONECT   10   11   42
CONECT   11   12   43   44
CONECT   12   13   45   46
CONECT   13   14   47   48
CONECT   14   15   49   50
CONECT   15   16   51   52
CONECT   16   17   53   54
CONECT   17   18   55   56
CONECT   18   19   19   20
CONECT   20   21
CONECT   21   22   57   58
CONECT   22   23   24   59
CONECT   23   60
CONECT   24   25   61   62
CONECT   25   63
END

HMDB0011568
     RDKit          3D
MG(18:2(9Z,12Z)/0:0/0:0)
 63 62  0  0  0  0  0  0  0  0999 V2000
    8.3960   -0.5435   -0.6625 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6480   -0.6488   -1.9525 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0752    0.6599   -2.4194 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1088    1.2685   -1.4576 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9160    0.3540   -1.1986 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0462    1.0484   -0.2520 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7184    0.6044    0.9356 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1384   -0.6340    1.5446 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1880   -1.6537    1.9215 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8912   -1.6649    1.7634 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0480   -0.6418    1.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0256   -0.0640    2.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8171    0.9860    1.4533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5855    0.4390    0.2751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5372   -0.6647    0.6802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5554   -0.2227    1.6680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4595    0.8829    1.2520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2939    0.5183    0.0777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2259   -0.6418   -0.3959 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1471    1.4074   -0.5185 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9947    1.2466   -1.5629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2572    0.5231   -1.3390 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.8637    0.4191   -2.6454 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2806   -0.8166   -0.7641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8788   -0.9685    0.5416 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5884    0.4931   -0.3396 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7897   -1.0801    0.1191 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3831   -1.0663   -0.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8853   -1.4474   -1.9718 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4029   -0.9525   -2.7366 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8437    1.3916   -2.6816 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5094    0.4450   -3.3602 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5553    1.6263   -0.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6812    2.1769   -1.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3174    0.2805   -2.1673 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1997   -0.6552   -0.9604 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6471    2.0301   -0.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0623    1.2936    1.5197 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8850   -1.1358    0.8540 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8433   -0.3833    2.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6355   -2.5543    2.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4034   -2.6004    2.1612 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3329   -1.2602    0.4695 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4557    0.0586    0.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5835   -0.8695    2.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5835    0.4974    2.9506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5016    1.3954    2.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1581    1.8044    1.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1972    1.2763   -0.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9486    0.0794   -0.5299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9448   -1.4747    1.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0222   -1.0225   -0.2387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2230   -1.1213    1.8546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1120   -0.0440    2.6910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9137    1.8401    1.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1381    1.0990    2.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2490    2.2519   -2.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4766    0.7158   -2.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9843    1.1819   -0.7696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2541   -0.2168   -3.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3068   -1.2466   -0.9238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6245   -1.4980   -1.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6696   -0.8187    1.1316 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  2  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
 22 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
  7 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 12 46  1  0
 13 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 15 52  1  0
 16 53  1  0
 16 54  1  0
 17 55  1  0
 17 56  1  0
 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
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(S)-1-Monolinolein	ChEBI
(S)-1-O-Linoleoylglycerol	ChEBI
1-(9Z,12Z)-Octadecadienoyl-sn-glycerol	ChEBI
1-(9Z,12Z-Octadecadienoyl)-sn-glycerol	ChEBI
1-Linoleoyl-sn-monoglyceride	ChEBI
MG (18:2(N-6)/0:0/0:0)	ChEBI
sn-1-Monolinoleoylglycerol	ChEBI
1-(9Z,12Z-Octadecadienoyl)-rac-glycerol	HMDB
1-LG	HMDB
1-Linoleoyl-glycerol	HMDB
1-Monoacylglyceride	HMDB
1-Monoacylglycerol	HMDB
a-Monoacylglycerol	HMDB
alpha-Monoacylglycerol	HMDB
MAG(18:2)	HMDB
MAG(18:2/0:0)	HMDB
MAG(18:2n6/0:0)	HMDB
MAG(18:2W6/0:0)	HMDB
MG(18:2)	HMDB
MG(18:2/0:0)	HMDB
MG(18:2n6/0:0)	HMDB
MG(18:2W6/0:0)	HMDB
1-Monolinoleoyl-rac-glycerol	HMDB
Glyceryl linoleic acid monoester	HMDB
MLG CPD	HMDB
Monolinolein	HMDB
(9Z,12Z)-2,3-Dihydroxypropyl octadecadienoate	HMDB
(±)-2,3-dihydroxypropyl 9(Z),12(Z)-octadecadienoate	HMDB
1-Glyceryl linoleate	HMDB
1-Linoleylglycerol	HMDB
1-Monolinolein	HMDB
1-O-(9Z,12Z-Octadecadienoyl)glycerol	HMDB
2,3-Dihydroxypropyl linoleate	HMDB
3-O-(9Z,12Z-Octadecadienoyl)glycerol	HMDB
Glycerol 1-monolinolate	HMDB
alpha-Glyceryl linoleate	HMDB
alpha-Monolinolein	HMDB
Α-glyceryl linoleate	HMDB
Α-monolinolein	HMDB

Chemical Formula

C₂₁H₃₈O₄

Average Molecular Weight

354.524

Monoisotopic Molecular Weight

354.277009704

IUPAC Name

(2S)-2,3-dihydroxypropyl (9Z,12Z)-octadeca-9,12-dienoate

Traditional Name

(2S)-2,3-dihydroxypropyl (9Z,12Z)-octadeca-9,12-dienoate

CAS Registry Number

67968-46-1

SMILES

[H][C@](O)(CO)COC(=O)CCCCCCC\C=C/C\C=C/CCCCC

InChI Identifier

InChI=1S/C21H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(24)25-19-20(23)18-22/h6-7,9-10,20,22-23H,2-5,8,11-19H2,1H3/b7-6-,10-9-/t20-/m0/s1

InChI Key

WECGLUPZRHILCT-GSNKCQISSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Lineolic acids and derivatives

Alternative Parents

Substituents

Octadecanoid
1-acyl-sn-glycerol
Monoradylglycerol
Monoacylglycerol
Fatty acid ester
Glycerolipid
1,2-diol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Primary alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

1-acyl-sn-glycerol (CHEBI:75561 )
1-monolinolein (CHEBI:75561 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0026 g/L	ALOGPS
logP	5.56	ALOGPS
logP	5.25	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	13.62	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	18	ChemAxon
Refractivity	105.54 m³·mol⁻¹	ChemAxon
Polarizability	43.43 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	197.013	31661259
DarkChem	[M-H]-	194.644	31661259
DeepCCS	[M+H]+	184.351	30932474
DeepCCS	[M-H]-	181.856	30932474
DeepCCS	[M-2H]-	216.286	30932474
DeepCCS	[M+Na]+	191.512	30932474
AllCCS	[M+H]+	195.5	32859911
AllCCS	[M+H-H2O]+	193.0	32859911
AllCCS	[M+NH4]+	197.8	32859911
AllCCS	[M+Na]+	198.4	32859911
AllCCS	[M-H]-	192.0	32859911
AllCCS	[M+Na-2H]-	194.2	32859911
AllCCS	[M+HCOO]-	196.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
MG(18:2(9Z,12Z)/0:0/0:0)	[H][C@](O)(CO)COC(=O)CCCCCCC\C=C/C\C=C/CCCCC	3055.6	Standard polar	33892256
MG(18:2(9Z,12Z)/0:0/0:0)	[H][C@](O)(CO)COC(=O)CCCCCCC\C=C/C\C=C/CCCCC	2476.5	Standard non polar	33892256
MG(18:2(9Z,12Z)/0:0/0:0)	[H][C@](O)(CO)COC(=O)CCCCCCC\C=C/C\C=C/CCCCC	2710.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
MG(18:2(9Z,12Z)/0:0/0:0),1TMS,isomer #1	CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](CO)O[Si](C)(C)C	2702.4	Semi standard non polar	33892256
MG(18:2(9Z,12Z)/0:0/0:0),1TMS,isomer #2	CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC[C@@H](O)CO[Si](C)(C)C	2726.8	Semi standard non polar	33892256
MG(18:2(9Z,12Z)/0:0/0:0),2TMS,isomer #1	CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](CO[Si](C)(C)C)O[Si](C)(C)C	2763.0	Semi standard non polar	33892256
MG(18:2(9Z,12Z)/0:0/0:0),1TBDMS,isomer #1	CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](CO)O[Si](C)(C)C(C)(C)C	2931.1	Semi standard non polar	33892256
MG(18:2(9Z,12Z)/0:0/0:0),1TBDMS,isomer #2	CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC[C@@H](O)CO[Si](C)(C)C(C)(C)C	2956.4	Semi standard non polar	33892256
MG(18:2(9Z,12Z)/0:0/0:0),2TBDMS,isomer #1	CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3225.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - MG(18:2(9Z,12Z)/0:0/0:0) GC-MS (2 TMS) - 70eV, Positive	splash10-0ul9-9671500000-4e4bb8e87a9cc2319269	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - MG(18:2(9Z,12Z)/0:0/0:0) GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - MG(18:2(9Z,12Z)/0:0/0:0) 10V, Positive-QTOF	splash10-00di-0009000000-89dbc87ac8de09803926	2017-10-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - MG(18:2(9Z,12Z)/0:0/0:0) 20V, Positive-QTOF	splash10-00di-0009000000-89dbc87ac8de09803926	2017-10-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - MG(18:2(9Z,12Z)/0:0/0:0) 40V, Positive-QTOF	splash10-0dxi-0069000000-d82efb02589dfc0e55dd	2017-10-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - MG(18:2(9Z,12Z)/0:0/0:0) 10V, Positive-QTOF	splash10-00di-0009000000-86c837f82a8c5364a0ef	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - MG(18:2(9Z,12Z)/0:0/0:0) 20V, Positive-QTOF	splash10-00di-0009000000-86c837f82a8c5364a0ef	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - MG(18:2(9Z,12Z)/0:0/0:0) 40V, Positive-QTOF	splash10-08h0-0089000000-33ccfd00c0b5d47d1ed9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - MG(18:2(9Z,12Z)/0:0/0:0) 10V, Positive-QTOF	splash10-03di-0009000000-1c0a6952088ee6edf835	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - MG(18:2(9Z,12Z)/0:0/0:0) 20V, Positive-QTOF	splash10-03di-0009000000-1c0a6952088ee6edf835	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - MG(18:2(9Z,12Z)/0:0/0:0) 40V, Positive-QTOF	splash10-01ot-9005000000-0ac8256b32d2fd4e2ed3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - MG(18:2(9Z,12Z)/0:0/0:0) 10V, Negative-QTOF	splash10-0w2c-9047000000-f966391c54be5370555b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - MG(18:2(9Z,12Z)/0:0/0:0) 20V, Negative-QTOF	splash10-03di-8090000000-cd4040e80d6ce4fcdeb7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - MG(18:2(9Z,12Z)/0:0/0:0) 40V, Negative-QTOF	splash10-08i0-9570000000-097dc95c4a2f0aad3d5b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - MG(18:2(9Z,12Z)/0:0/0:0) 10V, Positive-QTOF	splash10-06ri-3169000000-b12f9fb0cdb95b084dc7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - MG(18:2(9Z,12Z)/0:0/0:0) 20V, Positive-QTOF	splash10-070j-9452000000-1d6802fd0ab2b6fd2bdf	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - MG(18:2(9Z,12Z)/0:0/0:0) 40V, Positive-QTOF	splash10-0a59-9200000000-ef291e5afeed57919b27	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

All Tissues

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	37.6 +/- 36 uM	Adult (>18 years old)	Both	Normal	21359215	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	26476344	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	28587349	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	28587349	details

Associated Disorders and Diseases

Disease References

Colorectal cancer

Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Wang X, Wang J, Rao B, Deng L: Gut flora profiling and fecal metabolite composition of colorectal cancer patients and healthy individuals. Exp Ther Med. 2017 Jun;13(6):2848-2854. doi: 10.3892/etm.2017.4367. Epub 2017 Apr 20. [PubMed:28587349 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028281

KNApSAcK ID

Not Available

Chemspider ID

4941255

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6436630

PDB ID

Not Available

ChEBI ID

75561

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [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. 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. 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.

Enzymes

Enzyme Details

1. Monoglyceride lipase

General function:: Lipid transport and metabolism
Specific function:: Converts monoacylglycerides to free fatty acids and glycerol. Hydrolyzes the endocannabinoid 2-arachidonoylglycerol, and thereby contributes to the regulation of endocannabinoid signaling, nociperception and perception of pain (By similarity). Regulates the levels of fatty acids that serve as signaling molecules and promote cancer cell migration, invasion and tumor growth.
Gene Name:: MGLL
Uniprot ID:: Q99685
Molecular weight:: Not Available

Enzyme Details

2. Hormone-sensitive lipase

General function:: Involved in hydrolase activity
Specific function:: In adipose tissue and heart, it primarily hydrolyzes stored triglycerides to free fatty acids, while in steroidogenic tissues, it principally converts cholesteryl esters to free cholesterol for steroid hormone production.
Gene Name:: LIPE
Uniprot ID:: Q05469
Molecular weight:: 116596.715

Enzyme Details

3. 2-acylglycerol O-acyltransferase 2

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Catalyzes the formation of diacylglycerol from 2-monoacylglycerol and fatty acyl-CoA. Has a preference toward monoacylglycerols containing unsaturated fatty acids in an order of C18:3 > C18:2 > C18:1 > C18:0. Plays a central role in absorption of dietary fat in the small intestine by catalyzing the resynthesis of triacylglycerol in enterocytes. May play a role in diet-induced obesity.
Gene Name:: MOGAT2
Uniprot ID:: Q3SYC2
Molecular weight:: 38195.285

Enzyme Details

4. 2-acylglycerol O-acyltransferase 1

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Catalyzes the formation of diacylglycerol from 2-monoacylglycerol and fatty acyl-CoA. Probably not involved in absorption of dietary fat in the small intestine (By similarity).
Gene Name:: MOGAT1
Uniprot ID:: Q96PD6
Molecular weight:: 38812.19

Enzyme Details

5. 2-acylglycerol O-acyltransferase 3

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Catalyzes the formation of diacylglycerol from 2-monoacylglycerol and fatty acyl-CoA. Also able to catalyze the terminal step in triacylglycerol synthesis by using diacylglycerol and fatty acyl-CoA as substrates. Has a preference toward palmitoyl-CoA and oleoyl-CoA. May be involved in absorption of dietary fat in the small intestine by catalyzing the resynthesis of triacylglycerol in enterocytes.
Gene Name:: MOGAT3
Uniprot ID:: Q86VF5
Molecular weight:: 38729.84

Enzyme Details

6. Lysophosphatidic acid phosphatase type 6

General function:: Involved in acid phosphatase activity
Specific function:: Hydrolyzes lysophosphatidic acid to monoacylglycerol.
Gene Name:: ACP6
Uniprot ID:: Q9NPH0
Molecular weight:: 48853.955

Enzyme Details

7. Acylglycerol kinase, mitochondrial

General function:: Involved in NAD+ kinase activity
Specific function:: Lipid kinase that can phosphorylate both monoacylglycerol and diacylglycerol to form lysophosphatidic acid (LPA) and phosphatidic acid (PA), respectively. Does not phosphorylate sphingosine. Overexpression increases the formation and secretion of LPA, resulting in transactivation of EGFR and activation of the downstream MAPK signaling pathway, leading to increased cell growth
Gene Name:: AGK
Uniprot ID:: Q53H12
Molecular weight:: 47136.8

Enzyme Details

8. Ectonucleotide pyrophosphatase/phosphodiesterase family member 6

General function:: Involved in catalytic activity
Specific function:: Choline-specific glycerophosphodiester phosphodiesterase. The preferred substrate may be lysosphingomyelin (By similarity). Hydrolyzes lysophosphatidylcholine (LPC) to form monoacylglycerol and phosphorylcholine but not lysophosphatidic acid, showing it has a lysophospholipase C activity. Has a preference for LPC with short (12:0 and 14:0) or polyunsaturated (18:2 and 20:4) fatty acids. Also hydrolyzes glycerophosphorylcholine and sphingosylphosphorylcholine efficiently. Hydrolyzes the classical substrate for phospholipase C, p-nitrophenyl phosphorylcholine in vitro, while it does not hydrolyze the classical nucleotide phosphodiesterase substrate, p-nitrophenyl thymidine 5'-monophosphate. Does not hydrolyze diacyl phospholipids such as phosphatidylethanolamine, phosphatidylinositol, phosphatidylserine, phosphatidylglycerol and phosphatidic acid.
Gene Name:: ENPP6
Uniprot ID:: Q6UWR7
Molecular weight:: 50240.625

Showing metabocard for MG(18:2(9Z,12Z)/0:0/0:0) (HMDB0011568)

MOL for HMDB0011568 (MG(18:2(9Z,12Z)/0:0/0:0))

3D MOL for HMDB0011568 (MG(18:2(9Z,12Z)/0:0/0:0))

3D SDF for HMDB0011568 (MG(18:2(9Z,12Z)/0:0/0:0))

3D-SDF for HMDB0011568 (MG(18:2(9Z,12Z)/0:0/0:0))

PDB for HMDB0011568 (MG(18:2(9Z,12Z)/0:0/0:0))

3D PDB for HMDB0011568 (MG(18:2(9Z,12Z)/0:0/0:0))

SMILES for HMDB0011568 (MG(18:2(9Z,12Z)/0:0/0:0))

INCHI for HMDB0011568 (MG(18:2(9Z,12Z)/0:0/0:0))

Structure for HMDB0011568 (MG(18:2(9Z,12Z)/0:0/0:0))

3D Structure for HMDB0011568 (MG(18:2(9Z,12Z)/0:0/0:0))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes