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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

2006-08-13 23:27:52 UTC

Update Date

2022-03-07 02:49:21 UTC

HMDB ID

HMDB0004666

Secondary Accession Numbers

HMDB0011548
HMDB04666
HMDB11548

Metabolite Identification

Common Name

MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0)

Description

MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0), also known as 2-arachidonoylglycerol (2-AG), is a unique molecular species of monoacylglycerol isolated in 1995 from rat brain and canine gut as an endogenous ligand for the cannabinoid receptors. 2-AG is rapidly formed from arachidonic acid-containing phospholipids through increased phospholipid metabolism, such as enhanced inositol phospholipid turnover, in various tissues and cells upon stimulation. 2-AG binds to the cannabinoid receptors CB1 and CB2 and exhibits a variety of cannabimimetic activities in vitro and in vivo. 2-AG is an endogenous cannabinoid (endocannabinoid). Endocannabinoids are a class of fatty acid derivatives defined by their ability to interact with the specific cannabinoid receptors that were originally identified as the targets of delta9-tetrahydocannabinol (delta9-THC), the psychoactive component of cannabis. Endocannabinoids have been implicated in a growing number of important physiological and behavioral events. Endocannabinoids are amides, esters, and ethers of long-chain polyunsaturated fatty acids, which act as new lipidic mediators. 2-AG is one of the main endogenous agonists of cannabinoid receptors, able to mimic several pharmacological effects of delta9-THC, the active principle of Cannabis sativa preparations like hashish and marijuana. The activity of AEA and 2-AG at their receptors is limited by cellular uptake through an anandamide membrane transporter (AMT), followed by intracellular degradation. A fatty acid amide hydrolase (FAAH) is the main AEA hydrolase, whereas a monoacylglycerol lipase (MAGL) is critical in degrading 2-AG (PMID: 16515464 , 16278487 , 16678907 ).

Structure

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

MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0)
  Mrv1652304202019522D          

 28 27  0  0  0  0            999 V2000
   24.1439   -6.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1828   -7.0350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2216   -6.4802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1439   -5.3702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2603   -7.0350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4327   -8.1450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9380   -8.1589    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.7182   -8.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7182   -9.3290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0041   -8.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2899   -8.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5758   -8.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8617   -8.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0367   -8.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3225   -8.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6084   -8.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7834   -8.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0693   -8.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3552   -8.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5302   -8.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8160   -8.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1019   -8.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2769   -8.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5628   -8.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8486   -8.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1345   -8.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4204   -8.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7062   -8.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  2  6  1  0  0  0  0
  2  7  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
  8  6  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END

HMDB0004666
     RDKit          3D
MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0)
 65 64  0  0  0  0  0  0  0  0999 V2000
   -5.1689    1.5095    3.6260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1133    2.3998    2.9096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6631    1.8664    1.6522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7833    1.5912    0.5213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7396    0.5472    0.5552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2576   -0.8203    0.7624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1318   -1.7855   -0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5096   -1.8352   -1.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9148   -0.7082   -2.0251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6481   -0.5911   -2.3626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6242   -1.6751   -2.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0495   -2.1322   -3.3862 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2350   -2.0513   -3.6172 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2030   -1.5235   -2.6658 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8969   -0.3418   -3.2339 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1922   -0.3419   -3.3895 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0849   -1.4283   -3.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1141   -0.9903   -1.9902 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4248   -0.5495   -0.7354 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4407   -0.1387    0.2543 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6536   -0.2038   -0.0506 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1162    0.3181    1.5115 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0572    0.7177    2.4791 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8041    2.1635    2.8560 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9188    3.0035    1.7510 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9672   -0.1673    3.6862 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8879    0.2094    4.6548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1123    1.8405    3.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3663    1.7138    4.7540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3664    0.4574    3.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9362    2.7411    3.6134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5794    3.4041    2.7010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5015    2.6068    1.3527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2329    0.9063    1.9144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4666    1.4575   -0.3970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2731    2.5820    0.2144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9462    0.6650   -0.1839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1449    0.7478    1.5249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8108   -1.0283    1.7362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6088   -2.7602    0.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2963   -2.2971   -2.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7937   -2.7206   -1.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5639    0.1524   -2.3022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3214    0.3390   -2.8578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9922   -2.4946   -1.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8915   -1.1361   -1.4402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7448   -2.5501   -4.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6060   -2.4116   -4.6080 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9211   -2.3828   -2.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8570   -1.2626   -1.6566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2798    0.5364   -3.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6705    0.5695   -3.8197 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7644   -1.5576   -3.9752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7187   -2.4180   -2.8690 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7684   -1.8683   -1.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6696   -0.1369   -2.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7937    0.3295   -0.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8073   -1.3896   -0.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0629    0.5900    2.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7987    2.2832    3.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6018    2.4823    3.5691 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5411    2.5485    1.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9429   -0.1992    4.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2140   -1.2076    3.3975 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5385    1.0188    5.0868 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  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  1  0
 26 27  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  6 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
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 16 52  1  0
 17 53  1  0
 17 54  1  0
 18 55  1  0
 18 56  1  0
 19 57  1  0
 19 58  1  0
 23 59  1  0
 24 60  1  0
 24 61  1  0
 25 62  1  0
 26 63  1  0
 26 64  1  0
 27 65  1  0
M  END

MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0)
  Mrv1652304202019522D          

 28 27  0  0  0  0            999 V2000
   24.1439   -6.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1828   -7.0350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2216   -6.4802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1439   -5.3702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2603   -7.0350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4327   -8.1450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9380   -8.1589    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.7182   -8.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7182   -9.3290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0041   -8.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2899   -8.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5758   -8.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8617   -8.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0367   -8.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3225   -8.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6084   -8.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7834   -8.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0693   -8.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3552   -8.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5302   -8.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8160   -8.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1019   -8.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2769   -8.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5628   -8.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8486   -8.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1345   -8.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4204   -8.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7062   -8.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  2  6  1  0  0  0  0
  2  7  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
  8  6  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004666

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]C(CO)(CO)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C23H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(26)27-22(20-24)21-25/h6-7,9-10,12-13,15-16,22,24-25H,2-5,8,11,14,17-21H2,1H3/b7-6-,10-9-,13-12-,16-15-

> <INCHI_KEY>
RCRCTBLIHCHWDZ-DOFZRALJSA-N

> <FORMULA>
C23H38O4

> <MOLECULAR_WEIGHT>
378.5454

> <EXACT_MASS>
378.277009704

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
44.957697759251324

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3-dihydroxypropan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate

> <ALOGPS_LOGP>
5.65

> <JCHEM_LOGP>
5.412627913000001

> <ALOGPS_LOGS>
-5.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.979619367999383

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.278372842011322

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9827691988008223

> <JCHEM_POLAR_SURFACE_AREA>
66.75999999999999

> <JCHEM_REFRACTIVITY>
116.97789999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.37e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-arachidonoylglycerol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004666
     RDKit          3D
MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0)
 65 64  0  0  0  0  0  0  0  0999 V2000
   -5.1689    1.5095    3.6260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1133    2.3998    2.9096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6631    1.8664    1.6522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7833    1.5912    0.5213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7396    0.5472    0.5552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2576   -0.8203    0.7624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1318   -1.7855   -0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5096   -1.8352   -1.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9148   -0.7082   -2.0251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6481   -0.5911   -2.3626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6242   -1.6751   -2.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0495   -2.1322   -3.3862 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2350   -2.0513   -3.6172 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2030   -1.5235   -2.6658 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8969   -0.3418   -3.2339 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1922   -0.3419   -3.3895 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0849   -1.4283   -3.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1141   -0.9903   -1.9902 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4248   -0.5495   -0.7354 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4407   -0.1387    0.2543 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6536   -0.2038   -0.0506 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1162    0.3181    1.5115 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0572    0.7177    2.4791 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8041    2.1635    2.8560 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9188    3.0035    1.7510 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9672   -0.1673    3.6862 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8879    0.2094    4.6548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1123    1.8405    3.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3663    1.7138    4.7540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3664    0.4574    3.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9362    2.7411    3.6134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5794    3.4041    2.7010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5015    2.6068    1.3527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2329    0.9063    1.9144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4666    1.4575   -0.3970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2731    2.5820    0.2144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9462    0.6650   -0.1839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1449    0.7478    1.5249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8108   -1.0283    1.7362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6088   -2.7602    0.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2963   -2.2971   -2.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7937   -2.7206   -1.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5639    0.1524   -2.3022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3214    0.3390   -2.8578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9922   -2.4946   -1.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8915   -1.1361   -1.4402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7448   -2.5501   -4.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6060   -2.4116   -4.6080 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9211   -2.3828   -2.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8570   -1.2626   -1.6566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2798    0.5364   -3.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6705    0.5695   -3.8197 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7644   -1.5576   -3.9752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7187   -2.4180   -2.8690 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7684   -1.8683   -1.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6696   -0.1369   -2.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7937    0.3295   -0.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8073   -1.3896   -0.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0629    0.5900    2.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7987    2.2832    3.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6018    2.4823    3.5691 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5411    2.5485    1.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9429   -0.1992    4.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2140   -1.2076    3.3975 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5385    1.0188    5.0868 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  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  1  0
 26 27  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  6 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
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 16 52  1  0
 17 53  1  0
 17 54  1  0
 18 55  1  0
 18 56  1  0
 19 57  1  0
 19 58  1  0
 23 59  1  0
 24 60  1  0
 24 61  1  0
 25 62  1  0
 26 63  1  0
 26 64  1  0
 27 65  1  0
M  END

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0)                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  C   UNK     0      45.069 -12.096   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      43.275 -13.132   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      41.480 -12.096   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      45.069 -10.024   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      39.686 -13.132   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      41.874 -15.204   0.000  0.00  0.00           O+0
HETATM    7  H   UNK     0      44.684 -15.230   0.000  0.00  0.00           H+0
HETATM    8  C   UNK     0      40.541 -15.974   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      40.541 -17.414   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      39.208 -15.203   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      37.874 -15.974   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      36.541 -15.203   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      35.209 -15.974   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      33.669 -15.974   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      32.335 -15.203   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      31.002 -15.974   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      29.462 -15.974   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.129 -15.203   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      26.796 -15.974   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      25.256 -15.974   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      23.923 -15.203   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      22.590 -15.974   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      21.050 -15.974   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      19.717 -15.203   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      18.384 -15.974   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.051 -15.203   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.718 -15.974   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.385 -15.203   0.000  0.00  0.00           C+0
CONECT    1    2    4                                                       
CONECT    2    1    6    7    3                                             
CONECT    3    2    5                                                       
CONECT    4    1                                                            
CONECT    5    3                                                            
CONECT    6    2    8                                                       
CONECT    7    2                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   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                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   54    0
END

COMPND    HMDB0004666
HETATM    1  C1  UNL     1      -5.169   1.509   3.626  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.113   2.400   2.910  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.663   1.866   1.652  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.783   1.591   0.521  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.740   0.547   0.555  1.00  0.00           C  
HETATM    6  C6  UNL     1      -5.258  -0.820   0.762  1.00  0.00           C  
HETATM    7  C7  UNL     1      -5.132  -1.786  -0.082  1.00  0.00           C  
HETATM    8  C8  UNL     1      -4.510  -1.835  -1.382  1.00  0.00           C  
HETATM    9  C9  UNL     1      -3.915  -0.708  -2.025  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.648  -0.591  -2.363  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.624  -1.675  -2.100  1.00  0.00           C  
HETATM   12  C12 UNL     1      -1.049  -2.132  -3.386  1.00  0.00           C  
HETATM   13  C13 UNL     1       0.235  -2.051  -3.617  1.00  0.00           C  
HETATM   14  C14 UNL     1       1.203  -1.524  -2.666  1.00  0.00           C  
HETATM   15  C15 UNL     1       1.897  -0.342  -3.234  1.00  0.00           C  
HETATM   16  C16 UNL     1       3.192  -0.342  -3.389  1.00  0.00           C  
HETATM   17  C17 UNL     1       4.085  -1.428  -3.052  1.00  0.00           C  
HETATM   18  C18 UNL     1       5.114  -0.990  -1.990  1.00  0.00           C  
HETATM   19  C19 UNL     1       4.425  -0.550  -0.735  1.00  0.00           C  
HETATM   20  C20 UNL     1       5.441  -0.139   0.254  1.00  0.00           C  
HETATM   21  O1  UNL     1       6.654  -0.204  -0.051  1.00  0.00           O  
HETATM   22  O2  UNL     1       5.116   0.318   1.512  1.00  0.00           O  
HETATM   23  C21 UNL     1       6.057   0.718   2.479  1.00  0.00           C  
HETATM   24  C22 UNL     1       5.804   2.164   2.856  1.00  0.00           C  
HETATM   25  O3  UNL     1       5.919   3.003   1.751  1.00  0.00           O  
HETATM   26  C23 UNL     1       5.967  -0.167   3.686  1.00  0.00           C  
HETATM   27  O4  UNL     1       6.888   0.209   4.655  1.00  0.00           O  
HETATM   28  H1  UNL     1      -4.112   1.840   3.475  1.00  0.00           H  
HETATM   29  H2  UNL     1      -5.366   1.714   4.754  1.00  0.00           H  
HETATM   30  H3  UNL     1      -5.366   0.457   3.433  1.00  0.00           H  
HETATM   31  H4  UNL     1      -6.936   2.741   3.613  1.00  0.00           H  
HETATM   32  H5  UNL     1      -5.579   3.404   2.701  1.00  0.00           H  
HETATM   33  H6  UNL     1      -7.501   2.607   1.353  1.00  0.00           H  
HETATM   34  H7  UNL     1      -7.233   0.906   1.914  1.00  0.00           H  
HETATM   35  H8  UNL     1      -6.467   1.458  -0.397  1.00  0.00           H  
HETATM   36  H9  UNL     1      -5.273   2.582   0.214  1.00  0.00           H  
HETATM   37  H10 UNL     1      -3.946   0.665  -0.184  1.00  0.00           H  
HETATM   38  H11 UNL     1      -4.145   0.748   1.525  1.00  0.00           H  
HETATM   39  H12 UNL     1      -5.811  -1.028   1.736  1.00  0.00           H  
HETATM   40  H13 UNL     1      -5.609  -2.760   0.297  1.00  0.00           H  
HETATM   41  H14 UNL     1      -5.296  -2.297  -2.148  1.00  0.00           H  
HETATM   42  H15 UNL     1      -3.794  -2.721  -1.378  1.00  0.00           H  
HETATM   43  H16 UNL     1      -4.564   0.152  -2.302  1.00  0.00           H  
HETATM   44  H17 UNL     1      -2.321   0.339  -2.858  1.00  0.00           H  
HETATM   45  H18 UNL     1      -1.992  -2.495  -1.483  1.00  0.00           H  
HETATM   46  H19 UNL     1      -0.892  -1.136  -1.440  1.00  0.00           H  
HETATM   47  H20 UNL     1      -1.745  -2.550  -4.160  1.00  0.00           H  
HETATM   48  H21 UNL     1       0.606  -2.412  -4.608  1.00  0.00           H  
HETATM   49  H22 UNL     1       1.921  -2.383  -2.454  1.00  0.00           H  
HETATM   50  H23 UNL     1       0.857  -1.263  -1.657  1.00  0.00           H  
HETATM   51  H24 UNL     1       1.280   0.536  -3.520  1.00  0.00           H  
HETATM   52  H25 UNL     1       3.671   0.569  -3.820  1.00  0.00           H  
HETATM   53  H26 UNL     1       4.764  -1.558  -3.975  1.00  0.00           H  
HETATM   54  H27 UNL     1       3.719  -2.418  -2.869  1.00  0.00           H  
HETATM   55  H28 UNL     1       5.768  -1.868  -1.815  1.00  0.00           H  
HETATM   56  H29 UNL     1       5.670  -0.137  -2.395  1.00  0.00           H  
HETATM   57  H30 UNL     1       3.794   0.330  -0.967  1.00  0.00           H  
HETATM   58  H31 UNL     1       3.807  -1.390  -0.323  1.00  0.00           H  
HETATM   59  H32 UNL     1       7.063   0.590   2.029  1.00  0.00           H  
HETATM   60  H33 UNL     1       4.799   2.283   3.273  1.00  0.00           H  
HETATM   61  H34 UNL     1       6.602   2.482   3.569  1.00  0.00           H  
HETATM   62  H35 UNL     1       6.541   2.549   1.122  1.00  0.00           H  
HETATM   63  H36 UNL     1       4.943  -0.199   4.112  1.00  0.00           H  
HETATM   64  H37 UNL     1       6.214  -1.208   3.398  1.00  0.00           H  
HETATM   65  H38 UNL     1       6.538   1.019   5.087  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3   31   32
CONECT    3    4   33   34
CONECT    4    5   35   36
CONECT    5    6   37   38
CONECT    6    7    7   39
CONECT    7    8   40
CONECT    8    9   41   42
CONECT    9   10   10   43
CONECT   10   11   44
CONECT   11   12   45   46
CONECT   12   13   13   47
CONECT   13   14   48
CONECT   14   15   49   50
CONECT   15   16   16   51
CONECT   16   17   52
CONECT   17   18   53   54
CONECT   18   19   55   56
CONECT   19   20   57   58
CONECT   20   21   21   22
CONECT   22   23
CONECT   23   24   26   59
CONECT   24   25   60   61
CONECT   25   62
CONECT   26   27   63   64
CONECT   27   65
END

HMDB0004666
     RDKit          3D
MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0)
 65 64  0  0  0  0  0  0  0  0999 V2000
   -5.1689    1.5095    3.6260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1133    2.3998    2.9096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6631    1.8664    1.6522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7833    1.5912    0.5213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7396    0.5472    0.5552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2576   -0.8203    0.7624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1318   -1.7855   -0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5096   -1.8352   -1.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9148   -0.7082   -2.0251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6481   -0.5911   -2.3626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6242   -1.6751   -2.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0495   -2.1322   -3.3862 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2350   -2.0513   -3.6172 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2030   -1.5235   -2.6658 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8969   -0.3418   -3.2339 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1922   -0.3419   -3.3895 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0849   -1.4283   -3.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1141   -0.9903   -1.9902 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4248   -0.5495   -0.7354 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4407   -0.1387    0.2543 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6536   -0.2038   -0.0506 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1162    0.3181    1.5115 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0572    0.7177    2.4791 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8041    2.1635    2.8560 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9188    3.0035    1.7510 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9672   -0.1673    3.6862 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8879    0.2094    4.6548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1123    1.8405    3.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3663    1.7138    4.7540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3664    0.4574    3.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9362    2.7411    3.6134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5794    3.4041    2.7010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5015    2.6068    1.3527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2329    0.9063    1.9144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4666    1.4575   -0.3970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2731    2.5820    0.2144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9462    0.6650   -0.1839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1449    0.7478    1.5249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8108   -1.0283    1.7362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6088   -2.7602    0.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2963   -2.2971   -2.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7937   -2.7206   -1.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5639    0.1524   -2.3022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3214    0.3390   -2.8578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9922   -2.4946   -1.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8915   -1.1361   -1.4402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7448   -2.5501   -4.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6060   -2.4116   -4.6080 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9211   -2.3828   -2.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8570   -1.2626   -1.6566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2798    0.5364   -3.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6705    0.5695   -3.8197 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7644   -1.5576   -3.9752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7187   -2.4180   -2.8690 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7684   -1.8683   -1.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6696   -0.1369   -2.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7937    0.3295   -0.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8073   -1.3896   -0.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0629    0.5900    2.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7987    2.2832    3.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6018    2.4823    3.5691 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5411    2.5485    1.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9429   -0.1992    4.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2140   -1.2076    3.3975 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5385    1.0188    5.0868 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  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  1  0
 26 27  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  6 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
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 16 52  1  0
 17 53  1  0
 17 54  1  0
 18 55  1  0
 18 56  1  0
 19 57  1  0
 19 58  1  0
 23 59  1  0
 24 60  1  0
 24 61  1  0
 25 62  1  0
 26 63  1  0
 26 64  1  0
 27 65  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-glycerol	ChEBI
2-AG	ChEBI
2-Ara-GL	ChEBI
2-Arachidonoyl-glycerol	ChEBI
2-Arachidonyl-glycerol	ChEBI
2-Arachidonoyl-sn-glycerol	Kegg
(5Z,8Z,11Z,14Z)-2-Hydroxy-1-(hydroxymethyl)ethyl ester 5,8,11,14-eicosatetraenoate	HMDB
(5Z,8Z,11Z,14Z)-2-Hydroxy-1-(hydroxymethyl)ethyl ester 5,8,11,14-eicosatetraenoic acid	HMDB
(all-Z)-2-Hydroxy-1-(hydroxymethyl)ethyl ester 5,8,11,14-eicosatetraenoate	HMDB
(all-Z)-2-Hydroxy-1-(hydroxymethyl)ethyl ester 5,8,11,14-eicosatetraenoic acid	HMDB
1-Monoacylglyceride	HMDB
1-Monoacylglycerol	HMDB
2-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-rac-glycerol	HMDB
2-Arachidonyl glycerol	HMDB
2-Monoarachidonoylglycerolbeta-monoacylglycerol	HMDB
b-Monoacylglycerol	HMDB
beta-Monoacylglycerol	HMDB
MAG(20:4)	HMDB
MG(20:4)	HMDB
2-Arachidonoylglycerol	HMDB
Glyceryl 2-arachidonate	HMDB
2-Monoarachidonoylglycerol	HMDB
2-Arachidonylglycerol	HMDB
MAG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0)	HMDB
MAG(0:0/20:4n6/0:0)	HMDB
MAG(0:0/20:4W6/0:0)	HMDB
MAG(20:4(5Z,8Z,11Z,14Z))	HMDB
MAG(20:4n6)	HMDB
MAG(20:4W6)	HMDB
MG(0:0/20:4n6/0:0)	HMDB
MG(0:0/20:4W6/0:0)	HMDB
MG(20:4(5Z,8Z,11Z,14Z))	HMDB
MG(20:4n6)	HMDB
MG(20:4W6)	HMDB
MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0)	HMDB

Chemical Formula

C₂₃H₃₈O₄

Average Molecular Weight

378.5454

Monoisotopic Molecular Weight

378.277009704

IUPAC Name

1,3-dihydroxypropan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate

Traditional Name

2-arachidonoylglycerol

CAS Registry Number

53847-30-6

SMILES

[H]C(CO)(CO)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC

InChI Identifier

InChI=1S/C23H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(26)27-22(20-24)21-25/h6-7,9-10,12-13,15-16,22,24-25H,2-5,8,11,14,17-21H2,1H3/b7-6-,10-9-,13-12-,16-15-

InChI Key

RCRCTBLIHCHWDZ-DOFZRALJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as endocannabinoids. These are arachidonic acid derivatives containing either an N-acetylethanolamine(type 1) or a glycerol(types 2 and 3) moiety attached to the aliphatic tail.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Endocannabinoids

Sub Class

Not Available

Direct Parent

Endocannabinoids

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

endocannabinoid (CHEBI:52392 )
2-monoglyceride (CHEBI:52392 )
Fatty ethers (C13856 )
Monoacylglycerols (C13856 )
Monoacylglycerols (LMGL01010023 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21359215)
Cerebrospinal Fluid (CSF) (PMID: 19817812)

Tissue

All Tissues (HMDB: HMDB0004666)

Organ

Placenta (HMDB: HMDB0004666)

Excreta

Biofluid or Excreta

Feces (PMID: 28587349)
Urine (PMID: 32966057)

Cellular substructure

Membrane (HMDB: HMDB0004666)
Extracellular (HMDB: HMDB0004666)

Source

Exogenous

Exogenous (HMDB: HMDB0004666)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0004666)

Process

Not Available

Role

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	0.0014 g/L	ALOGPS
logP	5.65	ALOGPS
logP	5.41	ChemAxon
logS	-5.4	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	18	ChemAxon
Refractivity	116.98 m³·mol⁻¹	ChemAxon
Polarizability	44.96 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]+	204.109	31661259
DarkChem	[M-H]-	203.271	31661259
DeepCCS	[M+H]+	198.166	30932474
DeepCCS	[M-H]-	195.808	30932474
DeepCCS	[M-2H]-	229.869	30932474
DeepCCS	[M+Na]+	205.183	30932474
AllCCS	[M+H]+	201.7	32859911
AllCCS	[M+H-H2O]+	199.3	32859911
AllCCS	[M+NH4]+	204.0	32859911
AllCCS	[M+Na]+	204.6	32859911
AllCCS	[M-H]-	197.5	32859911
AllCCS	[M+Na-2H]-	200.0	32859911
AllCCS	[M+HCOO]-	202.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	7.45 minutes	32390414
Predicted by Siyang on May 30, 2022	23.2985 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.85 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	38.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3622.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	413.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	209.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	273.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	740.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1125.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	661.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	114.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2232.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	790.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	2058.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	800.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	548.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	365.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	519.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	9.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0)	[H]C(CO)(CO)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC	3169.9	Standard polar	33892256
MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0)	[H]C(CO)(CO)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC	2539.8	Standard non polar	33892256
MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0)	[H]C(CO)(CO)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC	2880.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0),1TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC(CO)CO[Si](C)(C)C	2902.4	Semi standard non polar	33892256
MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0),2TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC(CO[Si](C)(C)C)CO[Si](C)(C)C	2941.4	Semi standard non polar	33892256
MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0),1TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC(CO)CO[Si](C)(C)C(C)(C)C	3136.5	Semi standard non polar	33892256
MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0),2TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC(CO[Si](C)(C)C(C)(C)C)CO[Si](C)(C)C(C)(C)C	3416.7	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(0:0/20:4(5Z,8Z,11Z,14Z)/0:0) GC-MS (2 TMS) - 70eV, Positive	splash10-0l0i-5290110000-f742efe3985e3840860a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - MG(0:0/20:4(5Z,8Z,11Z,14Z)/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(0:0/20:4(5Z,8Z,11Z,14Z)/0:0) 10V, Positive-QTOF	splash10-0002-0009000000-3193f1e5874b95385d69	2017-10-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0) 20V, Positive-QTOF	splash10-004k-0009000000-627d06b5ba2360a06067	2017-10-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0) 40V, Positive-QTOF	splash10-00i2-0009000000-0762851e03f624970475	2017-10-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0) 10V, Positive-QTOF	splash10-004i-0009000000-5e905142605905a46679	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0) 20V, Positive-QTOF	splash10-0a90-0009000000-ae7594dce5d303ff168a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0) 40V, Positive-QTOF	splash10-0bti-0039000000-746b8a740d001af85c5a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0) 10V, Positive-QTOF	splash10-0udi-0000900000-e64013c0e57ed934df45	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0) 20V, Positive-QTOF	splash10-0udi-0000900000-e64013c0e57ed934df45	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0) 40V, Positive-QTOF	splash10-0fbf-0009300000-62825ca83031f6d152ec	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0) 10V, Positive-QTOF	splash10-0002-0009000000-c6ed117899d7fd7906f3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0) 20V, Positive-QTOF	splash10-004j-0009000000-d5b85743041436ea2e66	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0) 40V, Positive-QTOF	splash10-00i0-0009000000-7556d5d8a8a555162413	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0) 10V, Negative-QTOF	splash10-00fu-8029000000-9c1a42f92892713859ab	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0) 20V, Negative-QTOF	splash10-0kmu-9023000000-df51ee22c1d10b8fbdc2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0) 40V, Negative-QTOF	splash10-0a4r-9232000000-e481aacc04dad6bfc856	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Urine

Tissue Locations

All Tissues
Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	7.8 +/- 4.6 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.1596 +/- 0.1102 uM	Not Specified	Both	Normal	19817812	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.01848 +/- 0.00617 uM	Not Specified	Not Specified	Normal	21177788	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.01062 +/- 0.00458 uM	Not Specified	Not Specified	Normal	21177788	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
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.2095 +/- 0.14656 uM	Adult (>18 years old)	Both	epilepsy	19817812	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	28587349	details

Associated Disorders and Diseases

Disease References

Epilepsy
Romigi A, Bari M, Placidi F, Marciani MG, Malaponti M, Torelli F, Izzi F, Prosperetti C, Zannino S, Corte F, Chiaramonte C, Maccarrone M: Cerebrospinal fluid levels of the endocannabinoid anandamide are reduced in patients with untreated newly diagnosed temporal lobe epilepsy. Epilepsia. 2010 May;51(5):768-72. doi: 10.1111/j.1528-1167.2009.02334.x. Epub 2009 Oct 8. [PubMed:19817812 ]
Colorectal cancer
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

FDB023394

KNApSAcK ID

Not Available

Chemspider ID

4445451

KEGG Compound ID

C13856

BioCyc ID

CPD-12600

BiGG ID

Not Available

Wikipedia Link

2-Arachidonoylglycerol

METLIN ID

Not Available

PubChem Compound

5282280

PDB ID

Not Available

ChEBI ID

52392

Food Biomarker Ontology

Not Available

VMH ID

C13856

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Bari M, Battista N, Fezza F, Gasperi V, Maccarrone M: New insights into endocannabinoid degradation and its therapeutic potential. Mini Rev Med Chem. 2006 Mar;6(3):257-68. [PubMed:16515464 ]
Alger BE: Endocannabinoid identification in the brain: studies of breakdown lead to breakthrough, and there may be NO hope. Sci STKE. 2005 Nov 8;2005(309):pe51. [PubMed:16278487 ]
Sugiura T, Kishimoto S, Oka S, Gokoh M: Biochemistry, pharmacology and physiology of 2-arachidonoylglycerol, an endogenous cannabinoid receptor ligand. Prog Lipid Res. 2006 Sep;45(5):405-46. Epub 2006 Apr 19. [PubMed:16678907 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

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(0:0/20:4(5Z,8Z,11Z,14Z)/0:0) (HMDB0004666)

MOL for HMDB0004666 (MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0))

3D MOL for HMDB0004666 (MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0))

3D SDF for HMDB0004666 (MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0))

3D-SDF for HMDB0004666 (MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0))

PDB for HMDB0004666 (MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0))

3D PDB for HMDB0004666 (MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0))

SMILES for HMDB0004666 (MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0))

INCHI for HMDB0004666 (MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0))

Structure for HMDB0004666 (MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0))

3D Structure for HMDB0004666 (MG(0:0/20:4(5Z,8Z,11Z,14Z)/0:0))

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes