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Structure Database (LMSD)

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Common Name

N-arachidonoyl dihydroxypropylamine

Systematic Name

N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-(1,3-dihydroxy-propyl-2-amine)

Synonyms

AA dihydroxypropylamine
Arachidonoyl Serinol

LM ID

LMFA08020072

Formula

C₂₃H₃₉NO₃

Exact Mass

Calculate m/z

377.292994

Sum Composition

NA 23:4;O2

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View NP-MRD ID(NMR) spectrum

Classification

Biological Context

2-Arachidonoyl glycerol (2-AG) has been isolated from porcine brain, and has been characterized as the natural endocannabinoid ligand for the CB1 receptor.^1,2 Replacement of the sn-2 oxygen in the glycerol moiety of 2-AG with a nitrogen atom gives arachidonoyl serinol.³ Arachidonoyl serinol is much more stable than 2-AG. However, it is at least a log less potent as a CB1 receptor agonist than 2-AG.²

This information has been provided by Cayman Chemical

References

1. Khanolkar, A.D., Abadji, V., Lin, S., et al. Head group analogs of arachidonylethanolamide, the endogenous cannabinoid ligand. J. Med. Chem. 39(22), 4515-4519 (1996).

2. Sugiura, T., Kodaka, T., Kondo, S., et al. 2-Arachidonoylglycerol, a putative endogenous cannabinoid receptor ligand, induces rapid, transient elevation of intracellular free Ca2+ in neuroblastoma X glioma hybrid NG108-15 cells. Biochem. Biophys. Res. Commun. 229(1), 58-64 (1996).

3. Sugiura, T., Kodaka, T., Kondo, S., et al. Is the cannabinoid CB1 receptor a 2-arachidonoylglycerol receptor? Structural requirements for triggering a Ca2+ transient in NG108-15 cells. J. Biochem. 122(4), 890-895 (1997).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Head group analogs of arachidonylethanolamide, the endogenous cannabinoid ligand.,
J Med Chem, 1996

Pubmed ID: 8893848

String Representations

InChiKey (Click to copy)

QHELXIATGZYOIB-DOFZRALJSA-N

InChi (Click to copy)

InChI=1S/C23H39NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(27)24-22(20-25)21-26/h6-7,9-10,12-13,15-16,22,25-26H,2-5,8,11,14,17-21H2,1H3,(H,24,27)/b7-6-,10-9-,13-12-,16-15-

SMILES (Click to copy)

C(NC(CO)CO)(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC