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Structure Database (LMSD)

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Common Name

N-Oleoyl Dopamine

Systematic Name

N-[2-(3,4-dihydroxyphenyl)ethyl]-9Z-octadecenamide

Synonyms

OLDA

LM ID

LMFA08020140

Formula

C₂₆H₄₃NO₃

Exact Mass

Calculate m/z

417.324294

Sum Composition

NA 26:5;O2

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

N-Oleoyl dopamine (ODA) is a selective, endogenous vanilloid receptor 1 (VR1) agonist isolated from bovine brain.¹ Structurally, it is the amide of oleic acid and dopamine and is therefore a “hybrid” analog which incorporates components of both the anandamide-like and dopamine neurotransmitter pathways. ODA binds to the human recombinant VR1 with a Ki of 36 nM making it equipotent to capsaicin and slightly more potent than N-arachidonoyl dopamine in this assay.¹ It causes hyperalgesia and nocifensive behavior that is blocked by the VR1 antagonist iodo-resiniferatoxin. ODA is selective for VR1 based on observations that it has weak affinity for the rat CB1 receptor (Ki of 1.6 µM) and is a very weak inhibitor of FAAH. ODA is also a potent inhibitor of 5-lipoxygenase from rat basophilic leukemia-1 (RBL-1) cells, with a IC50 of 7.5 nM.^2,3

This information has been provided by Cayman Chemical

References

1. Chu, C.J., Huang, S.M., De Petrocellis, L., et al. N-oleoyldopamine, a novel endogenous capsaicin-like lipid that produces hyperalgesia. J. Biol. Chem. 278(16), 13633-13639 (2003).

2. Iwakami, S., Shibuya, M., Tseng, C.F., et al. Inhibition of arachidonate 5-lipoxygenase by phenolic compounds. Chem. Pharm. Bull. (Tokyo) 34(9), 3960-3963 (1986).

3. Tseng, C.F., Iwakami, S., Mikajiri, A., et al. Inhibition of in vitro prostaglandin and leukotriene biosyntheses by cinnamoyl-β-phenethylamine and N-acyldopamine derivatives. Chem. Pharm. Bull. (Tokyo) 40(2), 396-400 (1992).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Bos taurus (#9913)

Mammalia (#40674)

N-oleoyldopamine, a novel endogenous capsaicin-like lipid that produces hyperalgesia.,
J Biol Chem, 2003

Pubmed ID: 12569099

String Representations

InChiKey (Click to copy)

QQBPLXNESPTPNU-KTKRTIGZSA-N

InChi (Click to copy)

InChI=1S/C26H43NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-26(30)27-21-20-23-18-19-24(28)25(29)22-23/h9-10,18-19,22,28-29H,2-8,11-17,20-21H2,1H3,(H,27,30)/b10-9-

SMILES (Click to copy)

C(CCC/C=C\CCCCCCCC)CCCC(=O)NCCC1=CC(O)=C(O)C=C1