Structure Database (LMSD)

Common Name
N-oleoyl proline
Systematic Name
N-(9Z-octadecenoyl)-proline
Synonyms
LM ID
LMFA08020118
Formula
C23H41NO3
Exact Mass
Calculate m/z
379.308644
Sum Composition
NAPro 18:1
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty amides [FA08]
N-acyl amino acids [FA0805]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]
Carbocyclic fatty acids [FA0114]

Biological Context

N-Oleoyl proline is an N-acyl amine that has been detected in bovine brain extracts and D. melanogaster larvae using mass spectrometry.1,2 In a preclinical model of pain, mice lacking fatty acid amide hydrolase (FAAH KO) had decreased N-oleoyl proline levels in lumbar spinal cord after capsaicin administration (1 µg/10 µl).3 N-Oleoyl proline also has surfactant properties (critical micelle concentration = 4.8 µM).4

This information has been provided by Cayman Chemical

References

1. Carey, L.M., Slivicki, R.A., Leishman, E., et al. A pro-nociceptive phenotype unmasked in mice lacking fatty-acid amide hydrolase. Mol. Pain 12, (2016).
2. Sreenu, M., Nayak, R.R., Prasad, R.B.N., et al. Synthesis, surface and micellar properties of sodium N-oleoyl amino acids. Colloids Surf. A. Physicochem. Eng. Aspects 449, 74-81 (2014).
3. Tan, B., O'Dell, D.K., Yu, Y.W., et al. Identification of endogenous acyl amino acids based on a targeted lipidomics approach. J. Lipid. Res. 51(1), 112-119 (2010).
4. Tortoriello, G., Rhodes, B.P., Takacs, S.M., et al. Targeted lipidomics in Drosophila melanogaster identifies novel 2-monoacylglycerols and N-acyl amides. PLoS One 8(7), e67865 (2013).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Rattus norvegicus (#10116)
Mammalia (#40674)
Identification of endogenous acyl amino acids based on a targeted lipidomics approach.,
J Lipid Res, 2010
Pubmed ID: 19584404

String Representations

InChiKey (Click to copy)
WQCMZYCKACKLDL-YUQDSPFASA-N
InChi (Click to copy)
InChI=1S/C23H41NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-19-22(25)24-20-17-18-21(24)23(26)27/h9-10,21H,2-8,11-20H2,1H3,(H,26,27)/b10-9-/t21-/m0/s1
SMILES (Click to copy)
C1CCN(C(CCCCCCC/C=C\CCCCCCCC)=O)[C@]1([H])C(=O)O

Other Databases

CHEBI ID
165546
PubChem CID
52922068
Cayman ID
20369

Calculated Physicochemical Properties

Heavy Atoms 27
Rings 1
Aromatic Rings 0
Rotatable Bonds 16
Van der Waals Molecular Volume 423.55
Topological Polar Surface Area 57.61
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 4
logP 6.67
Molar Refractivity 112.82

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Created at
-
Updated at
19th Feb 2024