Structure Database (LMSD)

Common Name
Lauroleinic acid
Systematic Name
5Z-dodecenoic acid
Synonyms
  • C12:1n-7
  • Denticetic acid
LM ID
LMFA01030226
Formula
C12H22O2
Exact Mass
Calculate m/z
198.16198
Sum Composition
FA 12:1
Status
Curated
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Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]

Biological Context

5(Z)-Dodecenoic acid is a medium-chain unsaturated fatty acid. It is a precursor in the biosynthesis of the sex pheromone 5(Z)-dodecenal.1 5(Z)-Dodecenoic acid levels are increased in culture medium from MCF-7 breast cancer cells compared to KMST-6 fibroblasts.2 Levels of 5(Z)-dodecenoic acid are increased in the plasma of patients with medium-chain acyl-CoA dehydrogenase (MCAD) deficiency, an inborn error of metabolism characterized by hypoketotic hypoglycemia, medium-chain dicarboxylic aciduria, and intolerance to fasting.3

This information has been provided by Cayman Chemical

References

1. Onkenhout, W., Venizelos, V., van der Poel, P.F.H., et al. Identification and quantification of intermediates of unsaturated fatty acid metabolism in plasma of patients with fatty acid oxidation disorders. Clin. Chem. 41(10), 1467-1474 (1995).
2. Bestmann, H.J., Attygalle, A.B., Garbe, W., et al. Chemical structure and final steps of biosynthesis of the female sex pheromone of Gastropacha quercifolia (Lepidoptera: Lasiocampidae). Insect Biochem. Molec. Biol. 23(7), 793-799 (1993).
3. Tanaka, M., Hsuan, C., Oeki, M., et al. Identification of characteristic compounds of moderate volatility in breast cancer cell lines. PLoS One 15(6), e0235442 (2020).

Reactions

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References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
Identification of characteristic compounds of moderate volatility in breast cancer cell lines.,
PLoS One, 2020
Pubmed ID: 32598404
Gastropacha quercifolia (#1502188)
Insecta (#50557)
Chemical structure and final steps of biosynthesis of the female sex pheromone of Gastropacha quercifolia (Lepidoptera: Lasiocampidae),
Insec Biochem Mol Biol, 1993

String Representations

InChiKey (Click to copy)
IJBFSOLHRKELLR-FPLPWBNLSA-N
InChi (Click to copy)
InChI=1S/C12H22O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h7-8H,2-6,9-11H2,1H3,(H,13,14)/b8-7-
SMILES (Click to copy)
C(CCC/C=C\CCCCCC)(=O)O

Other Databases

LIPIDAT ID
1759
HMDB ID
HMDB0000529
CHEBI ID
86595
PubChem CID
5312378
PlantFA ID
10029
Cayman ID
35910

Calculated Physicochemical Properties

Heavy Atoms 14
Rings 0
Aromatic Rings 0
Rotatable Bonds 9
Van der Waals Molecular Volume 228.46
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 3.77
Molar Refractivity 59.39

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Created at
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Updated at
9th Jun 2022