Structure Database (LMSD)

Common Name
12S-hydroxy-16-heptadecynoic acid
Systematic Name
12S-hydroxy-16-heptadecynoic acid
Synonyms
LM ID
LMFA01050146
Formula
C17H30O3
Exact Mass
Calculate m/z
282.219495
Sum Composition
FA 17:2;O
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty Acids and Conjugates [FA01]
Hydroxy fatty acids [FA0105]
Unsaturated fatty acids [FA0103]

Biological Context

12(S)-hydroxy-16-Heptadecynoic acid is a mechanism-based inhibitor of cytochrome P450 ω-hydroxylase.1 It inhibits prostaglandin ω-hydroxylase with a Ki value of 1.8 µM.1

This information has been provided by Cayman Chemical

References

1. Burger, A., Clark, J.E., Nishimoto, M., et al. Mechanism-based inhibitors of prostaglandin w -hydrolase: (R)- and (S)-12-hydroxy-16-heptadecynoic acid and 2,2-dimethyl-12-hydroxy-16-heptadecynoic acid. J. Med. Chem. 36, 1418-1424 (1993).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Mechanism-based inhibitors of prostaglandin omega-hydroxylase: (R)- and (S)-12-hydroxy-16-heptadecynoic acid and 2,2-dimethyl-12-hydroxy-16-heptadecynoic acid.,
J Med Chem, 1993
Pubmed ID: 8496909

String Representations

InChiKey (Click to copy)
HBFCVDJQUPEEIC-MRXNPFEDSA-N
InChi (Click to copy)
InChI=1S/C17H30O3/c1-2-3-10-13-16(18)14-11-8-6-4-5-7-9-12-15-17(19)20/h1,16,18H,3-15H2,(H,19,20)/t16-/m1/s1
SMILES (Click to copy)
C(C[C@H](O)CCCC#C)CCCCCCCCC(=O)O

Other Databases

CHEBI ID
165400
LIPIDBANK ID
DFA8152
PubChem CID
5282972
Cayman ID
31570

Calculated Physicochemical Properties

Heavy Atoms 20
Rings 0
Aromatic Rings 0
Rotatable Bonds 14
Van der Waals Molecular Volume 321.11
Topological Polar Surface Area 57.53
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 4.42
Molar Refractivity 83.01

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Created at
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Updated at
3rd May 2022