Structure Database (LMSD)

Common Name
DL-9-hydroxy stearic acid
Systematic Name
9-hydroxy-octadecanoic acid
Synonyms
  • 9-HODA
  • 9-HSA
LM ID
LMFA02000127
Formula
C18H36O3
Exact Mass
Calculate m/z
300.266445
Sum Composition
FA 18:0;O
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Octadecanoids [FA02]
Other Octadecanoids [FA0200]
Fatty Acids and Conjugates [FA01]
Hydroxy fatty acids [FA0105]

Biological Context

9-hydroxy Stearic acid is a hydroxy fatty acid and an active metabolite of 9-PAHSA .1,2 It is formed from 9-PAHSA by liver and pancreatic carboxyl ester lipases.2 9-hydroxy Stearic acid (5 µM) inhibits histone deacetylase 1 (HDAC1) in HT-29 colon cancer cell lysates.3 It inhibits the proliferation of, and induces cell cycle arrest at the G0/G1 phase in, HT-29 cells when used at a concentration of 100 µM.1

This information has been provided by Cayman Chemical

References

1. Kolar, M.J., Kamat, S.S., Parsons, W.H., et al. Branched fatty acid esters of hydroxy fatty acids are preferred substrates of the MODY8 protein carboxyl ester lipase. Biochemistry 55(33), 4636-4641 (2016).
2. Calonghi, N., Cappadone, C., Pagnotta, E., et al. 9-Hydroxystearic acid upregulates p21WAF1 in HT29 cancer cells. Biochem. Biophys. Res. Commun. 314(1), 138-142 (2004).
3. Calonghi, N., Cappadone, C., Pagnotta, E., et al. Histone deacetylase 1: A target of 9-hydroxystearic acid in the inhibition of cell growth in human colon cancer. J. Lipid Res. 46(8), 1596-1603 (2005).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Malassezia furfur (#55194)
Malasseziomycetes (#1538075)
A study of the fatty acid metabolism of the yeast Pityrosporum ovale.,
Biochem J, 1968
Pubmed ID: 5691082
Homo sapiens (#9606)
Mammalia (#40674)
Identification of the peroxidation product hydroxystearic acid in Lewis lung carcinoma cells.,
Biochem Biophys Res Commun, 1991
Pubmed ID: 1872846

String Representations

InChiKey (Click to copy)
RKHXDCVAPIMDMG-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C18H36O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h17,19H,2-16H2,1H3,(H,20,21)
SMILES (Click to copy)
C(CCCCCC(O)CCCCCCCCC)CC(=O)O

Other Databases

HMDB ID
HMDB0061661
CHEBI ID
136638
PubChem CID
9570127
PlantFA ID
10263
Cayman ID
18016
GuidePharm ID
13240

Calculated Physicochemical Properties

Heavy Atoms 21
Rings 0
Aromatic Rings 0
Rotatable Bonds 16
Van der Waals Molecular Volume 343.69
Topological Polar Surface Area 57.53
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 5.59
Molar Refractivity 89.08

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Created at
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Updated at
18th Nov 2024