Structure Database (LMSD)

Common Name
3-keto stearic acid
Systematic Name
3-oxo-octadecanoic acid
Synonyms
LM ID
LMFA02000240
Formula
C18H34O3
Exact Mass
Calculate m/z
298.250795
Sum Composition
FA 18:1;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]
Oxo fatty acids [FA0106]

Biological Context

3-oxo Stearic acid is an intermediate in the dissociated (or type II) fatty acid biosynthesis that occurs in bacteria and plants.1 This β-keto fatty acid is generated following the reaction of hexadecenoyl-acyl-carrier-protein (ACP) with malonyl-ACP by the enzyme β-ketoacyl-ACP synthase II, which produces 3-oxo octadecenoyl-ACP.2 Removal of the ACP group by ACP hydrolase produces the free acid.

This information has been provided by Cayman Chemical

References

1. Marrakchi, H., Zhang, Y.M., and Rock, C.O. Mechanistic diversity and regulation of type II fatty acid synthesis. Biochem. Soc. Trans. 30(Pt 6), 1050-1055 (2002).
2. Parsons, J.B., and Rock, C.O. Bacterial lipids: Metabolism and membrane homeostasis. Prog. Lipid Res. 52(3), 249-276 (2013).

String Representations

InChiKey (Click to copy)
YQGGUZWHNVQJMF-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C18H34O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-17(19)16-18(20)21/h2-16H2,1H3,(H,20,21)
SMILES (Click to copy)
C(CCCCCCCCCCCCC)CC(=O)CC(=O)O

Other Databases

HMDB ID
HMDB0010736
CHEBI ID
50576
PubChem CID
5283005
Cayman ID
14807

Calculated Physicochemical Properties

Heavy Atoms 21
Rings 0
Aromatic Rings 0
Rotatable Bonds 16
Van der Waals Molecular Volume 341.05
Topological Polar Surface Area 54.37
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 3
logP 5.51
Molar Refractivity 87.57

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Updated at
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