Structure Database (LMSD)

Common Name
4-ene-Valproic acid
Systematic Name
2-propylpent-4-enoic acid
Synonyms
LM ID
LMFA01030982
Formula
C8H14O2
Exact Mass
Calculate m/z
142.09938
Sum Composition
FA 8:1
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View studies deposited in Metabolomics Workbench in which this molecule has been identified

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]
Branched fatty acids [FA0102]

Biological Context

(±)-2-propyl-4-Pentenoic acid (4-ene VPA) is a major metabolite of valproic acid .1 It undergoes β-oxidation to form reactive metabolites that induce hepatotoxicity in rats. 4-ene VPA is also neuroteratogenic, reducing forebrain size and inducing deformation of the neural tube in mouse embryos.2

This information has been provided by Cayman Chemical

References

1. Gofflot, F., Nassogne, M.C., Etzion, T., et al. In vitro neuroteratogenicity of valproic acid and 4-en-VPA. Neurotoxicol. Teratol. 17(4), 425-435 (1995).
2. Tang, W., and Abbott, F.S. A comparative investigation of 2-propyl-4-pentenoic acid (4-ene VPA) and its α-fluorinated analogue: Phase II metabolism and pharmacokinetics. Drug Metab. Dispos. 25(2), 219-227 (1997).

String Representations

InChiKey (Click to copy)
UMYDNZXEHYSVFY-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C8H14O2/c1-3-5-7(6-4-2)8(9)10/h3,7H,1,4-6H2,2H3,(H,9,10)
SMILES (Click to copy)
C=CCC(C(=O)O)CCC

Other Databases

KEGG ID
C16648
HMDB ID
HMDB0013897
CHEBI ID
80634
PubChem CID
104896
Cayman ID
23090

Calculated Physicochemical Properties

Heavy Atoms 10
Rings 0
Aromatic Rings 0
Rotatable Bonds 5
Van der Waals Molecular Volume 159.26
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 2.06
Molar Refractivity 40.85

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Updated at
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