Structure Database (LMSD)

Common Name
Valproic acid
Systematic Name
2-propylpentanoic acid
Synonyms
LM ID
LMFA01020291
Formula
C8H16O2
Exact Mass
Calculate m/z
144.11503
Sum Composition
FA 8:0
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View MassBank spectra

Classification

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

Biological Context

Valproic acid is an analog of the natural fatty acid valeric acid that inhibits class I histone deacetylases (HDACs) with IC50 values of approximately 2 mM.1 It decreases the number of axon branches in sensory neurons isolated from newborn rat dorsal root ganglia, an effect that is reversed by inositol-1,4,5-trisphosphate (1,4,5-IP3).2 In vivo, valproic acid inhibits amyloid-β deposition and neuritic plaque formation and decreases escape latency in Morris water maze, indicating improved memory performance, in the APP23 transgenic mouse model of Alzheimer's disease.3 Valproic acid has anticonvulsant activity in the pentylenetetrazole seizure threshold test in mice (ED50 = 0.71 mmol/kg) but induces neurotoxicity when administered at doses greater than or equal to 1.2 mmol/kg.4 Formulations containing valproic acid have been used in the treatment of bipolar disorder and various seizure disorders.

This information has been provided by Cayman Chemical

References

1. Williams, R.S.B., Cheng, L., Mudge, A.W., et al. A common mechanism of action for three mood-stabilizing drugs. Nature 417(6886), 292-295 (2002).
2. Göttlicher, M., Minucci, S., Zhu, P., et al. Valproic acid defines a novel class of HDAC inhibitors inducing differentiation of transformed cells. EMBO J. 20(24), 6969-6978 (2001).
3. Qing, H., He, G., Ly, P.T., et al. Valproic acid inhibits Aβ production, neuritic plaque formation, and behavioral deficits in Alzheimer’s disease mouse models. J. Exp. Med. 205(12), 2781-2789 (2008).
4. Elmazar, M.M., Hauck, R.S., and Nau, H. Anticonvulsant and neurotoxic activities of twelve analogues of valproic acid. J. Pharm. Sci. 82(12), 1255-1258 (1993).

String Representations

InChiKey (Click to copy)
NIJJYAXOARWZEE-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C8H16O2/c1-3-5-7(6-4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10)
SMILES (Click to copy)
C(=O)(O)C(CCC)CCC

Other Databases

Wikipedia
Valproic_acid
KEGG ID
C07185
HMDB ID
HMDB0001877
CHEBI ID
39867
PubChem CID
3121
Cayman ID
35739
PDB ID
2PP
GuidePharm ID
7009

Calculated Physicochemical Properties

Heavy Atoms 10
Rings 0
Aromatic Rings 0
Rotatable Bonds 5
Van der Waals Molecular Volume 161.90
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 2.29
Molar Refractivity 40.94

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Updated at
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