Record Information
Version1.0
Creation date2011-09-21 00:18:28 UTC
Update date2015-10-09 22:31:14 UTC
Primary IDFDB022722
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameValproic acid
DescriptionValproic acid (VPA) is considered to be a drug of first choice and one of the most frequently-prescribed antiepileptic drugs worldwide for the therapy of generalized and focal epilepsies, including special epileptic. It is a broad-spectrum antiepileptic drug and is usually well tolerated. Rarely, serious complications may occur in some patients, including hemorrhagic pancreatitis, coagulopathies, bone marrow suppression, VPA-induced hepatotoxicity and encephalopathy, but there is still a lack of knowledge about the incidence and occurrence of these special side effects. VPA has been approved for stabilization of manic episodes in patients with bipolar disorder. It is also used to treat migraine headaches and schizophrenia. As the use of VPA increases, the number of both accidental and intentional exposures increases. This is paralleled by more reports of VPA-induced toxicity. VPA is relatively contraindicated in pregnancy due to its teratogenicity. It is a known folate antagonist, which can cause neural tube defects. Thus, folic acid supplements may alleviate teratogenic problems. Women who become pregnant whilst taking valproate should be counselled as to its risks. VPA is an inhibitor of the enzyme histone deacetylase 1 (HDAC1). HDAC1 is needed for HIV to remain in infected cells. Patients treated with valproic acid in addition to highly active antiretroviral therapy (HAART) showed a median 75% reduction in latent HIV infection. VPA is believed to affect the function of the neurotransmitter GABA (as a GABA transaminase inhibitor) in the human brain. Valproic Acid dissociates to the valproate ion in the gastrointestinal tract. (PMID: 18201150, 17496767) [HMDB]
CAS Number99-66-1
Structure
Thumb
Synonyms
SynonymSource
2-N-Propyl-N-valeric acidChEBI
2-PROPYL-pentanoIC ACIDChEBI
2-Propylpentanoic acidChEBI
2-Propylvaleric acidChEBI
4-Heptanecarboxylic acidChEBI
Acide valproiqueChEBI
Acido valproicoChEBI
Acidum valproicumChEBI
DepakeneChEBI
Di-N-propylacetic acidChEBI
Di-N-propylessigsaeureChEBI
Dipropylacetic acidChEBI
DPAChEBI
N-DPAChEBI
ValproinsaeureChEBI
VPAChEBI
2-N-Propyl-N-valerateGenerator
2-PROPYL-pentanoateGenerator
2-PropylpentanoateGenerator
2-PropylvalerateGenerator
4-HeptanecarboxylateGenerator
Di-N-propylacetateGenerator
DipropylacetateGenerator
ValproateGenerator
(N-C3H7)2chcoohHMDB
(S)-2-Propyl-4-pentanoateHMDB
(S)-2-Propyl-4-pentanoic acidHMDB
Alti-valproicHMDB
Apo-divalproexHMDB
Apo-valproicHMDB
Apo-valproic syrupHMDB
AvuganeHMDB
BacecaHMDB
ConvulexHMDB
DelepsineHMDB
DepakinHMDB
Depakin chronoHMDB
DepakineHMDB
Depakine chronoHMDB
DeproicHMDB
Di-N-propylessigsaureHMDB
DivalproexHMDB
DOM-divalproexHMDB
Dom-valproateHMDB
DOM-valproicHMDB
Dom-valproic acidHMDB
DOM-valproic acid e.c.HMDB
Dom-valproic acid syrupHMDB
Epiject i.v.HMDB
EpilexHMDB
EpilimHMDB
EpivalHMDB
Epival erHMDB
ErgenylHMDB
Gen-divalproexHMDB
Kyselina 2-propylvalerovaHMDB
Med valproicHMDB
MylproinHMDB
MyproateHMDB
Myproic acidHMDB
N-Dipropylacetic acidHMDB
Novo-divalproexHMDB
Novo-valproicHMDB
Novo-valproic - eccHMDB
Novo-valproic soft gel capHMDB
Nu-valproicHMDB
PEACHMDB
Penta-valproicHMDB
PHL-ValproateHMDB
PHL-Valproic acidHMDB
PHL-Valproic acid e.c.HMDB
PMS-DivalproexHMDB
PMS-ValproateHMDB
PMS-Valproic acidHMDB
PMS-Valproic acid e.c.HMDB
Propylvaleric acidHMDB
Ratio-valproic - eccHMDB
S(-)-4-En-valproateHMDB
S(-)-4-En-valproic acidHMDB
S-2-N-Propyl-4-pentenoateHMDB
S-2-N-Propyl-4-pentenoic acidHMDB
Sandoz valproicHMDB
SavicolHMDB
SprinkleHMDB
ValcoteHMDB
ValparinHMDB
Valproic acid uspHMDB
Dipropyl acetateHMDB
Valproate, sodiumHMDB
Calcium, valproateHMDB
ConvulsofinHMDB
Semisodium valproateHMDB
Sodium valproateHMDB
Valproate calciumHMDB
Valproate, calciumHMDB
Valproic acid, sodium salt (2:1)HMDB
Acetate, dipropylHMDB
DepakoteHMDB
Divalproex sodiumHMDB
Magnesium valproateHMDB
Sodium, divalproexHMDB
Sodium, valproateHMDB
VupralHMDB
2 Propylpentanoic acidHMDB
Acid, propylisopropylaceticHMDB
Acid, valproicHMDB
Calcium valproateHMDB
Propylisopropylacetic acidHMDB
Valproate sodiumHMDB
Valproate, magnesiumHMDB
Valproate, semisodiumHMDB
(n-C3H7)2CHCOOHhmdb
(S)-2-propyl-4-pentanoatehmdb
(S)-2-propyl-4-pentanoic acidhmdb
2 PP (base)hmdb
2-n-Propyl-n-valeric acidhmdb
2-propyl-Pentanoatehmdb
2-propyl-Pentanoic acidhmdb
2-propylpentanoic acid (ACD/Name 4.0)hmdb
acide valproique [inn-french]hmdb
acido valproico [inn-spanish]hmdb
acidum valproicum [inn-latin]hmdb
APO-divalproexhmdb
Depakene Cap 250mghmdb
Depakene Cap 500mghmdb
Di-n-propylacetic acidhmdb
Di-n-propylessigsaurehmdb
Di-n-propylessigsaure [german]hmdb
Divalproex-125hmdb
Divalproex-250hmdb
Divalproex-500hmdb
DOM-valproic acid E.C.hmdb
DPA (van)hmdb
Epiject I.V.hmdb
Epival Ect 125mghmdb
Epival Ect 250mghmdb
Epival Ect 500mghmdb
Gen-Valproic - Cap 250mghmdb
Kyselina 2-propylvalerova [Czech]hmdb
N-dipropylacetic acidhmdb
nchembio815-comp21hmdb
Novo-Valproic - ECChmdb
Nu-Divalproex 125mghmdb
Nu-Divalproex 250mghmdb
Nu-Divalproex 500mghmdb
PHL-valproatehmdb
PHL-valproic acidhmdb
PHL-valproic acid E.C.hmdb
PMS-Divalproex (125mg)hmdb
PMS-Divalproex (500mg)hmdb
PMS-valproatehmdb
PMS-valproic acidhmdb
PMS-valproic acid E.C.hmdb
Ratio-Valproic - ECChmdb
Ratio-Valproic 50mg/mL Syruphmdb
Ratio-Valproic-Cap 250mghmdb
S-2-n-Propyl-4-pentenoatehmdb
S-2-n-Propyl-4-pentenoic acidhmdb
Sodium hydrogen divalproatehmdb
Sodium hydrogen divalproic acidhmdb
Valproate semisodique [french]hmdb
Valproate semisodiumhmdb
Valproato semisodico [spanish]hmdb
Valproatum seminatricum [latin]hmdb
Valproic acid [usan:ban:inn]hmdb
Valproic acid USPhmdb
Valproic acid USP24hmdb
Valproic-250hmdb
Predicted Properties
PropertyValueSource
Water Solubility2.36 g/LALOGPS
logP2.54ALOGPS
logP2.8ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)5.14ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity40.25 m³·mol⁻¹ChemAxon
Polarizability17 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC8H16O2
IUPAC name2-propylpentanoic acid
InChI IdentifierInChI=1S/C8H16O2/c1-3-5-7(6-4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10)
InChI KeyNIJJYAXOARWZEE-UHFFFAOYSA-N
Isomeric SMILESCCCC(CCC)C(O)=O
Average Molecular Weight144.2114
Monoisotopic Molecular Weight144.115029756
Classification
Description Belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMethyl-branched fatty acids
Alternative Parents
Substituents
  • Methyl-branched fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Route of exposure:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Indirect biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0fk9-9300000000-1a0314ea63d5a3c9bba1Spectrum
Predicted GC-MSValproic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004m-9300000000-e66da5fefd079f7426a4Spectrum
Predicted GC-MSValproic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00b9-9100000000-7bb11c5d52ffa09851f8Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-0udi-2900000000-156413e81733a6236c1fSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0f6y-2900000000-a769cafb885b78532cacSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0gbj-7900000000-46a522b9a26459334f5aSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0006-0900000000-39a45d4e3201082d9d89Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0002-9000000000-4ddd957d8c8dc2b1de03Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0006-0900000000-6ba582ae102c4721034dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0006-0900000000-58d9ba88010f1b370c58Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-3900000000-2d1032d7e8ac58235b4fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4j-9000000000-0d39870bc4521a42c50aSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00di-9000000000-3c4e21b69b8877d6df3eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-0900000000-39a45d4e3201082d9d89Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9000000000-4ddd957d8c8dc2b1de03Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-0900000000-6ba582ae102c4721034dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-0900000000-58d9ba88010f1b370c58Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-3900000000-2d1032d7e8ac58235b4fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4j-9000000000-0d39870bc4521a42c50aSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-3c4e21b69b8877d6df3eSpectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0006-0900000000-5b83f0d6c36f8249285aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-3900000000-be0e79e3b65dad2e2d08Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0005-9500000000-37d8981251a94cfd51e3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-b63be8686bbf9a96b2baSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-3900000000-25f23d80c7431c074a74Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0005-9500000000-144b6cc9fea5bae4f269Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052e-9100000000-eb5e97329782125f6615Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID3009
ChEMBL IDCHEMBL109
KEGG Compound IDC07185
Pubchem Compound ID3121
Pubchem Substance IDNot Available
ChEBI ID39867
Phenol-Explorer IDNot Available
DrugBank IDDB00313
HMDB IDHMDB01877
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET ID2PP
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDValproic acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Cytochrome P450, family 1, subfamily A, polypeptide 1CYP1A1A0N0X8
Cytochrome P450 2D6CYP2D6Q6NWU0
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference