VALPROIC ACID

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Trade Names
Synonyms
Status
Molecule Category Free-form
ATC N03AG01
UNII 614OI1Z5WI
EPA CompTox DTXSID6023733

Structure

InChI Key NIJJYAXOARWZEE-UHFFFAOYSA-N
Smiles CCCC(CCC)C(=O)O
InChI
InChI=1S/C8H16O2/c1-3-5-7(6-4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10)

Physicochemical Descriptors

Property Name Value
Molecular Formula C8H16O2
Molecular Weight 144.21
AlogP 2.29
Hydrogen Bond Acceptor 1.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 5.0
Polar Surface Area 37.3
Molecular species ACID
Aromatic Rings 0.0
Heavy Atoms 10.0

Metabolites Network

visNetwork

Bioactivity

Mechanism of Action Action Reference
Succinate semialdehyde dehydrogenase inhibitor INHIBITOR PubMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Kinase Protein Kinase CMGC protein kinase group CMGC protein kinase GSK family
- - - - 65
Enzyme Oxidoreductase
- 56100-56100 - - -
Enzyme Transferase
- - - - 41
Epigenetic regulator Eraser Histone deacetylase HDAC class I
- 39000-40000 - - 7
Epigenetic regulator Eraser Histone deacetylase HDAC class IIa
- - - - 7
Epigenetic regulator Eraser Histone deacetylase HDAC class IIb
- - - - 7
Epigenetic regulator Eraser Histone deacetylase HDAC class IV
- - - - 7
Membrane receptor
- - - - 81-93
Surface antigen
- - - - 81-93
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 10
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - - 20
Assay Description Organism Bioactivity Reference
Inhibition of GSK3-beta at 2 mM relative to control None 65.2 %
Inhibition of human HDAC in HeLa cells at 100 uM Homo sapiens 7.4 %
Antiproliferative activity against human A549 cells at 1 mM after 3 days Homo sapiens 24.0 %
Inhibition of TNF-alpha-induced tissue factor activity in HUVEC at 6 uM preincubated for 4 hrs assessed after 4 hrs of TNFalpha challenge by one stage clotting assay Homo sapiens 81.0 %
Inhibition of LPS-induced tissue factor activity in HUVEC at 6 uM preincubated for 4 hrs assessed after 4 hrs of LPS challenge by one stage clotting assay Homo sapiens 93.0 %
Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells at 100 uM by confocal microscopy Homo sapiens 19.6 %
Inhibition of human aquaporin 4 M23 isoform expressed in Xenopus laevis oocytes at 20 uM Homo sapiens 40.0 %
Inhibition of dihydrotestosterone (assayed at the Km) glucuronidation by human recombinant UGT2B15 (+/- 11% inhibition at 5mM VPA) Homo sapiens 41.0 %
Inhibition of propofol (assayed at the Km) glucuronidation by human recombinant UGT1A9 (+/- 15% inhibition at 5mM VPA) Homo sapiens 46.0 %
TP_TRANSPORTER: inhibition of PAH uptake (PAH: 2 uM, Valproic acid; 2000 uM) in Xenopus laevis oocytes Xenopus laevis 85.0 %
Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as reduction in E17-betaG uptake at 20 uM by scintillation counting Homo sapiens 25.2 %
Inhibition of human liver OATP1B3 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E17-betaG uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 9.6 %
Inhibition of human liver OATP2B1 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E3S uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 61.9 %
Time dependent inhibition of CYP1A2 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2B6 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2C9 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2C19 in human liver microsomes at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2D6 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP3A4 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2C8 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Antinociceptive activity in Albino Swiss CD-1 mouse assessed as inhibition of formalin-induced neurogenic pain response at 100 mg/kg, ip administered 30 mins before formalin injection measured up to 5 mins relative to control Mus musculus 15.7 %
Antinociceptive activity in Albino Swiss CD-1 mouse assessed as inhibition of formalin-induced neurogenic pain response at 150 mg/kg, ip administered 30 mins before formalin injection measured up to 5 mins relative to control Mus musculus 25.8 %
Antinociceptive activity in Albino Swiss CD-1 mouse assessed as inhibition of formalin-induced neurogenic pain response at 200 mg/kg, ip administered 30 mins before formalin injection measured up to 5 mins relative to control Mus musculus 29.2 %
Antinociceptive activity in Albino Swiss CD-1 mouse assessed as inhibition of capsaicin-induced nociception by measuring time spent licking injected paw at 200 mg/kg, ip administered 30 mins mins prior to capsaicin challenge measured for 5 mins relative to control Mus musculus 42.2 %
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus 9.7 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli -0.41 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 1.95 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 13.05 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 7.03 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 5.05 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans -4.42 %
IC50 for antiviral activity against SARS-CoV-2 in the Vero E6 cell line at 48 h by immunofluorescence-based assay (detecting the viral NP protein in the nucleus of the Vero E6 cells). Chlorocebus sabaeus 121.06 nM

Environmental Exposure

Environmental Exposure Map
Countries
Croatia
Czech Republic
Germany
Hungary
Romania
Serbia
Slovakia
Slovenia

Cross References

Resources Reference
ChEBI 39867
ChEMBL CHEMBL109
DrugBank DB00313
DrugCentral 2803
FDA SRS 614OI1Z5WI
Human Metabolome Database HMDB0001877
Guide to Pharmacology 7009
KEGG C07185
PDB 2PP
PharmGKB PA451846
PubChem 3121
SureChEMBL SCHEMBL2275
ZINC ZINC000003008621
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