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Showing metabocard for Valproic acid (HMDB0001877)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (25) Show 25 proteinsXML
enzymes (25) Show 25 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-02-24 11:11:14 UTC
Update Date2023-02-21 17:15:54 UTC
HMDB IDHMDB0001877
Secondary Accession Numbers
  • HMDB01877
Metabolite Identification
Common 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 ).
Structure
Data?1676999754
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001877 (Valproic acid)


  Mrv1652305271900322D          

 10  9  0  0  0  0            999 V2000
   -1.4289    0.1650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.1650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.1650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.2475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.9900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  8  1  0  0  0  0
  4  5  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
M  END
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3D MOL for HMDB0001877 (Valproic acid)

HMDB0001877
     RDKit          3D
Valproic acid
 26 25  0  0  0  0  0  0  0  0999 V2000
    2.8499    0.8540   -1.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3193    0.8024   -0.7455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1139    0.0535    0.5130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2394   -0.1274    1.0553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2765   -0.8441    0.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7223   -0.3553   -1.0171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2739    1.0578   -0.9997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0697   -0.9172    2.3476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4283   -0.4966    3.4548 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5144   -2.1555    2.2455 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0298    1.7250   -1.6600 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3777    0.8543   -0.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1522   -0.0566   -1.5789 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9293    0.3514   -1.6656 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9117    1.8218   -0.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6334   -0.9428    0.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7187    0.5697    1.3330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6515    0.8535    1.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9117   -1.9136    0.1146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2029   -1.0397    0.9168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6654   -0.9810   -1.2601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1123   -0.4796   -1.8891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2482    1.0928   -0.4758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5305    1.7497   -0.5851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4326    1.3395   -2.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2147   -2.8160    1.5563 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  4  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
 10 26  1  0
M  END
Download

3D SDF for HMDB0001877 (Valproic acid)


  Mrv1652305271900322D          

 10  9  0  0  0  0            999 V2000
   -1.4289    0.1650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.1650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.1650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.2475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.9900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  8  1  0  0  0  0
  4  5  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001877

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCC(CCC)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H16O2/c1-3-5-7(6-4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10)

> <INCHI_KEY>
NIJJYAXOARWZEE-UHFFFAOYSA-N

> <FORMULA>
C8H16O2

> <MOLECULAR_WEIGHT>
144.2114

> <EXACT_MASS>
144.115029756

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
16.996878483662726

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-propylpentanoic acid

> <ALOGPS_LOGP>
2.54

> <JCHEM_LOGP>
2.7984510709999997

> <ALOGPS_LOGS>
-1.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.144389811177235

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
40.2491

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.36e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
valproic acid

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0001877 (Valproic acid)

HMDB0001877
     RDKit          3D
Valproic acid
 26 25  0  0  0  0  0  0  0  0999 V2000
    2.8499    0.8540   -1.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3193    0.8024   -0.7455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1139    0.0535    0.5130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2394   -0.1274    1.0553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2765   -0.8441    0.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7223   -0.3553   -1.0171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2739    1.0578   -0.9997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0697   -0.9172    2.3476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4283   -0.4966    3.4548 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5144   -2.1555    2.2455 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0298    1.7250   -1.6600 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3777    0.8543   -0.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1522   -0.0566   -1.5789 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9293    0.3514   -1.6656 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9117    1.8218   -0.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6334   -0.9428    0.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7187    0.5697    1.3330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6515    0.8535    1.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9117   -1.9136    0.1146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2029   -1.0397    0.9168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6654   -0.9810   -1.2601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1123   -0.4796   -1.8891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2482    1.0928   -0.4758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5305    1.7497   -0.5851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4326    1.3395   -2.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2147   -2.8160    1.5563 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  4  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
 10 26  1  0
M  END
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PDB for HMDB0001877 (Valproic acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -2.667   0.308   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -0.462   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.308   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.462   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.308   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -2.772   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -4.312   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -2.002   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.001  -0.462   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       2.667   1.848   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    8    5                                                  
CONECT    5    4    9   10                                                  
CONECT    6    7    8                                                       
CONECT    7    6                                                            
CONECT    8    4    6                                                       
CONECT    9    5                                                            
CONECT   10    5                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for HMDB0001877 (Valproic acid)

COMPND    HMDB0001877
HETATM    1  C1  UNL     1       2.850   0.854  -1.020  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.319   0.802  -0.745  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.114   0.054   0.513  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.239  -0.127   1.055  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.277  -0.844   0.294  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.722  -0.355  -1.017  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.274   1.058  -1.000  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.070  -0.917   2.348  1.00  0.00           C  
HETATM    9  O1  UNL     1      -0.428  -0.497   3.455  1.00  0.00           O  
HETATM   10  O2  UNL     1       0.514  -2.156   2.246  1.00  0.00           O  
HETATM   11  H1  UNL     1       3.030   1.725  -1.660  1.00  0.00           H  
HETATM   12  H2  UNL     1       3.378   0.854  -0.066  1.00  0.00           H  
HETATM   13  H3  UNL     1       3.152  -0.057  -1.579  1.00  0.00           H  
HETATM   14  H4  UNL     1       0.929   0.351  -1.666  1.00  0.00           H  
HETATM   15  H5  UNL     1       0.912   1.822  -0.665  1.00  0.00           H  
HETATM   16  H6  UNL     1       1.633  -0.943   0.414  1.00  0.00           H  
HETATM   17  H7  UNL     1       1.719   0.570   1.333  1.00  0.00           H  
HETATM   18  H8  UNL     1      -0.652   0.853   1.450  1.00  0.00           H  
HETATM   19  H9  UNL     1      -0.912  -1.914   0.115  1.00  0.00           H  
HETATM   20  H10 UNL     1      -2.203  -1.040   0.917  1.00  0.00           H  
HETATM   21  H11 UNL     1      -2.665  -0.981  -1.260  1.00  0.00           H  
HETATM   22  H12 UNL     1      -1.112  -0.480  -1.889  1.00  0.00           H  
HETATM   23  H13 UNL     1      -3.248   1.093  -0.476  1.00  0.00           H  
HETATM   24  H14 UNL     1      -1.530   1.750  -0.585  1.00  0.00           H  
HETATM   25  H15 UNL     1      -2.433   1.340  -2.067  1.00  0.00           H  
HETATM   26  H16 UNL     1       0.215  -2.816   1.556  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3   14   15
CONECT    3    4   16   17
CONECT    4    5    8   18
CONECT    5    6   19   20
CONECT    6    7   21   22
CONECT    7   23   24   25
CONECT    8    9    9   10
CONECT   10   26
END
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SMILES for HMDB0001877 (Valproic acid)

CCCC(CCC)C(O)=O
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INCHI for HMDB0001877 (Valproic acid)

InChI=1S/C8H16O2/c1-3-5-7(6-4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
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
Chemical FormulaC8H16O2
Average Molecular Weight144.2114
Monoisotopic Molecular Weight144.115029756
IUPAC Name2-propylpentanoic acid
Traditional Namevalproic acid
CAS Registry Number99-66-1
SMILES
CCCC(CCC)C(O)=O
InChI Identifier
InChI=1S/C8H16O2/c1-3-5-7(6-4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10)
InChI KeyNIJJYAXOARWZEE-UHFFFAOYSA-N
Chemical Taxonomy
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
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological roleIndustrial applicationIndirect biological role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point222 °CNot Available
Water Solubility2 mg/mL at 20 °CNot Available
LogP2.75SANGSTER (1993)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+134.01131661259
DarkChem[M-H]-130.50931661259
AllCCS[M+H]+136.65232859911
AllCCS[M-H]-136.41132859911
DeepCCS[M+H]+137.54530932474
DeepCCS[M-H]-134.65930932474
DeepCCS[M-2H]-171.43930932474
DeepCCS[M+Na]+146.34930932474
AllCCS[M+H]+136.732859911
AllCCS[M+H-H2O]+132.632859911
AllCCS[M+NH4]+140.532859911
AllCCS[M+Na]+141.632859911
AllCCS[M-H]-136.432859911
AllCCS[M+Na-2H]-138.832859911
AllCCS[M+HCOO]-141.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Valproic acidCCCC(CCC)C(O)=O1906.7Standard polar33892256
Valproic acidCCCC(CCC)C(O)=O1083.8Standard non polar33892256
Valproic acidCCCC(CCC)C(O)=O1110.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Valproic acid,1TMS,isomer #1CCCC(CCC)C(=O)O[Si](C)(C)C1148.9Semi standard non polar33892256
Valproic acid,1TBDMS,isomer #1CCCC(CCC)C(=O)O[Si](C)(C)C(C)(C)C1373.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Valproic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-004m-9300000000-e66da5fefd079f7426a42017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Valproic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00b9-9100000000-7bb11c5d52ffa09851f82017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Valproic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Valproic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0fk9-9300000000-1a0314ea63d5a3c9bba12014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Valproic acid Quattro_QQQ 10V, N/A-QTOF (Annotated)splash10-0udi-2900000000-156413e81733a6236c1f2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valproic acid Quattro_QQQ 25V, N/A-QTOF (Annotated)splash10-0f6y-2900000000-a769cafb885b78532cac2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valproic acid Quattro_QQQ 40V, N/A-QTOF (Annotated)splash10-0gbj-7900000000-46a522b9a26459334f5a2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valproic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-0006-0900000000-39a45d4e3201082d9d892012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valproic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-0002-9000000000-4ddd957d8c8dc2b1de032012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valproic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-0006-0900000000-6ba582ae102c4721034d2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valproic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-0006-0900000000-58d9ba88010f1b370c582012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valproic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-0006-3900000000-2d1032d7e8ac58235b4f2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valproic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-0a4j-9000000000-0d39870bc4521a42c50a2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valproic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-00di-9000000000-3c4e21b69b8877d6df3e2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valproic acid LC-ESI-QQ , negative-QTOFsplash10-0006-0900000000-39a45d4e3201082d9d892017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valproic acid LC-ESI-QQ , negative-QTOFsplash10-0002-9000000000-4ddd957d8c8dc2b1de032017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valproic acid LC-ESI-QQ , negative-QTOFsplash10-0006-0900000000-6ba582ae102c4721034d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valproic acid LC-ESI-QQ , negative-QTOFsplash10-0006-0900000000-58d9ba88010f1b370c582017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valproic acid LC-ESI-QQ , negative-QTOFsplash10-0006-3900000000-2d1032d7e8ac58235b4f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valproic acid LC-ESI-QQ , negative-QTOFsplash10-0a4j-9000000000-0d39870bc4521a42c50a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valproic acid LC-ESI-QQ , negative-QTOFsplash10-00di-9000000000-3c4e21b69b8877d6df3e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valproic acid Linear Ion Trap , negative-QTOFsplash10-0006-0900000000-5b83f0d6c36f8249285a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Valproic acid 20V, Negative-QTOFsplash10-0006-0900000000-51a760d50a87d131ad672021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valproic acid 10V, Positive-QTOFsplash10-0002-3900000000-be0e79e3b65dad2e2d082017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valproic acid 20V, Positive-QTOFsplash10-0005-9500000000-37d8981251a94cfd51e32017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valproic acid 40V, Positive-QTOFsplash10-0006-9000000000-b63be8686bbf9a96b2ba2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valproic acid 10V, Negative-QTOFsplash10-0006-3900000000-25f23d80c7431c074a742017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valproic acid 20V, Negative-QTOFsplash10-0005-9500000000-144b6cc9fea5bae4f2692017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Valproic acid 40V, Negative-QTOFsplash10-052e-9100000000-eb5e97329782125f66152017-07-26Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue Locations
  • Brain
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified208.0 (3.5-416.0) uMAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00313
Phenol Explorer Compound IDNot Available
FooDB IDFDB022722
KNApSAcK IDNot Available
Chemspider ID3009
KEGG Compound IDC07185
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkValproic_Acid
METLIN ID2986
PubChem Compound3121
PDB IDNot Available
ChEBI ID39867
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Nemeroff CB: The role of GABA in the pathophysiology and treatment of anxiety disorders. Psychopharmacol Bull. 2003;37(4):133-46. [PubMed:15131523 ]
  2. Bell EC, Willson MC, Wilman AH, Dave S, Silverstone PH: Differential effects of chronic lithium and valproate on brain activation in healthy volunteers. Hum Psychopharmacol. 2005 Aug;20(6):415-24. [PubMed:16106488 ]
  3. Sztajnkrycer MD: Valproic acid toxicity: overview and management. J Toxicol Clin Toxicol. 2002;40(6):789-801. [PubMed:12475192 ]
  4. Seyfert S, Bernarding J, Braun J: Volume-selective 1H MR spectroscopy for in vivo detection of valproate in patients with epilepsy. Neuroradiology. 2003 May;45(5):295-9. Epub 2003 Mar 27. [PubMed:12669157 ]
  5. Eyal S, Lamb JG, Smith-Yockman M, Yagen B, Fibach E, Altschuler Y, White HS, Bialer M: The antiepileptic and anticancer agent, valproic acid, induces P-glycoprotein in human tumour cell lines and in rat liver. Br J Pharmacol. 2006 Oct;149(3):250-60. Epub 2006 Aug 7. [PubMed:16894351 ]
  6. Loscher W: Basic pharmacology of valproate: a review after 35 years of clinical use for the treatment of epilepsy. CNS Drugs. 2002;16(10):669-94. [PubMed:12269861 ]
  7. Huang YL, Hong HS, Wang ZW, Kuo TT: Fatal sodium valproate-induced hypersensitivity syndrome with lichenoid dermatitis and fulminant hepatitis. J Am Acad Dermatol. 2003 Aug;49(2):316-9. [PubMed:12894087 ]
  8. Anderson GD, Temkin NR, Chandler WL, Winn HR: Effect of valproate on hemostatic function in patients with traumatic brain injury. Epilepsy Res. 2003 Dec;57(2-3):111-9. [PubMed:15013052 ]
  9. Ho PC, Abbott FS, Zanger UM, Chang TK: Influence of CYP2C9 genotypes on the formation of a hepatotoxic metabolite of valproic acid in human liver microsomes. Pharmacogenomics J. 2003;3(6):335-42. [PubMed:14597963 ]
  10. Gerstner T, Bell N, Konig S: Oral valproic acid for epilepsy--long-term experience in therapy and side effects. Expert Opin Pharmacother. 2008 Feb;9(2):285-92. doi: 10.1517/14656566.9.2.285 . [PubMed:18201150 ]
  11. Russell S: Carnitine as an antidote for acute valproate toxicity in children. Curr Opin Pediatr. 2007 Apr;19(2):206-10. [PubMed:17496767 ]

Only showing the first 10 proteins. There are 25 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details
1. Cytochrome P450 3A4
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
Enzyme Details
2. Cytochrome P450 2C9
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
Enzyme Details
3. Cytochrome P450 2C19
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
Enzyme Details
4. Cytochrome P450 2E1
General function:
Involved in monooxygenase activity
Specific function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular weight:
56848.42
Enzyme Details
5. Cytochrome P450 3A43
General function:
Involved in monooxygenase activity
Specific function:
Exhibits low testosterone 6-beta-hydroxylase activity.
Gene Name:
CYP3A43
Uniprot ID:
Q9HB55
Molecular weight:
57756.285
Enzyme Details
6. Cytochrome P450 1B1
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Participates in the metabolism of an as-yet-unknown biologically active molecule that is a participant in eye development.
Gene Name:
CYP1B1
Uniprot ID:
Q16678
Molecular weight:
60845.33
Enzyme Details
7. Cytochrome P450 2C18
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP2C18
Uniprot ID:
P33260
Molecular weight:
55710.075
Enzyme Details
8. Cytochrome P450 2F1
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
May be involved in the metabolism of various pneumotoxicants including naphthalene. Is able to dealkylate ethoxycoumarin, propoxycoumarin, and pentoxyresorufin but possesses no activity toward ethoxyresorufin and only trace dearylation activity toward benzyloxyresorufin. Bioactivates 3-methylindole (3MI) by dehydrogenation to the putative electrophile 3-methylene-indolenine.
Gene Name:
CYP2F1
Uniprot ID:
P24903
Molecular weight:
55500.64
Enzyme Details
9. Cytochrome P450 4X1
General function:
Involved in monooxygenase activity
Specific function:
Not Available
Gene Name:
CYP4X1
Uniprot ID:
Q8N118
Molecular weight:
58874.62
Enzyme Details
10. Cytochrome P450 2B6
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular weight:
56277.81

Only showing the first 10 proteins. There are 25 proteins in total.

Show all enzymes and transporters