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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-18 18:55:05 UTC

Update Date

2023-02-21 17:30:11 UTC

HMDB ID

HMDB0060685

Secondary Accession Numbers

HMDB60685

Metabolite Identification

Common Name

3-Oxovalproic acid

Description

3-Oxovalproic acid is a metabolite of valproic acid. Valproic acid (VPA) is a chemical compound and an acid that has found clinical use as an anticonvulsant and mood-stabilizing drug, primarily in the treatment of epilepsy, bipolar disorder, and, less commonly, major depression. It is also used to treat migraine headaches and schizophrenia. VPA is a liquid at room temperature, but it can be reacted with a base such as sodium hydroxide to form the salt sodium valproate, which is a solid. (Wikipedia)

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-N-Propyl-3-oxopentanoic acid	Kegg
3-Keto-vpa	Kegg
2-N-Propyl-3-oxopentanoate	Generator
3-Oxovalproate	Generator
3-oxo-VPA	HMDB

Chemical Formula

C₈H₁₄O₃

Average Molecular Weight

158.195

Monoisotopic Molecular Weight

158.094294314

IUPAC Name

3-oxo-2-propylpentanoic acid

Traditional Name

3-oxo-vpa

CAS Registry Number

Not Available

SMILES

CCCC(C(O)=O)C(=O)CC

InChI Identifier

InChI=1S/C8H14O3/c1-3-5-6(8(10)11)7(9)4-2/h6H,3-5H2,1-2H3,(H,10,11)

InChI Key

PPYHXKUZTSZTQU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Short-chain keto acids and derivatives

Direct Parent

Short-chain keto acids and derivatives

Alternative Parents

Substituents

Beta-keto acid
Branched fatty acid
Methyl-branched fatty acid
Short-chain keto acid
Beta-hydroxy ketone
Fatty acyl
1,3-dicarbonyl compound
Ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

oxo carboxylic acid (CHEBI:80638 )
Branched fatty acids (C16652 )

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	11.3 g/L	ALOGPS
logP	1.53	ALOGPS
logP	2.13	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	4.53	ChemAxon
pKa (Strongest Basic)	-7.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	40.94 m³·mol⁻¹	ChemAxon
Polarizability	16.97 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	136.503	31661259
DarkChem	[M-H]-	133.025	31661259
DeepCCS	[M+H]+	135.672	30932474
DeepCCS	[M-H]-	131.843	30932474
DeepCCS	[M-2H]-	169.445	30932474
DeepCCS	[M+Na]+	144.845	30932474
AllCCS	[M+H]+	138.4	32859911
AllCCS	[M+H-H2O]+	134.4	32859911
AllCCS	[M+NH4]+	142.2	32859911
AllCCS	[M+Na]+	143.3	32859911
AllCCS	[M-H]-	136.3	32859911
AllCCS	[M+Na-2H]-	138.2	32859911
AllCCS	[M+HCOO]-	140.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.75 minutes	32390414
Predicted by Siyang on May 30, 2022	11.7975 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.96 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1754.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	357.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	132.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	219.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	141.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	471.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	507.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	74.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	943.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	375.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1177.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	274.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	358.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	335.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	287.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	56.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Oxovalproic acid	CCCC(C(O)=O)C(=O)CC	2290.4	Standard polar	33892256
3-Oxovalproic acid	CCCC(C(O)=O)C(=O)CC	1163.7	Standard non polar	33892256
3-Oxovalproic acid	CCCC(C(O)=O)C(=O)CC	1243.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Oxovalproic acid,1TMS,isomer #1	CCCC(C(=O)CC)C(=O)O[Si](C)(C)C	1254.9	Semi standard non polar	33892256
3-Oxovalproic acid,1TMS,isomer #2	CCCC(C(=O)O)=C(CC)O[Si](C)(C)C	1390.4	Semi standard non polar	33892256
3-Oxovalproic acid,1TMS,isomer #3	CC=C(O[Si](C)(C)C)C(CCC)C(=O)O	1345.3	Semi standard non polar	33892256
3-Oxovalproic acid,2TMS,isomer #1	CCCC(C(=O)O[Si](C)(C)C)=C(CC)O[Si](C)(C)C	1446.7	Semi standard non polar	33892256
3-Oxovalproic acid,2TMS,isomer #1	CCCC(C(=O)O[Si](C)(C)C)=C(CC)O[Si](C)(C)C	1450.6	Standard non polar	33892256
3-Oxovalproic acid,2TMS,isomer #1	CCCC(C(=O)O[Si](C)(C)C)=C(CC)O[Si](C)(C)C	1397.0	Standard polar	33892256
3-Oxovalproic acid,2TMS,isomer #2	CC=C(O[Si](C)(C)C)C(CCC)C(=O)O[Si](C)(C)C	1410.9	Semi standard non polar	33892256
3-Oxovalproic acid,2TMS,isomer #2	CC=C(O[Si](C)(C)C)C(CCC)C(=O)O[Si](C)(C)C	1390.5	Standard non polar	33892256
3-Oxovalproic acid,2TMS,isomer #2	CC=C(O[Si](C)(C)C)C(CCC)C(=O)O[Si](C)(C)C	1453.0	Standard polar	33892256
3-Oxovalproic acid,1TBDMS,isomer #1	CCCC(C(=O)CC)C(=O)O[Si](C)(C)C(C)(C)C	1476.7	Semi standard non polar	33892256
3-Oxovalproic acid,1TBDMS,isomer #2	CCCC(C(=O)O)=C(CC)O[Si](C)(C)C(C)(C)C	1626.8	Semi standard non polar	33892256
3-Oxovalproic acid,1TBDMS,isomer #3	CC=C(O[Si](C)(C)C(C)(C)C)C(CCC)C(=O)O	1569.1	Semi standard non polar	33892256
3-Oxovalproic acid,2TBDMS,isomer #1	CCCC(C(=O)O[Si](C)(C)C(C)(C)C)=C(CC)O[Si](C)(C)C(C)(C)C	1882.7	Semi standard non polar	33892256
3-Oxovalproic acid,2TBDMS,isomer #1	CCCC(C(=O)O[Si](C)(C)C(C)(C)C)=C(CC)O[Si](C)(C)C(C)(C)C	1840.6	Standard non polar	33892256
3-Oxovalproic acid,2TBDMS,isomer #1	CCCC(C(=O)O[Si](C)(C)C(C)(C)C)=C(CC)O[Si](C)(C)C(C)(C)C	1759.1	Standard polar	33892256
3-Oxovalproic acid,2TBDMS,isomer #2	CC=C(O[Si](C)(C)C(C)(C)C)C(CCC)C(=O)O[Si](C)(C)C(C)(C)C	1857.0	Semi standard non polar	33892256
3-Oxovalproic acid,2TBDMS,isomer #2	CC=C(O[Si](C)(C)C(C)(C)C)C(CCC)C(=O)O[Si](C)(C)C(C)(C)C	1818.7	Standard non polar	33892256
3-Oxovalproic acid,2TBDMS,isomer #2	CC=C(O[Si](C)(C)C(C)(C)C)C(CCC)C(=O)O[Si](C)(C)C(C)(C)C	1788.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Oxovalproic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6r-9300000000-a872e855ea302f48a027	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Oxovalproic acid GC-MS (1 TMS) - 70eV, Positive	splash10-0a4i-9110000000-05b7541bcf5d591a025f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Oxovalproic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Oxovalproic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxovalproic acid 10V, Positive-QTOF	splash10-0a4l-0900000000-8ac6fc41a00c23c58f36	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxovalproic acid 20V, Positive-QTOF	splash10-052f-9700000000-2049911b9994b308b7cb	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxovalproic acid 40V, Positive-QTOF	splash10-0a4i-9000000000-fcdaf98869410b8bf53b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxovalproic acid 10V, Negative-QTOF	splash10-0bt9-0900000000-afaa391c0668adf04ead	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxovalproic acid 20V, Negative-QTOF	splash10-0r00-9800000000-69c100806045528c7041	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxovalproic acid 40V, Negative-QTOF	splash10-0a4i-9000000000-a7ed3e77ae2186de2d78	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxovalproic acid 10V, Positive-QTOF	splash10-0a4i-9200000000-30a7c0f75cf45c8be103	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxovalproic acid 20V, Positive-QTOF	splash10-0a4i-9000000000-5012dccc5b71e9303275	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxovalproic acid 40V, Positive-QTOF	splash10-0a4i-9000000000-e90f11c79387829a2ca7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxovalproic acid 10V, Negative-QTOF	splash10-0a4i-9200000000-9bbdb4b643648865d8d7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxovalproic acid 20V, Negative-QTOF	splash10-053r-9200000000-242f931b403ffa5321af	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxovalproic acid 40V, Negative-QTOF	splash10-0a5c-9000000000-f350934c8a3355a86117	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Valproic Acid Metabolism Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C16652

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

173719

PDB ID

Not Available

ChEBI ID

80638

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 3-Oxovalproic acid (HMDB0060685)

MOL for HMDB0060685 (3-Oxovalproic acid)

3D MOL for HMDB0060685 (3-Oxovalproic acid)

3D SDF for HMDB0060685 (3-Oxovalproic acid)

3D-SDF for HMDB0060685 (3-Oxovalproic acid)

PDB for HMDB0060685 (3-Oxovalproic acid)

3D PDB for HMDB0060685 (3-Oxovalproic acid)

SMILES for HMDB0060685 (3-Oxovalproic acid)

INCHI for HMDB0060685 (3-Oxovalproic acid)

Structure for HMDB0060685 (3-Oxovalproic acid)

3D Structure for HMDB0060685 (3-Oxovalproic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra