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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-18 18:49:54 UTC

Update Date

2023-02-21 17:30:10 UTC

HMDB ID

HMDB0060683

Secondary Accession Numbers

HMDB60683

Metabolite Identification

Common Name

2-n-Propyl-4-oxopentanoic acid

Description

2-n-Propyl-4-oxopentanoic 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
4-Oxovalproic acid	Kegg
4-Keto-vpa	Kegg
4-Oxovalproate	Generator
2-N-Propyl-4-oxopentanoate	Generator

Chemical Formula

C₈H₁₄O₃

Average Molecular Weight

158.195

Monoisotopic Molecular Weight

158.094294314

IUPAC Name

4-oxo-2-propylpentanoic acid

Traditional Name

4-Keto-VPA

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C8H14O3/c1-3-4-7(8(10)11)5-6(2)9/h7H,3-5H2,1-2H3,(H,10,11)

InChI Key

HJRMYVTYHORJKC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Gamma-keto acids and derivatives

Direct Parent

Gamma-keto acids and derivatives

Alternative Parents

Substituents

Gamma-keto acid
Methyl-branched fatty acid
Short-chain keto acid
Branched fatty acid
Fatty acyl
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

oxo carboxylic acid (CHEBI:80641 )
Branched fatty acids (C16655 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060683)

Organ

Liver (HMDB: HMDB0060683)
Kidney (HMDB: HMDB0060683)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060683)

Source

Endogenous

Endogenous (HMDB: HMDB0060683)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Valproic Acid Metabolism Pathway (PathBank: SMP0000635)

Role

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	8.95 g/L	ALOGPS
logP	1.14	ALOGPS
logP	1.36	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	4.63	ChemAxon
pKa (Strongest Basic)	-7.3	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	40.86 m³·mol⁻¹	ChemAxon
Polarizability	16.91 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]+	137.079	31661259
DarkChem	[M-H]-	133.33	31661259
DeepCCS	[M+H]+	133.972	30932474
DeepCCS	[M-H]-	130.592	30932474
DeepCCS	[M-2H]-	167.649	30932474
DeepCCS	[M+Na]+	142.757	30932474
AllCCS	[M+H]+	137.9	32859911
AllCCS	[M+H-H2O]+	133.9	32859911
AllCCS	[M+NH4]+	141.6	32859911
AllCCS	[M+Na]+	142.7	32859911
AllCCS	[M-H]-	136.0	32859911
AllCCS	[M+Na-2H]-	137.9	32859911
AllCCS	[M+HCOO]-	140.2	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.	4.03 minutes	32390414
Predicted by Siyang on May 30, 2022	11.0308 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.02 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1651.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	335.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	129.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	200.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	121.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	419.2 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	444.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	69.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	879.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	352.5 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	1085.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	268.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	343.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	338.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	259.1 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	75.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-n-Propyl-4-oxopentanoic acid	CCCC(CC(C)=O)C(O)=O	2489.7	Standard polar	33892256
2-n-Propyl-4-oxopentanoic acid	CCCC(CC(C)=O)C(O)=O	1133.1	Standard non polar	33892256
2-n-Propyl-4-oxopentanoic acid	CCCC(CC(C)=O)C(O)=O	1266.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-n-Propyl-4-oxopentanoic acid,1TMS,isomer #1	CCCC(CC(C)=O)C(=O)O[Si](C)(C)C	1273.6	Semi standard non polar	33892256
2-n-Propyl-4-oxopentanoic acid,1TMS,isomer #2	CCCC(C=C(C)O[Si](C)(C)C)C(=O)O	1397.9	Semi standard non polar	33892256
2-n-Propyl-4-oxopentanoic acid,1TMS,isomer #3	C=C(CC(CCC)C(=O)O)O[Si](C)(C)C	1359.8	Semi standard non polar	33892256
2-n-Propyl-4-oxopentanoic acid,2TMS,isomer #1	CCCC(C=C(C)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1450.2	Semi standard non polar	33892256
2-n-Propyl-4-oxopentanoic acid,2TMS,isomer #1	CCCC(C=C(C)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1406.9	Standard non polar	33892256
2-n-Propyl-4-oxopentanoic acid,2TMS,isomer #1	CCCC(C=C(C)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1459.3	Standard polar	33892256
2-n-Propyl-4-oxopentanoic acid,2TMS,isomer #2	C=C(CC(CCC)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	1418.9	Semi standard non polar	33892256
2-n-Propyl-4-oxopentanoic acid,2TMS,isomer #2	C=C(CC(CCC)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	1443.0	Standard non polar	33892256
2-n-Propyl-4-oxopentanoic acid,2TMS,isomer #2	C=C(CC(CCC)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	1471.6	Standard polar	33892256
2-n-Propyl-4-oxopentanoic acid,1TBDMS,isomer #1	CCCC(CC(C)=O)C(=O)O[Si](C)(C)C(C)(C)C	1504.9	Semi standard non polar	33892256
2-n-Propyl-4-oxopentanoic acid,1TBDMS,isomer #2	CCCC(C=C(C)O[Si](C)(C)C(C)(C)C)C(=O)O	1636.8	Semi standard non polar	33892256
2-n-Propyl-4-oxopentanoic acid,1TBDMS,isomer #3	C=C(CC(CCC)C(=O)O)O[Si](C)(C)C(C)(C)C	1583.8	Semi standard non polar	33892256
2-n-Propyl-4-oxopentanoic acid,2TBDMS,isomer #1	CCCC(C=C(C)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1908.7	Semi standard non polar	33892256
2-n-Propyl-4-oxopentanoic acid,2TBDMS,isomer #1	CCCC(C=C(C)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1853.5	Standard non polar	33892256
2-n-Propyl-4-oxopentanoic acid,2TBDMS,isomer #1	CCCC(C=C(C)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1794.7	Standard polar	33892256
2-n-Propyl-4-oxopentanoic acid,2TBDMS,isomer #2	C=C(CC(CCC)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1873.8	Semi standard non polar	33892256
2-n-Propyl-4-oxopentanoic acid,2TBDMS,isomer #2	C=C(CC(CCC)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1868.2	Standard non polar	33892256
2-n-Propyl-4-oxopentanoic acid,2TBDMS,isomer #2	C=C(CC(CCC)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1811.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-n-Propyl-4-oxopentanoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9200000000-1bf9135c5fdb356b89f6	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-n-Propyl-4-oxopentanoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-0006-9200000000-b4bf3b0be34b2b9cc618	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-n-Propyl-4-oxopentanoic 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 - 2-n-Propyl-4-oxopentanoic acid 10V, Positive-QTOF	splash10-0a4l-1900000000-c9fe0c162cc9d094f5ed	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-n-Propyl-4-oxopentanoic acid 20V, Positive-QTOF	splash10-052f-9800000000-71519be759b69e835e47	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-n-Propyl-4-oxopentanoic acid 40V, Positive-QTOF	splash10-052g-9100000000-328f7640ed8dab5a3f08	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-n-Propyl-4-oxopentanoic acid 10V, Negative-QTOF	splash10-0a4i-0900000000-00228038be56fd38299c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-n-Propyl-4-oxopentanoic acid 20V, Negative-QTOF	splash10-0bt9-5900000000-7d5669fb3edc8d8d764d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-n-Propyl-4-oxopentanoic acid 40V, Negative-QTOF	splash10-0a4i-9100000000-e91fedd0dcff338a338e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-n-Propyl-4-oxopentanoic acid 10V, Positive-QTOF	splash10-02td-9500000000-749bf5c0521fd451f472	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-n-Propyl-4-oxopentanoic acid 20V, Positive-QTOF	splash10-00kg-9100000000-7ed49266f4dd55f8b4b1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-n-Propyl-4-oxopentanoic acid 40V, Positive-QTOF	splash10-052f-9000000000-575e3c8da2510e17a628	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-n-Propyl-4-oxopentanoic acid 10V, Negative-QTOF	splash10-066r-1900000000-9f5207e93205e5504d40	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-n-Propyl-4-oxopentanoic acid 20V, Negative-QTOF	splash10-0006-9300000000-e126a27e783f8fdb0d94	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-n-Propyl-4-oxopentanoic acid 40V, Negative-QTOF	splash10-0a4l-9000000000-7e312b33aef87b5fae1f	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

Not Available

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

C16655

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3731686

PDB ID

Not Available

ChEBI ID

Not Available

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 2-n-Propyl-4-oxopentanoic acid (HMDB0060683)

MOL for HMDB0060683 (2-n-Propyl-4-oxopentanoic acid)

3D MOL for HMDB0060683 (2-n-Propyl-4-oxopentanoic acid)

3D SDF for HMDB0060683 (2-n-Propyl-4-oxopentanoic acid)

3D-SDF for HMDB0060683 (2-n-Propyl-4-oxopentanoic acid)

PDB for HMDB0060683 (2-n-Propyl-4-oxopentanoic acid)

3D PDB for HMDB0060683 (2-n-Propyl-4-oxopentanoic acid)

SMILES for HMDB0060683 (2-n-Propyl-4-oxopentanoic acid)

INCHI for HMDB0060683 (2-n-Propyl-4-oxopentanoic acid)

Structure for HMDB0060683 (2-n-Propyl-4-oxopentanoic acid)

3D Structure for HMDB0060683 (2-n-Propyl-4-oxopentanoic 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