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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-11-30 15:51:25 UTC

Update Date

2023-02-21 17:17:57 UTC

HMDB ID

HMDB0013233

Secondary Accession Numbers

HMDB13233

Metabolite Identification

Common Name

Gamma-delta-Dioxovaleric acid

Description

Gamma-delta-Dioxovaleric acid, also known as 4-oxoglutarate semialdehyde or 4,5-dioxopentanoate, 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. Gamma-delta-Dioxovaleric acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Gamma-delta-Dioxovaleric acid.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4,5-Dioxopentanoate	ChEBI
4-Oxoglutarate semialdehyde	ChEBI
4,5-Dioxopentanoic acid	Generator
4-Oxoglutaric acid semialdehyde	Generator
g-delta-Dioxovalerate	Generator
g-delta-Dioxovaleric acid	Generator
gamma-delta-Dioxovalerate	Generator
Γ-δ-dioxovalerate	Generator
Γ-δ-dioxovaleric acid	Generator
4,5-Dioxovaleric acid	MeSH
gamma,delta-Dioxovalerate	MeSH
g-δ-dioxovalerate	Generator, HMDB
g-δ-dioxovaleric acid	Generator, HMDB

Chemical Formula

C₅H₆O₄

Average Molecular Weight

130.0987

Monoisotopic Molecular Weight

130.02660868

IUPAC Name

4,5-dioxopentanoic acid

Traditional Name

4,5-dioxopentanoic acid

CAS Registry Number

Not Available

SMILES

OC(=O)CCC(=O)C=O

InChI Identifier

InChI=1S/C5H6O4/c6-3-4(7)1-2-5(8)9/h3H,1-2H2,(H,8,9)

InChI Key

YHUFRVYVNKGICT-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
Short-chain keto acid
Alpha-ketoaldehyde
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dioxo monocarboxylic acid (CHEBI:17204 )

Ontology

Not Available

Endogenous (HMDB: HMDB0013233)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

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	58.7 g/L	ALOGPS
logP	-0.41	ALOGPS
logP	0.021	ChemAxon
logS	-0.35	ALOGPS
pKa (Strongest Acidic)	3.83	ChemAxon
pKa (Strongest Basic)	-8.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.44 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	27.94 m³·mol⁻¹	ChemAxon
Polarizability	11.22 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]+	126.518	31661259
DarkChem	[M-H]-	122.637	31661259
DeepCCS	[M+H]+	125.866	30932474
DeepCCS	[M-H]-	123.145	30932474
DeepCCS	[M-2H]-	159.831	30932474
DeepCCS	[M+Na]+	134.738	30932474
AllCCS	[M+H]+	129.8	32859911
AllCCS	[M+H-H2O]+	125.7	32859911
AllCCS	[M+NH4]+	133.7	32859911
AllCCS	[M+Na]+	134.8	32859911
AllCCS	[M-H]-	125.1	32859911
AllCCS	[M+Na-2H]-	127.7	32859911
AllCCS	[M+HCOO]-	130.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Gamma-delta-Dioxovaleric acid	OC(=O)CCC(=O)C=O	1928.9	Standard polar	33892256
Gamma-delta-Dioxovaleric acid	OC(=O)CCC(=O)C=O	936.9	Standard non polar	33892256
Gamma-delta-Dioxovaleric acid	OC(=O)CCC(=O)C=O	1106.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Gamma-delta-Dioxovaleric acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CCC(=O)C=O	1326.1	Semi standard non polar	33892256
Gamma-delta-Dioxovaleric acid,1TMS,isomer #2	C[Si](C)(C)OC(C=O)=CCC(=O)O	1400.7	Semi standard non polar	33892256
Gamma-delta-Dioxovaleric acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CC=C(C=O)O[Si](C)(C)C	1514.8	Semi standard non polar	33892256
Gamma-delta-Dioxovaleric acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CC=C(C=O)O[Si](C)(C)C	1413.2	Standard non polar	33892256
Gamma-delta-Dioxovaleric acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CC=C(C=O)O[Si](C)(C)C	1571.6	Standard polar	33892256
Gamma-delta-Dioxovaleric acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC(=O)C=O	1581.9	Semi standard non polar	33892256
Gamma-delta-Dioxovaleric acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(C=O)=CCC(=O)O	1680.6	Semi standard non polar	33892256
Gamma-delta-Dioxovaleric acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC=C(C=O)O[Si](C)(C)C(C)(C)C	1998.1	Semi standard non polar	33892256
Gamma-delta-Dioxovaleric acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC=C(C=O)O[Si](C)(C)C(C)(C)C	1845.7	Standard non polar	33892256
Gamma-delta-Dioxovaleric acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC=C(C=O)O[Si](C)(C)C(C)(C)C	1842.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Gamma-delta-Dioxovaleric acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9100000000-fc2cf6a68672c069c40d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gamma-delta-Dioxovaleric acid GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-7900000000-dcbbfde08d90d09b23d1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gamma-delta-Dioxovaleric acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gamma-delta-Dioxovaleric 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 - Gamma-delta-Dioxovaleric acid 10V, Positive-QTOF	splash10-03di-4900000000-080c9829311e7ab02b5d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gamma-delta-Dioxovaleric acid 20V, Positive-QTOF	splash10-03y1-9300000000-792d9d0b3040e058f709	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gamma-delta-Dioxovaleric acid 40V, Positive-QTOF	splash10-0a4i-9000000000-fdbc51824a0926161972	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gamma-delta-Dioxovaleric acid 10V, Negative-QTOF	splash10-004i-1900000000-7c344a5cd45bc790e0a5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gamma-delta-Dioxovaleric acid 20V, Negative-QTOF	splash10-0r2a-9800000000-66c52bb7dba441550970	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gamma-delta-Dioxovaleric acid 40V, Negative-QTOF	splash10-0a4i-9000000000-6ebdf3e036a8949b9262	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gamma-delta-Dioxovaleric acid 10V, Negative-QTOF	splash10-01ri-7900000000-51ce480395e9691cfa02	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gamma-delta-Dioxovaleric acid 20V, Negative-QTOF	splash10-0a4i-9000000000-64247810f585e9632354	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gamma-delta-Dioxovaleric acid 40V, Negative-QTOF	splash10-0a4l-9000000000-f48888a7d79528a136f3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gamma-delta-Dioxovaleric acid 10V, Positive-QTOF	splash10-06rl-9300000000-a9ac543d860aebfc6344	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gamma-delta-Dioxovaleric acid 20V, Positive-QTOF	splash10-0a4u-9000000000-6fa1912ca17ad42fd1c5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gamma-delta-Dioxovaleric acid 40V, Positive-QTOF	splash10-052f-9000000000-f952b2bfabcaede48037	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB029349

KNApSAcK ID

Not Available

Chemspider ID

106654

KEGG Compound ID

C02800

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

119412

PDB ID

HKV

ChEBI ID

17204

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 Gamma-delta-Dioxovaleric acid (HMDB0013233)

MOL for HMDB0013233 (Gamma-delta-Dioxovaleric acid)

3D MOL for HMDB0013233 (Gamma-delta-Dioxovaleric acid)

3D SDF for HMDB0013233 (Gamma-delta-Dioxovaleric acid)

3D-SDF for HMDB0013233 (Gamma-delta-Dioxovaleric acid)

PDB for HMDB0013233 (Gamma-delta-Dioxovaleric acid)

3D PDB for HMDB0013233 (Gamma-delta-Dioxovaleric acid)

SMILES for HMDB0013233 (Gamma-delta-Dioxovaleric acid)

INCHI for HMDB0013233 (Gamma-delta-Dioxovaleric acid)

Structure for HMDB0013233 (Gamma-delta-Dioxovaleric acid)

3D Structure for HMDB0013233 (Gamma-delta-Dioxovaleric acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra