Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-17 00:56:39 UTC

Update Date

2023-02-21 17:29:55 UTC

HMDB ID

HMDB0060365

Secondary Accession Numbers

HMDB60365

Metabolite Identification

Common Name

2,5-Dioxopentanoate

Description

2,5-Dioxopentanoate 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. 2,5-Dioxopentanoate is an extremely weak basic (essentially neutral) compound (based on its pKa). 2,5-Dioxopentanoate exists in all living organisms, ranging from bacteria to humans. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.

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-Oxoglutarate semialdehyde	ChEBI
2-Oxoglutaric acid semialdehyde	Generator
2,5-Dioxopentanoic acid	Generator
2,5-Dioxopentanoate	ChEBI

Chemical Formula

C₅H₆O₄

Average Molecular Weight

130.0987

Monoisotopic Molecular Weight

130.02660868

IUPAC Name

2,5-dioxopentanoic acid

Traditional Name

2-oxoglutarate semialdehyde

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

VHKNBDIQDAXGBL-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

Short-chain keto acid
Alpha-keto acid
Alpha-hydroxy ketone
Alpha-hydrogen aldehyde
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:17415 )

Ontology

Not Available

Not Available

Not Available

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	53.6 g/L	ALOGPS
logP	-0.02	ALOGPS
logP	-0.27	ChemAxon
logS	-0.38	ALOGPS
pKa (Strongest Acidic)	2.88	ChemAxon
pKa (Strongest Basic)	-7	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	27.96 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]+	127.695	31661259
DarkChem	[M-H]-	123.821	31661259
DeepCCS	[M+H]+	128.515	30932474
DeepCCS	[M-H]-	126.326	30932474
DeepCCS	[M-2H]-	162.284	30932474
DeepCCS	[M+Na]+	137.094	30932474
AllCCS	[M+H]+	130.2	32859911
AllCCS	[M+H-H2O]+	126.0	32859911
AllCCS	[M+NH4]+	134.0	32859911
AllCCS	[M+Na]+	135.1	32859911
AllCCS	[M-H]-	124.8	32859911
AllCCS	[M+Na-2H]-	127.4	32859911
AllCCS	[M+HCOO]-	130.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,5-Dioxopentanoate	OC(=O)C(=O)CCC=O	2153.9	Standard polar	33892256
2,5-Dioxopentanoate	OC(=O)C(=O)CCC=O	945.5	Standard non polar	33892256
2,5-Dioxopentanoate	OC(=O)C(=O)CCC=O	1121.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,5-Dioxopentanoate,1TMS,isomer #1	C[Si](C)(C)OC(=O)C(=O)CCC=O	1287.9	Semi standard non polar	33892256
2,5-Dioxopentanoate,1TMS,isomer #2	C[Si](C)(C)OC(=CCC=O)C(=O)O	1403.6	Semi standard non polar	33892256
2,5-Dioxopentanoate,1TMS,isomer #3	C[Si](C)(C)OC=CCC(=O)C(=O)O	1375.0	Semi standard non polar	33892256
2,5-Dioxopentanoate,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(=CCC=O)O[Si](C)(C)C	1429.6	Semi standard non polar	33892256
2,5-Dioxopentanoate,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(=CCC=O)O[Si](C)(C)C	1371.6	Standard non polar	33892256
2,5-Dioxopentanoate,2TMS,isomer #1	C[Si](C)(C)OC(=O)C(=CCC=O)O[Si](C)(C)C	1508.7	Standard polar	33892256
2,5-Dioxopentanoate,2TMS,isomer #2	C[Si](C)(C)OC=CCC(=O)C(=O)O[Si](C)(C)C	1461.9	Semi standard non polar	33892256
2,5-Dioxopentanoate,2TMS,isomer #2	C[Si](C)(C)OC=CCC(=O)C(=O)O[Si](C)(C)C	1401.1	Standard non polar	33892256
2,5-Dioxopentanoate,2TMS,isomer #2	C[Si](C)(C)OC=CCC(=O)C(=O)O[Si](C)(C)C	1567.4	Standard polar	33892256
2,5-Dioxopentanoate,2TMS,isomer #3	C[Si](C)(C)OC=CC=C(O[Si](C)(C)C)C(=O)O	1576.0	Semi standard non polar	33892256
2,5-Dioxopentanoate,2TMS,isomer #3	C[Si](C)(C)OC=CC=C(O[Si](C)(C)C)C(=O)O	1496.5	Standard non polar	33892256
2,5-Dioxopentanoate,2TMS,isomer #3	C[Si](C)(C)OC=CC=C(O[Si](C)(C)C)C(=O)O	1750.3	Standard polar	33892256
2,5-Dioxopentanoate,3TMS,isomer #1	C[Si](C)(C)OC=CC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1622.4	Semi standard non polar	33892256
2,5-Dioxopentanoate,3TMS,isomer #1	C[Si](C)(C)OC=CC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1521.7	Standard non polar	33892256
2,5-Dioxopentanoate,3TMS,isomer #1	C[Si](C)(C)OC=CC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1583.9	Standard polar	33892256
2,5-Dioxopentanoate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=O)CCC=O	1550.8	Semi standard non polar	33892256
2,5-Dioxopentanoate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=CCC=O)C(=O)O	1646.4	Semi standard non polar	33892256
2,5-Dioxopentanoate,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC=CCC(=O)C(=O)O	1631.4	Semi standard non polar	33892256
2,5-Dioxopentanoate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=CCC=O)O[Si](C)(C)C(C)(C)C	1883.6	Semi standard non polar	33892256
2,5-Dioxopentanoate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=CCC=O)O[Si](C)(C)C(C)(C)C	1789.0	Standard non polar	33892256
2,5-Dioxopentanoate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(=CCC=O)O[Si](C)(C)C(C)(C)C	1796.6	Standard polar	33892256
2,5-Dioxopentanoate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC=CCC(=O)C(=O)O[Si](C)(C)C(C)(C)C	1900.3	Semi standard non polar	33892256
2,5-Dioxopentanoate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC=CCC(=O)C(=O)O[Si](C)(C)C(C)(C)C	1846.6	Standard non polar	33892256
2,5-Dioxopentanoate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC=CCC(=O)C(=O)O[Si](C)(C)C(C)(C)C	1842.3	Standard polar	33892256
2,5-Dioxopentanoate,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC=CC=C(O[Si](C)(C)C(C)(C)C)C(=O)O	2034.9	Semi standard non polar	33892256
2,5-Dioxopentanoate,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC=CC=C(O[Si](C)(C)C(C)(C)C)C(=O)O	1926.1	Standard non polar	33892256
2,5-Dioxopentanoate,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC=CC=C(O[Si](C)(C)C(C)(C)C)C(=O)O	1973.1	Standard polar	33892256
2,5-Dioxopentanoate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=CC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2234.0	Semi standard non polar	33892256
2,5-Dioxopentanoate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=CC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2103.9	Standard non polar	33892256
2,5-Dioxopentanoate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=CC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1936.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-Dioxopentanoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-052u-9000000000-377953d8c75ca6f8b4f6	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-Dioxopentanoate GC-MS (1 TMS) - 70eV, Positive	splash10-0079-9200000000-11aa6a7e16f7cd819696	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-Dioxopentanoate 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 - 2,5-Dioxopentanoate 10V, Positive-QTOF	splash10-03e9-5900000000-b779cddec9f446feb30b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dioxopentanoate 20V, Positive-QTOF	splash10-07bv-9200000000-9df87f0c938c9f743049	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dioxopentanoate 40V, Positive-QTOF	splash10-0a4u-9000000000-03f1c95daea1111adde8	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dioxopentanoate 10V, Negative-QTOF	splash10-004i-3900000000-e272bd80213642423407	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dioxopentanoate 20V, Negative-QTOF	splash10-01s9-9500000000-b35a75d7fba0b28d73e4	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dioxopentanoate 40V, Negative-QTOF	splash10-000x-9000000000-1c3288e1517226f72749	2017-10-06	Wishart Lab	View Spectrum

NMR Spectra

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

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

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C00433

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

523

PDB ID

Not Available

ChEBI ID

17415

Food Biomarker Ontology

Not Available

VMH ID

25DOP

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

Enzyme Details

1. Aldehyde dehydrogenase, mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: Not Available
Gene Name:: ALDH2
Uniprot ID:: P05091
Molecular weight:: 56380.93

Reactions

2,5-Dioxopentanoate + NADP + Water → Oxoglutaric acid + NADPH + Hydrogen Ion	details

Enzyme Details

2. Fatty aldehyde dehydrogenase

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidation of long-chain aliphatic aldehydes to fatty acids. Active on a variety of saturated and unsaturated aliphatic aldehydes between 6 and 24 carbons in length. Responsible for conversion of the sphingosine 1-phosphate (S1P) degradation product hexadecenal to hexadecenoic acid.
Gene Name:: ALDH3A2
Uniprot ID:: P51648
Molecular weight:: 54847.36

Reactions

2,5-Dioxopentanoate + NADP + Water → Oxoglutaric acid + NADPH + Hydrogen Ion	details

Enzyme Details

3. Aldehyde dehydrogenase X, mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation.
Gene Name:: ALDH1B1
Uniprot ID:: P30837
Molecular weight:: 57248.96

Reactions

2,5-Dioxopentanoate + NADP + Water → Oxoglutaric acid + NADPH + Hydrogen Ion	details

Showing metabocard for 2,5-Dioxopentanoate (HMDB0060365)

MOL for HMDB0060365 (2,5-Dioxopentanoate)

3D MOL for HMDB0060365 (2,5-Dioxopentanoate)

3D SDF for HMDB0060365 (2,5-Dioxopentanoate)

3D-SDF for HMDB0060365 (2,5-Dioxopentanoate)

PDB for HMDB0060365 (2,5-Dioxopentanoate)

3D PDB for HMDB0060365 (2,5-Dioxopentanoate)

SMILES for HMDB0060365 (2,5-Dioxopentanoate)

INCHI for HMDB0060365 (2,5-Dioxopentanoate)

Structure for HMDB0060365 (2,5-Dioxopentanoate)

3D Structure for HMDB0060365 (2,5-Dioxopentanoate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions

Reactions