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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:54:44 UTC

Update Date

2023-02-21 17:26:57 UTC

HMDB ID

HMDB0039447

Secondary Accession Numbers

HMDB39447

Metabolite Identification

Common Name

2-Methyl-4-oxopentanedioic acid

Description

2-Methyl-4-oxopentanedioic acid 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. 2-Methyl-4-oxopentanedioic acid has been detected, but not quantified in, fruits. This could make 2-methyl-4-oxopentanedioic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2-Methyl-4-oxopentanedioic 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
2-Methyl-4-oxopentanedioate	Generator
2-Methyl-4-oxo-pentanedioic acid	HMDB
2-Methyl-4-oxoglutaric acid	HMDB

Chemical Formula

C₆H₈O₅

Average Molecular Weight

160.1247

Monoisotopic Molecular Weight

160.037173366

IUPAC Name

2-methyl-4-oxopentanedioic acid

Traditional Name

2-methyl-4-oxopentanedioic acid

CAS Registry Number

55601-64-4

SMILES

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

InChI Identifier

InChI=1S/C6H8O5/c1-3(5(8)9)2-4(7)6(10)11/h3H,2H2,1H3,(H,8,9)(H,10,11)

InChI Key

AVSMSTWODLACGT-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
Branched fatty acid
Short-chain keto acid
Methyl-branched fatty acid
Alpha-keto acid
Dicarboxylic acid or derivatives
Fatty acyl
Alpha-hydroxy ketone
Ketone
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0039447)
Cytoplasm (HMDB: HMDB0039447)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039447)

Source

Exogenous

Food

Food (HMDB: HMDB0039447)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0039447)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0039447)

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	29 g/L	ALOGPS
logP	-0.13	ALOGPS
logP	0.43	ChemAxon
logS	-0.74	ALOGPS
pKa (Strongest Acidic)	2.84	ChemAxon
pKa (Strongest Basic)	-9.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.67 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	33.46 m³·mol⁻¹	ChemAxon
Polarizability	13.89 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]+	136.624	31661259
DarkChem	[M-H]-	132.257	31661259
DeepCCS	[M+H]+	127.385	30932474
DeepCCS	[M-H]-	123.556	30932474
DeepCCS	[M-2H]-	161.053	30932474
DeepCCS	[M+Na]+	136.433	30932474
AllCCS	[M+H]+	135.6	32859911
AllCCS	[M+H-H2O]+	131.7	32859911
AllCCS	[M+NH4]+	139.3	32859911
AllCCS	[M+Na]+	140.4	32859911
AllCCS	[M-H]-	130.0	32859911
AllCCS	[M+Na-2H]-	131.9	32859911
AllCCS	[M+HCOO]-	133.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Methyl-4-oxopentanedioic acid	CC(CC(=O)C(O)=O)C(O)=O	2170.9	Standard polar	33892256
2-Methyl-4-oxopentanedioic acid	CC(CC(=O)C(O)=O)C(O)=O	1194.3	Standard non polar	33892256
2-Methyl-4-oxopentanedioic acid	CC(CC(=O)C(O)=O)C(O)=O	1390.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Methyl-4-oxopentanedioic acid,1TMS,isomer #1	CC(CC(=O)C(=O)O[Si](C)(C)C)C(=O)O	1404.7	Semi standard non polar	33892256
2-Methyl-4-oxopentanedioic acid,1TMS,isomer #2	CC(CC(=O)C(=O)O)C(=O)O[Si](C)(C)C	1441.2	Semi standard non polar	33892256
2-Methyl-4-oxopentanedioic acid,1TMS,isomer #3	CC(C=C(O[Si](C)(C)C)C(=O)O)C(=O)O	1525.8	Semi standard non polar	33892256
2-Methyl-4-oxopentanedioic acid,2TMS,isomer #1	CC(CC(=O)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1540.3	Semi standard non polar	33892256
2-Methyl-4-oxopentanedioic acid,2TMS,isomer #2	CC(C=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O	1560.3	Semi standard non polar	33892256
2-Methyl-4-oxopentanedioic acid,2TMS,isomer #3	CC(C=C(O[Si](C)(C)C)C(=O)O)C(=O)O[Si](C)(C)C	1610.7	Semi standard non polar	33892256
2-Methyl-4-oxopentanedioic acid,3TMS,isomer #1	CC(C=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1621.5	Semi standard non polar	33892256
2-Methyl-4-oxopentanedioic acid,3TMS,isomer #1	CC(C=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1576.3	Standard non polar	33892256
2-Methyl-4-oxopentanedioic acid,1TBDMS,isomer #1	CC(CC(=O)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	1662.6	Semi standard non polar	33892256
2-Methyl-4-oxopentanedioic acid,1TBDMS,isomer #2	CC(CC(=O)C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	1713.7	Semi standard non polar	33892256
2-Methyl-4-oxopentanedioic acid,1TBDMS,isomer #3	CC(C=C(O[Si](C)(C)C(C)(C)C)C(=O)O)C(=O)O	1772.2	Semi standard non polar	33892256
2-Methyl-4-oxopentanedioic acid,2TBDMS,isomer #1	CC(CC(=O)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1996.1	Semi standard non polar	33892256
2-Methyl-4-oxopentanedioic acid,2TBDMS,isomer #2	CC(C=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	2022.3	Semi standard non polar	33892256
2-Methyl-4-oxopentanedioic acid,2TBDMS,isomer #3	CC(C=C(O[Si](C)(C)C(C)(C)C)C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	2072.3	Semi standard non polar	33892256
2-Methyl-4-oxopentanedioic acid,3TBDMS,isomer #1	CC(C=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2246.3	Semi standard non polar	33892256
2-Methyl-4-oxopentanedioic acid,3TBDMS,isomer #1	CC(C=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2145.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methyl-4-oxopentanedioic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9200000000-7d80d7851cb528af10fe	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methyl-4-oxopentanedioic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00y0-9520000000-03429d83d71e1cd992fb	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methyl-4-oxopentanedioic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methyl-4-oxopentanedioic 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-Methyl-4-oxopentanedioic acid 10V, Positive-QTOF	splash10-0296-4900000000-62e469ad0d10805a679e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-4-oxopentanedioic acid 20V, Positive-QTOF	splash10-00kg-9600000000-aecadc734047f90c6ef4	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-4-oxopentanedioic acid 40V, Positive-QTOF	splash10-0006-9000000000-043e2f2fb8c4dd5b2787	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-4-oxopentanedioic acid 10V, Negative-QTOF	splash10-0a4i-1900000000-f9bd9f760324cff077e2	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-4-oxopentanedioic acid 20V, Negative-QTOF	splash10-01b9-8900000000-d6600af2c408c932d778	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-4-oxopentanedioic acid 40V, Negative-QTOF	splash10-00r6-9100000000-6e4f0879f03b8f446871	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-4-oxopentanedioic acid 10V, Negative-QTOF	splash10-066r-1900000000-61fdac584e1e6d67c690	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-4-oxopentanedioic acid 20V, Negative-QTOF	splash10-01ba-9100000000-7225deb1921bad0088e6	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-4-oxopentanedioic acid 40V, Negative-QTOF	splash10-0006-9000000000-5c710116a266dda99533	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-4-oxopentanedioic acid 10V, Positive-QTOF	splash10-014m-9400000000-26ca34f27f99fc9931b7	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-4-oxopentanedioic acid 20V, Positive-QTOF	splash10-00kf-9000000000-3f85864b61e3cc8118ef	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methyl-4-oxopentanedioic acid 40V, Positive-QTOF	splash10-0006-9000000000-d25fdf485458577c8d13	2021-09-25	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

Cytoplasm
Extracellular

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

FDB019046

KNApSAcK ID

Not Available

Chemspider ID

9237826

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11062673

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 2-Methyl-4-oxopentanedioic acid (HMDB0039447)

MOL for HMDB0039447 (2-Methyl-4-oxopentanedioic acid)

3D MOL for HMDB0039447 (2-Methyl-4-oxopentanedioic acid)

3D SDF for HMDB0039447 (2-Methyl-4-oxopentanedioic acid)

3D-SDF for HMDB0039447 (2-Methyl-4-oxopentanedioic acid)

PDB for HMDB0039447 (2-Methyl-4-oxopentanedioic acid)

3D PDB for HMDB0039447 (2-Methyl-4-oxopentanedioic acid)

SMILES for HMDB0039447 (2-Methyl-4-oxopentanedioic acid)

INCHI for HMDB0039447 (2-Methyl-4-oxopentanedioic acid)

Structure for HMDB0039447 (2-Methyl-4-oxopentanedioic acid)

3D Structure for HMDB0039447 (2-Methyl-4-oxopentanedioic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra