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

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2013-02-26 19:00:51 UTC

Update Date

2023-02-21 17:29:17 UTC

HMDB ID

HMDB0059731

Secondary Accession Numbers

HMDB59731

Metabolite Identification

Common Name

2,3-Methyleneglutaric acid

Description

2,3-Methyleneglutaric acid belongs to the class of organic compounds known as branched fatty acids. These are fatty acids containing a branched chain. 2,3-Methyleneglutaric acid is a weakly acidic compound (based on its pKa).

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,3-Methyleneglutarate	Generator
2,3-Dimethylidenepentanedioate	Generator

Chemical Formula

C₇H₈O₄

Average Molecular Weight

156.136

Monoisotopic Molecular Weight

156.042258744

IUPAC Name

2,3-dimethylidenepentanedioic acid

Traditional Name

2,3-dimethylidenepentanedioic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C7H8O4/c1-4(3-6(8)9)5(2)7(10)11/h1-3H2,(H,8,9)(H,10,11)

InChI Key

YNNMOGWGBFSMGB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as branched fatty acids. These are fatty acids containing a branched chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Branched fatty acids

Alternative Parents

Substituents

Branched fatty acid
Unsaturated fatty acid
Dicarboxylic 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

Not Available

Ontology

Not Available

Urine (PMID: 2338430)

Process

Not Available

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	6.8 g/L	ALOGPS
logP	0.77	ALOGPS
logP	0.44	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	3.85	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	36.84 m³·mol⁻¹	ChemAxon
Polarizability	14.02 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]+	134.242	31661259
DarkChem	[M-H]-	127.712	31661259
DeepCCS	[M+H]+	130.546	30932474
DeepCCS	[M-H]-	126.717	30932474
DeepCCS	[M-2H]-	164.133	30932474
DeepCCS	[M+Na]+	139.579	30932474
AllCCS	[M+H]+	135.6	32859911
AllCCS	[M+H-H2O]+	131.6	32859911
AllCCS	[M+NH4]+	139.3	32859911
AllCCS	[M+Na]+	140.3	32859911
AllCCS	[M-H]-	129.1	32859911
AllCCS	[M+Na-2H]-	130.9	32859911
AllCCS	[M+HCOO]-	133.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,3-Methyleneglutaric acid	OC(=O)CC(=C)C(=C)C(O)=O	2247.7	Standard polar	33892256
2,3-Methyleneglutaric acid	OC(=O)CC(=C)C(=C)C(O)=O	1195.5	Standard non polar	33892256
2,3-Methyleneglutaric acid	OC(=O)CC(=C)C(=C)C(O)=O	1401.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,3-Methyleneglutaric acid,1TMS,isomer #1	C=C(CC(=O)O[Si](C)(C)C)C(=C)C(=O)O	1424.5	Semi standard non polar	33892256
2,3-Methyleneglutaric acid,1TMS,isomer #2	C=C(CC(=O)O)C(=C)C(=O)O[Si](C)(C)C	1399.8	Semi standard non polar	33892256
2,3-Methyleneglutaric acid,2TMS,isomer #1	C=C(CC(=O)O[Si](C)(C)C)C(=C)C(=O)O[Si](C)(C)C	1486.6	Semi standard non polar	33892256
2,3-Methyleneglutaric acid,1TBDMS,isomer #1	C=C(CC(=O)O[Si](C)(C)C(C)(C)C)C(=C)C(=O)O	1654.5	Semi standard non polar	33892256
2,3-Methyleneglutaric acid,1TBDMS,isomer #2	C=C(CC(=O)O)C(=C)C(=O)O[Si](C)(C)C(C)(C)C	1621.9	Semi standard non polar	33892256
2,3-Methyleneglutaric acid,2TBDMS,isomer #1	C=C(CC(=O)O[Si](C)(C)C(C)(C)C)C(=C)C(=O)O[Si](C)(C)C(C)(C)C	1907.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Methyleneglutaric acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-8900000000-a00269f6739650fd2587	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Methyleneglutaric acid GC-MS (2 TMS) - 70eV, Positive	splash10-00tr-9430000000-6ba132b353a7ab90070a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Methyleneglutaric 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 - 2,3-Methyleneglutaric acid 10V, Positive-QTOF	splash10-000i-1900000000-abdc7d007b4022ebfe0a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Methyleneglutaric acid 20V, Positive-QTOF	splash10-000i-9500000000-bb3d7c402a217a13b10d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Methyleneglutaric acid 40V, Positive-QTOF	splash10-0uy0-9000000000-7393f6b402386ca77d04	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Methyleneglutaric acid 10V, Negative-QTOF	splash10-0bt9-1900000000-f570967b040100cb0746	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Methyleneglutaric acid 20V, Negative-QTOF	splash10-0900-4900000000-ed478e23a56a33b01af4	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Methyleneglutaric acid 40V, Negative-QTOF	splash10-066u-9100000000-1c7b8b244d782963dade	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Methyleneglutaric acid 10V, Negative-QTOF	splash10-02t9-9600000000-b461a396bd916581d3d7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Methyleneglutaric acid 20V, Negative-QTOF	splash10-02t9-9300000000-87822dd627e08ab815dd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Methyleneglutaric acid 40V, Negative-QTOF	splash10-014i-9000000000-98b77167e196e46d548d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Methyleneglutaric acid 10V, Positive-QTOF	splash10-03xs-8900000000-7ef8eb914626e79eac73	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Methyleneglutaric acid 20V, Positive-QTOF	splash10-014i-9000000000-4196763d964141c901e6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Methyleneglutaric acid 40V, Positive-QTOF	splash10-0uxr-9000000000-fbbd155568664f5390e7	2021-09-22	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

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	2338430	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

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

123510533

PDB ID

Not Available

ChEBI ID

89910

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

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 2,3-Methyleneglutaric acid (HMDB0059731)

MOL for HMDB0059731 (2,3-Methyleneglutaric acid)

3D MOL for HMDB0059731 (2,3-Methyleneglutaric acid)

3D SDF for HMDB0059731 (2,3-Methyleneglutaric acid)

3D-SDF for HMDB0059731 (2,3-Methyleneglutaric acid)

PDB for HMDB0059731 (2,3-Methyleneglutaric acid)

3D PDB for HMDB0059731 (2,3-Methyleneglutaric acid)

SMILES for HMDB0059731 (2,3-Methyleneglutaric acid)

INCHI for HMDB0059731 (2,3-Methyleneglutaric acid)

Structure for HMDB0059731 (2,3-Methyleneglutaric acid)

3D Structure for HMDB0059731 (2,3-Methyleneglutaric acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra