ContaminantDB: Mesaconic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-26 05:21:47 UTC

Update Date

2016-11-09 01:21:13 UTC

Accession Number

CHEM034952

Identification

Common Name

Mesaconic acid

Class

Small Molecule

Description

A dicarboxylic acid consisting of fumaric acid having a methyl substituent at the 2-position.

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(e)-2-Methyl-2-butenedioic acid	ChEBI
(e)-Citraconic acid	ChEBI
2-Methylfumaric acid	ChEBI
Citronic acid	ChEBI
Methylfumaric acid	ChEBI
trans-1-Propene-1,2-dicarboxylic acid	ChEBI
trans-2-Methyl-2-butenedioic acid	ChEBI
2-Methylfumarate	Kegg
(e)-2-Methyl-2-butenedioate	Generator
(e)-Citraconate	Generator
Citronate	Generator
Methylfumarate	Generator
trans-1-Propene-1,2-dicarboxylate	Generator
trans-2-Methyl-2-butenedioate	Generator
Mesaconate	Generator
(Z)-2-Methyl-2-butenedioic acid	HMDB
Citraconic acid	HMDB
Citraconic acid, (e)-isomer	HMDB
Citraconic acid, ammonium salt	HMDB
Citraconic acid, calcium salt	HMDB
Citraconic acid, sodium salt	HMDB
Methylmaleic acid	HMDB
Monomethylfumarate	HMDB
(2E)-2-Methyl-2-butenedioate	HMDB
(2E)-2-Methyl-2-butenedioic acid	HMDB

Chemical Formula

C₅H₆O₄

Average Molecular Mass

130.099 g/mol

Monoisotopic Mass

130.027 g/mol

CAS Registry Number

498-24-8

IUPAC Name

(2E)-2-methylbut-2-enedioic acid

Traditional Name

mesaconic acid

SMILES

C\C(=C/C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2+

InChI Key

HNEGQIOMVPPMNR-NSCUHMNNSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Methyl-branched fatty acids

Alternative Parents

Substituents

Methyl-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

dicarboxylic acid (CHEBI:16600 )
Dicarboxylic acids (LMFA01170116 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	15.9 g/L	ALOGPS
logP	0.21	ALOGPS
logP	0.35	ChemAxon
logS	-0.91	ALOGPS
pKa (Strongest Acidic)	3.72	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	2	ChemAxon
Refractivity	28.96 m³·mol⁻¹	ChemAxon
Polarizability	11.24 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-0002-1910000000-7b5cb889d8459c0edd01	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00di-9500000000-b21cd4d2b489173d2933	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-053r-2940000000-4329a46b213ac4abcca9	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-1910000000-7b5cb889d8459c0edd01	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9500000000-b21cd4d2b489173d2933	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-053r-2940000000-4329a46b213ac4abcca9	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-01q3-9200000000-99f5b89fc0026d764b2b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-05g3-9540000000-ba938fe63ed9356955c6	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000j-9400000000-e10edb30d7748a7adb05	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00m0-9000000000-6ef60fd2abfbb5741bca	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0159-9000000000-e14ffb74e5a8298232a3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-000i-9100000000-8749d95b95760456aeed	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-000i-9100000000-8749d95b95760456aeed	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-5900000000-48835a534a81752d3085	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-9100000000-dcbf0f65cbb6f9b6b578	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9000000000-632723c704c4db90a4b6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004r-5900000000-4b2260c72d18030ec912	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002r-9500000000-1fd59395c864782b12b9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014u-9000000000-b6d65140f365dabf3b3a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01p9-9400000000-ebf4634a042628bb8a44	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00ko-9000000000-e04449c635203c9d3da0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-1b2c407328e3780e996e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-ec20127c74818b1f634d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-8867d7b163c801abd185	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014l-9000000000-55fcd5974652df621054	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum