MiMeDB: Showing metabocard for Mesaconic acid (MMDBc0047913)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-23 23:14:42 UTC

Update Date

2022-09-01 02:01:26 UTC

Metabolite ID

MMDBc0047913

Metabolite Identification

Common Name

Mesaconic acid

Description

Mesaconic acid, also known as 2-methylfumarate or citronic acid, 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. Mesaconic acid is a dicarboxylic butenoic acid, with a methyl group in position 2 and the double bound between carbons 2 and 3. Mesaconic acid was first studied for its physical properties in 1874 by Jacobus van ‚Äòt Hoff (https://web.archive.org/web/20051117102410/http://dbhs.wvusd.k12.ca.us/webdocs/Chem-History/Van%27t-Hoff-1874.html). It is now known to be involved in the biosynthesis of vitamin B12 and it is also a competitor inhibitor of the reduction of fumarate.

Structure

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

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

Molecular Formula

C₅H₆O₄

Average Mass

130.0987

Monoisotopic Mass

130.02660868

IUPAC Name

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

Traditional Name

mesaconic acid

CAS Registry Number

498-24-8

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 )

Functional Ontology

Not Available

Physical Properties

State

Solid

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	Yes	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	Deposition Date	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	2014-06-16	View 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	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-053r-2940000000-4329a46b213ac4abcca9	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-1910000000-7b5cb889d8459c0edd01	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9500000000-b21cd4d2b489173d2933	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-053r-2940000000-4329a46b213ac4abcca9	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-01q3-9200000000-99f5b89fc0026d764b2b	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-05g3-9540000000-ba938fe63ed9356955c6	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000j-9400000000-e10edb30d7748a7adb05	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00m0-9000000000-6ef60fd2abfbb5741bca	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0159-9000000000-e14ffb74e5a8298232a3	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-000i-9100000000-8749d95b95760456aeed	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-000i-9100000000-8749d95b95760456aeed	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-5900000000-48835a534a81752d3085	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-9100000000-dcbf0f65cbb6f9b6b578	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9000000000-632723c704c4db90a4b6	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004r-5900000000-4b2260c72d18030ec912	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002r-9500000000-1fd59395c864782b12b9	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014u-9000000000-b6d65140f365dabf3b3a	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01p9-9400000000-ebf4634a042628bb8a44	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00ko-9000000000-e04449c635203c9d3da0	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-1b2c407328e3780e996e	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-ec20127c74818b1f634d	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-8867d7b163c801abd185	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014l-9000000000-55fcd5974652df621054	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2021-10-10	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane
Mitochondria

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0001634	Adenosine triphosphate	ADP	Succinate-coa ligase, adp-forming, beta subunit	Mesaconate- Coenzyme A Ligase (ADP-Forming), Mitochondrial	VMH	13783048
MMDBr0001635	Coenzyme A	Guanosine diphosphate	Succinate-coa ligase, alpha subunit	Mesaconate- Coenzyme A Ligase (GDP-Forming)	VMH	13783048
MMDBr0012679	Water	(S)-Citramalate	Not Available	Mesaconate hydratase	VMH	30371894
MMDBr0013154	(2S,3S)-3-methyl-L-aspartic acid	Mesaconic acid	Methylaspartate ammonia-lyase	Non-hydrolytic bond cleavage (or its reversal)	RHEA	34755880
MMDBr0016156	Mesaconic acid	Mesaconyl-CoA	Succinyl-CoA:mesaconate CoA-transferase	Transfer of CoA moiety	RHEA	34755880
MMDBr0016157	Mesaconic acid	Mesaconyl-CoA	Succinyl-CoA:mesaconate CoA-transferase	Transfer of CoA moiety	RHEA	34755880
MMDBr0038837	Mesaconyl-CoA	Mesaconic acid	Thioesterase TesA	Hydrolysis	RHEA	34755880
MMDBr0038978	Mesaconic acid	N-Mesaconyl-4R-hydroxysphinganine	Alkaline ceramidase YPC1	Hydrolysis	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	8	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	2	Human ; Human feces	Metabolic reconstruction
Bacteria/NULL	Firmicutes	1
Archaea/Archaea	Euryarchaeota	2
Bacteria	Firmicutes	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0000749

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

ChEBI ID

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Truscott RJ, Malegan D, McCairns E, Burke D, Hick L, Sims P, Halpern B, Tanaka K, Sweetman L, Nyhan WL, Hammond J, Bumack C, Haan EA, Danks DM: New metabolites in isovaleric acidemia. Clin Chim Acta. 1981 Mar 5;110(2-3):187-203. doi: 10.1016/0009-8981(81)90348-x. [PubMed:6452974 ]

Showing metabocard for Mesaconic acid (MMDBc0047913)

MOL for #<Metabolite:0x00007fe2d4506c20>

3D MOL for #<Metabolite:0x00007fe2d4506c20>

3D SDF for #<Metabolite:0x00007fe2d4506c20>

3D-SDF for #<Metabolite:0x00007fe2d4506c20>

PDB for #<Metabolite:0x00007fe2d4506c20>

3D PDB for #<Metabolite:0x00007fe2d4506c20>

SMILES for #<Metabolite:0x00007fe2d4506c20>

INCHI for #<Metabolite:0x00007fe2d4506c20>

Structure for #<Metabolite:0x00007fe2d4506c20>

3D Structure for #<Metabolite:0x00007fe2d4506c20>