P. aeruginosa Metabolome Database: Citraconic acid (PAMDB001792)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB001792

Identification

Name:

Citraconic acid

Description:

Mesaconic acid is one of several isomeric carboxylic acids obtained from citric acid. Is used as a fire retardant, recent studies revealed this acid is a competitive inhibitor of fumarate reduction.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

(Z)-2-Methyl-2-butenedioate
(Z)-2-Methyl-2-butenedioic acid
Citraconate
Methylmaleate
Methylmaleic acid

Chemical Formula:

C₅H₆O₄

Average Molecular Weight:

130.0987

Monoisotopic Molecular Weight:

130.02660868

InChI Key:

HNEGQIOMVPPMNR-IHWYPQMZSA-N

InChI:

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

CAS number:

498-23-7

IUPAC Name:

(2Z)-2-methylbut-2-enedioic acid

Traditional IUPAC Name:

citraconic acid

SMILES:

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

Chemical Taxonomy

Taxonomy Description

This compound 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
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dicarboxylic acid (CHEBI:17626 )
Dicarboxylic acids (LMFA01170099 )

Physical Properties

State:

Solid

Charge:

-2

Melting point:

88-94 °C

Experimental Properties:

Property	Value	Source
Water Solubility:	783.0 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	15.9 mg/mL	ALOGPS
logP	0.21	ALOGPS
logP	0.35	ChemAxon
logS	-0.91	ALOGPS
pKa (Strongest Acidic)	2.5	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	11.17 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

(R)-2-Methylmalate <> Citraconic acid + Water
Citraconic acid + Water <> D-Erythro-3-Methylmalate
Citraconic acid + Water > Citramalic acid

Pathways:

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-053s-9830000000-9984d183d92e149a6ab4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-000i-9100000000-707e9072305131e101d9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0006-9000000000-2a007e703ec5aa2df51a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-000f-9200000000-5095d8b00331302fe65f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-004i-2900000000-98ab39de610d4d7e428d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-000i-9000000000-1786e7db899e12344315	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-000i-9000000000-a1b543932fc265020973	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-d5dc2c9fdcd47f64c404	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-81b2f20752aef9eee2e9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-000i-9200000000-ddad81eb9311ec64a8c7	View in MoNA
1D NMR	1H NMR Spectrum	Not Available
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available

References

References:

Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. Pubmed: 17379776
Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A

Synthesis Reference:

Berg, Rudolph G. Catalytic preparation of citraconic and itaconic acids. U.S. (1972), 5 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
CHEBI ID	17626
HMDB ID	HMDB00634
Pubchem Compound ID	874
Kegg ID	C02226
ChemSpider ID	553689
Wikipedia ID	Not Available
BioCyc ID	Not Available

Citraconic acid (PAMDB001792)

Structure for Citraconic acid (PAMDB001792)