Milk Composition Database: Showing metabocard for Citraconic acid (BMDB0000634)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:34:01 UTC

Update Date

2020-05-05 18:39:50 UTC

MCDB ID

BMDB0000634

Secondary Accession Numbers

BMDB00634

Metabolite Identification

Common Name

Citraconic acid

Description

Citraconic acid, also known as 2-methylmaleate or methylmaleic 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. Citraconic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Citraconic acid exists in all living organisms, ranging from bacteria to humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(Z)-2-Methyl-2-butenedioic acid	ChEBI
2-Methyl-2-butenedioic acid	ChEBI
2-Methylmaleic acid	ChEBI
alpha-Methylmaleic acid	ChEBI
cis-2-Methylbutenedioic acid	ChEBI
cis-Methylbutenedioic acid	ChEBI
Citraconsaeure	ChEBI
Methyl-maleinsaeure	ChEBI
Methylmaleic acid	ChEBI
Citraconate	Kegg
(Z)-2-Methyl-2-butenedioate	Generator
2-Methyl-2-butenedioate	Generator
2-Methylmaleate	Generator
a-Methylmaleate	Generator
a-Methylmaleic acid	Generator
alpha-Methylmaleate	Generator
Α-methylmaleate	Generator
Α-methylmaleic acid	Generator
cis-2-Methylbutenedioate	Generator
cis-Methylbutenedioate	Generator
Methylmaleate	Generator
Citraconic acid, ammonium salt	HMDB
Citraconic acid, calcium salt	HMDB
Citraconic acid, sodium salt	HMDB
Methylfumaric acid	HMDB
(e)-2-Methyl-2-butenedioic acid	HMDB
Citraconic acid, (e)-isomer	HMDB
Mesaconic acid	HMDB
Monomethylfumarate	HMDB

Chemical Formula

C₅H₆O₄

Average Molecular Weight

130.0987

Monoisotopic Molecular Weight

130.02660868

IUPAC Name

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

Traditional Name

citraconic acid

CAS Registry Number

498-23-7

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-IHWYPQMZSA-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:17626 )
Dicarboxylic acids (LMFA01170099 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	88 - 94 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	783 mg/mL	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	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-MS (2 TMS)	splash10-053s-9830000000-9984d183d92e149a6ab4	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-9300000000-e6df22429c37d2a7f548	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-053s-9830000000-9984d183d92e149a6ab4	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-1910000000-5eda2b2a1e8b0386b997	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-01q3-9200000000-640fe5e61db043d72d25	2017-08-28	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 (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, Negative (Annotated)	splash10-000i-9100000000-707e9072305131e101d9	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0006-9000000000-2a007e703ec5aa2df51a	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-000f-9200000000-5095d8b00331302fe65f	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-004i-2900000000-98ab39de610d4d7e428d	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-000i-9000000000-1786e7db899e12344315	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-000i-9000000000-a1b543932fc265020973	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-d5dc2c9fdcd47f64c404	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-81b2f20752aef9eee2e9	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-000i-9200000000-ddad81eb9311ec64a8c7	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-2900000000-98ab39de610d4d7e428d	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-1786e7db899e12344315	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-a1b543932fc265020973	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-d5dc2c9fdcd47f64c404	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-81b2f20752aef9eee2e9	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-000i-9200000000-ddad81eb9311ec64a8c7	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 9V, positive	splash10-001i-9000000000-243e35b5f07a2e972851	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 4V, positive	splash10-03di-1900000000-e8a9dc6bff676e7ead5a	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 5V, positive	splash10-03di-1900000000-d2e84a4209df38673770	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 7V, positive	splash10-03di-2900000000-214b108bacb2c899d800	2020-07-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01q9-4900000000-86e2b44f3c8ee5a18c48	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02g9-9200000000-6d6e041c039e8649caf3	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kf-9000000000-7eeaf466a984bad3e0c8	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004r-6900000000-69d0c4409d2eb535ceeb	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002r-9400000000-a67e18d9101e6c4863ec	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00ko-9100000000-6c212f68da0a408b4ea1	2017-07-26	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-24	View Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Not Available	2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected but not Quantified	Not Applicable		PMID: 25599412	details
Detected but not Quantified	Not Applicable		PMID: 25599412	details

External Links

HMDB ID

HMDB0000634

DrugBank ID

DB04734

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Citraconic_acid

METLIN ID

5607

PubChem Compound

643798

PDB ID

Not Available

ChEBI ID

17626

References

Synthesis Reference

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

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28. [PubMed:25599412 ]

Showing metabocard for Citraconic acid (BMDB0000634)

Structure for BMDB0000634 (Citraconic acid)