Showing Compound Methylenebutanedioic acid (FDB012645)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:17 UTC

Update date

2019-11-26 03:07:18 UTC

Primary ID

FDB012645

Secondary Accession Numbers

FDB030947

Chemical Information

FooDB Name

Methylenebutanedioic acid

Description

Itaconic acid, also known as itaconate, belongs to the class of organic compounds known as branched fatty acids. These are fatty acids containing a branched chain. Itaconic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

CAS Number

97-65-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
2-Methylenesuccinic acid	ChEBI
2-Propene-1,2-dicarboxylic acid	ChEBI
Methylenebutanedioic acid	ChEBI
Methylenesuccinic acid	ChEBI
Propylenedicarboxylic acid	ChEBI
2-Methylenesuccinate	Generator
2-Propene-1,2-dicarboxylate	Generator
Methylenebutanedioate	Generator
Methylenesuccinate	Generator
Propylenedicarboxylate	Generator
Itaconate	Generator
2-Hydroxy-3-naphthoyl-2-naphthylamine	HMDB
Itaconic acid, copper salt	HMDB
Itaconic acid, disodium salt	HMDB
Itaconic acid, calcium salt	HMDB
Itaconic acid, sodium salt	HMDB
2-Hydroxy-3-Naphthoyl-2-Naphthylamine	biospider
2-methylidenebutanedioic acid	biospider
3-Carboxy-3-butenoic acid	biospider
Itaconic acid	db_source
Methylenesuccinic acid, 8CI	db_source

Predicted Properties

Property	Value	Source
Water Solubility	63 g/L	ALOGPS
logP	0	ALOGPS
logP	0.053	ChemAxon
logS	-0.31	ALOGPS
pKa (Strongest Acidic)	3.65	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	3	ChemAxon
Refractivity	27.91 m³·mol⁻¹	ChemAxon
Polarizability	11.06 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C5H6O4

IUPAC name

2-methylidenebutanedioic acid

InChI Identifier

InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h1-2H2,(H,6,7)(H,8,9)

InChI Key

LVHBHZANLOWSRM-UHFFFAOYSA-N

Isomeric SMILES

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

Average Molecular Weight

130.0987

Monoisotopic Molecular Weight

130.02660868

Classification

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

dicarboxylic acid (CHEBI:30838 )
Dicarboxylic acids (LMFA01170063 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Escherichia coli

Fungi:

Aspergillus:

Aspergillus terreus

Plant:

Biological location:

Subcellular:

Biofluid and excreta:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Biochemical pathway:

Lipid metabolism pathway

Chemical reaction:

Lipid peroxidation

Role

Biological role:

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 46.16%; H 4.65%; O 49.19%	DFC
Melting Point	Mp 167-168° (162-164° dec.)	DFC
Boiling Point	Not Available
Experimental Water Solubility	76.8 mg/mL at 20 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	Not Available
Experimental pKa	pKa2 5.14 (25°, 0.1M NaClO4)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-067j-4970000000-62c083c1889c0389bdc7	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-067j-4970000000-62c083c1889c0389bdc7	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-1910000000-691ec6088f9d55e9b158	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001c-9100000000-3218ae9ee6b97674a039	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-059i-9420000000-cf91095ef1210525cf5d	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-03y1-9400000000-8522d5eb5288a63433b1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-00kr-9000000000-8287612bcdd337cb94dd	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-02a9-9200000000-d17287465b81dab7939c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-004i-4900000000-8433e22f39cee33233c1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-000i-9000000000-5879e62dedd6aab4b1ca	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-000i-9000000000-464f41418a542f68cdb2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-96ec7055deb2e0402943	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-f4499898bdcf9c9eb9c4	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-000i-9100000000-dac578cf4d95b2206d4b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-4900000000-8433e22f39cee33233c1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-5879e62dedd6aab4b1ca	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-464f41418a542f68cdb2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-96ec7055deb2e0402943	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-f4499898bdcf9c9eb9c4	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-000i-9100000000-dac578cf4d95b2206d4b	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-4900000000-8dbdce71f36577627d67	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02g9-9300000000-72767f1807dfa80e809c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kf-9000000000-e26167424a1c652a920d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004r-5900000000-95e66a8f3b6c0bc3cec6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002r-9500000000-c8ab0cb1983e8213e622	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014u-9000000000-f54d12caffc54c552d2d	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

30838

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB02092

CRC / DFC (Dictionary of Food Compounds) ID

HJM97-X:HJM97-X

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

35130

KNApSAcK ID

C00033964

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Itaconic acid

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound Methylenebutanedioic acid (FDB012645)

Structure for FDB012645 (Methylenebutanedioic acid)