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	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Methylenebutanedioic acid, 2 TMS, GC-MS Spectrum	splash10-067j-4970000000-62c083c1889c0389bdc7	Spectrum
GC-MS	Methylenebutanedioic acid, non-derivatized, GC-MS Spectrum	splash10-067j-4970000000-62c083c1889c0389bdc7	Spectrum
GC-MS	Methylenebutanedioic acid, non-derivatized, GC-MS Spectrum	splash10-0002-1910000000-691ec6088f9d55e9b158	Spectrum
Predicted GC-MS	Methylenebutanedioic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001c-9100000000-3218ae9ee6b97674a039	Spectrum
Predicted GC-MS	Methylenebutanedioic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-059i-9420000000-cf91095ef1210525cf5d	Spectrum
Predicted GC-MS	Methylenebutanedioic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Methylenebutanedioic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-03y1-9400000000-8522d5eb5288a63433b1	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-00kr-9000000000-8287612bcdd337cb94dd	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-02a9-9200000000-d17287465b81dab7939c	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-004i-4900000000-8433e22f39cee33233c1	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-000i-9000000000-5879e62dedd6aab4b1ca	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-000i-9000000000-464f41418a542f68cdb2	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-96ec7055deb2e0402943	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-f4499898bdcf9c9eb9c4	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-000i-9100000000-dac578cf4d95b2206d4b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-4900000000-8433e22f39cee33233c1	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-5879e62dedd6aab4b1ca	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-464f41418a542f68cdb2	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-96ec7055deb2e0402943	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-f4499898bdcf9c9eb9c4	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-000i-9100000000-dac578cf4d95b2206d4b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-3a323040e2c2c85076cf	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-000i-9000000000-d3d15eaac40f45cd1f12	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Negative	splash10-000i-9000000000-2834a749f71c5924616c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-b8ad1fa3bcacc46e663c	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-4900000000-8dbdce71f36577627d67	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02g9-9300000000-72767f1807dfa80e809c	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kf-9000000000-e26167424a1c652a920d	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004r-5900000000-95e66a8f3b6c0bc3cec6	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002r-9500000000-c8ab0cb1983e8213e622	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014u-9000000000-f54d12caffc54c552d2d	2015-05-27	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	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)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum