Showing Compound fumarate (FDB030865)

Record Information

Version

1.0

Creation date

2015-05-07 20:19:52 UTC

Update date

2020-09-17 15:38:22 UTC

Primary ID

FDB030865

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

fumarate

Description

Fumaric acid, also known as E297 or fumarsaeure, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Fumaric acid is a weakly acidic compound (based on its pKa). Fumaric acid exists in all living species, ranging from bacteria to humans. Within humans, fumaric acid participates in a number of enzymatic reactions. In particular, fumaric acid can be biosynthesized from L-malic acid; which is catalyzed by the enzyme fumarate hydratase, mitochondrial. In addition, fumaric acid can be biosynthesized from succinic acid through the action of the enzyme mutant succinate dehydrogenase. A butenedioic acid in which the C=C double bond has E geometry. In humans, fumaric acid is involved in the metabolic disorder called the glutaminolysis and cancer pathway. Fumaric acid is an odorless and sour tasting compound. Outside of the human body, Fumaric acid is found, on average, in the highest concentration within a few different foods, such as sweet cherries, star fruits, and milk (cow) and in a lower concentration in grape wines. Fumaric acid has also been detected, but not quantified in, several different foods, such as cow milks, apples, fishes, garden rhubarbs, and common sages. This could make fumaric acid a potential biomarker for the consumption of these foods. Fumaric acid is a potentially toxic compound. Fumaric acid, with regard to humans, has been found to be associated with several diseases such as rheumatoid arthritis, eosinophilic esophagitis, and lung cancer; fumaric acid has also been linked to several inborn metabolic disorders including 2-ketoglutarate dehydrogenase complex deficiency and fumarase deficiency.

CAS Number

110-17-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(2E)-2-Butenedioic acid	ChEBI
(e)-2-Butenedioic acid	ChEBI
e297	ChEBI
Fumarsaeure	ChEBI
trans-1,2-Ethylenedicarboxylic acid	ChEBI
trans-But-2-enedioic acid	ChEBI
trans-Butenedioic acid	ChEBI
(2E)-2-Butenedioate	Generator
(e)-2-Butenedioate	Generator
trans-1,2-Ethylenedicarboxylate	Generator
trans-But-2-enedioate	Generator
trans-Butenedioate	Generator
Fumarate	Generator
(2E)-But-2-enedioate	HMDB
(2E)-But-2-enedioic acid	HMDB
2-(e)-Butenedioate	HMDB
2-(e)-Butenedioic acid	HMDB
Allomaleate	HMDB
Allomaleic acid	HMDB
Boletate	HMDB
Boletic acid	HMDB
FC 33	HMDB
Lichenate	HMDB
Lichenic acid	HMDB
trans-2-Butenedioate	HMDB
trans-2-Butenedioic acid	HMDB
Furamag	HMDB
Mafusol	HMDB
Fumaric acid	HMDB

Predicted Properties

Property	Value	Source
Water Solubility	24.1 g/L	ALOGPS
logP	0.21	ALOGPS
logP	-0.041	ChemAxon
logS	-0.68	ALOGPS
pKa (Strongest Acidic)	3.55	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	24.61 m³·mol⁻¹	ChemAxon
Polarizability	9.35 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

C4H4O4

IUPAC name

(2E)-but-2-enedioic acid

InChI Identifier

InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+

InChI Key

VZCYOOQTPOCHFL-OWOJBTEDSA-N

Isomeric SMILES

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

Average Molecular Weight

116.0722

Monoisotopic Molecular Weight

116.010958616

Classification

Description

belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Dicarboxylic acids and derivatives

Direct Parent

Dicarboxylic acids and derivatives

Alternative Parents

Substituents

Fatty acyl
Fatty acid
Unsaturated fatty acid
Dicarboxylic acid or derivatives
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

butenedioic acid (CHEBI:18012 )

Ontology

Physiological effect

Health effect:

Observation:

Skin irritation

Health condition:

Nervous system disorders:

Seizure

Respiratory, thoracic and mediastinal disorders:

Cough

Gastrointestinal disorders:

Cancer:

Lung cancer

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Synthetic:

Personal care product

Biological:

Animal

Fungi:

Aspergillus

Plant:

Biological location:

Organ and components:

Prostate

Biofluid and excreta:

Cell and elements:

Extracellular

Subcellular:

Process

Naturally occurring process:

Biological process:

Cellular process:

Cell signaling

Role

Biological role:

Environmental role:

Air pollutant

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
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-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-0002-2940000000-e988056514d4ce4acc27	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-0002-2960000000-a5ebaf2bbade922838ec	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-0002-2950000000-32afa4d45e0e72b174b4	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0002-0950000000-fe0f05c02c783d0b6f6b	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-006t-9530000000-0fc03f31f09dc8dbf4c6	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0002-3690000000-75089756992cdbe841e3	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-9100000000-2cf649749b42cc0c610c	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0007-0890000000-b1c35cd55deb81254f66	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-2940000000-e988056514d4ce4acc27	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-2960000000-a5ebaf2bbade922838ec	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-2950000000-32afa4d45e0e72b174b4	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0950000000-fe0f05c02c783d0b6f6b	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-006t-9530000000-0fc03f31f09dc8dbf4c6	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0002-3690000000-75089756992cdbe841e3	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0940000000-177fdb9168659029ffaa	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ba-9200000000-52f88e04bac0ff8cdf17	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00di-8920000000-06da44f348d0fe0358b3	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-00di-9100000000-57f13cd433a6fe4bf0b3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0229-9600000000-cd9e2979d0bb1e2a62f2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-03k9-8900000000-dc50dbf8a50872383d54	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positive	splash10-0002-9100000000-b47e534bc82a6ed36e7c	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-9800000000-dbf34563376daeb2901f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00xs-9200000000-113bf08cdc77707ed3ad	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00fr-9000000000-f32d7ec65e8649bc2b0a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-2900000000-408d53a9fff7acc8ca23	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-6900000000-f149e9e5a34e27dd4d4e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fxt-9000000000-cae5f71dc27daaf17d9e	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-0092-9000000000-003dd2d9303272b2ebea	JSpectraViewer \| MoNA
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
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

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

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

Not Available

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

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound fumarate (FDB030865)

Structure for FDB030865 (fumarate)