Showing Compound Maleylacetoacetic acid (FDB022817)

Record Information

Version

1.0

Creation date

2011-09-21 00:20:06 UTC

Update date

2020-04-21 18:02:19 UTC

Primary ID

FDB022817

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Maleylacetoacetic acid

Description

4-Fumarylacetoacetic acid, also known as fumarylacetoacetate, belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain. 4-Fumarylacetoacetic acid has been detected, but not quantified in, several different foods, such as greenthread teas (Thelesperma), butternuts (Juglans cinerea), arabica coffees (Coffea arabica), hickory nuts (Carya), and chanterelles (Cantharellus cibarius). This could make 4-fumarylacetoacetic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4-Fumarylacetoacetic acid.

CAS Number

5698-52-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Fumarylacetoacetone	ChEBI
Fumarylacetoacetate	Kegg
Fumarylacetoacetic acid	Generator
4-Fumarylacetoacetate	Generator
4-Fumaryl-acetoacetate	HMDB
(2E)-4,6-Dioxo-2-octenedioic acid	HMDB
4-Fumarylacetoacetic acid	HMDB
4-Maleylacetoacetate	hmdb
4-Maleylacetoacetic acid	hmdb
Maleylacetoacetate	hmdb

Predicted Properties

Property	Value	Source
Water Solubility	1.65 g/L	ALOGPS
logP	-0.19	ALOGPS
logP	0.4	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	3.05	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	108.74 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	44.4 m³·mol⁻¹	ChemAxon
Polarizability	17.28 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C8H8O6

IUPAC name

(2E)-4,6-dioxooct-2-enedioic acid

InChI Identifier

InChI=1S/C8H8O6/c9-5(1-2-7(11)12)3-6(10)4-8(13)14/h1-2H,3-4H2,(H,11,12)(H,13,14)/b2-1+

InChI Key

GACSIVHAIFQKTC-OWOJBTEDSA-N

Isomeric SMILES

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

Average Molecular Weight

200.1455

Monoisotopic Molecular Weight

200.032087988

Classification

Description

Belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Medium-chain keto acids and derivatives

Direct Parent

Medium-chain keto acids and derivatives

Alternative Parents

Substituents

Medium-chain keto acid
Beta-keto acid
1,3-diketone
Beta-hydroxy ketone
Dicarboxylic acid or derivatives
Unsaturated fatty acid
1,3-dicarbonyl compound
Fatty acyl
Enone
Acryloyl-group
Alpha,beta-unsaturated ketone
Ketone
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

oxo dicarboxylic acid (CHEBI:30907 )
beta-diketone (CHEBI:30907 )
Dicarboxylic acids (LMFA01170066 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
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

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	4-Fumarylacetoacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0007-9300000000-7b2ae90eb353073cb652	Spectrum
Predicted GC-MS	4-Fumarylacetoacetic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05bu-7092000000-254fb0c9b4683fd48ef1	Spectrum
Predicted GC-MS	4-Fumarylacetoacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Fumarylacetoacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fsi-1920000000-f36f976fb4a0271e936b	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-6900000000-692cbcc9f99aac913e42	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00rj-9200000000-8e21be4180492b988f54	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4j-1900000000-ea634f49698a94be6311	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-5900000000-4d5261faac7c9dc29c36	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9500000000-17b0a81ad882f626ac2a	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0bt9-3900000000-0353447aa417ab1cef29	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-9600000000-fabbd099eded8f7879a9	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-9000000000-e4bd7674e02d56b3573f	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001r-4900000000-80aa92977bd40f96e740	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kb-9100000000-7d688d7f7d7a804690a3	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-c0d2eba6487ff950c63d	2021-09-24	View Spectrum