ChemFOnt: Showing chemical card for 2,5-Furandicarboxylic acid (CFc000002191)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:01 UTC

Chemfont ID

CFc000002191

Molecule Identification

Common Name

2,5-Furandicarboxylic acid

Definition

2,5-Furandicarboxylic acid is a normal urinary metabolite in humans. (PMID:14708889 , 8087979 , 2338430 , 3711221 ). Dietary studies show that the furan derivatives or their precursors are of exogenous origin. They are originated from furan derivatives found in food prepared by strong heating. This may explain the absence of 2,5-furandicarboxylic acid in urine of breastfed children, and the absence of these acids in the urine of rats, pigs, cows, oxs, rabbits, and monkeys (PMID 4630229 ). 2,5-Furandicarboxylic acid is also a microbial metabolite, a product of the oxidation of hydroxymethylfurfural (HMF) by the enzyme furfural/HMF oxidoreductase which is found in the bacterium Cupriavidus basilensis. Cupriavidus basilensis is a gram-negative soil bacterium of the genus Cupriavidus and the family Burkholderiaceae. 2,5-Furandicarboxylic acid increases with the level of fructose consumed (PMID:20194784 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2,5-Dicarboxyfuran	ChEBI
Dehydromucic acid	ChEBI
Furane-alpha,alpha'-dicarboxylic acid	ChEBI
Furan-2,5-dicarboxylate	Kegg
Dehydromucate	Generator
Furane-a,alpha'-dicarboxylate	Generator
Furane-a,alpha'-dicarboxylic acid	Generator
Furane-alpha,alpha'-dicarboxylate	Generator
Furane-α,alpha'-dicarboxylate	Generator
Furane-α,alpha'-dicarboxylic acid	Generator
Furan-2,5-dicarboxylic acid	Generator
2,5-Furandicarboxylate	Generator
(1,5-Dimethylhexyl)hydrazine	HMDB
Dehydroschleimsaeure	HMDB
Furan 2,5-dicarboxylate	HMDB
Furan 2,5-dicarboxylic acid	HMDB
Furan-2,5-dicarbonsaeure	HMDB
Furane-a,a'-dicarboxylate	HMDB
Furane-a,a'-dicarboxylic acid	HMDB
FDCA CPD	MeSH, HMDB
2,5-Furandicarboxylic acid	ChEBI

Chemical Formula

C₆H₄O₅

Average Molecular Weight

156.093

Monoisotopic Molecular Weight

156.005873238

IUPAC Name

furan-2,5-dicarboxylic acid

Traditional Name

2,5-furandicarboxylic acid

CAS Registry Number

3238-40-2

SMILES

OC(=O)C1=CC=C(O1)C(O)=O

InChI Identifier

InChI=1S/C6H4O5/c7-5(8)3-1-2-4(11-3)6(9)10/h1-2H,(H,7,8)(H,9,10)

InChI Key

CHTHALBTIRVDBM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furoic acids. These are organic compounds containing a furoic acid moiety, with a structure characterized by a furan ring bearing a carboxylic acid group at the C2 or C3 carbon atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Furans

Sub Class

Furoic acid and derivatives

Direct Parent

Furoic acids

Alternative Parents

Substituents

Furoic acid
Dicarboxylic acid or derivatives
Heteroaromatic compound
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

dicarboxylic acid (CHEBI:84212 )
furans (CHEBI:84212 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 8087979)

Source

Endogenous

Endogenous (HMDB: HMDB0004812)

Microbe

Microbe (HMDB: HMDB0004812)
Cupriavidus basilensis (HMDB: HMDB0004812)

Exogenous

Exogenous (HMDB: HMDB0004812)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	11.8 g/L	ALOGPS
logP	0.66	ALOGPS
logP	0.27	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	-4.6	ChemAxon
pKa (Strongest Basic)	11.11	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	87.74 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	32.84 m³·mol⁻¹	ChemAxon
Polarizability	13.05 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon