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Record Information
Version3.6
Creation Date2006-08-24 09:50:04 UTC
Update Date2016-02-11 01:06:51 UTC
HMDB IDHMDB04812
Secondary Accession Numbers
  • HMDB00578
Metabolite Identification
Common Name2,5-Furandicarboxylic acid
Description2,5-Furandicarboxylic acid is a normal urinary metabolite in humans. (PMIDs 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 rat, pig, cow, ox, rabbit, and monkey. (PMID 4630229 ).
Structure
Thumb
Synonyms
ValueSource
2,5-DicarboxyfuranChEBI
2,5-Furandicarboxylic acidChEBI
Dehydromucic acidChEBI
Furane-alpha,alpha'-dicarboxylic acidChEBI
Furan-2,5-dicarboxylateGenerator
2,5-FurandicarboxylateGenerator
DehydromucateGenerator
Furane-a,alpha'-dicarboxylateGenerator
Furane-a,alpha'-dicarboxylic acidGenerator
Furane-alpha,alpha'-dicarboxylateGenerator
Furane-α,alpha'-dicarboxylateGenerator
Furane-α,alpha'-dicarboxylic acidGenerator
(1,5-Dimethylhexyl)hydrazineHMDB
DehydroschleimsaeureHMDB
Furan 2,5-dicarboxylateHMDB
Furan 2,5-dicarboxylic acidHMDB
Furan-2,5-dicarbonsaeureHMDB
Furane-a,a'-dicarboxylateHMDB
Furane-a,a'-dicarboxylic acidHMDB
Chemical FormulaC6H4O5
Average Molecular Weight156.093
Monoisotopic Molecular Weight156.005873238
IUPAC Namefuran-2,5-dicarboxylic acid
Traditional Name2,5-furandicarboxylic acid
CAS Registry Number3238-40-2
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 KeyInChIKey=CHTHALBTIRVDBM-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as furoic acid derivatives. 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassFurans
Sub ClassFuroic acid derivatives
Direct ParentFuroic acid derivatives
Alternative Parents
Substituents
  • Furoate
  • Dicarboxylic acid or derivatives
  • Heteroaromatic compound
  • Oxacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Microbial
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point342 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1 mg/mL at 18 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility11.8 mg/mLALOGPS
logP0.66ALOGPS
logP0.27ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)2.76ChemAxon
pKa (Strongest Basic)-6.1ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area87.74 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity32.84 m3·mol-1ChemAxon
Polarizability13.05 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0900000000-2edf2743af7ee90a29aeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000l-9200000000-a9709e652d30a2063847View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00ku-9000000000-c9fcb98abb314bb78c67View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
UrineDetected and Quantified2.7 (0.1-9.1) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified6.9 (3.7-10.1) umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified1.5 (0.1-12.0) umol/mmol creatinineChildren (1-13 years old)Both
Normal
details
UrineDetected and Quantified1.7 (0.1-8.7) umol/mmol creatinineChildren (1-13 years old)Both
Normal
details
UrineDetected and Quantified1.9 (0.1-5.4) umol/mmol creatinineAdolescent (13-18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023423
KNApSAcK IDNot Available
Chemspider ID69178
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04812
Metagene LinkHMDB04812
METLIN ID7076
PubChem Compound76720
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceGonis, George; Amstutz, E. D. Preparation of furan-2,5-dicarboxylic acid. Journal of Organic Chemistry (1962), 27 2946-7.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [8087979 ]
  2. Pettersen JE, Jellum E: The identification and metabolic origin of 2-furoylglycine and 2,5-furandicarboxylic acid in human urine. Clin Chim Acta. 1972 Oct;41:199-207. [4630229 ]