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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-24 09:50:04 UTC
Update Date2017-12-07 01:54:08 UTC
HMDB IDHMDB0004812
Secondary Accession Numbers
  • HMDB00578
  • HMDB04812
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
Dehydromucic acidChEBI
Furane-alpha,alpha'-dicarboxylic acidChEBI
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
Furan-2,5-dicarboxylateHMDB
Furan-2,5-dicarboxylic acidHMDB
Furane-a,a'-dicarboxylateHMDB
Furane-a,a'-dicarboxylic acidHMDB
FDCA CPDMeSH
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 KeyCHTHALBTIRVDBM-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassFurans
Sub ClassFuroic acid and derivatives
Direct ParentFuroic 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 FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Biofluid and excreta:

Source:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity32.84 m³·mol⁻¹ChemAxon
Polarizability13.05 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a5i-6900000000-d288769ec5810d63b1b2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0229-9480000000-8391a736007498218310View in MoNA
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0900000000-c2840f2e7256d798d4faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-0900000000-c3d20c4a56763ab0900cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000j-9100000000-0e380e427de8c76266bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-ec73c307d1a6f5bd94d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0w29-2900000000-0b5e65af058aa2ef6db6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00lr-9200000000-41c982464657e52513deView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    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 IDCPD-14105
    BiGG IDNot Available
    Wikipedia Link2,5-Furandicarboxylic_acid
    METLIN ID7076
    PubChem Compound76720
    PDB IDNot Available
    ChEBI ID84212
    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. [PubMed: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. [PubMed:4630229 ]