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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-24 09:50:04 UTC
Update Date2023-05-30 20:55:53 UTC
HMDB IDHMDB0004812
Secondary Accession Numbers
  • HMDB0000578
  • HMDB00578
  • HMDB04812
Metabolite Identification
Common Name2,5-Furandicarboxylic acid
Description2,5-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
Data?1676999823
Synonyms
ValueSource
2,5-DicarboxyfuranChEBI
Dehydromucic acidChEBI
Furane-alpha,alpha'-dicarboxylic acidChEBI
Furan-2,5-dicarboxylateKegg
DehydromucateGenerator
Furane-a,alpha'-dicarboxylateGenerator
Furane-a,alpha'-dicarboxylic acidGenerator
Furane-alpha,alpha'-dicarboxylateGenerator
Furane-α,alpha'-dicarboxylateGenerator
Furane-α,alpha'-dicarboxylic acidGenerator
Furan-2,5-dicarboxylic acidGenerator
2,5-FurandicarboxylateGenerator
(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
FDCA CPDMeSH, HMDB
2,5-Furandicarboxylic acidChEBI
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
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.
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point342 °CNot Available
Boiling Point419.20 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1 mg/mL at 18 °CNot Available
LogP-0.020 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility11.8 g/LALOGPS
logP0.66ALOGPS
logP0.27ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)-4.6ChemAxon
pKa (Strongest Basic)11.11ChemAxon
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+132.83831661259
DarkChem[M-H]-127.59231661259
DeepCCS[M+H]+128.61530932474
DeepCCS[M-H]-124.78830932474
DeepCCS[M-2H]-162.09830932474
DeepCCS[M+Na]+137.58930932474
AllCCS[M+H]+132.332859911
AllCCS[M+H-H2O]+127.732859911
AllCCS[M+NH4]+136.532859911
AllCCS[M+Na]+137.732859911
AllCCS[M-H]-125.232859911
AllCCS[M+Na-2H]-126.432859911
AllCCS[M+HCOO]-127.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2,5-Furandicarboxylic acidOC(=O)C1=CC=C(O1)C(O)=O1995.9Standard polar33892256
2,5-Furandicarboxylic acidOC(=O)C1=CC=C(O1)C(O)=O1342.2Standard non polar33892256
2,5-Furandicarboxylic acidOC(=O)C1=CC=C(O1)C(O)=O1457.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2,5-Furandicarboxylic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=C(C(=O)O)O11584.6Semi standard non polar33892256
2,5-Furandicarboxylic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=C(C(=O)O[Si](C)(C)C)O11654.9Semi standard non polar33892256
2,5-Furandicarboxylic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(C(=O)O)O11852.5Semi standard non polar33892256
2,5-Furandicarboxylic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)O12143.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2,5-Furandicarboxylic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a5i-6900000000-d288769ec5810d63b1b22017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,5-Furandicarboxylic acid GC-MS (2 TMS) - 70eV, Positivesplash10-0229-9480000000-8391a7360074982183102017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,5-Furandicarboxylic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,5-Furandicarboxylic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,5-Furandicarboxylic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-000i-0900000000-2edf2743af7ee90a29ae2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,5-Furandicarboxylic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-000l-9200000000-a9709e652d30a20638472012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,5-Furandicarboxylic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-00ku-9000000000-c9fcb98abb314bb78c672012-07-25HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,5-Furandicarboxylic acid 10V, Positive-QTOFsplash10-0a4r-0900000000-c2840f2e7256d798d4fa2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,5-Furandicarboxylic acid 20V, Positive-QTOFsplash10-052r-0900000000-c3d20c4a56763ab0900c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,5-Furandicarboxylic acid 40V, Positive-QTOFsplash10-000j-9100000000-0e380e427de8c76266bf2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,5-Furandicarboxylic acid 10V, Negative-QTOFsplash10-0udi-0900000000-ec73c307d1a6f5bd94d22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,5-Furandicarboxylic acid 20V, Negative-QTOFsplash10-0w29-2900000000-0b5e65af058aa2ef6db62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,5-Furandicarboxylic acid 40V, Negative-QTOFsplash10-00lr-9200000000-41c982464657e52513de2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,5-Furandicarboxylic acid 10V, Negative-QTOFsplash10-02t9-9500000000-ea0c20378ff74ce1345f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,5-Furandicarboxylic acid 20V, Negative-QTOFsplash10-014i-9100000000-4520e50e1c56f67826812021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,5-Furandicarboxylic acid 40V, Negative-QTOFsplash10-014i-9000000000-eb1155a9bb1577d1bb892021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,5-Furandicarboxylic acid 10V, Positive-QTOFsplash10-0a4r-1900000000-9fe216ad8db30c7901bb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,5-Furandicarboxylic acid 20V, Positive-QTOFsplash10-0002-9600000000-bfeb15a5dbae92e0bbcd2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,5-Furandicarboxylic acid 40V, Positive-QTOFsplash10-000i-9000000000-524d51557840cf7b7f3c2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, experimental)2021-10-10Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal 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
UrineDetected and Quantified1.39 (0.64-3.43) umol/mmol creatinineNewborn (0-30 days old)Both
Normal
    • Analysis of 40 NI...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023423
KNApSAcK IDNot Available
Chemspider ID69178
KEGG Compound IDC20450
BioCyc IDCPD-14105
BiGG IDNot Available
Wikipedia Link2,5-Furandicarboxylic_acid
METLIN ID7076
PubChem Compound76720
PDB IDNot Available
ChEBI ID84212
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1435791
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. Boulat O, Gradwohl M, Matos V, Guignard JP, Bachmann C: Organic acids in the second morning urine in a healthy Swiss paediatric population. Clin Chem Lab Med. 2003 Dec;41(12):1642-58. [PubMed:14708889 ]
  2. 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 ]
  3. 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 ]
  4. Liebich HM, Forst C: Basic profiles of organic acids in urine. J Chromatogr. 1990 Jan 26;525(1):1-14. [PubMed:2338430 ]
  5. Koopman F, Wierckx N, de Winde JH, Ruijssenaars HJ: Identification and characterization of the furfural and 5-(hydroxymethyl)furfural degradation pathways of Cupriavidus basilensis HMF14. Proc Natl Acad Sci U S A. 2010 Mar 16;107(11):4919-24. doi: 10.1073/pnas.0913039107. Epub 2010 Mar 1. [PubMed:20194784 ]
  6. Heindl A, Dietel P, Spiteller G: Distinction between urinary acids originating from nutrition and those produced in the human body. J Chromatogr. 1986 Apr 25;377:3-14. doi: 10.1016/s0378-4347(00)80756-2. [PubMed:3711221 ]