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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:02 UTC
HMDB IDHMDB00617
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-Furoic acid
DescriptionFuroic acid is a metabolite that appears in the urine of workers occupationally exposed to furfural and is a marker of exposure to this compound. Furfural is a heterocyclic aldehyde that is commonly used as a solvent in industry. It is readily absorbed into the body via the lungs and has significant skin absorption. Furfural is an irritant of the eyes, mucous membranes, and skin and is a central nervous system depressant. Furfural as a confirmed animal carcinogen with unknown relevance to humans (It has been suggested that is a substance that produces hepatic cirrhosis). Once in the body, furfural is metabolized rapidly via oxidation to the metabolite furoic acid, which is then conjugated with glycine and excreted in the urine in both free and conjugated forms. (PMID: 3751566 , 4630229 , 12587683 ).
Structure
Thumb
Synonyms
ValueSource
2-CarboxyfuranChEBI
2-Furancarboxylic acidChEBI
2-Furanoic acidChEBI
Acide 2-furoiqueChEBI
acido 2-FuroicoChEBI
alpha-Furancarboxylic acidChEBI
alpha-Furoic acidChEBI
Furan-2-carbonsaeureChEBI
Pyromucic acidChEBI
2-FuroateGenerator
2-FurancarboxylateGenerator
2-FuranoateGenerator
a-FurancarboxylateGenerator
a-Furancarboxylic acidGenerator
alpha-FurancarboxylateGenerator
α-furancarboxylateGenerator
α-furancarboxylic acidGenerator
a-FuroateGenerator
a-Furoic acidGenerator
alpha-FuroateGenerator
α-furoateGenerator
α-furoic acidGenerator
PyromucateGenerator
b-FurancarboxylateHMDB
b-Furancarboxylic acidHMDB
b-FuroateHMDB
b-Furoic acidHMDB
beta-FurancarboxylateHMDB
beta-Furancarboxylic acidHMDB
beta-FuroateHMDB
beta-Furoic acidHMDB
FurancarboxylateHMDB
Furancarboxylic acidHMDB
FuroateHMDB
Furoic acidHMDB
Chemical FormulaC5H4O3
Average Molecular Weight112.0835
Monoisotopic Molecular Weight112.016043994
IUPAC Namefuran-2-carboxylic acid
Traditional Namefuroic acid
CAS Registry Number88-14-2
SMILES
OC(=O)C1=CC=CO1
InChI Identifier
InChI=1S/C5H4O3/c6-5(7)4-2-1-3-8-4/h1-3H,(H,6,7)
InChI KeyInChIKey=SMNDYUVBFMFKNZ-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
  • Heteroaromatic compound
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point133.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility37.1 mg/mL at 15 °CNot Available
LogP0.64POMONA (1987)
Predicted Properties
PropertyValueSource
Water Solubility27.1 mg/mLALOGPS
logP0.98ALOGPS
logP0.69ChemAxon
logS-0.62ALOGPS
pKa (Strongest Acidic)3.12ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area50.44 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity25.71 m3·mol-1ChemAxon
Polarizability9.79 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-004i-2900000000-0a68833fc4193e1f8cedView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-014i-9000000000-29104923ddd1637492b6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-014i-9000000000-f5839ae3e2498c8ed422View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-014m-9000000000-add36932dee552c27460View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-03di-3900000000-1400c95fd6fa180f3477View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-014i-9000000000-3ef00380e59fd05e13d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-014i-9000000000-793fd8d927620ba879c4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-00kb-9000000000-41d0eb8e5d92a9c18133View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0002-9000000000-b316782c64a0bd01cfa4View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified5.0 (5.0-5.0) umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified10.0 (1.6-28.0) umol/mmol creatinineNewborn (0-30 days old)BothNormal 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 IDFDB000951
KNApSAcK IDC00000151
Chemspider ID10251740
KEGG Compound IDC01546
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00617
Metagene LinkHMDB00617
METLIN ID2266
PubChem Compound6919
PDB IDFOA
ChEBI ID30845
References
Synthesis ReferenceHurd, Charles D.; Garrett, J. W.; Osborne, E. N. Furan reactions. IV. Furoic acid from furfural. Journal of the American Chemical Society (1933), 55 1082-4.
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 ]
  3. Todoriki H, Hayashi T, Naruse H: High-performance liquid chromatographic method for screening disorders of aromatic acid metabolism using a multi-detection system. J Chromatogr. 1984 Oct 12;310(2):273-81. [6511847 ]
  4. Tan ZB, Tonks CE, O'Donnell GE, Geyer R: An improved HPLC analysis of the metabolite furoic acid in the urine of workers occupationally exposed to furfural. J Anal Toxicol. 2003 Jan-Feb;27(1):43-6. [12587683 ]
  5. Groeseneken D, van Vlem E, Veulemans H, Masschelein R: Gas chromatographic determination of methoxyacetic and ethoxyacetic acid in urine. Br J Ind Med. 1986 Jan;43(1):62-5. [3947564 ]
  6. Hall IH, Wong OT, Reynolds DJ, Chang JJ: The hypolipidemic effects of 2-furoic acid in Sprague-Dawley rats. Arch Pharm (Weinheim). 1993 Jan;326(1):15-23. [8447721 ]
  7. Shimizu A, Kanisawa M: Experimental studies on hepatic cirrhosis and hepatocarcinogenesis. I. Production of hepatic cirrhosis by furfural administration. Acta Pathol Jpn. 1986 Jul;36(7):1027-38. [3751566 ]