Showing Compound Card for Furoic acid (CDB005774)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesXML
Record Information
Version1.0
Created at2020-04-27 16:55:15 UTC
Updated at2021-01-04 18:59:27 UTC
CannabisDB IDCDB005774
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameFuroic acid
Description2-Furoic acid, also known as alpha-Furoic acid or Pyromucic acid, 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. 2-Furoic acid exists as a white to off-white crystalline solid. It has a sweet, oily, herbaceious or earthy odor. It is most widely found in food products as a preservative (acting as a bacteriocide and fungicide) and a flavoring agent. Other uses for 2-furoic acid include nylon preparation and optic technologies. 2-Furoic acid is also a metabolite that appears in the urine of individuals 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. Furfural is also found in many processed foods and beverages such as cocoa, coffee, tea, beer, wine and bread (due to thermal decomposition of carbohydrates). Furfural 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 leads to hepatic cirrhosis). Once in the body, furfural is metabolized rapidly via oxidation to the metabolite 2-Furoic acid, which may then be conjugated with glycine and excreted in the urine in both free and conjugated forms. (PMID: 3751566 , 4630229 , 12587683 ). As a result, 2-Furoic acid is a biomarker for the exposure to furfural and the consumption of beer, wine, bread and cocoa. 2-Furoic acid may also cause mutagenic effects in bacteria and yeasts, leading to damage and irritation to the gastrointestinal tract, respiratory tract, skin, and eyes. Furoic acid is one of many compounds found in cannabis smoke and is formed during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
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-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
2-FuroateGenerator
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
Furan-3-carboxylicHMDB
2-Furoic acid, sodium saltHMDB
Furan-2-ylacetateHMDB
Furan-2-carboxylateHMDB
Furan-2-carboxylic acidHMDB
2-Furoic acidKEGG
Chemical FormulaC5H4O3
Average Molecular Weight112.08
Monoisotopic Molecular Weight112.016
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 KeySMNDYUVBFMFKNZ-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
  • Heteroaromatic compound
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • 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

Route of exposure:

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point133.5 °CNot Available
Boiling Point230 to 232 °CWikipedia
Water Solubility37.1 mg/mL at 15 °CNot Available
logP0.64POMONA (1987)
Predicted Properties
PropertyValueSource
logP0.98ALOGPS
logP0.69ChemAxon
logS-0.62ALOGPS
pKa (Strongest Acidic)-6.5ChemAxon
pKa (Strongest Basic)6.41ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area50.44 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity25.71 m³·mol⁻¹ChemAxon
Polarizability9.8 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSFuroic acid, 1 TMS, GC-MS Spectrumsplash10-004i-2900000000-0a68833fc4193e1f8cedSpectrum
GC-MSFuroic acid, non-derivatized, GC-MS Spectrumsplash10-004i-2900000000-0a68833fc4193e1f8cedSpectrum
GC-MSFuroic acid, non-derivatized, GC-MS Spectrumsplash10-004j-4900000000-ea5ecbab959d0d5c46f2Spectrum
Predicted GC-MSFuroic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01p6-9200000000-29936ed9a6e09458beebSpectrum
Predicted GC-MSFuroic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00ds-9200000000-deea8b11e937a3c9a0b6Spectrum
Predicted GC-MSFuroic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFuroic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-014i-9000000000-29104923ddd1637492b62012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-014i-9000000000-f5839ae3e2498c8ed4222012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-014m-9000000000-add36932dee552c274602012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-03di-3900000000-1400c95fd6fa180f34772012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-014i-9000000000-3ef00380e59fd05e13d72012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-014i-9000000000-793fd8d927620ba879c42012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-00kb-9000000000-41d0eb8e5d92a9c181332012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0002-9000000000-b316782c64a0bd01cfa42012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-3900000000-1400c95fd6fa180f34772017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-9000000000-3ef00380e59fd05e13d72017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-9000000000-793fd8d927620ba879c42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00kb-9000000000-41d0eb8e5d92a9c181332017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9000000000-b316782c64a0bd01cfa42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 4V, positivesplash10-03di-0900000000-e56f9404be174f6936362020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 8V, positivesplash10-03di-4900000000-d5a109e334b699d07fd42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 12V, positivesplash10-0002-9200000000-5ffc1a1c60bdd1e1607f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 16V, positivesplash10-0002-9000000000-c8b314b1b859572c98102020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 20V, positivesplash10-0002-9000000000-557bd61baaf69da1bbf32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 12V, positivesplash10-0002-9000000000-dc124ecf6a6750677b102020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-8900000000-0e807897f25b2ae739ec2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ot-9400000000-a38fb6802bc09c6a697f2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uy1-9000000000-88ac4d1b946f0141be712017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1900000000-23013259dcdc1acd43162017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xr-9600000000-197797d0dbb1a04c891c2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kr-9000000000-b09281ae3a89c2ed52ed2017-09-01View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0000617
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000951
KNApSAcK IDC00000151
Chemspider ID10251740
KEGG Compound IDC01546
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Furoic_acid
METLIN ID2266
PubChem Compound6919
PDB IDNot Available
ChEBI ID30845
References
General References
  1. 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. doi: 10.1111/j.1440-1827.1986.tb00212.x. [PubMed:3751566 ]
  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. doi: 10.1016/0009-8981(72)90512-8. [PubMed:4630229 ]
  3. 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. doi: 10.1093/jat/27.1.43. [PubMed:12587683 ]