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Showing NP-Card for 2-Furoic acid (NP0001107)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:41:44 UTC
NP-MRD IDNP0001107
Secondary Accession NumbersNone
Natural Product 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 ). 2-Furoic acid is a biomarker for the consumption of beer
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001107 (2-Furoic acid)


  Mrv1652309272007342D          

  8  8  0  0  0  0            999 V2000
10001.406610000.5262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.121410000.1143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.021010000.6081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.353610000.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6085 9999.3385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.4335 9999.3385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.688410000.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.411310001.3512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  0  0  0  0
  1  7  1  0  0  0  0
  1  8  2  0  0  0  0
M  END
Download

3D MOL for NP0001107 (2-Furoic acid)

HMDB0000617
     RDKit          3D
2-Furoic acid
 12 12  0  0  0  0  0  0  0  0999 V2000
    2.3612   -1.1913    0.9492 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7882   -0.3178    0.2518 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5545    0.6167   -0.4152 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3179   -0.2984    0.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4493    0.5912   -0.5680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7809    0.2710   -0.4008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7676   -0.8307    0.4381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5339   -1.1134    0.7239 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9260    1.3892    0.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0876    1.4194   -1.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6373    0.7736   -0.8323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6913   -1.3094    0.7492 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  4  1  0
  3  9  1  0
  5 10  1  0
  6 11  1  0
  7 12  1  0
M  END
Download

3D SDF for NP0001107 (2-Furoic acid)


  Mrv1652309272007342D          

  8  8  0  0  0  0            999 V2000
10001.406610000.5262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.121410000.1143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.021010000.6081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.353610000.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6085 9999.3385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.4335 9999.3385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.688410000.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.411310001.3512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  0  0  0  0
  1  7  1  0  0  0  0
  1  8  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0001107

> <DATABASE_NAME>
NP-MRD

> <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_KEY>
SMNDYUVBFMFKNZ-UHFFFAOYSA-N

> <FORMULA>
C5H4O3

> <MOLECULAR_WEIGHT>
112.0835

> <EXACT_MASS>
112.016043994

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
9.795118389590135

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
furan-2-carboxylic acid

> <ALOGPS_LOGP>
0.98

> <JCHEM_LOGP>
0.6910753679999999

> <ALOGPS_LOGS>
-0.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
-6.5094420345971225

> <JCHEM_PKA_STRONGEST_BASIC>
6.412956533041503

> <JCHEM_POLAR_SURFACE_AREA>
50.44

> <JCHEM_REFRACTIVITY>
25.7051

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.71e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
furoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0001107 (2-Furoic acid)

HMDB0000617
     RDKit          3D
2-Furoic acid
 12 12  0  0  0  0  0  0  0  0999 V2000
    2.3612   -1.1913    0.9492 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7882   -0.3178    0.2518 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5545    0.6167   -0.4152 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3179   -0.2984    0.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4493    0.5912   -0.5680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7809    0.2710   -0.4008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7676   -0.8307    0.4381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5339   -1.1134    0.7239 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9260    1.3892    0.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0876    1.4194   -1.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6373    0.7736   -0.8323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6913   -1.3094    0.7492 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  4  1  0
  3  9  1  0
  5 10  1  0
  6 11  1  0
  7 12  1  0
M  END
Download

PDB for NP0001107 (2-Furoic acid)

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8669.2928667.649   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8670.6278666.880   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8666.7068667.802   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0    8665.4608666.896   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8665.9368665.432   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8667.4768665.432   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8667.9528666.896   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8669.3018669.189   0.000  0.00  0.00           O+0
CONECT    1    2    7    8                                                  
CONECT    2    1                                                            
CONECT    3    4    7                                                       
CONECT    4    5    3                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    3    1                                                  
CONECT    8    1                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END
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3D PDB for NP0001107 (2-Furoic acid)

COMPND    HMDB0000617
HETATM    1  O1  UNL     1       2.361  -1.191   0.949  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.788  -0.318   0.252  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.554   0.617  -0.415  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.318  -0.298   0.153  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.449   0.591  -0.568  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.781   0.271  -0.401  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.768  -0.831   0.438  1.00  0.00           C  
HETATM    8  O3  UNL     1      -0.534  -1.113   0.724  1.00  0.00           O  
HETATM    9  H1  UNL     1       2.926   1.389   0.129  1.00  0.00           H  
HETATM   10  H2  UNL     1      -0.088   1.419  -1.177  1.00  0.00           H  
HETATM   11  H3  UNL     1      -2.637   0.774  -0.832  1.00  0.00           H  
HETATM   12  H4  UNL     1      -2.691  -1.309   0.749  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3    9
CONECT    4    5    5    8
CONECT    5    6   10
CONECT    6    7    7   11
CONECT    7    8   12
END
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SMILES for NP0001107 (2-Furoic acid)

OC(=O)C1=CC=CO1
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INCHI for NP0001107 (2-Furoic acid)

InChI=1S/C5H4O3/c6-5(7)4-2-1-3-8-4/h1-3H,(H,6,7)
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View in JSmol
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 Mass112.0835 Da
Monoisotopic Mass112.01604 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aloe africanaLOTUS Database
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Aspergillus stellatusLOTUS Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
Cercospora beticolaLOTUS Database
CervidaeFooDB
Cervus canadensisFooDB
Codonopsis pilosulaLOTUS Database
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Eucalyptus viminalisKNApSAcK Database
Forsythia viridissimaLOTUS Database
Gallus gallusFooDB
Grosmannia crassivaginataLOTUS Database
Homalomena occultaLOTUS Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
Ophiocordyceps sinensisLOTUS Database
OryctolagusFooDB
Osbeckia chinensisLOTUS Database
Ovis ariesFooDB
Phaseolus vulgarisKNApSAcK Database
PhasianidaeFooDB
Phasianus colchicusFooDB
Phomopsis velataLOTUS Database
Solanum lycopersicumLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Vitis viniferaLOTUS Database
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point133.5 °CNot Available
Boiling Point230.00 to 232.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility37.1 mg/mL at 15 °CNot Available
LogP0.64Not Available
Predicted Properties
PropertyValueSource
Water Solubility27.1 g/LALOGPS
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
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
Good Scents IDrw1040161
References
General References
  1. 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. [PubMed:12587683 ]
  2. 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. [PubMed:3947564 ]
  3. 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. [PubMed:8447721 ]