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Showing NP-Card for 3-Furoic acid (NP0000220)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:39:35 UTC
NP-MRD IDNP0000220
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Furoic acid
Description3-Furoic acid is an organic acid regularly occurring in urine of healthy individuals. (PMID 2338430 ). 3-Furoic acid is also a compound found in honey and honeydew samples (PMID 11403496 ), and is a structural analog of nicotinic acid (niacin, a vitamin of the B complex). (PMID 12563315 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000220 (3-Furoic acid)

3-Furoic acid.mol
  Mrv1652305261923572D          

  8  8  0  0  0  0            999 V2000
   -0.4125   -1.2535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6674   -0.4689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6674   -0.4689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -1.2535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  1  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
M  END
Download

3D MOL for NP0000220 (3-Furoic acid)

HMDB0000444
     RDKit          3D
3-Furoic acid
 12 12  0  0  0  0  0  0  0  0999 V2000
    1.8549   -1.5143    0.6696 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5084   -0.3384    0.3247 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4849    0.6051    0.1865 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0974   -0.0706    0.0990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0083   -0.8802    0.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1281   -0.1327   -0.1307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7127    1.0698   -0.3984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4001    1.1564   -0.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1981    0.4743   -0.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9580   -1.9239    0.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1455   -0.4790   -0.1528 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2090    2.0334   -0.4374 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  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  4  2  0
  3  9  1  0
  5 10  1  0
  6 11  1  0
  8 12  1  0
M  END
Download

3D SDF for NP0000220 (3-Furoic acid)

3-Furoic acid.mol
  Mrv1652305261923572D          

  8  8  0  0  0  0            999 V2000
   -0.4125   -1.2535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6674   -0.4689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6674   -0.4689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -1.2535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  1  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000220

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C5H4O3/c6-5(7)4-1-2-8-3-4/h1-3H,(H,6,7)

> <INCHI_KEY>
IHCCAYCGZOLTEU-UHFFFAOYSA-N

> <FORMULA>
C5H4O3

> <MOLECULAR_WEIGHT>
112.0835

> <EXACT_MASS>
112.016043994

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
9.678148318377772

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
furan-3-carboxylic acid

> <ALOGPS_LOGP>
0.75

> <JCHEM_LOGP>
0.7710742443333334

> <ALOGPS_LOGS>
-0.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.311645800455931

> <JCHEM_PKA_STRONGEST_BASIC>
-3.076295353853603

> <JCHEM_POLAR_SURFACE_AREA>
50.44

> <JCHEM_REFRACTIVITY>
25.827600000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.01e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-furoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000220 (3-Furoic acid)

HMDB0000444
     RDKit          3D
3-Furoic acid
 12 12  0  0  0  0  0  0  0  0999 V2000
    1.8549   -1.5143    0.6696 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5084   -0.3384    0.3247 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4849    0.6051    0.1865 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0974   -0.0706    0.0990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0083   -0.8802    0.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1281   -0.1327   -0.1307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7127    1.0698   -0.3984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4001    1.1564   -0.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1981    0.4743   -0.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9580   -1.9239    0.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1455   -0.4790   -0.1528 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2090    2.0334   -0.4374 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  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  4  2  0
  3  9  1  0
  5 10  1  0
  6 11  1  0
  8 12  1  0
M  END
Download

PDB for NP0000220 (3-Furoic acid)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 3-Furoic acid.mol                                 
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  O   UNK     0      -0.770  -2.340   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.246  -0.875   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.030   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.246  -0.875   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.770  -2.340   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.570   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.334   2.340   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       1.334   2.340   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4    1                                                       
CONECT    6    3    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END
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3D PDB for NP0000220 (3-Furoic acid)

COMPND    HMDB0000444
HETATM    1  O1  UNL     1       1.855  -1.514   0.670  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.508  -0.338   0.325  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.485   0.605   0.186  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.097  -0.071   0.099  1.00  0.00           C  
HETATM    5  C3  UNL     1      -1.008  -0.880   0.188  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.128  -0.133  -0.131  1.00  0.00           C  
HETATM    7  O3  UNL     1      -1.713   1.070  -0.398  1.00  0.00           O  
HETATM    8  C5  UNL     1      -0.400   1.156  -0.276  1.00  0.00           C  
HETATM    9  H1  UNL     1       3.198   0.474  -0.538  1.00  0.00           H  
HETATM   10  H2  UNL     1      -0.958  -1.924   0.466  1.00  0.00           H  
HETATM   11  H3  UNL     1      -3.146  -0.479  -0.153  1.00  0.00           H  
HETATM   12  H4  UNL     1       0.209   2.033  -0.437  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3    9
CONECT    4    5    8    8
CONECT    5    6    6   10
CONECT    6    7   11
CONECT    7    8
CONECT    8   12
END
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SMILES for NP0000220 (3-Furoic acid)

OC(=O)C1=COC=C1
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INCHI for NP0000220 (3-Furoic acid)

InChI=1S/C5H4O3/c6-5(7)4-1-2-8-3-4/h1-3H,(H,6,7)
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View in JSmol
Synonyms
ValueSource
3-CarboxyfuranChEBI
3-Furancarboxylic acidChEBI
3-FurancarboxylateGenerator
3-FuroateGenerator
3-FuranoateHMDB
3-Furanoic acidHMDB
Chemical FormulaC5H4O3
Average Mass112.0835 Da
Monoisotopic Mass112.01604 Da
IUPAC Namefuran-3-carboxylic acid
Traditional Name3-furoic acid
CAS Registry Number488-93-7
SMILES
OC(=O)C1=COC=C1
InChI Identifier
InChI=1S/C5H4O3/c6-5(7)4-1-2-8-3-4/h1-3H,(H,6,7)
InChI KeyIHCCAYCGZOLTEU-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 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
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brachystemma calycinumLOTUS Database
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Euonymus europaeaLOTUS Database
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
Penicillium herqueiLOTUS Database
Peristeria elataLOTUS Database
Phaseolus vulgarisLOTUS Database
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Tripterygium wilfordiiLOTUS 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
  • Furan-3-carboxylic acid
  • Furan-3-carboxylic acid or derivatives
  • 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 Point120 - 122 °CNot Available
Boiling Point229.00 to 230.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility64 mg/mLNot Available
LogP1.03Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility30.1 g/LALOGPS
logP0.75ALOGPS
logP0.77ChemAxon
logS-0.57ALOGPS
pKa (Strongest Acidic)4.31ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area50.44 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity25.83 m³·mol⁻¹ChemAxon
Polarizability9.68 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000444
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022049
KNApSAcK IDNot Available
Chemspider ID9849
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Furoic acid
METLIN ID5433
PubChem Compound10268
PDB IDNot Available
ChEBI ID30846
Good Scents IDrw1044231
References
General References
  1. Nozal MJ, Bernal JL, Toribio L, Jimenez JJ, Martin MT: High-performance liquid chromatographic determination of methyl anthranilate, hydroxymethylfurfural and related compounds in honey. J Chromatogr A. 2001 May 11;917(1-2):95-103. [PubMed:11403496 ]
  2. Salis S, Spano N, Ciulu M, Floris I, Pilo MI, Sanna G: Electrochemical Determination of the "Furanic Index" in Honey. Molecules. 2021 Jul 6;26(14). pii: molecules26144115. doi: 10.3390/molecules26144115. [PubMed:34299390 ]
  3. Sampaio-Dias IE, Reis-Mendes A, Costa VM, Garcia-Mera X, Brea J, Loza MI, Pires-Lima BL, Alcoholado C, Algarra M, Rodriguez-Borges JE: Discovery of New Potent Positive Allosteric Modulators of Dopamine D2 Receptors: Insights into the Bioisosteric Replacement of Proline to 3-Furoic Acid in the Melanostatin Neuropeptide. J Med Chem. 2021 May 13;64(9):6209-6220. doi: 10.1021/acs.jmedchem.1c00252. Epub 2021 Apr 16. [PubMed:33861612 ]
  4. Nomura H, Ueyama J, Kondo T, Saito I, Murata K, Iwata T, Wakusawa S, Kamijima M: Quantitation of neonicotinoid metabolites in human urine using GC-MS. J Chromatogr B Analyt Technol Biomed Life Sci. 2013 Dec 15;941:109-15. doi: 10.1016/j.jchromb.2013.10.012. Epub 2013 Oct 18. [PubMed:24189204 ]
  5. Foo Wong Y, Makahleh A, Al Azzam KM, Yahaya N, Saad B, Sulaiman SA: Micellar electrokinetic chromatography method for the simultaneous determination of furanic compounds in honey and vegetable oils. Talanta. 2012 Aug 15;97:23-31. doi: 10.1016/j.talanta.2012.03.056. Epub 2012 Apr 27. [PubMed:22841043 ]
  6. Rocamora-Reverte L, Carrasco-Garcia E, Ceballos-Torres J, Prashar S, Kaluderovic GN, Ferragut JA, Gomez-Ruiz S: Study of the anticancer properties of tin(IV) carboxylate complexes on a panel of human tumor cell lines. ChemMedChem. 2012 Feb 6;7(2):301-10. doi: 10.1002/cmdc.201100432. Epub 2011 Dec 13. [PubMed:22170592 ]