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Showing NP-Card for 5-hydroxyfuran-2-carboxylic acid (NP0252609)

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Record Information
Version1.0
Created at2022-09-07 16:10:32 UTC
Updated at2022-09-07 16:10:32 UTC
NP-MRD IDNP0252609
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-hydroxyfuran-2-carboxylic acid
Description5-Hydroxy-2-furoic 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. 5-hydroxyfuran-2-carboxylic acid is found in Pyricularia grisea. It was first documented in 2007 (PMID: 17439666). 5-Hydroxy-2-furoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0252609 (5-hydroxyfuran-2-carboxylic acid)


  Mrv0541 06081214512D          

  9  9  0  0  0  0            999 V2000
   -0.1467    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  4  9  2  0  0  0  0
M  END
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3D MOL for NP0252609 (5-hydroxyfuran-2-carboxylic acid)

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3D SDF for NP0252609 (5-hydroxyfuran-2-carboxylic acid)

  Mrv0541 06081214512D          

  9  9  0  0  0  0            999 V2000
   -0.1467    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  4  9  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0252609

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=CC=C(O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C5H4O4/c6-4-2-1-3(9-4)5(7)8/h1-2,6H,(H,7,8)

> <INCHI_KEY>
JVUTYZQGCHCOPB-UHFFFAOYSA-N

> <FORMULA>
C5H4O4

> <MOLECULAR_WEIGHT>
128.0829

> <EXACT_MASS>
128.010958616

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
10.85476857727577

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-hydroxyfuran-2-carboxylic acid

> <ALOGPS_LOGP>
0.81

> <JCHEM_LOGP>
0.476801055

> <ALOGPS_LOGS>
-0.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.287584372617771

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1341256897095877

> <JCHEM_PKA_STRONGEST_BASIC>
-5.2088140406705135

> <JCHEM_POLAR_SURFACE_AREA>
70.67

> <JCHEM_REFRACTIVITY>
26.9393

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.89e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxyfuran-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0252609 (5-hydroxyfuran-2-carboxylic acid)
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PDB for NP0252609 (5-hydroxyfuran-2-carboxylic acid)
HEADER    PROTEIN                                 08-JUN-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-JUN-12         0                                  
HETATM    1  O   UNK     0      -0.274   4.390   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.393   4.390   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.306   1.175   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.735  -1.536   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8    4                                                       
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END

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3D PDB for NP0252609 (5-hydroxyfuran-2-carboxylic acid)
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SMILES for NP0252609 (5-hydroxyfuran-2-carboxylic acid)
OC(=O)C1=CC=C(O)O1
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INCHI for NP0252609 (5-hydroxyfuran-2-carboxylic acid)
InChI=1S/C5H4O4/c6-4-2-1-3(9-4)5(7)8/h1-2,6H,(H,7,8)
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Synonyms
ValueSource
5-Hydroxy-2-furoateGenerator
5-Hydroxyfuran-2-carboxylateGenerator
Chemical FormulaC5H4O4
Average Mass128.0829 Da
Monoisotopic Mass128.01096 Da
IUPAC Name5-hydroxyfuran-2-carboxylic acid
Traditional Name5-hydroxyfuran-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C1=CC=C(O)O1
InChI Identifier
InChI=1S/C5H4O4/c6-4-2-1-3(9-4)5(7)8/h1-2,6H,(H,7,8)
InChI KeyJVUTYZQGCHCOPB-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Magnaporthe griseaLOTUS 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
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.81ALOGPS
logP0.48ChemAxon
logS-0.65ALOGPS
pKa (Strongest Acidic)3.13ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area70.67 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity26.94 m³·mol⁻¹ChemAxon
Polarizability10.85 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0059784  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3373337  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound4161539  
PDB IDNot Available
ChEBI ID86395  
Good Scents IDNot Available
References
General References
  1. Castrillo JI, Zeef LA, Hoyle DC, Zhang N, Hayes A, Gardner DC, Cornell MJ, Petty J, Hakes L, Wardleworth L, Rash B, Brown M, Dunn WB, Broadhurst D, O'Donoghue K, Hester SS, Dunkley TP, Hart SR, Swainston N, Li P, Gaskell SJ, Paton NW, Lilley KS, Kell DB, Oliver SG: Growth control of the eukaryote cell: a systems biology study in yeast. J Biol. 2007;6(2):4. doi: 10.1186/jbiol54. [PubMed:17439666  ] 
  2. LOTUS database [Link]