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Showing NP-Card for 2,5-Furandicarboxylic acid (NP0000965)

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Record Information
Version2.0
Created at2006-08-24 09:50:04 UTC
Updated at2021-08-19 23:58:37 UTC
NP-MRD IDNP0000965
Secondary Accession NumbersNone
Natural Product Identification
Common Name2,5-Furandicarboxylic acid
Description2,5-Furandicarboxylic acid is a normal urinary metabolite in humans. (PMID:14708889 , 8087979 , 2338430 , 3711221 ). Dietary studies show that the furan derivatives or their precursors are of exogenous origin. They are originated from furan derivatives found in food prepared by strong heating. This may explain the absence of 2,5-furandicarboxylic acid in urine of breastfed children, and the absence of these acids in the urine of rats, pigs, cows, oxs, rabbits, and monkeys (PMID 4630229 ). 2,5-Furandicarboxylic acid is also a microbial metabolite, a product of the oxidation of hydroxymethylfurfural (HMF) by the enzyme furfural/HMF oxidoreductase which is found in the bacterium Cupriavidus basilensis. Cupriavidus basilensis is a gram-negative soil bacterium of the genus Cupriavidus and the family Burkholderiaceae. 2,5-Furandicarboxylic acid increases with the level of fructose consumed (PMID:20194784 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000965 (2,5-Furandicarboxylic acid)


  Mrv1652305261923562D          

 11 11  0  0  0  0            999 V2000
   18.4535  -18.0980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3231  -18.0980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3883  -18.8801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0120  -19.4571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7647  -19.4571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8404  -18.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9362  -18.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0558  -18.3951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7209  -18.3951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8009  -17.6105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9758  -17.6105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  7  1  0  0  0  0
  3  8  1  0  0  0  0
  3  9  1  0  0  0  0
  4  6  2  0  0  0  0
  5  7  2  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  2  0  0  0  0
  9 11  2  0  0  0  0
 10 11  1  0  0  0  0
M  END
Download

3D MOL for NP0000965 (2,5-Furandicarboxylic acid)

HMDB0004812
     RDKit          3D
2,5-Furandicarboxylic acid
 15 15  0  0  0  0  0  0  0  0999 V2000
   -2.6953   -1.4168   -1.3630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4206   -0.7504   -0.3379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4337   -0.4928    0.5564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0507   -0.2706   -0.1219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5951    0.4800    0.9675 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7436    0.6759    0.7090 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0641    0.0543   -0.5039 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3786    0.0303   -1.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5285   -0.5632   -2.2188 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4449    0.6578   -0.5246 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0524   -0.4794   -0.9255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6097   -1.0163    1.3932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1874    0.8100    1.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4501    1.2142    1.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4350    1.0671    0.3796 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  9  2  0
  8 10  1  0
  7 11  1  0
 11  4  1  0
  3 12  1  0
  5 13  1  0
  6 14  1  0
 10 15  1  0
M  END
Download

3D SDF for NP0000965 (2,5-Furandicarboxylic acid)


  Mrv1652305261923562D          

 11 11  0  0  0  0            999 V2000
   18.4535  -18.0980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3231  -18.0980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3883  -18.8801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0120  -19.4571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7647  -19.4571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8404  -18.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9362  -18.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0558  -18.3951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7209  -18.3951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8009  -17.6105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9758  -17.6105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  7  1  0  0  0  0
  3  8  1  0  0  0  0
  3  9  1  0  0  0  0
  4  6  2  0  0  0  0
  5  7  2  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  2  0  0  0  0
  9 11  2  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000965

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H4O5/c7-5(8)3-1-2-4(11-3)6(9)10/h1-2H,(H,7,8)(H,9,10)

> <INCHI_KEY>
CHTHALBTIRVDBM-UHFFFAOYSA-N

> <FORMULA>
C6H4O5

> <MOLECULAR_WEIGHT>
156.093

> <EXACT_MASS>
156.005873238

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
13.046469592857386

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
furan-2,5-dicarboxylic acid

> <ALOGPS_LOGP>
0.66

> <JCHEM_LOGP>
0.26865939966666663

> <ALOGPS_LOGS>
-1.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
-3.849455376352089

> <JCHEM_PKA_STRONGEST_ACIDIC>
-4.6183288380633245

> <JCHEM_PKA_STRONGEST_BASIC>
11.109116533631033

> <JCHEM_POLAR_SURFACE_AREA>
87.74000000000001

> <JCHEM_REFRACTIVITY>
32.838800000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.18e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,5-furandicarboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000965 (2,5-Furandicarboxylic acid)

HMDB0004812
     RDKit          3D
2,5-Furandicarboxylic acid
 15 15  0  0  0  0  0  0  0  0999 V2000
   -2.6953   -1.4168   -1.3630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4206   -0.7504   -0.3379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4337   -0.4928    0.5564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0507   -0.2706   -0.1219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5951    0.4800    0.9675 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7436    0.6759    0.7090 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0641    0.0543   -0.5039 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3786    0.0303   -1.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5285   -0.5632   -2.2188 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4449    0.6578   -0.5246 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0524   -0.4794   -0.9255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6097   -1.0163    1.3932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1874    0.8100    1.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4501    1.2142    1.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4350    1.0671    0.3796 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  9  2  0
  8 10  1  0
  7 11  1  0
 11  4  1  0
  3 12  1  0
  5 13  1  0
  6 14  1  0
 10 15  1  0
M  END
Download

PDB for NP0000965 (2,5-Furandicarboxylic acid)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  O   UNK     0      34.447 -33.783   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      26.736 -33.783   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      30.591 -35.243   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      33.622 -36.320   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      27.561 -36.320   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      33.302 -34.814   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      27.881 -34.814   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      31.837 -34.338   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      29.346 -34.338   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      31.362 -32.873   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      29.821 -32.873   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2    7                                                            
CONECT    3    8    9                                                       
CONECT    4    6                                                            
CONECT    5    7                                                            
CONECT    6    1    4    8                                                  
CONECT    7    2    5    9                                                  
CONECT    8    3    6   10                                                  
CONECT    9    3    7   11                                                  
CONECT   10    8   11                                                       
CONECT   11    9   10                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for NP0000965 (2,5-Furandicarboxylic acid)

COMPND    HMDB0004812
HETATM    1  O1  UNL     1      -2.695  -1.417  -1.363  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.421  -0.750  -0.338  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.434  -0.493   0.556  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.051  -0.271  -0.122  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.595   0.480   0.967  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.744   0.676   0.709  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.064   0.054  -0.504  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.379   0.030  -1.130  1.00  0.00           C  
HETATM    9  O3  UNL     1       2.529  -0.563  -2.219  1.00  0.00           O  
HETATM   10  O4  UNL     1       3.445   0.658  -0.525  1.00  0.00           O  
HETATM   11  O5  UNL     1      -0.052  -0.479  -0.926  1.00  0.00           O  
HETATM   12  H1  UNL     1      -3.610  -1.016   1.393  1.00  0.00           H  
HETATM   13  H2  UNL     1      -1.187   0.810   1.799  1.00  0.00           H  
HETATM   14  H3  UNL     1       1.450   1.214   1.321  1.00  0.00           H  
HETATM   15  H4  UNL     1       3.435   1.067   0.380  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   12
CONECT    4    5    5   11
CONECT    5    6   13
CONECT    6    7    7   14
CONECT    7    8   11
CONECT    8    9    9   10
CONECT   10   15
END
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SMILES for NP0000965 (2,5-Furandicarboxylic acid)

OC(=O)C1=CC=C(O1)C(O)=O
Download

INCHI for NP0000965 (2,5-Furandicarboxylic acid)

InChI=1S/C6H4O5/c7-5(8)3-1-2-4(11-3)6(9)10/h1-2H,(H,7,8)(H,9,10)
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View in JSmol
Synonyms
ValueSource
2,5-DicarboxyfuranChEBI
Dehydromucic acidChEBI
Furane-alpha,alpha'-dicarboxylic acidChEBI
Furan-2,5-dicarboxylateKegg
DehydromucateGenerator
Furane-a,alpha'-dicarboxylateGenerator
Furane-a,alpha'-dicarboxylic acidGenerator
Furane-alpha,alpha'-dicarboxylateGenerator
Furane-α,alpha'-dicarboxylateGenerator
Furane-α,alpha'-dicarboxylic acidGenerator
Furan-2,5-dicarboxylic acidGenerator
2,5-FurandicarboxylateGenerator
FDCA CPDHMDB
(1,5-Dimethylhexyl)hydrazineHMDB
DehydroschleimsaeureHMDB
Furan 2,5-dicarboxylateHMDB
Furan 2,5-dicarboxylic acidHMDB
Furan-2,5-dicarbonsaeureHMDB
Furane-a,a'-dicarboxylateHMDB
Furane-a,a'-dicarboxylic acidHMDB
2,5-Furandicarboxylic acidChEBI
Chemical FormulaC6H4O5
Average Mass156.0930 Da
Monoisotopic Mass156.00587 Da
IUPAC Namefuran-2,5-dicarboxylic acid
Traditional Name2,5-furandicarboxylic acid
CAS Registry Number3238-40-2
SMILES
OC(=O)C1=CC=C(O1)C(O)=O
InChI Identifier
InChI=1S/C6H4O5/c7-5(8)3-1-2-4(11-3)6(9)10/h1-2H,(H,7,8)(H,9,10)
InChI KeyCHTHALBTIRVDBM-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, simulated)V.dorna832021-08-24View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, simulated)v.dorna83@yahoo.comNot AvailableNot Available2021-08-11View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Phomopsis velataLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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
  • Dicarboxylic acid or derivatives
  • Heteroaromatic compound
  • Oxacycle
  • 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 Point342 °CNot Available
Boiling Point419.20 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1 mg/mL at 18 °CNot Available
LogP-0.020 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility11.8 g/LALOGPS
logP0.66ALOGPS
logP0.27ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)-4.6ChemAxon
pKa (Strongest Basic)11.11ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area87.74 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity32.84 m³·mol⁻¹ChemAxon
Polarizability13.05 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0004812
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023423
KNApSAcK IDNot Available
Chemspider ID69178
KEGG Compound IDC20450
BioCyc IDCPD-14105
BiGG IDNot Available
Wikipedia Link2,5-Furandicarboxylic_acid
METLIN ID7076
PubChem Compound76720
PDB IDNot Available
ChEBI ID84212
Good Scents IDrw1435791
References
General References
  1. 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. [PubMed:4630229 ]