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Showing NP-Card for Bikojic acid (NP0337713)

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Record Information
Version2.0
Created at2024-09-11 12:03:46 UTC
Updated at2024-09-11 12:03:47 UTC
NP-MRD IDNP0337713
Secondary Accession NumbersNone
Natural Product Identification
Common NameBikojic acid
DescriptionBikojic acid, also known as BGY-F or bikojate, belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone. Bikojic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Bikojic acid has been detected, but not quantified in, fats and oils. This could make bikojic acid a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0337713 (Bikojic acid)


  Mrv0541 05061307312D          

 20 21  0  0  0  0            999 V2000
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  2  0  0  0  0
  5  3  1  0  0  0  0
  6  2  2  0  0  0  0
  6  4  1  0  0  0  0
  7  1  1  0  0  0  0
  8  2  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  2  0  0  0  0
 12 10  2  0  0  0  0
 12 11  1  0  0  0  0
 13  3  1  0  0  0  0
 14  4  1  0  0  0  0
 15  7  2  0  0  0  0
 16  8  2  0  0  0  0
 17  9  1  0  0  0  0
 18 10  1  0  0  0  0
 19  5  1  0  0  0  0
 19 11  1  0  0  0  0
 20  6  1  0  0  0  0
 20 12  1  0  0  0  0
M  END
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3D MOL for NP0337713 (Bikojic acid)

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3D SDF for NP0337713 (Bikojic acid)

  Mrv0541 05061307312D          

 20 21  0  0  0  0            999 V2000
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  2  0  0  0  0
  5  3  1  0  0  0  0
  6  2  2  0  0  0  0
  6  4  1  0  0  0  0
  7  1  1  0  0  0  0
  8  2  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  2  0  0  0  0
 12 10  2  0  0  0  0
 12 11  1  0  0  0  0
 13  3  1  0  0  0  0
 14  4  1  0  0  0  0
 15  7  2  0  0  0  0
 16  8  2  0  0  0  0
 17  9  1  0  0  0  0
 18 10  1  0  0  0  0
 19  5  1  0  0  0  0
 19 11  1  0  0  0  0
 20  6  1  0  0  0  0
 20 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0337713

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1=CC(=O)C(O)=C(O1)C1=C(O)C(=O)C=C(CO)O1

> <INCHI_IDENTIFIER>
InChI=1S/C12H10O8/c13-3-5-1-7(15)9(17)11(19-5)12-10(18)8(16)2-6(4-14)20-12/h1-2,13-14,17-18H,3-4H2

> <INCHI_KEY>
SBAWSKBDCSMRPE-UHFFFAOYSA-N

> <FORMULA>
C12H10O8

> <MOLECULAR_WEIGHT>
282.203

> <EXACT_MASS>
282.037567296

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
25.472285027314303

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-hydroxy-2-[3-hydroxy-6-(hydroxymethyl)-4-oxo-4H-pyran-2-yl]-6-(hydroxymethyl)-4H-pyran-4-one

> <ALOGPS_LOGP>
-0.68

> <JCHEM_LOGP>
-1.4819595273333337

> <ALOGPS_LOGS>
-2.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.956821289502566

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.8905326607627195

> <JCHEM_PKA_STRONGEST_BASIC>
-3.085698413237351

> <JCHEM_POLAR_SURFACE_AREA>
133.52

> <JCHEM_REFRACTIVITY>
70.70340000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.29e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-2-[3-hydroxy-6-(hydroxymethyl)-4-oxopyran-2-yl]-6-(hydroxymethyl)pyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0337713 (Bikojic acid)
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PDB for NP0337713 (Bikojic acid)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -5.335   0.000   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1    5    7                                                       
CONECT    2    6    8                                                       
CONECT    3    5   13                                                       
CONECT    4    6   14                                                       
CONECT    5    1    3   19                                                  
CONECT    6    2    4   20                                                  
CONECT    7    1    9   15                                                  
CONECT    8    2   10   16                                                  
CONECT    9    7   11   17                                                  
CONECT   10    8   12   18                                                  
CONECT   11    9   12   19                                                  
CONECT   12   10   11   20                                                  
CONECT   13    3                                                            
CONECT   14    4                                                            
CONECT   15    7                                                            
CONECT   16    8                                                            
CONECT   17    9                                                            
CONECT   18   10                                                            
CONECT   19    5   11                                                       
CONECT   20    6   12                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

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3D PDB for NP0337713 (Bikojic acid)
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SMILES for NP0337713 (Bikojic acid)
OCC1=CC(=O)C(O)=C(O1)C1=C(O)C(=O)C=C(CO)O1
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INCHI for NP0337713 (Bikojic acid)
InChI=1S/C12H10O8/c13-3-5-1-7(15)9(17)11(19-5)12-10(18)8(16)2-6(4-14)20-12/h1-2,13-14,17-18H,3-4H2
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View in JSmol
Synonyms
ValueSource
BikojateGenerator
6,6'-Bis(5-hydroxy-2-hydroxymethyl-4H-pyran-4-one)HMDB
BGY-FHMDB
BGY-F compoundMeSH
Chemical FormulaC12H10O8
Average Mass282.2030 Da
Monoisotopic Mass282.03757 Da
IUPAC Name3-hydroxy-2-[3-hydroxy-6-(hydroxymethyl)-4-oxo-4H-pyran-2-yl]-6-(hydroxymethyl)-4H-pyran-4-one
Traditional Name3-hydroxy-2-[3-hydroxy-6-(hydroxymethyl)-4-oxopyran-2-yl]-6-(hydroxymethyl)pyran-4-one
CAS Registry NumberNot Available
SMILES
OCC1=CC(=O)C(O)=C(O1)C1=C(O)C(=O)C=C(CO)O1
InChI Identifier
InChI=1S/C12H10O8/c13-3-5-1-7(15)9(17)11(19-5)12-10(18)8(16)2-6(4-14)20-12/h1-2,13-14,17-18H,3-4H2
InChI KeySBAWSKBDCSMRPE-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPyrans  
Sub ClassPyranones and derivatives  
Direct ParentPyranones and derivatives  
Alternative Parents
Substituents
  • Pyranone
    • 

  • Heteroaromatic compound
    • 

  • Cyclic ketone
    • 

  • Oxacycle
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Aromatic alcohol
    • 

  • Primary alcohol
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
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
logP-0.68ALOGPS
logP-1.5ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)7.89ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area133.52 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity70.7 m³·mol⁻¹ChemAxon
Polarizability25.47 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0034034  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012274  
KNApSAcK IDNot Available
Chemspider ID30777040  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound89014314  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available