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Showing NP-Card for 6,7,8-Trihydroxycoumarin (NP0063259)

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Record Information
Version2.0
Created at2022-04-28 07:42:37 UTC
Updated at2022-04-28 07:42:37 UTC
NP-MRD IDNP0063259
Secondary Accession NumbersNone
Natural Product Identification
Common Name6,7,8-Trihydroxycoumarin
Description6,7,8-Trihydroxy-2H-chromen-2-one belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton. 6,7,8-Trihydroxy-2H-chromen-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa). 6,7,8-Trihydroxy-2h-chromen-2-one is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 6,7-dihydroxy-2h-chromen-2-one. This aromatic-hydroxylation-of-fused-benzene-ring-pattern2 occurs in humans. 6,7,8-Trihydroxycoumarin is found in Fraxinus japonica Seringe Blume , Pelargonium reniforme and Pelargonium sidoides . It is generated by cyp1a2, cyp2b6, and cyp2c9 enzymes via an aromatic-hydroxylation-of-fused-benzene-ring-pattern2 reaction.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0063259 (6,7,8-Trihydroxycoumarin)


  Mrv1652308221903522D          

 14 15  0  0  0  0            999 V2000
    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
    2.8579    0.0000    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
    3.5724   -0.4125    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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  4  1  1  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  2  1  0  0  0  0
  7  5  2  0  0  0  0
  8  7  1  0  0  0  0
  9  4  1  0  0  0  0
  9  8  2  0  0  0  0
 10  5  1  0  0  0  0
 11  6  2  0  0  0  0
 12  7  1  0  0  0  0
 13  8  1  0  0  0  0
 14  6  1  0  0  0  0
 14  9  1  0  0  0  0
M  END
Download

3D MOL for NP0063259 (6,7,8-Trihydroxycoumarin)

     RDKit          3D

 20 21  0  0  0  0  0  0  0  0999 V2000
   -3.8746   -1.3566   -0.0273 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7867   -0.6920   -0.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9250    0.6783   -0.1629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7766    1.4477   -0.2365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5717    0.7873   -0.2353 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6054    1.5125   -0.3073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8400    0.8984   -0.3094 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0251    1.6549   -0.3833 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8872   -0.4673   -0.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1534   -1.0691   -0.2413 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7323   -1.2126   -0.1652 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8545   -2.5909   -0.0950 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5038   -0.5942   -0.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6177   -1.2972   -0.0943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9104    1.1498   -0.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8425    2.5334   -0.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5710    2.6032   -0.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9259    1.2353   -0.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1905   -2.0809   -0.1882 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0239   -3.1402   -0.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  5 13  1  0
  8 18  1  0
 10 19  1  0
 12 20  1  0
  3 15  1  0
  4 16  1  0
  6 17  1  0
M  END
Download

3D SDF for NP0063259 (6,7,8-Trihydroxycoumarin)


  Mrv1652308221903522D          

 14 15  0  0  0  0            999 V2000
    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
    2.8579    0.0000    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
    3.5724   -0.4125    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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  4  1  1  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  2  1  0  0  0  0
  7  5  2  0  0  0  0
  8  7  1  0  0  0  0
  9  4  1  0  0  0  0
  9  8  2  0  0  0  0
 10  5  1  0  0  0  0
 11  6  2  0  0  0  0
 12  7  1  0  0  0  0
 13  8  1  0  0  0  0
 14  6  1  0  0  0  0
 14  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0063259

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=C(O)C(O)=C2OC(=O)C=CC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H6O5/c10-5-3-4-1-2-6(11)14-9(4)8(13)7(5)12/h1-3,10,12-13H

> <INCHI_KEY>
NSDVPAHANCHBFV-UHFFFAOYSA-N

> <FORMULA>
C9H6O5

> <MOLECULAR_WEIGHT>
194.142

> <EXACT_MASS>
194.021523293

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
17.179523550081065

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,7,8-trihydroxy-2H-chromen-2-one

> <ALOGPS_LOGP>
1.29

> <JCHEM_LOGP>
1.5226636503333333

> <ALOGPS_LOGS>
-1.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.259460991773052

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.486004047560995

> <JCHEM_PKA_STRONGEST_BASIC>
-4.393874049594843

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
47.4913

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.48e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,7,8-trihydroxychromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0063259 (6,7,8-Trihydroxycoumarin)

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PDB for NP0063259 (6,7,8-Trihydroxycoumarin)
HEADER    PROTEIN                                 22-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-AUG-19         0                                  
HETATM    1  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -0.770   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       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2    4                                                       
CONECT    2    1    6                                                       
CONECT    3    4    5                                                       
CONECT    4    1    3    9                                                  
CONECT    5    3    7   10                                                  
CONECT    6    2   11   14                                                  
CONECT    7    5    8   12                                                  
CONECT    8    7    9   13                                                  
CONECT    9    4    8   14                                                  
CONECT   10    5                                                            
CONECT   11    6                                                            
CONECT   12    7                                                            
CONECT   13    8                                                            
CONECT   14    6    9                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

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3D PDB for NP0063259 (6,7,8-Trihydroxycoumarin)
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SMILES for NP0063259 (6,7,8-Trihydroxycoumarin)
OC1=C(O)C(O)=C2OC(=O)C=CC2=C1
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INCHI for NP0063259 (6,7,8-Trihydroxycoumarin)
InChI=1S/C9H6O5/c10-5-3-4-1-2-6(11)14-9(4)8(13)7(5)12/h1-3,10,12-13H
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View in JSmol
SynonymsNot Available
Chemical FormulaC9H6O5
Average Mass194.1420 Da
Monoisotopic Mass194.02152 Da
IUPAC Name6,7,8-trihydroxy-2H-chromen-2-one
Traditional Name6,7,8-trihydroxychromen-2-one
CAS Registry NumberNot Available
SMILES
OC1=C(O)C(O)=C2OC(=O)C=CC2=C1
InChI Identifier
InChI=1S/C9H6O5/c10-5-3-4-1-2-6(11)14-9(4)8(13)7(5)12/h1-3,10,12-13H
InChI KeyNSDVPAHANCHBFV-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Fraxinus japonica Seringe BlumePlant
Pelargonium reniformePlant
Pelargonium sidoidesPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassCoumarins and derivatives  
Sub ClassHydroxycoumarins  
Direct Parent7-hydroxycoumarins  
Alternative Parents
Substituents
  • 7-hydroxycoumarin
    • 

  • Benzopyran
    • 

  • 1-benzopyran
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Pyranone
    • 

  • Benzenoid
    • 

  • Pyran
    • 

  • Heteroaromatic compound
    • 

  • Lactone
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Polyol
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
logP1.29ALOGPS
logP1.52ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)7.49ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity47.49 m³·mol⁻¹ChemAxon
Polarizability17.18 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0132253  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9994589  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11819936  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available