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Showing NP-Card for 6,8-Dihydroxy-7-methoxycoumarin (NP0063079)

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Record Information
Version2.0
Created at2022-04-28 07:34:23 UTC
Updated at2022-04-28 07:34:23 UTC
NP-MRD IDNP0063079
Secondary Accession NumbersNone
Natural Product Identification
Common Name6,8-Dihydroxy-7-methoxycoumarin
Description6,8-Dihydroxy-7-methoxy-2H-chromen-2-one belongs to the class of organic compounds known as hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the coumarin skeleton. 6,8-Dihydroxy-7-methoxy-2H-chromen-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa). It is generated by cyp1a2, cyp2a6, cyp2b6, cyp2c9, and cyp2e1 enzymes via an aromatic-hydroxylation-of-fused-benzene-ring-pattern1 reaction. 6,8-Dihydroxy-7-methoxy-2h-chromen-2-one is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 8-hydroxy-7-methoxy-2h-chromen-2-one. 6,8-Dihydroxy-7-methoxycoumarin is found in Pelargonium sidoides . This aromatic-hydroxylation-of-fused-benzene-ring-pattern1 occurs in humans.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0063079 (6,8-Dihydroxy-7-methoxycoumarin)


  Mrv1652308221900402D          

 15 16  0  0  0  0            999 V2000
    4.2868   -2.4750    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
    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
    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
    3.5724   -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
    2.8579   -2.4750    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
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  5  2  1  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  3  1  0  0  0  0
  9  5  1  0  0  0  0
  9  8  2  0  0  0  0
 10  6  2  0  0  0  0
 10  8  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  2  0  0  0  0
 13  8  1  0  0  0  0
 14  1  1  0  0  0  0
 14 10  1  0  0  0  0
 15  7  1  0  0  0  0
 15  9  1  0  0  0  0
M  END
Download

3D MOL for NP0063079 (6,8-Dihydroxy-7-methoxycoumarin)

     RDKit          3D

 23 24  0  0  0  0  0  0  0  0999 V2000
   -3.4684   -0.2197    0.8258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7445   -0.1510   -0.3846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3801    0.1031   -0.3302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8853    1.3907   -0.3637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7946    2.4335   -0.4539 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4805    1.5813   -0.3065 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3638    0.5350   -0.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7312    0.6929   -0.1586 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5448   -0.4176   -0.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9946   -1.6827   -0.0402 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7606   -2.7017    0.0420 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7028   -1.7793   -0.0981 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8834   -0.7569   -0.1830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4880   -0.9642   -0.2398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9338   -2.2644   -0.2034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5563   -1.2764    1.1767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4692    0.2281    0.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9093    0.3210    1.6161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5330    3.4072   -0.4847 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8758    2.6031   -0.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1350    1.6917   -0.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6205   -0.3390   -0.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9304   -2.4346   -0.2437 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14  3  1  0
 13  7  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  5 19  1  0
  6 20  1  0
  8 21  1  0
  9 22  1  0
 15 23  1  0
M  END
Download

3D SDF for NP0063079 (6,8-Dihydroxy-7-methoxycoumarin)


  Mrv1652308221900402D          

 15 16  0  0  0  0            999 V2000
    4.2868   -2.4750    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
    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
    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
    3.5724   -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
    2.8579   -2.4750    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
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  5  2  1  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  3  1  0  0  0  0
  9  5  1  0  0  0  0
  9  8  2  0  0  0  0
 10  6  2  0  0  0  0
 10  8  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  2  0  0  0  0
 13  8  1  0  0  0  0
 14  1  1  0  0  0  0
 14 10  1  0  0  0  0
 15  7  1  0  0  0  0
 15  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0063079

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C2C=CC(=O)OC2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C10H8O5/c1-14-10-6(11)4-5-2-3-7(12)15-9(5)8(10)13/h2-4,11,13H,1H3

> <INCHI_KEY>
MUAREBTUSYHSDU-UHFFFAOYSA-N

> <FORMULA>
C10H8O5

> <MOLECULAR_WEIGHT>
208.169

> <EXACT_MASS>
208.037173358

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
19.137610416953777

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.69

> <JCHEM_LOGP>
1.668557706333333

> <ALOGPS_LOGS>
-1.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.531386472418049

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.939516981040203

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2027162256885005

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
51.97360000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.04e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,8-dihydroxy-7-methoxychromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0063079 (6,8-Dihydroxy-7-methoxycoumarin)

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PDB for NP0063079 (6,8-Dihydroxy-7-methoxycoumarin)
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       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -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  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000  -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       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2    3    5                                                       
CONECT    3    2    7                                                       
CONECT    4    5    6                                                       
CONECT    5    2    4    9                                                  
CONECT    6    4   10   11                                                  
CONECT    7    3   12   15                                                  
CONECT    8    9   10   13                                                  
CONECT    9    5    8   15                                                  
CONECT   10    6    8   14                                                  
CONECT   11    6                                                            
CONECT   12    7                                                            
CONECT   13    8                                                            
CONECT   14    1   10                                                       
CONECT   15    7    9                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

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3D PDB for NP0063079 (6,8-Dihydroxy-7-methoxycoumarin)
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SMILES for NP0063079 (6,8-Dihydroxy-7-methoxycoumarin)
COC1=C(O)C=C2C=CC(=O)OC2=C1O
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INCHI for NP0063079 (6,8-Dihydroxy-7-methoxycoumarin)
InChI=1S/C10H8O5/c1-14-10-6(11)4-5-2-3-7(12)15-9(5)8(10)13/h2-4,11,13H,1H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC10H8O5
Average Mass208.1690 Da
Monoisotopic Mass208.03717 Da
IUPAC Name6,8-dihydroxy-7-methoxy-2H-chromen-2-one
Traditional Name6,8-dihydroxy-7-methoxychromen-2-one
CAS Registry NumberNot Available
SMILES
COC1=C(O)C=C2C=CC(=O)OC2=C1O
InChI Identifier
InChI=1S/C10H8O5/c1-14-10-6(11)4-5-2-3-7(12)15-9(5)8(10)13/h2-4,11,13H,1H3
InChI KeyMUAREBTUSYHSDU-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
Pelargonium sidoidesPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the coumarin skeleton.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassCoumarins and derivatives  
Sub ClassHydroxycoumarins  
Direct ParentHydroxycoumarins  
Alternative Parents
Substituents
  • Hydroxycoumarin
    • 

  • Benzopyran
    • 

  • 1-benzopyran
    • 

  • Anisole
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Alkyl aryl ether
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • Pyranone
    • 

  • Benzenoid
    • 

  • Pyran
    • 

  • Heteroaromatic compound
    • 

  • Lactone
    • 

  • Ether
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • 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
logP1.69ALOGPS
logP1.67ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)9.94ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity51.97 m³·mol⁻¹ChemAxon
Polarizability19.14 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0130546  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID809093  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound928135  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available