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Showing NP-Card for 8-hydroxycoumarin (NP0285212)

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Record Information
Version2.0
Created at2022-09-09 13:17:00 UTC
Updated at2022-09-09 13:17:00 UTC
NP-MRD IDNP0285212
Secondary Accession NumbersNone
Natural Product Identification
Common Name8-hydroxycoumarin
Description8-Hydroxy-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. 8-hydroxycoumarin is found in Murraya paniculata. 8-Hydroxy-2H-chromen-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0285212 (8-hydroxycoumarin)


  Mrv1652308231920582D          

 12 13  0  0  0  0            999 V2000
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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    0.8250    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    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
    0.0000    3.3000    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    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  5  4  2  0  0  0  0
  6  2  1  0  0  0  0
  6  4  1  0  0  0  0
  7  3  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
  9  7  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  2  0  0  0  0
 12  8  1  0  0  0  0
 12  9  1  0  0  0  0
M  END
Download

3D MOL for NP0285212 (8-hydroxycoumarin)

     RDKit          3D

 18 19  0  0  0  0  0  0  0  0999 V2000
    3.0849    2.1663   -0.1170 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2357    1.2446   -0.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6807   -0.0414    0.1027 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7389   -1.0400    0.1734 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3996   -0.6578    0.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6040   -1.6210    0.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9427   -1.3015    0.0615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3173    0.0194   -0.0933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3177    0.9654   -0.1562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6729    2.2999   -0.3118 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0209    0.6593   -0.0728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9665    1.5701   -0.1339 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7315   -0.3128    0.1715 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9715   -2.0811    0.2931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2825   -2.6667    0.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6892   -2.0783    0.1160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3676    0.2678   -0.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6361    2.6078   -0.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5 11  2  0
 11 12  1  0
 12  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
 11  9  1  0
  4  5  1  0
 10 18  1  0
  8 17  1  0
  7 16  1  0
  6 15  1  0
  3 13  1  0
  4 14  1  0
M  END
Download

3D SDF for NP0285212 (8-hydroxycoumarin)


  Mrv1652308231920582D          

 12 13  0  0  0  0            999 V2000
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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    0.8250    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    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
    0.0000    3.3000    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    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  5  4  2  0  0  0  0
  6  2  1  0  0  0  0
  6  4  1  0  0  0  0
  7  3  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
  9  7  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  2  0  0  0  0
 12  8  1  0  0  0  0
 12  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0285212

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=CC2=C1OC(=O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C9H6O3/c10-7-3-1-2-6-4-5-8(11)12-9(6)7/h1-5,10H

> <INCHI_KEY>
DPTUTXWBBUARQB-UHFFFAOYSA-N

> <FORMULA>
C9H6O3

> <MOLECULAR_WEIGHT>
162.1421

> <EXACT_MASS>
162.031694058

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
15.280367432094511

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8-hydroxy-2H-chromen-2-one

> <ALOGPS_LOGP>
1.70

> <JCHEM_LOGP>
2.1297942936666665

> <ALOGPS_LOGS>
-1.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.147009170648023

> <JCHEM_PKA_STRONGEST_BASIC>
-4.361547153026582

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
43.529500000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.39e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-hydroxychromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0285212 (8-hydroxycoumarin)

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PDB for NP0285212 (8-hydroxycoumarin)
HEADER    PROTEIN                                 23-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-AUG-19         0                                  
HETATM    1  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   2.310   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       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    6                                                       
CONECT    3    1    7                                                       
CONECT    4    5    6                                                       
CONECT    5    4    8                                                       
CONECT    6    2    4    9                                                  
CONECT    7    3    9   10                                                  
CONECT    8    5   11   12                                                  
CONECT    9    6    7   12                                                  
CONECT   10    7                                                            
CONECT   11    8                                                            
CONECT   12    8    9                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

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3D PDB for NP0285212 (8-hydroxycoumarin)
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SMILES for NP0285212 (8-hydroxycoumarin)
OC1=CC=CC2=C1OC(=O)C=C2
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INCHI for NP0285212 (8-hydroxycoumarin)
InChI=1S/C9H6O3/c10-7-3-1-2-6-4-5-8(11)12-9(6)7/h1-5,10H
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View in JSmol
SynonymsNot Available
Chemical FormulaC9H6O3
Average Mass162.1421 Da
Monoisotopic Mass162.03169 Da
IUPAC Name8-hydroxy-2H-chromen-2-one
Traditional Name8-hydroxychromen-2-one
CAS Registry NumberNot Available
SMILES
OC1=CC=CC2=C1OC(=O)C=C2
InChI Identifier
InChI=1S/C9H6O3/c10-7-3-1-2-6-4-5-8(11)12-9(6)7/h1-5,10H
InChI KeyDPTUTXWBBUARQB-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Murraya paniculataLOTUS Database
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
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Pyranone
    • 

  • Benzenoid
    • 

  • Pyran
    • 

  • Heteroaromatic compound
    • 

  • Lactone
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • 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
logP1.7ALOGPS
logP2.13ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)10.15ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity43.53 m³·mol⁻¹ChemAxon
Polarizability15.28 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0140949  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB093208  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound122783  
PDB ID8CM  
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]