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Showing NP-Card for 4-Hydroxy-2H-1-benzopyran-2-one (NP0333934)

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Record Information
Version2.0
Created at2024-09-09 21:19:56 UTC
Updated at2024-09-09 21:19:56 UTC
NP-MRD IDNP0333934
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Hydroxy-2H-1-benzopyran-2-one
Description4-Hydroxycoumarin is an important fungal metabolite from the precursor coumarin, and its production leads to further fermentative production of the natural anticoagulant dicoumarol. 4-Hydroxy-2H-1-benzopyran-2-one is found in beer and grape wine.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0333934 (4-Hydroxy-2H-1-benzopyran-2-one)


  Mrv1652305221920152D          

 12 13  0  0  0  0            999 V2000
    1.4289    0.8250    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
    2.1434    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
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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
  4  2  1  0  0  0  0
  6  3  2  0  0  0  0
  7  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  4  2  0  0  0  0
  8  6  1  0  0  0  0
  9  5  2  0  0  0  0
 10  7  2  0  0  0  0
 11  9  1  0  0  0  0
 12  8  1  0  0  0  0
 12  9  1  0  0  0  0
M  END
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3D MOL for NP0333934 (4-Hydroxy-2H-1-benzopyran-2-one)

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3D SDF for NP0333934 (4-Hydroxy-2H-1-benzopyran-2-one)

  Mrv1652305221920152D          

 12 13  0  0  0  0            999 V2000
    1.4289    0.8250    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
    2.1434    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
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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
  4  2  1  0  0  0  0
  6  3  2  0  0  0  0
  7  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  4  2  0  0  0  0
  8  6  1  0  0  0  0
  9  5  2  0  0  0  0
 10  7  2  0  0  0  0
 11  9  1  0  0  0  0
 12  8  1  0  0  0  0
 12  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333934

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(=O)C2=CC=CC=C2O1

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

> <INCHI_KEY>
OWBBAPRUYLEWRR-UHFFFAOYSA-N

> <FORMULA>
C9H6O3

> <MOLECULAR_WEIGHT>
162.144

> <EXACT_MASS>
162.031694053

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
15.322089662670098

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxy-4H-chromen-4-one

> <ALOGPS_LOGP>
0.75

> <JCHEM_LOGP>
1.8054621266666664

> <ALOGPS_LOGS>
-1.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.566893062815414

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.476946968368113

> <JCHEM_PKA_STRONGEST_BASIC>
-5.512864169633001

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
52.566600000000015

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.55e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxycoumarin

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0333934 (4-Hydroxy-2H-1-benzopyran-2-one)
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PDB for NP0333934 (4-Hydroxy-2H-1-benzopyran-2-one)
HEADER    PROTEIN                                 22-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-19         0                                  
HETATM    1  C   UNK     0       2.667   1.540   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       4.001   2.310   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       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   1.540   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   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    6                                                       
CONECT    4    2    8                                                       
CONECT    5    7    9                                                       
CONECT    6    3    7    8                                                  
CONECT    7    5    6   10                                                  
CONECT    8    4    6   12                                                  
CONECT    9    5   11   12                                                  
CONECT   10    7                                                            
CONECT   11    9                                                            
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 NP0333934 (4-Hydroxy-2H-1-benzopyran-2-one)
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SMILES for NP0333934 (4-Hydroxy-2H-1-benzopyran-2-one)
OC1=CC(=O)C2=CC=CC=C2O1
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INCHI for NP0333934 (4-Hydroxy-2H-1-benzopyran-2-one)
InChI=1S/C9H6O3/c10-7-5-9(11)12-8-4-2-1-3-6(7)8/h1-5,11H
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View in JSmol
SynonymsNot Available
Chemical FormulaC9H6O3
Average Mass162.1440 Da
Monoisotopic Mass162.03169 Da
IUPAC Name2-hydroxy-4H-chromen-4-one
Traditional Name4-hydroxycoumarin
CAS Registry NumberNot Available
SMILES
OC1=CC(=O)C2=CC=CC=C2O1
InChI Identifier
InChI=1S/C9H6O3/c10-7-5-9(11)12-8-4-2-1-3-6(7)8/h1-5,11H
InChI KeyOWBBAPRUYLEWRR-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 coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassCoumarins and derivatives  
Sub ClassNot Available
Direct ParentCoumarins and derivatives  
Alternative Parents
Substituents
  • Chromone
    • 

  • Coumarin
    • 

  • Benzopyran
    • 

  • 1-benzopyran
    • 

  • Pyranone
    • 

  • Pyran
    • 

  • Benzenoid
    • 

  • Heteroaromatic compound
    • 

  • Vinylogous acid
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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
logP0.75ALOGPS
logP1.81ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)5.48ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity52.57 m³·mol⁻¹ChemAxon
Polarizability15.32 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB010971  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14101  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available