Np mrd loader

Showing NP-Card for 4-hydroxy-2H-chromen-2-one (NP0331897)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2023-09-28 20:01:37 UTC
Updated at2024-09-03 04:17:20 UTC
NP-MRD IDNP0331897
Natural Product DOIhttps://doi.org/10.57994/1003
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-hydroxy-2H-chromen-2-one
Description4-Hydroxy-2H-chromen-2-one, also known as 4-coumarinol or 4-hydroxy-2H-1-benzopyran-2-one, belongs to the class of organic compounds known as 4-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to C4-position the coumarin skeleton. 4-Hydroxy-2H-chromen-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa). A hydroxycoumarin that is coumarin in which the hydrogen at position 4 is replaced by a hydroxy group.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0331897 (4-hydroxy-2H-chromen-2-one)


  Mrv1652308231918412D          

 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  2  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  1  0  0  0  0
 10  7  1  0  0  0  0
 11  9  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 NP0331897 (4-hydroxy-2H-chromen-2-one)

     RDKit          3D

 18 19  0  0  0  0  0  0  0  0999 V2000
    2.9347   -2.4447    0.5031 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0405   -1.5583    0.3284 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4131   -0.2502    0.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4523    0.7481   -0.0473 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8245    2.0595   -0.2289 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1389    0.3531   -0.0471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9048    1.2715   -0.2335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2293    0.8885   -0.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4983   -0.4430   -0.0463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5209   -1.3853    0.1406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1724   -0.9737    0.1395 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7758   -1.8489    0.3150 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4459    0.0611    0.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2521    2.8541   -0.3751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6455    2.3180   -0.3800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0388    1.5786   -0.3768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5337   -0.8005   -0.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7343   -2.4280    0.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
  2 12  1  0
 12 11  1  0
 11 10  2  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  6  2  0
  6  4  1  0
  6 11  1  0
  5 14  1  0
  3 13  1  0
 10 18  1  0
  9 17  1  0
  8 16  1  0
  7 15  1  0
M  END
Download

3D SDF for NP0331897 (4-hydroxy-2H-chromen-2-one)


  Mrv1652308231918412D          

 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  2  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  1  0  0  0  0
 10  7  1  0  0  0  0
 11  9  2  0  0  0  0
 12  8  1  0  0  0  0
 12  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331897

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(=O)OC2=CC=CC=C12

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

> <INCHI_KEY>
VXIXUWQIVKSKSA-UHFFFAOYSA-N

> <FORMULA>
C9H6O3

> <MOLECULAR_WEIGHT>
162.144

> <EXACT_MASS>
162.031694053

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
15.242528371516123

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.01

> <JCHEM_LOGP>
1.029812716333333

> <ALOGPS_LOGS>
-1.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.295473229551473

> <JCHEM_PKA_STRONGEST_BASIC>
-7.043560009396393

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
43.440900000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.78e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-coumarin

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0331897 (4-hydroxy-2H-chromen-2-one)

Download
PDB for NP0331897 (4-hydroxy-2H-chromen-2-one)
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       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

Download
3D PDB for NP0331897 (4-hydroxy-2H-chromen-2-one)
Download
SMILES for NP0331897 (4-hydroxy-2H-chromen-2-one)
OC1=CC(=O)OC2=CC=CC=C12
Download
INCHI for NP0331897 (4-hydroxy-2H-chromen-2-one)
InChI=1S/C9H6O3/c10-7-5-9(11)12-8-4-2-1-3-6(7)8/h1-5,10H
Download
View in JSmol
Synonyms
ValueSource
4-CoumarinolChEBI
4-Hydroxy-2-chromenoneChEBI
4-Hydroxy-2H-1-benzopyran-2-oneChEBI
4-Hydroxy-2H-benzo[b]pyran-2-oneChEBI
Benzotetronic acidChEBI
BenzotetronateGenerator
4-Hydroxycoumarin (old)HMDB
4-OH CoumarinHMDB
4-HYDROXY-2H-chromen-2-oneChEBI
Chemical FormulaC9H6O3
Average Mass162.1440 Da
Monoisotopic Mass162.03169 Da
IUPAC Name4-hydroxy-2H-chromen-2-one
Traditional Name4-hydroxy-coumarin
CAS Registry NumberNot Available
SMILES
OC1=CC(=O)OC2=CC=CC=C12
InChI Identifier
InChI=1S/C9H6O3/c10-7-5-9(11)12-8-4-2-1-3-6(7)8/h1-5,10H
InChI KeyVXIXUWQIVKSKSA-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-09View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-09View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-09View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-09View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-09-28View Spectrum
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
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600, CD3OD, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-09View Spectrum
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 4-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to C4-position the coumarin skeleton.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassCoumarins and derivatives  
Sub ClassHydroxycoumarins  
Direct Parent4-hydroxycoumarins  
Alternative Parents
Substituents
  • 4-hydroxycoumarin
    • 

  • Benzopyran
    • 

  • 1-benzopyran
    • 

  • Pyranone
    • 

  • Pyran
    • 

  • Benzenoid
    • 

  • Heteroaromatic compound
    • 

  • Vinylogous acid
    • 

  • Lactone
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organic oxide
    • 

  • 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
logP1.01ALOGPS
logP1.03ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)5.3ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity43.44 m³·mol⁻¹ChemAxon
Polarizability15.24 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0137904  
DrugBank IDDB03410  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB093015  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC20414  
BioCyc IDCPD-12111  
BiGG IDNot Available
Wikipedia Link4-Hydroxycoumarin  
METLIN IDNot Available
PubChem Compound54682930  
PDB IDNot Available
ChEBI ID40070  
Good Scents IDNot Available
References
General References