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Showing NP-Card for Isourolithin A (NP0084140)

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Record Information
Version2.0
Created at2022-04-29 04:57:51 UTC
Updated at2022-04-29 04:57:51 UTC
NP-MRD IDNP0084140
Secondary Accession NumbersNone
Natural Product Identification
Common NameIsourolithin A
Description3,9-Dihydroxy-6H-benzo[c]chromen-6-one 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). Isourolithin A is found in Punica granatum and Trogopterus xanthipes. 3,9-Dihydroxy-6H-benzo[c]chromen-6-one is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0084140 (Isourolithin A)


  Mrv1652311121915542D          

 17 19  0  0  0  0            999 V2000
   -1.0326    1.2530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2076    1.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2049    0.5385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0299    0.5385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4423    1.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0299    1.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2049    1.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2674    1.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6799    0.5385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5049    0.5385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9174    1.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5049    1.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6799    1.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2674   -0.1760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6799   -0.8904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4423   -0.1760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9174    2.6819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
  4 16  1  0  0  0  0
 12 17  1  0  0  0  0
M  END
Download

3D MOL for NP0084140 (Isourolithin A)

     RDKit          3D

 25 27  0  0  0  0  0  0  0  0999 V2000
    0.7145   -3.4322    1.0852 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2554   -2.3023    0.7764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9925   -1.9727    0.8614 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4474   -0.7885    0.5336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8079   -0.4962    0.6489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3316    0.7332    0.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7006    0.9891    0.4457 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4498    1.6970   -0.1468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0969    1.4531   -0.2773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    0.2183    0.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7472   -0.0920   -0.0462 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6209    0.8475   -0.5004 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9714    0.5310   -0.6059 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9156    1.4439   -1.0622 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3887   -0.7309   -0.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5097   -1.6720    0.2095 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1751   -1.3749    0.3191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4828   -1.2681    1.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2509    0.7681   -0.3989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8863    2.6538   -0.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5005    2.2631   -0.6442 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2929    1.8244   -0.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7106    2.3764   -1.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4276   -0.9848   -0.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8214   -2.6843    0.5018 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4 10  2  0
 10  9  1  0
  9  8  2  0
 10 11  1  0
 11 17  2  0
 17 16  1  0
 16 15  2  0
 15 13  1  0
 13 14  1  0
 13 12  2  0
 17  2  1  0
  2  1  2  0
  2  3  1  0
  8  6  1  0
 12 11  1  0
  3  4  1  0
  7 19  1  0
  5 18  1  0
  9 21  1  0
  8 20  1  0
 16 25  1  0
 15 24  1  0
 14 23  1  0
 12 22  1  0
M  END
Download

3D SDF for NP0084140 (Isourolithin A)


  Mrv1652311121915542D          

 17 19  0  0  0  0            999 V2000
   -1.0326    1.2530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2076    1.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2049    0.5385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0299    0.5385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4423    1.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0299    1.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2049    1.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2674    1.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6799    0.5385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5049    0.5385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9174    1.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5049    1.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6799    1.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2674   -0.1760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6799   -0.8904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4423   -0.1760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9174    2.6819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
  4 16  1  0  0  0  0
 12 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0084140

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC2=C(C=C1)C1=C(C=CC(O)=C1)C(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C13H8O4/c14-7-2-4-10-11(5-7)9-3-1-8(15)6-12(9)17-13(10)16/h1-6,14-15H

> <INCHI_KEY>
WDGSXHQNUPZEHA-UHFFFAOYSA-N

> <FORMULA>
C13H8O4

> <MOLECULAR_WEIGHT>
228.203

> <EXACT_MASS>
228.042258738

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
22.211138825781212

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,9-dihydroxy-6H-benzo[c]chromen-6-one

> <ALOGPS_LOGP>
2.21

> <JCHEM_LOGP>
2.318196798

> <ALOGPS_LOGS>
-2.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.426068758184085

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.544547827031298

> <JCHEM_PKA_STRONGEST_BASIC>
-6.085422647906854

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
60.90090000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.67e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,9-dihydroxybenzo[c]chromen-6-one

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0084140 (Isourolithin A)

Download
PDB for NP0084140 (Isourolithin A)
HEADER    PROTEIN                                 12-NOV-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-NOV-19         0                                  
HETATM    1  O   UNK     0      -1.928   2.339   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.388   2.339   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.382   1.005   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.922   1.005   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.692   2.339   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.922   3.673   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.382   3.673   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.232   2.339   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.002   1.005   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.542   1.005   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.312   2.339   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.542   3.673   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.002   3.673   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.232  -0.329   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.002  -1.662   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.692  -0.329   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       7.312   5.006   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   16                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    5    9   13                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12    8                                                       
CONECT   14    9   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    4                                                       
CONECT   17   12                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

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3D PDB for NP0084140 (Isourolithin A)
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SMILES for NP0084140 (Isourolithin A)
OC1=CC2=C(C=C1)C1=C(C=CC(O)=C1)C(=O)O2
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INCHI for NP0084140 (Isourolithin A)
InChI=1S/C13H8O4/c14-7-2-4-10-11(5-7)9-3-1-8(15)6-12(9)17-13(10)16/h1-6,14-15H
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View in JSmol
Synonyms
ValueSource
3,9-dihydroxy-urolithin
isourolithin A
Chemical FormulaC13H8O4
Average Mass228.2030 Da
Monoisotopic Mass228.04226 Da
IUPAC Name3,9-dihydroxy-6H-benzo[c]chromen-6-one
Traditional Name3,9-dihydroxybenzo[c]chromen-6-one
CAS Registry NumberNot Available
SMILES
OC1=CC2=C(C=C1)C1=C(C=CC(O)=C1)C(=O)O2
InChI Identifier
InChI=1S/C13H8O4/c14-7-2-4-10-11(5-7)9-3-1-8(15)6-12(9)17-13(10)16/h1-6,14-15H
InChI KeyWDGSXHQNUPZEHA-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
Punica granatumPlant
Trogopterus xanthipesLOTUS Database
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
  • Coumarin
    • 

  • Isocoumarin
    • 

  • Benzopyran
    • 

  • 2-benzopyran
    • 

  • 1-benzopyran
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Pyranone
    • 

  • Benzenoid
    • 

  • Pyran
    • 

  • Heteroaromatic compound
    • 

  • Lactone
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen 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
logP2.21ALOGPS
logP2.32ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)7.54ChemAxon
pKa (Strongest Basic)-6.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity60.9 m³·mol⁻¹ChemAxon
Polarizability22.21 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0142418  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB093368  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10376459  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available