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Showing NP-Card for 4,8-dihydroxy-3,4-dihydro-2h-naphthalen-1-one (NP0260769)

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Record Information
Version2.0
Created at2022-09-08 03:01:33 UTC
Updated at2022-09-08 03:01:34 UTC
NP-MRD IDNP0260769
Secondary Accession NumbersNone
Natural Product Identification
Common Name4,8-dihydroxy-3,4-dihydro-2h-naphthalen-1-one
Description(S)-Isosclerone belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane (S)-Isosclerone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (S)-Isosclerone has been detected, but not quantified in, nuts. 4,8-dihydroxy-3,4-dihydro-2h-naphthalen-1-one is found in Aspergillus diversus, Aspergillus fumigatus, Colletotrichum gloeosporioides, Cytospora eucalypticola, Diplogelasinospora grovesii, Engelhardia roxburghiana, Garcinia atroviridis, Juglans mandshurica, Juglans regia, Pyricularia grisea, Sclerotinia sclerotiorum and Trichocladium griseum. This could make (S)-isosclerone a potential biomarker for the consumption of these foods.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0260769 (4,8-dihydroxy-3,4-dihydro-2h-naphthalen-1-one)


  Mrv0541 05061310362D          

 13 14  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
    1.4289    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
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    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
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    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
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    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  1  0  0  0  0
  6  2  1  0  0  0  0
  7  4  1  0  0  0  0
  7  6  1  0  0  0  0
  8  3  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 10  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  2  0  0  0  0
M  END
Download

3D MOL for NP0260769 (4,8-dihydroxy-3,4-dihydro-2h-naphthalen-1-one)

     RDKit          3D

 23 24  0  0  0  0  0  0  0  0999 V2000
   -0.0218    2.6776    0.6270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3765    1.6192    0.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6865    1.3934   -0.5906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3014    0.1205   -0.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3894   -1.0428    0.0013 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7726   -1.7714    1.1518 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0438   -0.7546   -0.0089 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9078   -1.8233   -0.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2845   -1.6234   -0.0527 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8149   -0.3532   -0.0325 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9447    0.7360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4604    1.9831    0.0186 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5896    0.5223    0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4112    2.2210   -0.3337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6001    1.4294   -1.7050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1571   -0.1479   -0.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8080    0.3576    0.8720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5841   -1.7610   -0.8491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4773   -1.2340    1.9223 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5689   -2.8500   -0.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9853   -2.4624   -0.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8681   -0.1230   -0.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1179    2.8867    0.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 13  1  0
 13  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  7  5  1  0
 11 13  1  0
  6 19  1  0
  5 18  1  6
  4 16  1  0
  4 17  1  0
  3 14  1  0
  3 15  1  0
  8 20  1  0
  9 21  1  0
 10 22  1  0
 12 23  1  0
M  END
Download

3D SDF for NP0260769 (4,8-dihydroxy-3,4-dihydro-2h-naphthalen-1-one)


  Mrv0541 05061310362D          

 13 14  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
    1.4289    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
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    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
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    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
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    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  1  0  0  0  0
  6  2  1  0  0  0  0
  7  4  1  0  0  0  0
  7  6  1  0  0  0  0
  8  3  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 10  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0260769

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1CCC(=O)C2=C1C=CC=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O3/c11-7-4-5-9(13)10-6(7)2-1-3-8(10)12/h1-3,7,11-12H,4-5H2

> <INCHI_KEY>
ZXYYTDCENDYKBR-UHFFFAOYSA-N

> <FORMULA>
C10H10O3

> <MOLECULAR_WEIGHT>
178.1846

> <EXACT_MASS>
178.062994186

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
17.823674283477672

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,8-dihydroxy-1,2,3,4-tetrahydronaphthalen-1-one

> <ALOGPS_LOGP>
0.70

> <JCHEM_LOGP>
1.3967482796666668

> <ALOGPS_LOGS>
-1.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.325448703108634

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.79664148009184

> <JCHEM_PKA_STRONGEST_BASIC>
-3.144565390501521

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
47.823100000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.39e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,8-dihydroxy-3,4-dihydro-2H-naphthalen-1-one

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0260769 (4,8-dihydroxy-3,4-dihydro-2h-naphthalen-1-one)

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PDB for NP0260769 (4,8-dihydroxy-3,4-dihydro-2h-naphthalen-1-one)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   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       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    6                                                       
CONECT    3    1    8                                                       
CONECT    4    5    7                                                       
CONECT    5    4    9                                                       
CONECT    6    2    7   10                                                  
CONECT    7    4    6   11                                                  
CONECT    8    3   10   12                                                  
CONECT    9    5   10   13                                                  
CONECT   10    6    8    9                                                  
CONECT   11    7                                                            
CONECT   12    8                                                            
CONECT   13    9                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

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3D PDB for NP0260769 (4,8-dihydroxy-3,4-dihydro-2h-naphthalen-1-one)
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SMILES for NP0260769 (4,8-dihydroxy-3,4-dihydro-2h-naphthalen-1-one)
OC1CCC(=O)C2=C1C=CC=C2O
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INCHI for NP0260769 (4,8-dihydroxy-3,4-dihydro-2h-naphthalen-1-one)
InChI=1S/C10H10O3/c11-7-4-5-9(13)10-6(7)2-1-3-8(10)12/h1-3,7,11-12H,4-5H2
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Synonyms
ValueSource
(4S)-4,8-Dihydroxy-alpha-tetraloneHMDB
Chemical FormulaC10H10O3
Average Mass178.1846 Da
Monoisotopic Mass178.06299 Da
IUPAC Name4,8-dihydroxy-1,2,3,4-tetrahydronaphthalen-1-one
Traditional Name4,8-dihydroxy-3,4-dihydro-2H-naphthalen-1-one
CAS Registry NumberNot Available
SMILES
OC1CCC(=O)C2=C1C=CC=C2O
InChI Identifier
InChI=1S/C10H10O3/c11-7-4-5-9(13)10-6(7)2-1-3-8(10)12/h1-3,7,11-12H,4-5H2
InChI KeyZXYYTDCENDYKBR-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
Aspergillus diversusLOTUS Database
Aspergillus fumigatusLOTUS Database
Colletotrichum gloeosporioidesLOTUS Database
Cytospora eucalypticolaLOTUS Database
Diplogelasinospora grovesiiLOTUS Database
Engelhardia roxburghianaLOTUS Database
Garcinia atroviridisLOTUS Database
Juglans mandshuricaLOTUS Database
Juglans regiaLOTUS Database
Magnaporthe griseaLOTUS Database
Sclerotinia sclerotiorumLOTUS Database
Trichocladium griseumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassTetralins  
Sub ClassNot Available
Direct ParentTetralins  
Alternative Parents
Substituents
  • Tetralin
    • 

  • Aryl alkyl ketone
    • 

  • Aryl ketone
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Vinylogous acid
    • 

  • Secondary alcohol
    • 

  • Ketone
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic 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
logP0.7ALOGPS
logP1.4ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)9.8ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity47.82 m³·mol⁻¹ChemAxon
Polarizability17.82 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0038712  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB018120  
KNApSAcK IDC00031466  
Chemspider ID8617670  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10442251  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]