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Showing NP-Card for (3s,4s)-3,4,6,8-tetrahydroxy-3,4-dihydro-2h-naphthalen-1-one (NP0226716)

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Record Information
Version2.0
Created at2022-09-06 05:50:47 UTC
Updated at2022-09-06 05:50:47 UTC
NP-MRD IDNP0226716
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3s,4s)-3,4,6,8-tetrahydroxy-3,4-dihydro-2h-naphthalen-1-one
Description4-Hydroxyscytalone 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. (3s,4s)-3,4,6,8-tetrahydroxy-3,4-dihydro-2h-naphthalen-1-one is found in Leptosphaeria maculans and Verticillium dahliae. (3s,4s)-3,4,6,8-tetrahydroxy-3,4-dihydro-2h-naphthalen-1-one was first documented in 2009 (PMID: 23983534). Based on a literature review a small amount of articles have been published on 4-Hydroxyscytalone (PMID: 35850839) (PMID: 33266016).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0226716 ((3s,4s)-3,4,6,8-tetrahydroxy-3,4-dihydro-2h-naphthalen-1-one)


  Mrv1652309062207502D          

 15 16  0  0  1  0            999 V2000
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   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
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   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   -1.6500    0.0000 C   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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
  8 15  1  0  0  0  0
  2 15  1  0  0  0  0
M  END
Download

3D MOL for NP0226716 ((3s,4s)-3,4,6,8-tetrahydroxy-3,4-dihydro-2h-naphthalen-1-one)

     RDKit          3D

 25 26  0  0  0  0  0  0  0  0999 V2000
   -0.8993    2.7710    0.9605 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9567    1.5891    0.4922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3052    1.0194    0.2579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1909   -0.3775   -0.3124 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4056   -1.0252   -0.1308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -1.1810    0.3814 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1937   -2.4917   -0.0755 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1804   -0.5537    0.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3387   -1.2328   -0.1418 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5417   -0.5875   -0.3616 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7223   -1.2658   -0.6467 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5791    0.7865   -0.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4216    1.5134   -0.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4663    2.8828    0.0493 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2497    0.8238    0.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7998    0.9567    1.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8787    1.6720   -0.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9938   -0.3361   -1.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2536   -1.9881    0.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3069   -1.1902    1.4747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6137   -2.6506   -0.8607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3143   -2.2978   -0.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2837   -1.5269    0.1634 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5192    1.2898   -0.4684 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3078    3.4004   -0.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 15  1  0
 15 13  2  0
 13 14  1  0
 13 12  1  0
 12 10  2  0
 10 11  1  0
 10  9  1  0
  9  8  2  0
  8  6  1  0
  6  7  1  0
  6  4  1  0
  8 15  1  0
  5 19  1  0
  4 18  1  6
  3 16  1  0
  3 17  1  0
 14 25  1  0
 12 24  1  0
 11 23  1  0
  9 22  1  0
  6 20  1  1
  7 21  1  0
M  END
Download

3D SDF for NP0226716 ((3s,4s)-3,4,6,8-tetrahydroxy-3,4-dihydro-2h-naphthalen-1-one)


  Mrv1652309062207502D          

 15 16  0  0  1  0            999 V2000
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   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
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   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   -1.6500    0.0000 C   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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
  8 15  1  0  0  0  0
  2 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0226716

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1CC(=O)C2=C(O)C=C(O)C=C2[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O5/c11-4-1-5-9(6(12)2-4)7(13)3-8(14)10(5)15/h1-2,8,10-12,14-15H,3H2/t8-,10-/m0/s1

> <INCHI_KEY>
BHKWJBLOULPVEY-WPRPVWTQSA-N

> <FORMULA>
C10H10O5

> <MOLECULAR_WEIGHT>
210.185

> <EXACT_MASS>
210.052823422

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
19.632104769948214

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,4S)-3,4,6,8-tetrahydroxy-1,2,3,4-tetrahydronaphthalen-1-one

> <JCHEM_LOGP>
0.17418681099999994

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.321483331293024

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.681559990521737

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3134497972462214

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
51.0115

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4S)-3,4,6,8-tetrahydroxy-3,4-dihydro-2H-naphthalen-1-one

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0226716 ((3s,4s)-3,4,6,8-tetrahydroxy-3,4-dihydro-2h-naphthalen-1-one)

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PDB for NP0226716 ((3s,4s)-3,4,6,8-tetrahydroxy-3,4-dihydro-2h-naphthalen-1-one)
HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    8    2                                                  
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

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3D PDB for NP0226716 ((3s,4s)-3,4,6,8-tetrahydroxy-3,4-dihydro-2h-naphthalen-1-one)
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SMILES for NP0226716 ((3s,4s)-3,4,6,8-tetrahydroxy-3,4-dihydro-2h-naphthalen-1-one)
O[C@H]1CC(=O)C2=C(O)C=C(O)C=C2[C@@H]1O
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INCHI for NP0226716 ((3s,4s)-3,4,6,8-tetrahydroxy-3,4-dihydro-2h-naphthalen-1-one)
InChI=1S/C10H10O5/c11-4-1-5-9(6(12)2-4)7(13)3-8(14)10(5)15/h1-2,8,10-12,14-15H,3H2/t8-,10-/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC10H10O5
Average Mass210.1850 Da
Monoisotopic Mass210.05282 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
O[C@H]1CC(=O)C2=C(O)C=C(O)C=C2[C@@H]1O
InChI Identifier
InChI=1S/C10H10O5/c11-4-1-5-9(6(12)2-4)7(13)3-8(14)10(5)15/h1-2,8,10-12,14-15H,3H2/t8-,10-/m0/s1
InChI KeyBHKWJBLOULPVEY-WPRPVWTQSA-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
Leptosphaeria maculansLOTUS Database
Verticillium dahliaeLOTUS 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
    • 

  • Phenol
    • 

  • Vinylogous acid
    • 

  • 1,2-diol
    • 

  • Ketone
    • 

  • Secondary alcohol
    • 

  • Polyol
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organic oxide
    • 

  • 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
logP0.17ChemAxon
pKa (Strongest Acidic)7.68ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Rotatable Bond Count0ChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID34543015  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound71588318  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Yu YH, Chen JY, Yi WT, Li MM, Li X, Zeng HT, Yuan T: [Secondary metabolites of endophyte Hypoxylon sp. HD-2014 from Uncaria rhynchophylla]. Zhongguo Zhong Yao Za Zhi. 2022 Jul;47(14):3816-3821. doi: 10.19540/j.cnki.cjcmm.20220225.201. [PubMed:35850839  ] 
  2. Girich EV, Yurchenko AN, Smetanina OF, Trinh PTH, Ngoc NTD, Pivkin MV, Popov RS, Pislyagin EA, Menchinskaya ES, Chingizova EA, Afiyatullov SS, Yurchenko EA: Neuroprotective Metabolites from Vietnamese Marine Derived Fungi of Aspergillus and Penicillium Genera. Mar Drugs. 2020 Nov 30;18(12):608. doi: 10.3390/md18120608. [PubMed:33266016  ] 
  3. Jang YW, Lee IK, Kim YS, Seok SJ, Yu SH, Yun BS: Chemical Constituents of the Fruiting Body of Xylaria polymorpha. Mycobiology. 2009 Sep;37(3):207-10. doi: 10.4489/MYCO.2009.37.3.207. Epub 2009  Sep 30. [PubMed:23983534  ] 
  4. LOTUS database [Link]