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Showing NP-Card for cis-1,2-dihydronaphthalene-1,2-diol (NP0002834)

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Record Information
Version1.0
Created at2020-11-23 19:41:36 UTC
Updated at2021-08-12 19:52:16 UTC
NP-MRD IDNP0002834
Secondary Accession NumbersNone
Natural Product Identification
Common Namecis-1,2-dihydronaphthalene-1,2-diol
Provided ByBMRBBMRB logo
Description(1R, 2S)-cis 1,2 dihydroxy-1,2-dihydronaphthalene is also known as (1R,2S)-1,2-dihydronaphthalene-1,2-diol. It was first documented in 2008 (PMID: 17984079). Based on a literature review very few articles have been published on (1R, 2S)-cis 1,2 dihydroxy-1,2-dihydronaphthalene.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002834 (cis-1,2-dihydronaphthalene-1,2-diol)

NDH
  Mrv0541 02241213582D          

 14 15  0  0  0  0            999 V2000
   -0.4602    1.4532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4602    0.6282    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1747    0.2157    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8891    0.6282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1747   -0.6093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4602   -1.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2543   -0.6093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2543    0.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9687    0.6282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9687   -1.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6832   -0.6093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6832    0.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0353    0.7296    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3744    0.7644    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  2  8  1  0  0  0  0
  2 13  1  1  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  3 14  1  1  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 12  2  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
M  END
Download

3D MOL for NP0002834 (cis-1,2-dihydronaphthalene-1,2-diol)

NP0002834
     RDKit          3D

 22 23  0  0  0  0  0  0  0  0999 V2000
   -3.2181   -0.5015    0.3403 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8658   -0.8054    0.6591 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3115   -1.7591   -0.2881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1371   -1.6140   -0.8432 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7399   -0.4835   -0.5759 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9984   -0.3868   -1.1742 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8225    0.6753   -0.8898 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3462    1.6113   -0.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1128    1.5171    0.5812 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2544    0.4434    0.3064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0735    0.3872    0.9353 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8631    1.4962    0.4514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8331   -1.1077    0.8231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9044   -1.3833    1.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8837   -2.6697   -0.5810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2429   -2.3553   -1.5485 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3166   -1.1527   -1.8604 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8046    0.8185   -1.3108 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0013    2.4659    0.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7349    2.2586    1.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9543    0.5782    2.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3298    1.9674   -0.2561 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11  2  1  0
 10  5  1  0
  1 13  1  0
  2 14  1  1
  3 15  1  0
  4 16  1  0
  6 17  1  0
  7 18  1  0
  8 19  1  0
  9 20  1  0
 11 21  1  1
 12 22  1  0
M  END
Download

3D SDF for NP0002834 (cis-1,2-dihydronaphthalene-1,2-diol)

NDH
  Mrv0541 02241213582D          

 14 15  0  0  0  0            999 V2000
   -0.4602    1.4532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4602    0.6282    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1747    0.2157    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8891    0.6282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1747   -0.6093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4602   -1.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2543   -0.6093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2543    0.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9687    0.6282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9687   -1.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6832   -0.6093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6832    0.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0353    0.7296    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3744    0.7644    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  2  8  1  0  0  0  0
  2 13  1  1  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  3 14  1  1  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 12  2  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0002834

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(O)C=CC2=C(C=CC=C2)[C@@]1([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O2/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-6,9-12H/t9-,10+/m0/s1

> <INCHI_KEY>
QPUHWUSUBHNZCG-VHSXEESVSA-N

> <FORMULA>
C10H10O2

> <MOLECULAR_WEIGHT>
162.1852

> <EXACT_MASS>
162.068079564

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
16.888569251050434

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S)-1,2-dihydronaphthalene-1,2-diol

> <ALOGPS_LOGP>
0.63

> <JCHEM_LOGP>
0.9964711513333333

> <ALOGPS_LOGS>
-0.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.72139267788548

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.200535653234656

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3681565168836514

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
47.37980000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.25e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S)-1,2-dihydronaphthalene-1,2-diol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0002834 (cis-1,2-dihydronaphthalene-1,2-diol)

NP0002834
     RDKit          3D

 22 23  0  0  0  0  0  0  0  0999 V2000
   -3.2181   -0.5015    0.3403 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8658   -0.8054    0.6591 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3115   -1.7591   -0.2881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1371   -1.6140   -0.8432 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7399   -0.4835   -0.5759 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9984   -0.3868   -1.1742 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8225    0.6753   -0.8898 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3462    1.6113   -0.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1128    1.5171    0.5812 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2544    0.4434    0.3064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0735    0.3872    0.9353 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8631    1.4962    0.4514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8331   -1.1077    0.8231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9044   -1.3833    1.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8837   -2.6697   -0.5810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2429   -2.3553   -1.5485 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3166   -1.1527   -1.8604 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8046    0.8185   -1.3108 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0013    2.4659    0.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7349    2.2586    1.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9543    0.5782    2.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3298    1.9674   -0.2561 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11  2  1  0
 10  5  1  0
  1 13  1  0
  2 14  1  1
  3 15  1  0
  4 16  1  0
  6 17  1  0
  7 18  1  0
  8 19  1  0
  9 20  1  0
 11 21  1  1
 12 22  1  0
M  END
Download

PDB for NP0002834 (cis-1,2-dihydronaphthalene-1,2-diol)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: NDH                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -0.859   2.713   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.859   1.173   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.193   0.403   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -3.526   1.173   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.193  -1.137   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.859  -1.907   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.475  -1.137   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.475   0.403   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.808   1.173   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.808  -1.907   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.142  -1.137   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.142   0.403   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0      -1.933   1.362   0.000  0.00  0.00           H+0
HETATM   14  H   UNK     0      -2.566   1.427   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    8   13                                             
CONECT    3    2    4    5   14                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    2    7    9                                                  
CONECT    9    8   12                                                       
CONECT   10    7   11                                                       
CONECT   11   10   12                                                       
CONECT   12    9   11                                                       
CONECT   13    2                                                            
CONECT   14    3                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END
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3D PDB for NP0002834 (cis-1,2-dihydronaphthalene-1,2-diol)

COMPND    NP0002834
HETATM    1  O1  UNL     1      -3.218  -0.501   0.340  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.866  -0.805   0.659  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.312  -1.759  -0.288  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.137  -1.614  -0.843  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.740  -0.484  -0.576  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.998  -0.387  -1.174  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.822   0.675  -0.890  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.346   1.611  -0.005  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.113   1.517   0.581  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.254   0.443   0.306  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.073   0.387   0.935  1.00  0.00           C  
HETATM   12  O2  UNL     1      -1.863   1.496   0.451  1.00  0.00           O  
HETATM   13  H1  UNL     1      -3.833  -1.108   0.823  1.00  0.00           H  
HETATM   14  H2  UNL     1      -1.904  -1.383   1.667  1.00  0.00           H  
HETATM   15  H3  UNL     1      -1.884  -2.670  -0.581  1.00  0.00           H  
HETATM   16  H4  UNL     1       0.243  -2.355  -1.549  1.00  0.00           H  
HETATM   17  H5  UNL     1       2.317  -1.153  -1.860  1.00  0.00           H  
HETATM   18  H6  UNL     1       3.805   0.818  -1.311  1.00  0.00           H  
HETATM   19  H7  UNL     1       3.001   2.466   0.229  1.00  0.00           H  
HETATM   20  H8  UNL     1       0.735   2.259   1.282  1.00  0.00           H  
HETATM   21  H9  UNL     1      -0.954   0.578   2.058  1.00  0.00           H  
HETATM   22  H10 UNL     1      -1.330   1.967  -0.256  1.00  0.00           H  
CONECT    1    2   13
CONECT    2    3   11   14
CONECT    3    4    4   15
CONECT    4    5   16
CONECT    5    6    6   10
CONECT    6    7   17
CONECT    7    8    8   18
CONECT    8    9   19
CONECT    9   10   10   20
CONECT   10   11
CONECT   11   12   21
CONECT   12   22
END
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SMILES for NP0002834 (cis-1,2-dihydronaphthalene-1,2-diol)

[H][C@]1(O)C=CC2=C(C=CC=C2)[C@@]1([H])O
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INCHI for NP0002834 (cis-1,2-dihydronaphthalene-1,2-diol)

InChI=1S/C10H10O2/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-6,9-12H/t9-,10+/m0/s1
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Synonyms
ValueSource
(1R,2S)-1,2-Dihydronaphthalene-1,2-diolKegg
(1R, 2S)-cis 1,2 DIHYDROXY-1,2-dihydronaphthaleneChEBI
Chemical FormulaC10H10O2
Average Mass162.1852 Da
Monoisotopic Mass162.06808 Da
IUPAC Name(1R,2S)-1,2-dihydronaphthalene-1,2-diol
Traditional Name(1R,2S)-1,2-dihydronaphthalene-1,2-diol
CAS Registry NumberNot Available
SMILES
[H][C@]1(O)C=CC2=C(C=CC=C2)[C@@]1([H])O
InChI Identifier
InChI=1S/C10H10O2/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-6,9-12H/t9-,10+/m0/s1
InChI KeyQPUHWUSUBHNZCG-VHSXEESVSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as naphthalenes. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNot Available
Direct ParentNaphthalenes
Alternative Parents
Substituents
  • Naphthalene
  • Secondary alcohol
  • 1,2-diol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic 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
logP0.63ALOGPS
logP1ChemAxon
logS-0.86ALOGPS
pKa (Strongest Acidic)13.2ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity47.38 m³·mol⁻¹ChemAxon
Polarizability16.89 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDDB08264
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID389268
KEGG Compound IDC04314
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID44343
Good Scents IDNot Available
References
General References
  1. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]