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Showing NP-Card for Naphthalene-1,2-diol (NP0084242)

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Record Information
Version2.0
Created at2022-04-29 05:02:18 UTC
Updated at2022-04-29 05:02:18 UTC
NP-MRD IDNP0084242
Secondary Accession NumbersNone
Natural Product Identification
Common NameNaphthalene-1,2-diol
DescriptionNaphthalene-1,2-diol, also known as 1,2-naphthalenediol or 1,2-naphthohydroquinone, belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position. Naphthalene-1,2-diol is an extremely weak basic (essentially neutral) compound (based on its pKa). Naphthalene-1,2-diol exists in all living organisms, ranging from bacteria to humans. Naphthalene-1,2-diol is found in Mus musculus and Paraburkholderia phymatum. These are hydroxylated naphthalenes.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0084242 (Naphthalene-1,2-diol)

D1N
  Mrv0541 02241213322D          

 12 13  0  0  0  0            999 V2000
   -0.9076   -1.0564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1931   -1.4689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1931   -2.2939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5213   -2.7064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2358   -2.2939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2358   -1.4689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5213   -1.0564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5213   -0.2314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9503   -1.0564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6648   -1.4689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6648   -2.2939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9503   -2.7064    0.0000 C   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
  2  7  1  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
  5 12  1  0  0  0  0
  6  7  2  0  0  0  0
  6  9  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
M  END
Download

3D MOL for NP0084242 (Naphthalene-1,2-diol)

     RDKit          3D

 20 21  0  0  0  0  0  0  0  0999 V2000
    3.4503    0.8563    0.1976 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1781    0.2738    0.1545 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0014   -1.0821    0.2907 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7539   -1.6652    0.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3846   -0.9074    0.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6331   -1.5036    0.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7300   -0.6877   -0.1552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5848    0.6755   -0.2949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3187    1.2573   -0.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2074    0.4633   -0.0693 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0420    1.0504   -0.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2666    2.4057   -0.1607 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2806    0.2963    0.3305 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8906   -1.6839    0.4333 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6422   -2.7531    0.3616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7490   -2.5919    0.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7215   -1.1355   -0.1894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4471    1.3299   -0.4411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2699    2.3381   -0.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5404    3.0638   -0.2958 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11  2  1  0
 10  5  1  0
  1 13  1  0
  3 14  1  0
  4 15  1  0
  6 16  1  0
  7 17  1  0
  8 18  1  0
  9 19  1  0
 12 20  1  0
M  END
Download

3D SDF for NP0084242 (Naphthalene-1,2-diol)

D1N
  Mrv0541 02241213322D          

 12 13  0  0  0  0            999 V2000
   -0.9076   -1.0564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1931   -1.4689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1931   -2.2939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5213   -2.7064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2358   -2.2939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2358   -1.4689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5213   -1.0564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5213   -0.2314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9503   -1.0564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6648   -1.4689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6648   -2.2939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9503   -2.7064    0.0000 C   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
  2  7  1  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
  5 12  1  0  0  0  0
  6  7  2  0  0  0  0
  6  9  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0084242

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C2C=CC=CC2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C10H8O2/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-6,11-12H

> <INCHI_KEY>
NXPPAOGUKPJVDI-UHFFFAOYSA-N

> <FORMULA>
C10H8O2

> <MOLECULAR_WEIGHT>
160.1693

> <EXACT_MASS>
160.0524295

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
16.401054634685195

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
naphthalene-1,2-diol

> <ALOGPS_LOGP>
2.06

> <JCHEM_LOGP>
2.3555919293333325

> <ALOGPS_LOGS>
-2.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.48981457507725

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.039398871788492

> <JCHEM_PKA_STRONGEST_BASIC>
-6.308095120997241

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
46.47000000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.10e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,2-dihydroxynaphthalene

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0084242 (Naphthalene-1,2-diol)

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PDB for NP0084242 (Naphthalene-1,2-diol)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: D1N                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -1.694  -1.972   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.360  -2.742   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.360  -4.282   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.973  -5.052   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.307  -4.282   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.307  -2.742   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.973  -1.972   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.973  -0.432   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.641  -1.972   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.974  -2.742   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.974  -4.282   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.641  -5.052   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7    9                                                  
CONECT    7    2    6    8                                                  
CONECT    8    7                                                            
CONECT    9    6   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12    5   11                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

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3D PDB for NP0084242 (Naphthalene-1,2-diol)
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SMILES for NP0084242 (Naphthalene-1,2-diol)
OC1=CC=C2C=CC=CC2=C1O
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INCHI for NP0084242 (Naphthalene-1,2-diol)
InChI=1S/C10H8O2/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-6,11-12H
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View in JSmol
Synonyms
ValueSource
1,2-DihydroxynaphthaleneChEBI
1,2-NaphthalenediolChEBI
1,2-NaphthohydroquinoneChEBI
beta-NaphthohydroquinoneChEBI
b-NaphthohydroquinoneGenerator
Β-naphthohydroquinoneGenerator
1,2-Dihydroxynaphthalene monohydrateHMDB
Chemical FormulaC10H8O2
Average Mass160.1693 Da
Monoisotopic Mass160.05243 Da
IUPAC Namenaphthalene-1,2-diol
Traditional Name1,2-dihydroxynaphthalene
CAS Registry NumberNot Available
SMILES
OC1=CC=C2C=CC=CC2=C1O
InChI Identifier
InChI=1S/C10H8O2/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-6,11-12H
InChI KeyNXPPAOGUKPJVDI-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
Mus musculusLOTUS Database
Paraburkholderia phymatum-
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassNaphthalenes  
Sub ClassNaphthols and derivatives  
Direct ParentNaphthols and derivatives  
Alternative Parents
Substituents
  • 1-naphthol
    • 

  • 2-naphthol
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • 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
logP2.06ALOGPS
logP2.36ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)9.04ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity46.47 m³·mol⁻¹ChemAxon
Polarizability16.4 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0060497  
DrugBank IDDB07610  
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC03012  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11318  
PDB IDNot Available
ChEBI ID17435  
Good Scents IDNot Available
References
General References