Np mrd loader

Showing NP-Card for 1-Naphthol (NP0001236)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2009-04-06 16:19:51 UTC
Updated at2024-09-03 04:22:01 UTC
NP-MRD IDNP0001236
Natural Product DOIhttps://doi.org/10.57994/2710
Secondary Accession NumbersNone
Natural Product Identification
Common Name1-Naphthol
Description1-Naphthol (1N) is a metabolite of carbaryl and naphthalene that is an intermediate in Metabolism of xenobiotics by cytochrome P450. It is generated by spontaneous reaction from (1R,2S)-Naphthalene epoxide then is it converted to 1,4-Dihydroxynaphthalene. Although 1-Naphthol is not persistent in the body, a single urine sample may adequately predict exposure over several months to chlorpyrifos, which is a broad-spectrum organophosphate insecticide. In adult men, TCPY and 1N were associated with reduced testosterone levels (PMID:16357596 , 15579421 ).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0001236 (1-Naphthol)


  Mrv1652309042000342D          

 11 12  0  0  0  0            999 V2000
   11.0320   -6.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0320   -7.3803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3174   -6.1428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3174   -7.7928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6030   -6.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6030   -7.3803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4609   -6.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4609   -7.3803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7464   -6.1428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7464   -7.7928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3174   -5.3178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  2  0  0  0  0
  8  7  1  0  0  0  0
  9  7  2  0  0  0  0
 10  8  2  0  0  0  0
  1  9  1  0  0  0  0
  2 10  1  0  0  0  0
  2  1  1  0  0  0  0
 11  3  1  0  0  0  0
M  END
Download

3D MOL for NP0001236 (1-Naphthol)

Download
3D SDF for NP0001236 (1-Naphthol)

  Mrv1652309042000342D          

 11 12  0  0  0  0            999 V2000
   11.0320   -6.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0320   -7.3803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3174   -6.1428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3174   -7.7928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6030   -6.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6030   -7.3803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4609   -6.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4609   -7.3803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7464   -6.1428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7464   -7.7928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3174   -5.3178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  2  0  0  0  0
  8  7  1  0  0  0  0
  9  7  2  0  0  0  0
 10  8  2  0  0  0  0
  1  9  1  0  0  0  0
  2 10  1  0  0  0  0
  2  1  1  0  0  0  0
 11  3  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001236

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=C2C=CC=CC2=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H8O/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7,11H

> <INCHI_KEY>
KJCVRFUGPWSIIH-UHFFFAOYSA-N

> <FORMULA>
C10H8O

> <MOLECULAR_WEIGHT>
144.1699

> <EXACT_MASS>
144.057514878

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
15.452427185666625

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
naphthalen-1-ol

> <ALOGPS_LOGP>
2.79

> <JCHEM_LOGP>
2.659157251

> <ALOGPS_LOGS>
-2.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.601542384963208

> <JCHEM_PKA_STRONGEST_BASIC>
-5.594382962192555

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
44.48910000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.47e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
naphthol

> <JCHEM_VEBER_RULE>
1

$$$$

Download
3D-SDF for NP0001236 (1-Naphthol)
Download
PDB for NP0001236 (1-Naphthol)
HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      20.593 -12.237   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.593 -13.777   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      19.259 -11.467   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      19.259 -14.547   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.926 -12.237   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.926 -13.777   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      23.260 -12.237   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      23.260 -13.777   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.927 -11.467   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.927 -14.547   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      19.259  -9.927   0.000  0.00  0.00           O+0
CONECT    1    3    9    2                                                  
CONECT    2    4   10    1                                                  
CONECT    3    1    5   11                                                  
CONECT    4    2    6                                                       
CONECT    5    3    6                                                       
CONECT    6    4    5                                                       
CONECT    7    8    9                                                       
CONECT    8    7   10                                                       
CONECT    9    7    1                                                       
CONECT   10    8    2                                                       
CONECT   11    3                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END

Download
3D PDB for NP0001236 (1-Naphthol)
Download
SMILES for NP0001236 (1-Naphthol)
OC1=C2C=CC=CC2=CC=C1
Download
INCHI for NP0001236 (1-Naphthol)
InChI=1S/C10H8O/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7,11H
Download
View in JSmol
Synonyms
ValueSource
1-HydroxynaphthaleneChEBI
1-NaphthalenolChEBI
alpha-HydroxynaphthaleneChEBI
alpha-NaphtholChEBI
a-HydroxynaphthaleneGenerator
Α-hydroxynaphthaleneGenerator
a-NaphtholGenerator
Α-naphtholGenerator
1-Naphthyl alcoholHMDB
alpha-Naphthyl alcoholHMDB
BASF ursol ernHMDB
Durafur developer DHMDB
Fouramine ernHMDB
Fourrine 99HMDB
Fourrine ernHMDB
Furro erHMDB
Nako TRBHMDB
Naphthol-1HMDB
Naphthyl-1-olHMDB
Tertral ernHMDB
Ursol ernHMDB
Zoba ernHMDB
1-Naphthol, 1-(14)C-labeledHMDB
1-Naphthol, 2-(13)C-labeledHMDB
1-Naphthol, ion(1+)HMDB
1-Naphthol, sodium saltHMDB
1-Naphthol, potassium saltHMDB
1-Naphthol, lithium saltHMDB
Chemical FormulaC10H8O
Average Mass144.1699 Da
Monoisotopic Mass144.05751 Da
IUPAC Namenaphthalen-1-ol
Traditional Namenaphthol
CAS Registry Number90-15-3
SMILES
OC1=C2C=CC=CC2=CC=C1
InChI Identifier
InChI=1S/C10H8O/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7,11H
InChI KeyKJCVRFUGPWSIIH-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)ztmnb@umsystem.eduSumner lab, University of MissouriZach Tretter2024-06-03View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)ztmnb@umsystem.eduSumner lab, University of MissouriZach Tretter2024-06-03View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)ztmnb@umsystem.eduSumner lab, University of MissouriZach Tretter2024-06-03View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)ztmnb@umsystem.eduSumner lab, University of MissouriZach Tretter2024-06-03View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, CD3OD, experimental)ztmnb@umsystem.eduSumner lab, University of MissouriZach Tretter2024-06-03View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)ztmnb@umsystem.eduSumner lab, University of MissouriZach Tretter2024-06-03View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 800.148940889, CD3OD, simulated)ztmnb@umsystem.eduSumner lab, University of MissouriZach Tretter2024-06-03View Spectrum
Species
Species of Origin
Species NameSourceReference
Cannabis sativaCannabisDB
      Not Available
Juglans nigra
Selaginella sinensis
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
    • 

  • 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
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.95 g/LALOGPS
logP2.79ALOGPS
logP2.66ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)9.6ChemAxon
pKa (Strongest Basic)-5.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity44.49 m³·mol⁻¹ChemAxon
Polarizability15.45 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0012138  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB005841  
KNApSAcK IDC00052604  
Chemspider ID6739  
KEGG Compound IDC11714  
BioCyc IDNAPHTHOL  
BiGG IDNot Available
Wikipedia Link1-Naphthol  
METLIN IDNot Available
PubChem Compound7005  
PDB ID1NP  
ChEBI ID10319  
Good Scents IDrw1155611  
References
General References
  1. Meeker JD, Ryan L, Barr DB, Hauser R: Exposure to nonpersistent insecticides and male reproductive hormones. Epidemiology. 2006 Jan;17(1):61-8. [PubMed:16357596  ] 
  2. Meeker JD, Barr DB, Serdar B, Rappaport SM, Hauser R: Utility of urinary 1-naphthol and 2-naphthol levels to assess environmental carbaryl and naphthalene exposure in an epidemiology study. J Expo Sci Environ Epidemiol. 2007 Jul;17(4):314-20. doi: 10.1038/sj.jes.7500502. Epub 2006 May 24. [PubMed:16721410  ] 
  3. Massey KA, Van Engelen DL, Warner IM: Determination of carbaryl as its primary metabolite, 1-naphthol, by reversed-phase high-performance liquid chromatography with fluorometric detection. Talanta. 1995 Oct;42(10):1457-63. doi: 10.1016/0039-9140(95)01595-3. [PubMed:18966375  ] 
  4. Kapuci M, Ulker Z, Gurkan S, Alpsoy L: Determination of cytotoxic and genotoxic effects of naphthalene, 1-naphthol and 2-naphthol on human lymphocyte culture. Toxicol Ind Health. 2014 Feb;30(1):82-9. doi: 10.1177/0748233712451772. Epub 2012 Jun 27. [PubMed:22740618  ]