Hmdb loader

Showing metabocard for 1-Naphthol (HMDB0012138)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Show more...Show more...Show more...Show more...
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2009-04-06 16:19:51 UTC
Update Date2023-02-21 17:17:39 UTC
HMDB IDHMDB0012138
Secondary Accession Numbers
  • HMDB12138
Metabolite 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
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0012138 (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 HMDB0012138 (1-Naphthol)

HMDB0012138
     RDKit          3D
1-Naphthol
 19 20  0  0  0  0  0  0  0  0999 V2000
   -1.5357    2.3852    0.2646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3405    1.0297    0.0991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4341    0.1764   -0.0324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2224   -1.1677   -0.1962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9445   -1.6713   -0.2307 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1378   -0.8357   -0.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4123   -1.3834   -0.1418 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5080   -0.5607   -0.0141 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3709    0.7972    0.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0761    1.2965    0.1867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0590    0.5276    0.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8325    3.0733    0.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4358    0.5985   -0.0020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0906   -1.8368   -0.2996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7932   -2.7565   -0.3634 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4910   -2.4527   -0.2741 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4877   -1.0131   -0.0489 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2329    1.4411    0.2531 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9714    2.3524    0.3167 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  2  1  0
 11  6  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  5 15  1  0
  7 16  1  0
  8 17  1  0
  9 18  1  0
 10 19  1  0
M  END
Download

3D SDF for HMDB0012138 (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>
HMDB0012138

> <DATABASE_NAME>
hmdb

> <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 HMDB0012138 (1-Naphthol)

HMDB0012138
     RDKit          3D
1-Naphthol
 19 20  0  0  0  0  0  0  0  0999 V2000
   -1.5357    2.3852    0.2646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3405    1.0297    0.0991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4341    0.1764   -0.0324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2224   -1.1677   -0.1962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9445   -1.6713   -0.2307 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1378   -0.8357   -0.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4123   -1.3834   -0.1418 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5080   -0.5607   -0.0141 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3709    0.7972    0.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0761    1.2965    0.1867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0590    0.5276    0.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8325    3.0733    0.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4358    0.5985   -0.0020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0906   -1.8368   -0.2996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7932   -2.7565   -0.3634 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4910   -2.4527   -0.2741 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4877   -1.0131   -0.0489 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2329    1.4411    0.2531 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9714    2.3524    0.3167 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  2  1  0
 11  6  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  5 15  1  0
  7 16  1  0
  8 17  1  0
  9 18  1  0
 10 19  1  0
M  END
Download

PDB for HMDB0012138 (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 HMDB0012138 (1-Naphthol)

COMPND    HMDB0012138
HETATM    1  O1  UNL     1      -1.536   2.385   0.265  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.340   1.030   0.099  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.434   0.176  -0.032  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.222  -1.168  -0.196  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.944  -1.671  -0.231  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.138  -0.836  -0.102  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.412  -1.383  -0.142  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.508  -0.561  -0.014  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.371   0.797   0.153  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.076   1.296   0.187  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.059   0.528   0.065  1.00  0.00           C  
HETATM   12  H1  UNL     1      -0.832   3.073   0.367  1.00  0.00           H  
HETATM   13  H2  UNL     1      -3.436   0.599  -0.002  1.00  0.00           H  
HETATM   14  H3  UNL     1      -3.091  -1.837  -0.300  1.00  0.00           H  
HETATM   15  H4  UNL     1      -0.793  -2.757  -0.363  1.00  0.00           H  
HETATM   16  H5  UNL     1       1.491  -2.453  -0.274  1.00  0.00           H  
HETATM   17  H6  UNL     1       3.488  -1.013  -0.049  1.00  0.00           H  
HETATM   18  H7  UNL     1       3.233   1.441   0.253  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.971   2.352   0.317  1.00  0.00           H  
CONECT    1    2   12
CONECT    2    3    3   11
CONECT    3    4   13
CONECT    4    5    5   14
CONECT    5    6   15
CONECT    6    7    7   11
CONECT    7    8   16
CONECT    8    9    9   17
CONECT    9   10   18
CONECT   10   11   11   19
END
Download

SMILES for HMDB0012138 (1-Naphthol)

OC1=C2C=CC=CC2=CC=C1
Download

INCHI for HMDB0012138 (1-Naphthol)

InChI=1S/C10H8O/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7,11H
Download
View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC10H8O
Average Molecular Weight144.1699
Monoisotopic Molecular Weight144.057514878
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
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
Ontology
Physiological effect
Health effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological roleEnvironmental roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point94.00 to 95.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point279.00 to 280.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility866 mg/L @ 24C (exp)The Good Scents Company Information System
LogP2.850The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
 details
UrineDetected and Quantified0.00117 umol/mmol creatinineAdult (>18 years old)Male
Normal		 details
UrineDetected and Quantified0.001595 umol/mmol creatinineNot AvailableNot AvailableNormal details
UrineDetected and Quantified0.0015 (0.0013-0.0017) umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.00232 (0.00112-0.00282) umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal
    • National Health a...
 details
UrineDetected and Quantified0.00147 (0.00118-0.00176) umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal
    • National Health a...
 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.001956 umol/mmol creatinineAdult (>18 years old)Male
Subfertility		 details
UrineDetected and Quantified0.0016 (0.0014-0.0019) umol/mmol creatinineAdult (>18 years old)MaleIdiopathic infertility details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDM00538
MarkerDB IDMDB00029786
Good Scents IDrw1155611
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
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. Hauser R, Meeker JD, Park S, Silva MJ, Calafat AM: Temporal variability of urinary phthalate metabolite levels in men of reproductive age. Environ Health Perspect. 2004 Dec;112(17):1734-40. [PubMed:15579421 ]