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Record Information
Version3.6
Creation Date2009-04-06 16:19:51 UTC
Update Date2016-02-11 01:23:39 UTC
HMDB IDHMDB12138
Secondary Accession NumbersNone
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
Synonyms
ValueSource
1-NaphthalenolChEBI
alpha-HydroxynaphthaleneChEBI
alpha-NaphtholChEBI
a-HydroxynaphthaleneGenerator
α-hydroxynaphthaleneGenerator
a-NaphtholGenerator
α-naphtholGenerator
1-HydroxynaphthaleneHMDB
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
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 KeyInChIKey=KJCVRFUGPWSIIH-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity44.49 m3·mol-1ChemAxon
Polarizability15.45 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-17872f169fc1a3b9a589View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-7ff94ab855e29de86608View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-2900000000-54aee2dee46145420c78View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-3cb1d47c2a60e27a99d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-027fc605a3ec221e62c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-1900000000-9d25f4653afbb98405fdView in MoNA
MSMass Spectrum (Electron Ionization)splash10-00kf-2900000000-464e7ef19c6bd0e23869View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
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
BiofluidStatusValueAgeSexConditionReferenceDetails
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
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB005841
KNApSAcK IDNot Available
Chemspider ID6739
KEGG Compound IDC11714
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link1-naphthol
NuGOwiki LinkHMDB12138
Metagene LinkHMDB12138
METLIN IDNot Available
PubChem Compound7005
PDB ID1NP
ChEBI ID10319
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
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. [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. [15579421 ]