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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2009-04-06 16:19:51 UTC
Update Date2017-12-07 02:35:55 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
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-labeledMeSH
1-Naphthol, 2-(13)C-labeledMeSH
1-Naphthol, ion(1+)MeSH
1-Naphthol, sodium saltMeSH
1-Naphthol, potassium saltMeSH
1-Naphthol, lithium saltMeSH
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
DescriptionThis compound belongs to the class of chemical entities known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassNaphthalenes
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
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

Physiological effect

Health effect:

  Health condition:

    Psychiatric disorders:

    Gastrointestinal disorders:

    Nervous system disorders:

    General disorders and administration site conditions:

    Musculoskeletal and connective tissue disorders:

    Metabolism and nutrition disorders:

    Vascular disorders:

  Observation:

Role

Indirect biological role:

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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-3900000000-61210a72d0e1913d7c72View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kf-0900000000-c0995f3a682409c43837View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0g4i-9850000000-192f1a8f4045c6c2e6a6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , negativesplash10-0006-0900000000-4e151ced4980c51dbed0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-014i-0900000000-8fc12807dac2f94e7abaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-014i-0900000000-c536d76de8d3df4d5774View in MoNA
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 AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    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
    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. [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 ]