Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2009-04-06 16:19:51 UTC
Update Date2021-10-13 05:33:55 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
Data?1582753018
Synonyms
ValueSource
1-HydroxynaphthaleneChEBI
1-NaphthalenolChEBI
alpha-HydroxynaphthaleneChEBI
alpha-NaphtholChEBI
a-HydroxynaphthaleneGenerator
Α-hydroxynaphthaleneGenerator
a-NaphtholGenerator
Α-naphtholGenerator
1-Naphthol, 1-(14)C-labeledMeSH
1-Naphthol, 2-(13)C-labeledMeSH
1-Naphthol, ion(1+)MeSH
1-Naphthol, lithium saltMeSH
1-Naphthol, potassium saltMeSH
1-Naphthol, sodium saltMeSH
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 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
Disposition
Biological locationRoute of exposureSource
Process
Role
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
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+128.78431661259
DarkChem[M-H]-125.78231661259
DeepCCS[M+H]+129.89330932474
DeepCCS[M-H]-126.9730932474
DeepCCS[M-2H]-163.65830932474
DeepCCS[M+Na]+139.10530932474
AllCCS[M+H]+128.532859911
AllCCS[M+H-H2O]+123.732859911
AllCCS[M+NH4]+133.032859911
AllCCS[M+Na]+134.332859911
AllCCS[M-H]-126.232859911
AllCCS[M+Na-2H]-126.932859911
AllCCS[M+HCOO]-127.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1-NaphtholOC1=C2C=CC=CC2=CC=C12521.0Standard polar33892256
1-NaphtholOC1=C2C=CC=CC2=CC=C11426.6Standard non polar33892256
1-NaphtholOC1=C2C=CC=CC2=CC=C11512.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1-Naphthol,1TMS,isomer #1C[Si](C)(C)OC1=CC=CC2=CC=CC=C121515.8Semi standard non polar33892256
1-Naphthol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CC2=CC=CC=C121776.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 1-Naphthol EI-B (Non-derivatized)splash10-014l-3900000000-61210a72d0e1913d7c722017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1-Naphthol EI-B (Non-derivatized)splash10-014l-3900000000-61210a72d0e1913d7c722018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Naphthol GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kf-0900000000-c0995f3a682409c438372017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Naphthol GC-MS (1 TMS) - 70eV, Positivesplash10-0g4i-9850000000-192f1a8f4045c6c2e6a62017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Naphthol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-00kf-2900000000-464e7ef19c6bd0e238692014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Naphthol APCI-ITFT , negative-QTOFsplash10-0006-0900000000-4e151ced4980c51dbed02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Naphthol ESI-ITFT , positive-QTOFsplash10-014i-0900000000-8fc12807dac2f94e7aba2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Naphthol APCI-ITFT , positive-QTOFsplash10-014i-0900000000-c536d76de8d3df4d57742017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Naphthol 45V, Negative-QTOFsplash10-0006-0900000000-95369892ad06085feeaa2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Naphthol 60V, Negative-QTOFsplash10-0006-0900000000-4359d09beb852a6b4d8d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Naphthol 45V, Positive-QTOFsplash10-0002-0900000000-81d05a973c3d900077c62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Naphthol 60V, Positive-QTOFsplash10-014j-0900000000-f42d4778921cb7d4089a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Naphthol 30V, Positive-QTOFsplash10-0002-0900000000-5eddad361f7fcd8098bf2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Naphthol 15V, Positive-QTOFsplash10-0002-0900000000-5d003cf06a82f555ebda2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Naphthol 75V, Positive-QTOFsplash10-0uxr-1900000000-6b7e7dbf4dd9988bdb692021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Naphthol 90V, Positive-QTOFsplash10-0udi-1900000000-8f3c86f1fed8a21368e12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Naphthol 15V, Negative-QTOFsplash10-0006-0900000000-ec57dc12ddf60a2741f02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Naphthol 15V, Positive-QTOFsplash10-014i-0900000000-751c55e1dc2b820d2fb82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Naphthol 45V, Positive-QTOFsplash10-014i-0900000000-0809d3facff6212072ef2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Naphthol 60V, Positive-QTOFsplash10-0gb9-1900000000-f5b727eb0fe4a390c0432021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Naphthol 30V, Positive-QTOFsplash10-014i-0900000000-49134c89950d7d99c9d12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Naphthol 75V, Negative-QTOFsplash10-00kf-0900000000-b57369b32440fe60da1d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Naphthol 35V, Positive-QTOFsplash10-014i-0900000000-8fc12807dac2f94e7aba2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Naphthol 90V, Negative-QTOFsplash10-014i-0900000000-8a33e2a4035f1d5db4c62021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Naphthol 10V, Positive-QTOFsplash10-0002-0900000000-17872f169fc1a3b9a5892015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Naphthol 20V, Positive-QTOFsplash10-0002-0900000000-7ff94ab855e29de866082015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Naphthol 40V, Positive-QTOFsplash10-0fb9-2900000000-54aee2dee46145420c782015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Naphthol 10V, Negative-QTOFsplash10-0006-0900000000-3cb1d47c2a60e27a99d52015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Naphthol 20V, Negative-QTOFsplash10-0006-0900000000-027fc605a3ec221e62c92015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Naphthol 40V, Negative-QTOFsplash10-0006-1900000000-9d25f4653afbb98405fd2015-04-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
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)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 ]