1-Hydroxypyrene (CHEM002931)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (15)XML
Record Information
Version1.0
Creation Date2014-08-29 04:48:18 UTC
Update Date2026-04-02 23:29:43 UTC
Accession NumberCHEM002931
Identification
Common Name1-Hydroxypyrene
ClassSmall Molecule
Description1-Hydroxypyrene is a metabolite of the noncarcinogen pyrene found in urine that is always a component of PAH mixtures. 1-hydroxypyrene is an accepted biomarker of carcinogenic Polycyclic aromatic hydrocarbons (PAH) dose PAH are a diverse group of environmental carcinogens formed during the incomplete combustion of organic matter. PAHs are believed to play an important role as causes of human cancer, particularly in certain occupational settings and in cigarette smokers. (1, 2).
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • Suspected Compounds
  • T3DB toxins
  • Tobacco Smoke Compounds
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Animal Toxin
  • Cigarette Toxin
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Hydroxy pyreneHMDB
1-PyrenolHMDB
Pyren-1-olHMDB
Chemical FormulaC16H12O
Average Molecular Mass220.266 g/mol
Monoisotopic Mass220.089 g/mol
CAS Registry Number5315-79-7
IUPAC Name1,5-dihydropyren-1-ol
Traditional Name1,5-dihydropyren-1-ol
SMILESOC1C=CC2=CCC3=C4C(C=CC1=C24)=CC=C3
InChI IdentifierInChI=1S/C16H12O/c17-14-9-7-12-5-4-10-2-1-3-11-6-8-13(14)16(12)15(10)11/h1-3,5-9,14,17H,4H2
InChI KeyCDYIVSAQQUIYKS-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenanthrols. Phenanthrols are compounds containing a phenanthrene (or its hydrogenated derivative) to which a hydroxyl group is attached.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenanthrenes and derivatives
Sub ClassPhenanthrols
Direct ParentPhenanthrols
Alternative Parents
Substituents
  • Phenanthrol
  • Phenalen
  • Naphthalene
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point180°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.017 g/LALOGPS
logP3.43ALOGPS
logP3.05ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)13.96ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity71.11 m³·mol⁻¹ChemAxon
Polarizability24.36 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-0290000000-e4b302a0328797592df1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0udi-3090000000-65cbe803b057aa263256Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0090000000-58858cf49733150cb6a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-0190000000-bff0e85d413a5f49e8ebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0390000000-2d4824111e5b0b9bd928Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-479ab5f08a52648242bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-fd07aed54a4ca5a37d3eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-1890000000-7233fddab6fc48b66023Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThis is a toxic chemical found in cigarettes or generated by tobacco combustion.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0013139
FooDB IDFDB029309
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia Link1-Hydroxypyrene
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID53481631
Kegg Compound IDC14519
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Hecht SS, Carmella SG, Le KA, Murphy SE, Li YS, Le C, Jensen J, Hatsukami DK: Effects of reduced cigarette smoking on levels of 1-hydroxypyrene in urine. Cancer Epidemiol Biomarkers Prev. 2004 May;13(5):834-42.
2. Carmella SG, Le KA, Hecht SS: Improved method for determination of 1-hydroxypyrene in human urine. Cancer Epidemiol Biomarkers Prev. 2004 Jul;13(7):1261-4.