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
Version4.0
StatusDetected and Quantified
Creation Date2009-11-30 15:49:50 UTC
Update Date2017-12-07 02:39:20 UTC
HMDB IDHMDB0013139
Secondary Accession Numbers
  • HMDB13139
Metabolite Identification
Common Name1-Hydroxypyrene
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(PMID: 15159317 ). 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. (PMID: 15247141 ).
Structure
Thumb
Synonyms
ValueSource
1-Hydroxy pyreneHMDB
1-PyrenolHMDB
Pyren-1-olHMDB
Chemical FormulaC16H12O
Average Molecular Weight220.2659
Monoisotopic Molecular Weight220.088815006
IUPAC Name1,5-dihydropyren-1-ol
Traditional Name1,5-dihydropyren-1-ol
CAS Registry Number5315-79-7
SMILES
OC1C=CC2=CCC3=C4C(C=CC1=C24)=CC=C3
InChI Identifier
InChI=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
DescriptionThis compound belongs to the class of chemical entities known as phenanthrols. These are compounds containing a phenanthrene (or its hydrogenated derivative) to which a hydroxyl group is attached.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassPhenanthrenes and derivatives
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
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

Role

Indirect biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point180 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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 RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-0290000000-e4b302a0328797592df1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0udi-3090000000-65cbe803b057aa263256View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0090000000-58858cf49733150cb6a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-0190000000-bff0e85d413a5f49e8ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0390000000-2d4824111e5b0b9bd928View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-479ab5f08a52648242bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-fd07aed54a4ca5a37d3eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-1890000000-7233fddab6fc48b66023View in MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Adult (>18 years old)BothNormal details
UrineDetected and Quantified0.000115-0.000230 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not Quantified Adult (>18 years old)MaleNormal details
UrineDetected and Quantified0.000023-0.000034 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.000115-0.000230 umol/mmol creatinineAdult (>18 years old)BothSmokers details
UrineDetected and Quantified0.000690-0.00460 umol/mmol creatinineAdult (>18 years old)MaleRoofers and Asphalt workers details
UrineDetected and Quantified0.0000585 (0.0000539-0.0000642) umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal
    • National Health a...
details
UrineDetected and Quantified0.0000924 (0.00008-0.000106) umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal
    • National Health a...
details
Abnormal Concentrations
Not Available
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 IDFDB029309
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC14519
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481631
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not 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. [PubMed:15159317 ]
  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. [PubMed:15247141 ]

Enzymes

General function:
Not Available
Specific function:
N5-glutamine methyltransferase responsible for the methylation of the GGQ triplet of the mitochondrial translation release factor MTRF1L.
Gene Name:
HEMK1
Uniprot ID:
Q9Y5R4
Molecular weight:
Not Available
Reactions
1-Hydroxypyrene + S-Adenosylmethionine → 1-Methoxypyrene + S-Adenosylhomocysteinedetails
General function:
Not Available
Specific function:
Probable methyltransferase (By similarity).
Gene Name:
METTL2B
Uniprot ID:
Q6P1Q9
Molecular weight:
Not Available
Reactions
1-Hydroxypyrene + S-Adenosylmethionine → 1-Methoxypyrene + S-Adenosylhomocysteinedetails
General function:
Not Available
Specific function:
Probable methyltransferase (By similarity).
Gene Name:
METTL6
Uniprot ID:
Q8TCB7
Molecular weight:
Not Available
Reactions
1-Hydroxypyrene + S-Adenosylmethionine → 1-Methoxypyrene + S-Adenosylhomocysteinedetails
General function:
Not Available
Specific function:
Methyltransferase that may act on DNA.
Gene Name:
WBSCR22
Uniprot ID:
O43709
Molecular weight:
Not Available
Reactions
1-Hydroxypyrene + S-Adenosylmethionine → 1-Methoxypyrene + S-Adenosylhomocysteinedetails