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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2009-11-30 15:49:50 UTC
Update Date2022-09-22 18:34:21 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 (PAHs) dose (PMID: 15159317 ). PAHs 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
Data?1594220313
Synonyms
ValueSource
1-PyrenolHMDB
3-HydroxypyreneHMDB
3-PyrenolHMDB
1-HydroxypyreneHMDB
Chemical FormulaC16H10O
Average Molecular Weight218.255
Monoisotopic Molecular Weight218.073164942
IUPAC Namepyren-1-ol
Traditional Name1-hydroxypyrene
CAS Registry Number5315-79-7
SMILES
OC1=C2C=CC3=CC=CC4=CC=C(C=C1)C2=C34
InChI Identifier
InChI=1S/C16H10O/c17-14-9-7-12-5-4-10-2-1-3-11-6-8-13(14)16(12)15(10)11/h1-9,17H
InChI KeyBIJNHUAPTJVVNQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrenes. Pyrenes are compounds containing a pyrene moiety, which consists four fused benzene rings, resulting in a flat aromatic system.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPyrenes
Sub ClassNot Available
Direct ParentPyrenes
Alternative Parents
Substituents
  • Pyrene
  • Phenanthrol
  • Phenanthrene
  • 1-naphthol
  • 2-naphthol
  • Naphthalene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point180 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.017 g/LALOGPS
logP4.73ALOGPS
logP3.98ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)9.5ChemAxon
pKa (Strongest Basic)-5.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity68.7 m³·mol⁻¹ChemAxon
Polarizability23.82 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-186.62430932474
DeepCCS[M+Na]+161.57430932474
AllCCS[M+H]+147.932859911
AllCCS[M+H-H2O]+143.732859911
AllCCS[M+NH4]+151.932859911
AllCCS[M+Na]+153.032859911
AllCCS[M-H]-152.532859911
AllCCS[M+Na-2H]-151.432859911
AllCCS[M+HCOO]-150.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1-HydroxypyreneOC1=C2C=CC3=CC=CC4=CC=C(C=C1)C2=C343546.5Standard polar33892256
1-HydroxypyreneOC1=C2C=CC3=CC=CC4=CC=C(C=C1)C2=C342332.8Standard non polar33892256
1-HydroxypyreneOC1=C2C=CC3=CC=CC4=CC=C(C=C1)C2=C342529.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1-Hydroxypyrene,1TMS,isomer #1C[Si](C)(C)OC1=CC=C2C=CC3=CC=CC4=CC=C1C2=C342521.1Semi standard non polar33892256
1-Hydroxypyrene,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C=CC3=CC=CC4=CC=C1C2=C342713.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1-Hydroxypyrene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-014r-8970000000-40fc4b6e45c866b2bd2f2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Hydroxypyrene 30V, Negative-QTOFsplash10-014i-0090000000-32d7fc1e9496a014be132021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Hydroxypyrene 15V, Negative-QTOFsplash10-014i-0090000000-ccdb95123ae27f15b2d92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Hydroxypyrene 35V, Negative-QTOFsplash10-01p9-8900000000-d7fb06c75b7742268bcb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Hydroxypyrene 60V, Negative-QTOFsplash10-014i-0090000000-76159160dbafe39067672021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Hydroxypyrene 35V, Positive-QTOFsplash10-0udi-0290000000-44903726070f8e7913662021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Hydroxypyrene 75V, Negative-QTOFsplash10-014i-0090000000-2f4c18fb811cae661c7b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Hydroxypyrene 90V, Negative-QTOFsplash10-014i-0290000000-6f8a43619aaa6ec7f0fc2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxypyrene 10V, Positive-QTOFsplash10-014i-0090000000-eeef28d1f76288438c2f2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxypyrene 20V, Positive-QTOFsplash10-014i-0390000000-7c020fbe6bc1cfd8eb562019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxypyrene 40V, Positive-QTOFsplash10-002f-0900000000-c2c938983da6fcdfb7f22019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxypyrene 10V, Negative-QTOFsplash10-014i-0090000000-2e0296cc63a8c10e4c8c2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxypyrene 20V, Negative-QTOFsplash10-014i-0090000000-2af676a028e8eed73c1c2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxypyrene 40V, Negative-QTOFsplash10-00kr-0980000000-810aa845f9fc4e69775b2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxypyrene 10V, Negative-QTOFsplash10-014i-0090000000-842f5e4c16cf0c3170f22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxypyrene 20V, Negative-QTOFsplash10-014i-0090000000-842f5e4c16cf0c3170f22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxypyrene 40V, Negative-QTOFsplash10-014r-0960000000-138614f2b4c885a6a3d42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxypyrene 10V, Positive-QTOFsplash10-014i-0090000000-d2d36af96689ffc25e5c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxypyrene 20V, Positive-QTOFsplash10-014i-0090000000-d2d36af96689ffc25e5c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxypyrene 40V, Positive-QTOFsplash10-00kr-0950000000-8cd557a66f397723cd502021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.000115-0.000230 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>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
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029309
KNApSAcK IDNot Available
Chemspider ID20100
KEGG Compound IDC14519
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link1-Hydroxypyrene
METLIN IDNot Available
PubChem Compound21387
PDB IDNot Available
ChEBI ID34093
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00029785
Good Scents 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