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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-10 22:58:31 UTC
Update Date2021-09-26 22:54:40 UTC
HMDB IDHMDB0245929
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-Methylcholanthrene
Description3-Methylcholanthrene, also known as 20-MC or 3-MC, belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene. Based on a literature review a significant number of articles have been published on 3-Methylcholanthrene. This compound has been identified in human blood as reported by (PMID: 31557052 ). 3-methylcholanthrene is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 3-Methylcholanthrene is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
1,2-Dihydro-3-methylbenz(J)aceanthryleneChEBI
20-MCChEBI
20-MethylcholanthreneChEBI
3-MCChEBI
3-MCAChEBI
3-Methyl-1,2-dihydrobenzo[J]aceanthryleneChEBI
MCChEBI
MCAChEBI
MethylcholanthreneChEBI
20 MethylcholanthreneHMDB
3 MethylcholanthreneHMDB
3-MethylcholanthreneMeSH
Chemical FormulaC21H16
Average Molecular Weight268.359
Monoisotopic Molecular Weight268.125200515
IUPAC Name16-methylpentacyclo[11.6.1.0²,¹¹.0⁵,¹⁰.0¹⁷,²⁰]icosa-1,3,5,7,9,11,13(20),14,16-nonaene
Traditional Namemethylcholanthrene
CAS Registry NumberNot Available
SMILES
CC1=C2CCC3=C4C=CC5=CC=CC=C5C4=CC(C=C1)=C23
InChI Identifier
InChI=1S/C21H16/c1-13-6-7-15-12-20-17-5-3-2-4-14(17)8-9-18(20)19-11-10-16(13)21(15)19/h2-9,12H,10-11H2,1H3
InChI KeyPPQNQXQZIWHJRB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenanthrenes and derivatives
Sub ClassNot Available
Direct ParentPhenanthrenes and derivatives
Alternative Parents
Substituents
  • Phenanthrene
  • Anthracene
  • Aromatic hydrocarbon
  • Polycyclic hydrocarbon
  • Unsaturated hydrocarbon
  • Hydrocarbon
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP6.49ALOGPS
logP6.02ChemAxon
logS-8.4ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity88.73 m³·mol⁻¹ChemAxon
Polarizability32.28 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-202.18430932474
DeepCCS[M+Na]+177.44230932474
AllCCS[M+H]+165.832859911
AllCCS[M+H-H2O]+162.032859911
AllCCS[M+NH4]+169.332859911
AllCCS[M+Na]+170.332859911
AllCCS[M-H]-172.732859911
AllCCS[M+Na-2H]-171.332859911
AllCCS[M+HCOO]-169.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-MethylcholanthreneCC1=C2CCC3=C4C=CC5=CC=CC=C5C4=CC(C=C1)=C233775.2Standard polar33892256
3-MethylcholanthreneCC1=C2CCC3=C4C=CC5=CC=CC=C5C4=CC(C=C1)=C232924.7Standard non polar33892256
3-MethylcholanthreneCC1=C2CCC3=C4C=CC5=CC=CC=C5C4=CC(C=C1)=C232981.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methylcholanthrene GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gbc-0190000000-afc590869cb6f6efd3122021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methylcholanthrene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylcholanthrene 10V, Positive-QTOFsplash10-014i-0090000000-fdb3e07f4b0226761ebf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylcholanthrene 20V, Positive-QTOFsplash10-014i-0090000000-56bd18515809a57785422016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylcholanthrene 40V, Positive-QTOFsplash10-0udl-0190000000-0f3383de07a19008b9e52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylcholanthrene 10V, Negative-QTOFsplash10-014i-0090000000-0bd51147fbef889cf8f52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylcholanthrene 20V, Negative-QTOFsplash10-014i-0090000000-c9ab90a6e50c33834a112016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylcholanthrene 40V, Negative-QTOFsplash10-0gbi-0090000000-b6f7111aec63c7114f6f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylcholanthrene 10V, Positive-QTOFsplash10-014i-0090000000-1ce8311e5103e80214822021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylcholanthrene 20V, Positive-QTOFsplash10-014i-0090000000-1ce8311e5103e80214822021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylcholanthrene 40V, Positive-QTOFsplash10-014i-0090000000-73250167e3e864199f572021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylcholanthrene 10V, Negative-QTOFsplash10-014i-0090000000-b6b0e372b8ee3bd14aa22021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylcholanthrene 20V, Negative-QTOFsplash10-014i-0090000000-b6b0e372b8ee3bd14aa22021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylcholanthrene 40V, Negative-QTOFsplash10-014i-0090000000-b4160a36094acd60de152021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID1611
KEGG Compound IDC14470
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethylcholanthrene
METLIN IDNot Available
PubChem Compound1674
PDB IDNot Available
ChEBI ID34342
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]