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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-10 23:19:31 UTC
Update Date2021-09-26 22:55:17 UTC
HMDB IDHMDB0246296
Secondary Accession NumbersNone
Metabolite Identification
Common Name4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)-2-methoxyphenol
Description4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)-2-methoxyphenol, also known as 4'-hydroxy-3'-methoxynomifensine or nomifensine M2, belongs to the class of organic compounds known as 4-phenyltetrahydroisoquinolines. 4-phenyltetrahydroisoquinolines are compounds containing a phenyl group attached to the C4-atom of a tetrahydroisoquinoline moiety. Based on a literature review very few articles have been published on 4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)-2-methoxyphenol. This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-(8-amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)-2-methoxyphenol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)-2-methoxyphenol 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
4'-Hydroxy-3'-methoxynomifensineHMDB
Nomifensine m2HMDB
Chemical FormulaC17H20N2O2
Average Molecular Weight284.359
Monoisotopic Molecular Weight284.152477892
IUPAC Name4-(8-amino-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)-2-methoxyphenol
Traditional Name4-(8-amino-2-methyl-3,4-dihydro-1H-isoquinolin-4-yl)-2-methoxyphenol
CAS Registry NumberNot Available
SMILES
COC1=C(O)C=CC(=C1)C1CN(C)CC2=C1C=CC=C2N
InChI Identifier
InChI=1S/C17H20N2O2/c1-19-9-13(11-6-7-16(20)17(8-11)21-2)12-4-3-5-15(18)14(12)10-19/h3-8,13,20H,9-10,18H2,1-2H3
InChI KeyFFBKUHDJNORZBU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 4-phenyltetrahydroisoquinolines. 4-Phenyltetrahydroisoquinolines are compounds containing a phenyl group attached to the C4-atom of a tetrahydroisoquinoline moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrahydroisoquinolines
Sub Class4-phenyltetrahydroisoquinolines
Direct Parent4-phenyltetrahydroisoquinolines
Alternative Parents
Substituents
  • 4-phenyltetrahydroisoquinoline
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Aralkylamine
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Ether
  • Azacycle
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Organooxygen compound
  • Primary amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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
logP2.16ALOGPS
logP2.04ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)10.04ChemAxon
pKa (Strongest Basic)8.29ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.72 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity85.62 m³·mol⁻¹ChemAxon
Polarizability31.36 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+165.41730932474
DeepCCS[M-H]-163.05930932474
DeepCCS[M-2H]-196.34130932474
DeepCCS[M+Na]+171.56830932474
AllCCS[M+H]+166.732859911
AllCCS[M+H-H2O]+163.032859911
AllCCS[M+NH4]+170.132859911
AllCCS[M+Na]+171.132859911
AllCCS[M-H]-173.432859911
AllCCS[M+Na-2H]-173.132859911
AllCCS[M+HCOO]-173.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)-2-methoxyphenolCOC1=C(O)C=CC(=C1)C1CN(C)CC2=C1C=CC=C2N3968.6Standard polar33892256
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)-2-methoxyphenolCOC1=C(O)C=CC(=C1)C1CN(C)CC2=C1C=CC=C2N2497.6Standard non polar33892256
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)-2-methoxyphenolCOC1=C(O)C=CC(=C1)C1CN(C)CC2=C1C=CC=C2N2604.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)-2-methoxyphenol,2TMS,isomer #1COC1=CC(C2CN(C)CC3=C(N[Si](C)(C)C)C=CC=C32)=CC=C1O[Si](C)(C)C2632.5Semi standard non polar33892256
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)-2-methoxyphenol,2TMS,isomer #1COC1=CC(C2CN(C)CC3=C(N[Si](C)(C)C)C=CC=C32)=CC=C1O[Si](C)(C)C2731.8Standard non polar33892256
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)-2-methoxyphenol,2TMS,isomer #1COC1=CC(C2CN(C)CC3=C(N[Si](C)(C)C)C=CC=C32)=CC=C1O[Si](C)(C)C3131.3Standard polar33892256
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)-2-methoxyphenol,2TMS,isomer #2COC1=CC(C2CN(C)CC3=C2C=CC=C3N([Si](C)(C)C)[Si](C)(C)C)=CC=C1O2599.5Semi standard non polar33892256
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)-2-methoxyphenol,2TMS,isomer #2COC1=CC(C2CN(C)CC3=C2C=CC=C3N([Si](C)(C)C)[Si](C)(C)C)=CC=C1O2886.4Standard non polar33892256
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)-2-methoxyphenol,2TMS,isomer #2COC1=CC(C2CN(C)CC3=C2C=CC=C3N([Si](C)(C)C)[Si](C)(C)C)=CC=C1O3204.3Standard polar33892256
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)-2-methoxyphenol,3TMS,isomer #1COC1=CC(C2CN(C)CC3=C2C=CC=C3N([Si](C)(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C2615.5Semi standard non polar33892256
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)-2-methoxyphenol,3TMS,isomer #1COC1=CC(C2CN(C)CC3=C2C=CC=C3N([Si](C)(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C2836.6Standard non polar33892256
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)-2-methoxyphenol,3TMS,isomer #1COC1=CC(C2CN(C)CC3=C2C=CC=C3N([Si](C)(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C2953.8Standard polar33892256
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)-2-methoxyphenol,2TBDMS,isomer #1COC1=CC(C2CN(C)CC3=C(N[Si](C)(C)C(C)(C)C)C=CC=C32)=CC=C1O[Si](C)(C)C(C)(C)C3049.7Semi standard non polar33892256
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)-2-methoxyphenol,2TBDMS,isomer #1COC1=CC(C2CN(C)CC3=C(N[Si](C)(C)C(C)(C)C)C=CC=C32)=CC=C1O[Si](C)(C)C(C)(C)C3251.2Standard non polar33892256
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)-2-methoxyphenol,2TBDMS,isomer #1COC1=CC(C2CN(C)CC3=C(N[Si](C)(C)C(C)(C)C)C=CC=C32)=CC=C1O[Si](C)(C)C(C)(C)C3351.1Standard polar33892256
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)-2-methoxyphenol,2TBDMS,isomer #2COC1=CC(C2CN(C)CC3=C2C=CC=C3N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O3008.3Semi standard non polar33892256
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)-2-methoxyphenol,2TBDMS,isomer #2COC1=CC(C2CN(C)CC3=C2C=CC=C3N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O3364.7Standard non polar33892256
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)-2-methoxyphenol,2TBDMS,isomer #2COC1=CC(C2CN(C)CC3=C2C=CC=C3N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O3358.1Standard polar33892256
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)-2-methoxyphenol,3TBDMS,isomer #1COC1=CC(C2CN(C)CC3=C2C=CC=C3N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C3210.9Semi standard non polar33892256
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)-2-methoxyphenol,3TBDMS,isomer #1COC1=CC(C2CN(C)CC3=C2C=CC=C3N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C3496.5Standard non polar33892256
4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)-2-methoxyphenol,3TBDMS,isomer #1COC1=CC(C2CN(C)CC3=C2C=CC=C3N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C3231.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)-2-methoxyphenol GC-MS (Non-derivatized) - 70eV, Positivesplash10-014l-0690000000-d90d2100399c2802cd6c2021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)-2-methoxyphenol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)-2-methoxyphenol GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)-2-methoxyphenol GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)-2-methoxyphenol GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)-2-methoxyphenol GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)-2-methoxyphenol 10V, Positive-QTOFsplash10-000i-0090000000-01771098ca2c96c89d932021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)-2-methoxyphenol 20V, Positive-QTOFsplash10-000i-0290000000-02f66e4970d807d479ce2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)-2-methoxyphenol 40V, Positive-QTOFsplash10-000f-1980000000-bf093e25bba2fdbd2eff2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)-2-methoxyphenol 10V, Negative-QTOFsplash10-001i-0390000000-8f6692974cd1ba2e69c52021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)-2-methoxyphenol 20V, Negative-QTOFsplash10-001i-0490000000-1f0d77f33f1a2d606b182021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(8-Amino-1,2,3,4-tetrahydro-2-methyl-4-isoquinolinyl)-2-methoxyphenol 40V, Negative-QTOFsplash10-001i-0390000000-3324a7f775b0e00c71e52021-10-12Wishart 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 ID143057
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound162959
PDB IDNot Available
ChEBI IDNot Available
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 ]