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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:53:22 UTC
Update Date2022-03-07 03:17:43 UTC
HMDB IDHMDB0060319
Secondary Accession Numbers
  • HMDB60319
Metabolite Identification
Common Name(S)-N-Methylcoclaurine
Description(S)-N-Methylcoclaurine belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached (S)-N-Methylcoclaurine is a very strong basic compound (based on its pKa) (S)-N-Methylcoclaurine exists in all living organisms, ranging from bacteria to humans. These are organic compounds containing an isoquinoline to which a benzyl group is attached.
Structure
Data?1563866043
Synonyms
ValueSource
(S)-1,2,3,4-Tetrahydro-1-[(4-hydroxyphenyl)methyl]-6-methoxy-2-methyl-7-isoquinolinolChEBI
Chemical FormulaC18H21NO3
Average Molecular Weight299.3642
Monoisotopic Molecular Weight299.152143543
IUPAC Name(1S)-1-[(4-hydroxyphenyl)methyl]-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol
Traditional Name(S)-N-methylcoclaurine
CAS Registry NumberNot Available
SMILES
COC1=C(O)C=C2[C@H](CC3=CC=C(O)C=C3)N(C)CCC2=C1
InChI Identifier
InChI=1S/C18H21NO3/c1-19-8-7-13-10-18(22-2)17(21)11-15(13)16(19)9-12-3-5-14(20)6-4-12/h3-6,10-11,16,20-21H,7-9H2,1-2H3/t16-/m0/s1
InChI KeyBOKVLBSSPUTWLV-INIZCTEOSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIsoquinolines and derivatives
Sub ClassBenzylisoquinolines
Direct ParentBenzylisoquinolines
Alternative Parents
Substituents
  • Benzylisoquinoline
  • Tetrahydroisoquinoline
  • Anisole
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Aralkylamine
  • Monocyclic benzene moiety
  • Benzenoid
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Ether
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Not AvailableNot 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
Water Solubility0.29 g/LALOGPS
logP2.69ALOGPS
logP3.13ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)9.87ChemAxon
pKa (Strongest Basic)8.2ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area52.93 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity87.37 m³·mol⁻¹ChemAxon
Polarizability33.25 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
DarkChem[M+H]+171.15231661259
DarkChem[M-H]-173.26531661259
DeepCCS[M+H]+180.36530932474
DeepCCS[M-H]-178.00730932474
DeepCCS[M-2H]-211.92330932474
DeepCCS[M+Na]+187.14930932474
AllCCS[M+H]+173.532859911
AllCCS[M+H-H2O]+170.032859911
AllCCS[M+NH4]+176.832859911
AllCCS[M+Na]+177.732859911
AllCCS[M-H]-177.732859911
AllCCS[M+Na-2H]-177.532859911
AllCCS[M+HCOO]-177.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(S)-N-MethylcoclaurineCOC1=C(O)C=C2[C@H](CC3=CC=C(O)C=C3)N(C)CCC2=C14034.1Standard polar33892256
(S)-N-MethylcoclaurineCOC1=C(O)C=C2[C@H](CC3=CC=C(O)C=C3)N(C)CCC2=C12642.7Standard non polar33892256
(S)-N-MethylcoclaurineCOC1=C(O)C=C2[C@H](CC3=CC=C(O)C=C3)N(C)CCC2=C12714.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(S)-N-Methylcoclaurine,1TMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C)[C@H](CC1=CC=C(O)C=C1)N(C)CC22630.9Semi standard non polar33892256
(S)-N-Methylcoclaurine,1TMS,isomer #2COC1=CC2=C(C=C1O)[C@H](CC1=CC=C(O[Si](C)(C)C)C=C1)N(C)CC22623.2Semi standard non polar33892256
(S)-N-Methylcoclaurine,2TMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C)[C@H](CC1=CC=C(O[Si](C)(C)C)C=C1)N(C)CC22608.9Semi standard non polar33892256
(S)-N-Methylcoclaurine,1TBDMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)[C@H](CC1=CC=C(O)C=C1)N(C)CC22894.8Semi standard non polar33892256
(S)-N-Methylcoclaurine,1TBDMS,isomer #2COC1=CC2=C(C=C1O)[C@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N(C)CC22885.0Semi standard non polar33892256
(S)-N-Methylcoclaurine,2TBDMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)[C@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N(C)CC23070.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (S)-N-Methylcoclaurine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-0900000000-086f09f17db300a597242017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-N-Methylcoclaurine GC-MS (2 TMS) - 70eV, Positivesplash10-01t9-1490200000-98a8949aca2ab22179162017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-N-Methylcoclaurine 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 - (S)-N-Methylcoclaurine 10V, Positive-QTOFsplash10-0udi-0019000000-c0d82165ca1fb9b38f352017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-N-Methylcoclaurine 20V, Positive-QTOFsplash10-0l06-0942000000-baf99463c63a33e3ae7b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-N-Methylcoclaurine 40V, Positive-QTOFsplash10-05r0-4920000000-116ece8d4676b862dbb52017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-N-Methylcoclaurine 10V, Negative-QTOFsplash10-0002-0090000000-c6fad313f45df56a53962017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-N-Methylcoclaurine 20V, Negative-QTOFsplash10-0002-0090000000-bf4c2bfd38d87099b5c62017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-N-Methylcoclaurine 40V, Negative-QTOFsplash10-0h00-1690000000-4cf29ba63cf2e71c858c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-N-Methylcoclaurine 10V, Positive-QTOFsplash10-0udi-0009000000-1d8c7ea64ca3af7aef5e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-N-Methylcoclaurine 20V, Positive-QTOFsplash10-1000-0494000000-c1be3351bd3522398f962021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-N-Methylcoclaurine 40V, Positive-QTOFsplash10-006y-4950000000-a6e2e5d2269bf93939e82021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-N-Methylcoclaurine 10V, Negative-QTOFsplash10-0002-0090000000-cf6f68fb1a2e8ad8e4162021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-N-Methylcoclaurine 20V, Negative-QTOFsplash10-0002-0090000000-3677eb70c67fa707ba172021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-N-Methylcoclaurine 40V, Negative-QTOFsplash10-004i-1690000000-049aecb2081c4545a6d42021-10-12Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
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 IDC00025268
Chemspider IDNot Available
KEGG Compound IDC05176
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440584
PDB IDNot Available
ChEBI ID17041
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. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the rate-limiting conversions of tyrosine to DOPA, DOPA to DOPA-quinone and possibly 5,6-dihydroxyindole to indole-5,6 quinone.
Gene Name:
TYR
Uniprot ID:
P14679
Molecular weight:
60392.69
Reactions
(S)-N-Methylcoclaurine + Oxygen + Reduced acceptor → (S)-3-Hydroxy-N-methylcoclaurine + Water + Acceptordetails