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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-09-04 13:13:28 UTC
Update Date2021-09-14 15:47:52 UTC
HMDB IDHMDB0006921
Secondary Accession Numbers
  • HMDB06921
Metabolite Identification
Common Name(S)-3-Hydroxy-N-methylcoclaurine
Description(S)-3-Hydroxy-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)-3-Hydroxy-N-methylcoclaurine exists in all living organisms, ranging from bacteria to humans (S)-3-Hydroxy-N-methylcoclaurine has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make (S)-3-hydroxy-N-methylcoclaurine a potential biomarker for the consumption of these foods (S)-3-Hydroxy-N-methylcoclaurine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on (S)-3-Hydroxy-N-methylcoclaurine.
Structure
Data?1582752415
Synonyms
ValueSource
3'-Hydroxy-(S)-N-methylcoclaurineChEBI
3'-Hydroxy-N-methyl-(S)-coclaurineChEBI
(S)-3'-Hydroxy-N-methylcoclaurineKegg
Chemical FormulaC18H21NO4
Average Molecular Weight315.3636
Monoisotopic Molecular Weight315.147058165
IUPAC Name4-{[(1S)-7-hydroxy-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl}benzene-1,2-diol
Traditional Name4-benzene-1,2-diol
CAS Registry NumberNot Available
SMILES
COC1=C(O)C=C2[C@H](CC3=CC(O)=C(O)C=C3)N(C)CCC2=C1
InChI Identifier
InChI=1S/C18H21NO4/c1-19-6-5-12-9-18(23-2)17(22)10-13(12)14(19)7-11-3-4-15(20)16(21)8-11/h3-4,8-10,14,20-22H,5-7H2,1-2H3/t14-/m0/s1
InChI KeyDAUPWJBRVZCBQB-AWEZNQCLSA-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
  • Catechol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Ether
  • Azacycle
  • 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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
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 Solubility0.23 g/LALOGPS
logP2.27ALOGPS
logP2.76ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)7.22ChemAxon
pKa (Strongest Basic)10.9ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area73.16 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity89.35 m³·mol⁻¹ChemAxon
Polarizability34.24 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]+174.57531661259
DarkChem[M-H]-176.54231661259
DeepCCS[M+H]+184.5730932474
DeepCCS[M-H]-182.21230932474
DeepCCS[M-2H]-216.2530932474
DeepCCS[M+Na]+191.47830932474
AllCCS[M+H]+176.932859911
AllCCS[M+H-H2O]+173.532859911
AllCCS[M+NH4]+180.032859911
AllCCS[M+Na]+180.932859911
AllCCS[M-H]-180.132859911
AllCCS[M+Na-2H]-179.932859911
AllCCS[M+HCOO]-179.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(S)-3-Hydroxy-N-methylcoclaurineCOC1=C(O)C=C2[C@H](CC3=CC(O)=C(O)C=C3)N(C)CCC2=C14246.6Standard polar33892256
(S)-3-Hydroxy-N-methylcoclaurineCOC1=C(O)C=C2[C@H](CC3=CC(O)=C(O)C=C3)N(C)CCC2=C12832.5Standard non polar33892256
(S)-3-Hydroxy-N-methylcoclaurineCOC1=C(O)C=C2[C@H](CC3=CC(O)=C(O)C=C3)N(C)CCC2=C12959.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(S)-3-Hydroxy-N-methylcoclaurine,1TMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C)[C@H](CC1=CC=C(O)C(O)=C1)N(C)CC22809.5Semi standard non polar33892256
(S)-3-Hydroxy-N-methylcoclaurine,1TMS,isomer #2COC1=CC2=C(C=C1O)[C@H](CC1=CC=C(O)C(O[Si](C)(C)C)=C1)N(C)CC22799.7Semi standard non polar33892256
(S)-3-Hydroxy-N-methylcoclaurine,1TMS,isomer #3COC1=CC2=C(C=C1O)[C@H](CC1=CC=C(O[Si](C)(C)C)C(O)=C1)N(C)CC22804.7Semi standard non polar33892256
(S)-3-Hydroxy-N-methylcoclaurine,2TMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C)[C@H](CC1=CC=C(O[Si](C)(C)C)C(O)=C1)N(C)CC22747.6Semi standard non polar33892256
(S)-3-Hydroxy-N-methylcoclaurine,2TMS,isomer #2COC1=CC2=C(C=C1O[Si](C)(C)C)[C@H](CC1=CC=C(O)C(O[Si](C)(C)C)=C1)N(C)CC22737.3Semi standard non polar33892256
(S)-3-Hydroxy-N-methylcoclaurine,2TMS,isomer #3COC1=CC2=C(C=C1O)[C@H](CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)N(C)CC22782.8Semi standard non polar33892256
(S)-3-Hydroxy-N-methylcoclaurine,3TMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C)[C@H](CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)N(C)CC22789.7Semi standard non polar33892256
(S)-3-Hydroxy-N-methylcoclaurine,1TBDMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)[C@H](CC1=CC=C(O)C(O)=C1)N(C)CC23072.3Semi standard non polar33892256
(S)-3-Hydroxy-N-methylcoclaurine,1TBDMS,isomer #2COC1=CC2=C(C=C1O)[C@H](CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)N(C)CC23059.2Semi standard non polar33892256
(S)-3-Hydroxy-N-methylcoclaurine,1TBDMS,isomer #3COC1=CC2=C(C=C1O)[C@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)N(C)CC23068.3Semi standard non polar33892256
(S)-3-Hydroxy-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(O)=C1)N(C)CC23212.3Semi standard non polar33892256
(S)-3-Hydroxy-N-methylcoclaurine,2TBDMS,isomer #2COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)[C@H](CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)N(C)CC23210.2Semi standard non polar33892256
(S)-3-Hydroxy-N-methylcoclaurine,2TBDMS,isomer #3COC1=CC2=C(C=C1O)[C@H](CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)N(C)CC23221.2Semi standard non polar33892256
(S)-3-Hydroxy-N-methylcoclaurine,3TBDMS,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(O[Si](C)(C)C(C)(C)C)=C1)N(C)CC23422.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (S)-3-Hydroxy-N-methylcoclaurine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-0900000000-16905ec7b37acd6da6f02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-3-Hydroxy-N-methylcoclaurine GC-MS (3 TMS) - 70eV, Positivesplash10-02t9-1390040000-7c86603d65085d54ab9c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-3-Hydroxy-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)-3-Hydroxy-N-methylcoclaurine 10V, Positive-QTOFsplash10-014i-0019000000-9ed95170816cfe1fcfad2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-Hydroxy-N-methylcoclaurine 20V, Positive-QTOFsplash10-000l-0952000000-7be95e26bc54ea0a159f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-Hydroxy-N-methylcoclaurine 40V, Positive-QTOFsplash10-00r2-5920000000-6983aa56eb6bde4d90502017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-Hydroxy-N-methylcoclaurine 10V, Negative-QTOFsplash10-03di-0009000000-63223a01156e31029e0a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-Hydroxy-N-methylcoclaurine 20V, Negative-QTOFsplash10-03di-0069000000-d962fb4fb99d68aa9cc92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-Hydroxy-N-methylcoclaurine 40V, Negative-QTOFsplash10-00bd-0590000000-b1ff4042511719f550f12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-Hydroxy-N-methylcoclaurine 10V, Positive-QTOFsplash10-014i-0019000000-941d7d018f05d7b7b5e92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-Hydroxy-N-methylcoclaurine 20V, Positive-QTOFsplash10-0ap3-0593000000-427edfb835dd38b010f32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-Hydroxy-N-methylcoclaurine 40V, Positive-QTOFsplash10-03di-0930000000-66fc76acde1decbe2f142021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-Hydroxy-N-methylcoclaurine 10V, Negative-QTOFsplash10-03di-0009000000-a9f6ec6e6fe2a282293c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-Hydroxy-N-methylcoclaurine 20V, Negative-QTOFsplash10-03di-0359000000-1ccd91cadb6625f9a2f22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-3-Hydroxy-N-methylcoclaurine 40V, Negative-QTOFsplash10-0006-0490000000-a697489aa89c42118f242021-09-24Wishart 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 IDFDB024153
KNApSAcK IDNot Available
Chemspider ID389490
KEGG Compound IDC05202
BioCyc ID3-HYDROXY-N-METHYL-S-COCLAURINE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440591
PDB IDNot Available
ChEBI ID17079
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 ReferencesNot Available

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