Showing metabocard for (S)-Reticuline (BMDB0003601)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:05:31 UTC
Update Date2020-04-22 15:12:34 UTC
BMDB IDBMDB0003601
Secondary Accession Numbers
  • BMDB03601
Metabolite Identification
Common Name(S)-Reticuline
Description(S)-Reticuline, also known as reticulin, belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached. Based on a literature review a significant number of articles have been published on (S)-Reticuline.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+)-ReticulineChEBI
(S)-(+)-ReticulineChEBI
L-(+)-ReticulineChEBI
ReticlineChEBI
ReticulinHMDB
ReticulineHMDB
S-(+)-ReticulineHMDB
(1S)-1,2,3,4-Tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-7-isoquinolinolHMDB
(S)-ReticuleneHMDB
(S)-ReticulineHMDB
Chemical FormulaC19H23NO4
Average Molecular Weight329.3902
Monoisotopic Molecular Weight329.162708229
IUPAC Name(1S)-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol
Traditional Name(+,-)-reticuline
CAS Registry Number485-19-8
SMILES
COC1=C(O)C=C(C[C@@H]2N(C)CCC3=CC(OC)=C(O)C=C23)C=C1
InChI Identifier
InChI=1S/C19H23NO4/c1-20-7-6-13-10-19(24-3)17(22)11-14(13)15(20)8-12-4-5-18(23-2)16(21)9-12/h4-5,9-11,15,21-22H,6-8H2,1-3H3/t15-/m0/s1
InChI KeyBHLYRWXGMIUIHG-HNNXBMFYSA-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
  • Methoxyphenol
  • Tetrahydroisoquinoline
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 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
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.71ALOGPS
logP3.1ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)9.76ChemAxon
pKa (Strongest Basic)7.81ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area62.16 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity93.84 m³·mol⁻¹ChemAxon
Polarizability36.15 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-0900000000-480c5be967ad0cdfe3a1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-08fr-1290200000-e4ec7775ca969ba4d67dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-efd80efd0b57900a92daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f7p-0934000000-7c33a1bd7de9666c1d8fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fk9-1920000000-12f84a978a4144057a4dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-4d4cbd0c33fe742e473fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0029000000-2bde34377f488f00c9fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06zc-0191000000-c4dcb047f808604a6e88View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0019000000-e3b1ce90ac36f283f151View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000x-0932000000-ab4976b621ab97468da0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0imj-0921000000-bc3bc4c37bf770f60e62View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-48c9693a0346ebfa2d97View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0169000000-ecf1a66856c22584f73cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00wa-0492000000-ef65d9cac11130e20cb8View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0003601
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002089
KNApSAcK IDC00001910
Chemspider ID388724
KEGG Compound IDC02105
BioCyc IDS-RETICULINE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6967
PubChem Compound439653
PDB IDNot Available
ChEBI ID16718
References
Synthesis ReferenceVanderlaan, Douglas G.; Schwartz, Martin A. Synthesis and oxidative coupling of (±)-3-oxoreticuline. Journal of Organic Chemistry (1985), 50(6), 743-7.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available