(S)-Reticuline (CHEM022754)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:50:55 UTC
Update Date2016-11-09 01:17:34 UTC
Accession NumberCHEM022754
Identification
Common Name(S)-Reticuline
ClassSmall Molecule
DescriptionThe (S)-enantiomer of reticuline.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical 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 Mass329.390 g/mol
Monoisotopic Mass329.163 g/mol
CAS Registry Number485-19-8
IUPAC Name(1S)-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol
Traditional Name(+,-)-reticuline
SMILESCOC1=C(O)C=C(C[C@@H]2N(C)CCC3=CC(OC)=C(O)C=C23)C=C1
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.17 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-0900000000-480c5be967ad0cdfe3a1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-08fr-1290200000-e4ec7775ca969ba4d67dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-efd80efd0b57900a92daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f7p-0934000000-7c33a1bd7de9666c1d8fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fk9-1920000000-12f84a978a4144057a4dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-4d4cbd0c33fe742e473fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0029000000-2bde34377f488f00c9fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06zc-0191000000-c4dcb047f808604a6e88Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0019000000-e3b1ce90ac36f283f151Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000x-0932000000-ab4976b621ab97468da0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0imj-0921000000-bc3bc4c37bf770f60e62Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-48c9693a0346ebfa2d97Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0169000000-ecf1a66856c22584f73cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00wa-0492000000-ef65d9cac11130e20cb8Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0003601
FooDB IDFDB002089
Phenol Explorer IDNot Available
KNApSAcK IDC00001910
BiGG IDNot Available
BioCyc IDS-RETICULINE
METLIN ID6967
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID388724
ChEBI ID16718
PubChem Compound ID439653
Kegg Compound IDC02105
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Vanderlaan, Douglas G.; Schwartz, Martin A. Synthesis and oxidative coupling of (±)-3-oxoreticuline. Journal of Organic Chemistry (1985), 50(6), 743-7.
2. Al-Amri AM, Smith RM, El-Haj BM, Juma'a MH: The GC-MS detection and characterization of reticuline as a marker of opium use. Forensic Sci Int. 2004 Mar 10;140(2-3):175-83.
3. Al-Amri AM, Smith RM, El-Haj BM, Juma'a MH: The GC-MS detection and characterization of reticuline as a marker of opium use. Forensic Sci Int. 2004 May 28;142(1):61-9.
4. Poeaknapo C, Schmidt J, Brandsch M, Drager B, Zenk MH: Endogenous formation of morphine in human cells. Proc Natl Acad Sci U S A. 2004 Sep 28;101(39):14091-6. Epub 2004 Sep 21.
5. Poeaknapo C: Mammalian morphine: de novo formation of morphine in human cells. Med Sci Monit. 2005 May;11(5):MS6-17. Epub 2005 Apr 28.
6. Boettcher C, Fellermeier M, Boettcher C, Drager B, Zenk MH: How human neuroblastoma cells make morphine. Proc Natl Acad Sci U S A. 2005 Jun 14;102(24):8495-500. Epub 2005 Jun 3.