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(S)-Reticuline (FDB002089)

Record Information
Version1.0
Creation date2010-04-08 22:05:14 UTC
Update date2019-11-26 02:56:59 UTC
Primary IDFDB002089
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(S)-Reticuline
DescriptionAlkaloid from Papaver somniferum (opium poppy) and Annona reticulata (custard apple) (S)-reticuline is an endogenous precursors of morphine. (PMID 15383669); (S)-Reticuline is a key intermediate in the synthesis of morphine, the major active metabolite of opium poppy. ; "Endogenous morphine" has been long isolated and authenticated by mass spectrometry in trace amounts from animal and human specific tissue or fluids. (PMID: 15874902); Recently, human neuroblastoma cells (SH-SY5Y) were shown capable of synthesizing morphine as well. (S)-reticuline undergoes a change of configuration at C-1 during its transformation to salutaridinol and thebaine. From thebaine, there is a bifurcate pathway leading to morphine proceeding via codeine or oripavine, in both plants and mammals. (PMID 15937106); Reticular fibers or reticulin is a histological term used to describe a type of fiber in connective tissue composed of type III collagen. Reticular fibers crosslink to form a fine meshwork (reticulum). This network acts as a supporting mesh in soft tissues such as liver, bone marrow, and the tissues and organs of the lymphatic system. (S)-Reticuline is found in many foods, some of which are tarragon, common bean, tinda, and other bread.
CAS Number485-19-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
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
Polarizability35.87 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC19H23NO4
IUPAC name1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol
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
InChI KeyBHLYRWXGMIUIHG-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(O)C=C(CC2N(C)CCC3=CC(OC)=C(O)C=C23)C=C1
Average Molecular Weight329.3902
Monoisotopic Molecular Weight329.162708229
Classification
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
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(S)-Reticuline, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-0900000000-480c5be967ad0cdfe3a1Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-57d1783ea6cc84614e742015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f7p-0935000000-d0a70dcdeb3adb4803952015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0hg5-1930000000-5051808ad28ed244d20d2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-80869c170e5a10af825d2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0029000000-da2d34d4cf98c8009fd32015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01x3-1191000000-89cd33861be80103c0812015-05-27View Spectrum
NMRNot Available
ChemSpider ID388724
ChEMBL IDCHEMBL235212
KEGG Compound IDC02105
Pubchem Compound ID439653
Pubchem Substance IDNot Available
ChEBI ID16718
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03601
CRC / DFC (Dictionary of Food Compounds) IDCFD80-P:CFD84-T
EAFUS IDNot Available
Dr. Duke ID(+)-RETICULINE|RETICULINE
BIGG IDNot Available
KNApSAcK IDC00001910
HET IDREN
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDReticulin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / Bioactivities
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.