Record Information
Version1.0
Creation date2010-04-08 22:05:14 UTC
Update date2018-01-23 18:50:24 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
Synonyms
SynonymSource
(R,S)-ReticulineChEBI
Reticuline hydrochloride, (+,-)-isomerMeSH
Reticuline perchlorateMeSH
Reticuline, (+,-)-isomerMeSH
Reticuline, (R)-isomerMeSH
Reticuline, 14C-labeled, (+,-)-isomerMeSH
(+)-reticulinebiospider
(s)-(+)-reticulinebiospider
(s)-reticulinebiospider
D-ReticulineHMDB
L-(+)-ReticulineChEBI
RENbiospider
ReticlineChEBI
ReticulinHMDB
ReticulineHMDB
S-(+)-ReticulineHMDB
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
DescriptionThis compound 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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 69.28%; H 7.04%; N 4.25%; O 19.43%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +132 (MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
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-0009000000-57d1783ea6cc84614e74View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f7p-0935000000-d0a70dcdeb3adb480395View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0hg5-1930000000-5051808ad28ed244d20dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-80869c170e5a10af825dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0029000000-da2d34d4cf98c8009fd3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01x3-1191000000-89cd33861be80103c081View in MoNA
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
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
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
analgesic35480 An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti dopaminergic48561 A drug that binds to but does not activate dopamine receptors, thereby blocking the actions of dopamine or exogenous agonists.DUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
central nervous system stimulant35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
convulsantDUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
hyperthermicDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
pyrogenicDUKE
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.