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Showing Compound (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
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
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
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
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
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Analgesic35480 An agent that relieves pain by reducing or blocking pain signals in the brain, commonly used to manage acute or chronic pain, inflammation, and fever, with therapeutic applications in surgery, injury, and disease treatment.DUKE
Anti bacterial33282 An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.DUKE
Anti dopaminergic48561 An agent that blocks dopamine receptors, reducing dopamine activity. It plays a biological role in regulating mood, motivation, and movement. Therapeutically, it's used to manage schizophrenia, bipolar disorder, and nausea, as well as to treat conditions like Tourette's syndrome and restless leg syndrome.DUKE
Anti-spasmodic52217 An agent that relaxes smooth muscle, reducing muscle spasms and cramps. It plays a biological role in regulating muscle tone and is therapeutically applied to treat conditions such as irritable bowel syndrome, menstrual cramps, and muscle spasms, providing relief from abdominal pain and discomfort.DUKE
Central nervous system stimulant35470 An agent that increases alertness and activity by enhancing neurotransmitter release, used therapeutically to manage attention deficit hyperactivity disorder (ADHD), narcolepsy, and fatigue, and to improve cognitive function and mood.DUKE
ConvulsantAn agent that induces convulsions and/or epileptic seizures, acting as a stimulant at low doses. It has no therapeutic applications due to its high risk of causing seizures and excitotoxicity, and is the opposite of an anticonvulsant.DUKE
Fungicide24127 An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.DUKE
HyperthermicA state of abnormally high body temperature. Biologically, it can occur as a response to infection or inflammation. Therapeutically, hyperthermia is applied to treat cancer, as high temperatures can damage cancer cells. Key medical uses include oncology, where hyperthermia is used in combination with radiation or chemotherapy to enhance treatment efficacy.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
PyrogenicAn agent that induces fever, stimulating the immune system. It plays a biological role in fighting infection and has therapeutic applications in immunotherapy and vaccine development. Key medical uses include treating certain infections and cancers, as well as stimulating the immune system in immunocompromised patients.DUKE
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.