AFCDB: (S)-Reticuline (FDB002089)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:14 UTC

Update date

2019-11-26 02:56:59 UTC

Primary ID

FDB002089

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(S)-Reticuline

Description

Alkaloid 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 Number

485-19-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.17 g/L	ALOGPS
logP	2.71	ALOGPS
logP	3.1	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	9.76	ChemAxon
pKa (Strongest Basic)	7.81	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	62.16 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	93.84 m³·mol⁻¹	ChemAxon
Polarizability	35.87 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C19H23NO4

IUPAC name

1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol

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

InChI Key

BHLYRWXGMIUIHG-UHFFFAOYSA-N

Isomeric SMILES

COC1=C(O)C=C(CC2N(C)CCC3=CC(OC)=C(O)C=C23)C=C1

Average Molecular Weight

329.3902

Monoisotopic Molecular Weight

329.162708229

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoquinolines and derivatives

Sub Class

Benzylisoquinolines

Direct Parent

Benzylisoquinolines

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzylisoquinoline alkaloid (CHEBI:26533 )
isoquinolinol (CHEBI:26533 )
benzyltetrahydroisoquinoline (CHEBI:26533 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 69.28%; H 7.04%; N 4.25%; O 19.43%	DFC
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]D +132 (MeOH)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	(S)-Reticuline, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-0900000000-480c5be967ad0cdfe3a1	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0009000000-57d1783ea6cc84614e74	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f7p-0935000000-d0a70dcdeb3adb480395	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0hg5-1930000000-5051808ad28ed244d20d	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0009000000-80869c170e5a10af825d	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0029000000-da2d34d4cf98c8009fd3	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01x3-1191000000-89cd33861be80103c081	2015-05-27	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

16718

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB03601

CRC / DFC (Dictionary of Food Compounds) ID

CFD80-P:CFD84-T

EAFUS ID

Not Available

Dr. Duke ID

(+)-RETICULINE|RETICULINE

BIGG ID

Not Available

KNApSAcK ID

C00001910

HET ID

REN

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Reticulin

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
analgesic	35480	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 bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti dopaminergic	48561	A drug that binds to but does not activate dopamine receptors, thereby blocking the actions of dopamine or exogenous agonists.	DUKE
anti spasmodic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
central nervous system stimulant	35470	A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.	DUKE
convulsant			DUKE
fungicide	24127	A substance used to destroy fungal pests.	DUKE
hyperthermic			DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
pyrogenic			DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not 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.

(S)-Reticuline (FDB002089)

Structure for FDB002089 ((S)-Reticuline)