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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-08-13 01:15:00 UTC
Update Date2021-09-14 15:48:20 UTC
HMDB IDHMDB0003601
Secondary Accession Numbers
  • HMDB03601
Metabolite Identification
Common Name(S)-Reticuline
Description(S)-Reticuline is an endogenous precursor of morphine (PMID: 15383669 ). (S)-Reticuline is a key intermediate in the synthesis of morphine, the major active metabolite of the 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 ). 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 into 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 ).
Structure
Data?1594848955
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 Weight329.3902
Monoisotopic Molecular Weight329.162708229
IUPAC Name(1S)-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol
Traditional Name(+,-)-reticuline
CAS Registry Number485-19-8
SMILES
COC1=C(O)C=C(C[C@@H]2N(C)CCC3=CC(OC)=C(O)C=C23)C=C1
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/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
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+176.37731661259
DarkChem[M-H]-178.31231661259
DeepCCS[M-2H]-218.62830932474
DeepCCS[M+Na]+193.85630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(S)-ReticulineCOC1=C(O)C=C(C[C@@H]2N(C)CCC3=CC(OC)=C(O)C=C23)C=C14346.7Standard polar33892256
(S)-ReticulineCOC1=C(O)C=C(C[C@@H]2N(C)CCC3=CC(OC)=C(O)C=C23)C=C12766.7Standard non polar33892256
(S)-ReticulineCOC1=C(O)C=C(C[C@@H]2N(C)CCC3=CC(OC)=C(O)C=C23)C=C12817.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(S)-Reticuline,1TMS,isomer #1COC1=CC2=C(C=C1O)[C@H](CC1=CC=C(OC)C(O[Si](C)(C)C)=C1)N(C)CC22743.3Semi standard non polar33892256
(S)-Reticuline,1TMS,isomer #2COC1=CC=C(C[C@H]2C3=CC(O[Si](C)(C)C)=C(OC)C=C3CCN2C)C=C1O2735.7Semi standard non polar33892256
(S)-Reticuline,2TMS,isomer #1COC1=CC=C(C[C@H]2C3=CC(O[Si](C)(C)C)=C(OC)C=C3CCN2C)C=C1O[Si](C)(C)C2720.9Semi standard non polar33892256
(S)-Reticuline,1TBDMS,isomer #1COC1=CC2=C(C=C1O)[C@H](CC1=CC=C(OC)C(O[Si](C)(C)C(C)(C)C)=C1)N(C)CC22980.3Semi standard non polar33892256
(S)-Reticuline,1TBDMS,isomer #2COC1=CC=C(C[C@H]2C3=CC(O[Si](C)(C)C(C)(C)C)=C(OC)C=C3CCN2C)C=C1O2973.1Semi standard non polar33892256
(S)-Reticuline,2TBDMS,isomer #1COC1=CC=C(C[C@H]2C3=CC(O[Si](C)(C)C(C)(C)C)=C(OC)C=C3CCN2C)C=C1O[Si](C)(C)C(C)(C)C3152.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (S)-Reticuline GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-0900000000-480c5be967ad0cdfe3a12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-Reticuline GC-MS (2 TMS) - 70eV, Positivesplash10-08fr-1290200000-e4ec7775ca969ba4d67d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-Reticuline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Reticuline 10V, Positive-QTOFsplash10-001i-0009000000-efd80efd0b57900a92da2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Reticuline 20V, Positive-QTOFsplash10-0f7p-0934000000-7c33a1bd7de9666c1d8f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Reticuline 40V, Positive-QTOFsplash10-0fk9-1920000000-12f84a978a4144057a4d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Reticuline 10V, Negative-QTOFsplash10-004i-0009000000-4d4cbd0c33fe742e473f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Reticuline 20V, Negative-QTOFsplash10-004i-0029000000-2bde34377f488f00c9fb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Reticuline 40V, Negative-QTOFsplash10-06zc-0191000000-c4dcb047f808604a6e882016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Reticuline 10V, Positive-QTOFsplash10-001i-0019000000-e3b1ce90ac36f283f1512021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Reticuline 20V, Positive-QTOFsplash10-000x-0932000000-ab4976b621ab97468da02021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Reticuline 40V, Positive-QTOFsplash10-0imj-0921000000-bc3bc4c37bf770f60e622021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Reticuline 10V, Negative-QTOFsplash10-004i-0009000000-48c9693a0346ebfa2d972021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Reticuline 20V, Negative-QTOFsplash10-004i-0169000000-ecf1a66856c22584f73c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Reticuline 40V, Negative-QTOFsplash10-00wa-0492000000-ef65d9cac11130e20cb82021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)FemaleEpithelial ovarian cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002089
KNApSAcK IDC00001910
Chemspider ID388724
KEGG Compound IDC02105
BioCyc IDS-RETICULINE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6967
PubChem Compound439653
PDB IDNot Available
ChEBI ID16718
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceVanderlaan, Douglas G.; Schwartz, Martin A. Synthesis and oxidative coupling of (±)-3-oxoreticuline. Journal of Organic Chemistry (1985), 50(6), 743-7.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:15036439 ]
  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 May 28;142(1):61-9. [PubMed:15272474 ]
  3. 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. [PubMed:15383669 ]
  4. 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. [PubMed:15874902 ]
  5. 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. [PubMed:15937106 ]