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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:48:40 UTC
Update Date2019-07-23 06:35:15 UTC
HMDB IDHMDB0041933
Secondary Accession Numbers
  • HMDB41933
Metabolite Identification
Common NameMitragynine
DescriptionMitragynine itself acts primarily via -opioid receptors, although its oxidation product mitragynine-pseudoindoxyl, which is likely to be a major component of kratom that has been aged or stored for extended periods, acts as a fairly selective -opioid agonist with little affinity for receptors. Another alkaloid with a major contribution to the opioid activity of the kratom plant is the related compound 7-hydroxymitragynine, which while present in the plant in much smaller quantities than mitragynine, is a much more potent opioid agonist.
Structure
Data?1563863715
Synonyms
ValueSource
Mitragynine ethanedisulfonateMeSH
SK And F-12711MeSH
Mitragynine monohydrochlorideMeSH
SK And F 12711MeSH
Mitragynine, (3beta,16E,20beta)-isomerMeSH
Mitragynine, (16E)-isomerMeSH
Mitragynine, (3beta,16E)-isomerMeSH
Chemical FormulaC23H30N2O4
Average Molecular Weight398.4953
Monoisotopic Molecular Weight398.220557458
IUPAC Namemethyl (2E)-2-[(2S,3S,12bS)-3-ethyl-8-methoxy-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate
Traditional Namemitragynine
CAS Registry Number6202-22-8
SMILES
[H][C@@]12C[C@@H]([C@H](CC)CN1CCC1=C2NC2=C1C(OC)=CC=C2)C(=C/OC)\C(=O)OC
InChI Identifier
InChI=1S/C23H30N2O4/c1-5-14-12-25-10-9-15-21-18(7-6-8-20(21)28-3)24-22(15)19(25)11-16(14)17(13-27-2)23(26)29-4/h6-8,13-14,16,19,24H,5,9-12H2,1-4H3/b17-13+/t14-,16+,19+/m1/s1
InChI KeyLELBFTMXCIIKKX-QVRQZEMUSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as corynanthean-type alkaloids. These are alkaloids with a structure based on the corynanthean nucleus, which is a tetracycle characterized by an indole fused to a quinolizidine. Additionally, the quinolizidine ring system is substituted to a 2-methylpropyl group and one ethyl group.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassCorynanthean-type alkaloids
Sub ClassNot Available
Direct ParentCorynanthean-type alkaloids
Alternative Parents
Substituents
  • Corynanthean skeleton
  • Beta-carboline
  • Pyridoindole
  • Quinolizine
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Anisole
  • Alkyl aryl ether
  • Aralkylamine
  • Piperidine
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Vinylogous ester
  • Methyl ester
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tertiary aliphatic amine
  • Tertiary amine
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid derivative
  • Ether
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.03 g/LALOGPS
logP4ALOGPS
logP3.3ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)16.67ChemAxon
pKa (Strongest Basic)7.33ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.79 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity112.91 m³·mol⁻¹ChemAxon
Polarizability43.29 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02ar-1149000000-68ad2024bca19f46b22fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0019000000-4a3248fba1292cfe9ecfJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00l2-1259000000-0c7ecfb4c67c6865e62eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-1359000000-e92aafb89a073659ee2eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-8e6dc3406d97e509a68bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6t-0009000000-3aa17544a9b8f0ba9317JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00e9-2049000000-c8eb7cdb83396a685cb1JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00001751
Chemspider ID2298865
KEGG Compound IDC09226
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMitragynine
METLIN IDNot Available
PubChem Compound3034396
PDB IDNot Available
ChEBI ID6956
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available