Mitragynine

Details

• Internal ID: a2d6d920-c797-4429-b26b-c76fd02c9704
• Taxonomy: Alkaloids and derivatives > Corynanthean-type alkaloids
• IUPAC Name: methyl (E)-2-[(2S,3S,12bS)-3-ethyl-8-methoxy-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate
• SMILES (Canonical): CCC1CN2CCC3=C(C2CC1C(=COC)C(=O)OC)NC4=C3C(=CC=C4)OC
• SMILES (Isomeric): CC[C@@H]1CN2CCC3=C([C@@H]2C[C@@H]1/C(=C\OC)/C(=O)OC)NC4=C3C(=CC=C4)OC
• InChI: 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 Key: LELBFTMXCIIKKX-QVRQZEMUSA-N
• Popularity: 271 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₀N₂O₄
• Molecular Weight: 398.50 g/mol
• Exact Mass: 398.22055744 g/mol
• Topological Polar Surface Area (TPSA): 63.80 Ų
• XlogP: 3.40

Synonyms

• 4098-40-2
• (-)-Mitragynine
• MITRAGYNINE PICRATE
• CHEBI:6956
• Skf 12711
• 9-Methoxycorynantheidine
• SK&F 12711
• UNII-EP479K822J
• CHEMBL299031
• HSDB 7901
• EP479K822J
• (E)-Methyl 2-((2S,3S,12bS)-3-ethyl-8-methoxy-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)-3-methoxyacrylate
• Mitragynin
• Mitragynine [MI]
• Mitragynine - 95%
• MITRAGYNINE [WHO-DD]
• SCHEMBL875799
• SCHEMBL875800
• DTXSID701032140
• BDBM50474152
• Mitragynine 100 microg/mL in Methanol
• 16,17-Didehydro-9,17-dimethoxy-17,18-seco-20-alpha-yohimban-16-carboxylic acid methyl ester
• BM164595
• methyl (E)-2-[(2S,3S,12bS)-3-ethyl-8-methoxy-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate
• C09226
• Q414299
• (16E,20-beta)-16,17-didehydro-9,17-dimethoxycorynan-16-carboxylic acid methyl ester
• (.ALPHA.E,2S,3S,12.BETA.S)-3-ETHYL-1,2,3,4,6,7,12,12B-OCTAHYDRO-8-METHOXY-.ALPHA.-(METHOXYMETHYLENE)-INDOLO(2,3-A)QUINOLIZINE-2-ACETIC ACID METHYL ESTER
• Corynan-16-carboxylic acid, 16,17-didehydro-9,17-dimethoxy-, methyl ester, (16E,20.beta.)-
• INDOLO(2,3-A)QUINOLIZINE-2-ACETIC ACID, 3-ETHYL-1,2,3,4,6,7,12,12B-OCTAHYDRO-8-METHOXY-.ALPHA.-(METHOXYMETHYLENE)-, METHYL ESTER, (.ALPHA.E,2S,3S,12BS)-
• methyl (2E)-2-[(2S,4S,5S)-5-ethyl-12-methoxy-7,17-diazatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),11,13,15-tetraen-4-yl]-3-methoxyprop-2-enoate
• methyl(e)-2-[(2s,3s,12bs)-3-ethyl-8-methoxy-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL236	P41143	Delta opioid receptor	60.26 nM	Ki	PMID: 11960505
CHEMBL237	P41145	Kappa opioid receptor	116 nM; 198 nM	Ki; Ki	via Super-PRED; via Super-PRED
CHEMBL233	P35372	Mu opioid receptor	39.2 nM; 161 nM	EC50; Ki	via Super-PRED; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.62%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.89%	94.45%
CHEMBL2535	P11166	Glucose transporter	95.81%	98.75%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.23%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.46%	95.56%
CHEMBL2581	P07339	Cathepsin D	92.33%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.58%	97.25%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	88.82%	91.79%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	87.56%	89.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.03%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.21%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.51%	86.33%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	83.38%	97.50%
CHEMBL5028	O14672	ADAM10	83.35%	97.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.71%	94.33%
CHEMBL255	P29275	Adenosine A2b receptor	82.27%	98.59%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.62%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.59%	99.23%

Plants that contains it

• Cryptocarya lividula
• Euphorbia pannonica
• Ixeris chinensis
• Knautia tatarica
• Mitragyna speciosa
• Penstemon gentianoides
• Picris conyzoides

Cross-Links

• PubChem: 3034396
• NPASS: NPC148183
• ChEMBL: CHEMBL299031
• LOTUS: LTS0222902
• wikiData: Q414299