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Mitragynine
- Family: Plantae - Rubiaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Indole Alkaloid
| Canonical Smiles | CO/C=C(\[C@H]1C[C@@H]2N(C[C@H]1CC)CCc1c2[nH]c2c1c(OC)ccc2)/C(=O)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 |
| InChIKey | LELBFTMXCIIKKX-QVRQZEMUSA-N |
| Formula | C23H30N2O4 |
| HBA | 5 |
| HBD | 1 |
| MW | 398.5 |
| Rotatable Bonds | 5 |
| TPSA | 63.79 |
| LogP | 3.83 |
| Number Rings | 4 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 29 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.52 |
| Exact Mass | 398.22 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Mitragyna inermis | Rubiaceae | Plantae | 170023 |
Showing of synonyms
Mitragynine
4098-40-2
(-)-Mitragynine
Skf 12711
Mitragynin
9-Methoxycorynantheidine
Mitragynine [MI]
SK&F 12711
UNII-EP479K822J
HSDB 7901
EP479K822J
MITRAGYNINE [WHO-DD]
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
16,17-Didehydro-9,17-dimethoxy-17,18-seco-20-alpha-yohimban-16-carboxylic acid methyl ester
Kratom alkaloids
(.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
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 (2E)-2-((2S,4S,5S)-5-ethyl-12-methoxy-7,17-diazatetracyclo(8.7.0.0,.0,)heptadeca-1(10),11(16),12,14-tetraen-4-yl)-3-methoxyprop-2-enoic acid
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 (2E)-2-[(2S,4S,5S)-5-ethyl-12-methoxy-7,17-diazatetracyclo[8.7.0.0,.0,]heptadeca-1(10),11(16),12,14-tetraen-4-yl]-3-methoxyprop-2-enoic acid
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
SK&F-12711
(E)-methyl 2-((2S,3S,12bR)-3-ethyl-8-methoxy-1,2,3,4,6,7,12,12b-\ octahydroindolo(2,3-a)quinolizin-2-yl)-3-methoxyacrylate ethanol solvate
(E)-methyl 2-[(2S,3S,12bR)-3-ethyl-8-methoxy-1,2,3,4,6,7,12,12b-\ octahydroindolo[2,3-a]quinolizin-2-yl]-3-methoxyacrylate ethanol solvate
SK And F 12711
SK And F-12711
(alphaE,2S,3S,12betaS)-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
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, (ALPHAE,2S,3S,12BS)-
CHEBI:6956
MITRAGYNINE PICRATE
CHEMBL299031
(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
Mitragynine (100?g/mL in Methanol)
Mitragynine - 95%
Mitragynine - 97%
SCHEMBL875799
GTPL13149
Mitragynine, 1mg/ml in Methanol
LELBFTMXCIIKKX-QVRQZEMUSA-N
DTXSID701032140
GLXC-02988
Mitragynine, 0.1mg/ml in Methanol
MSK40382
BDBM50474152
FM26024
Mitragynine 100 microg/mL in Methanol
NCGC00488797-01
1ST40382
BM164595
DB-299985
C09226
Q414299
(a-E,2S,3S,12bS)-3-Ethyl-1,2,3,4,6,7,12 ,12b-octahydro-8-methoxy-a-(methoxymethylene)-indolo[2 ,3-a]quinolizine-2-acetic acid methyl ester
(E)-methyl2-((2s,3s,12bs)-3-ethyl-8-methoxy-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)-3-methoxyacrylate
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
- Toklo PM, Alowanou GG, et al. (2023). UPLC-QToF-ESI-MS identification and anthelmintic activity of Mitragyna inermis (Willd.) Kuntze (Rubiaceae). Heliyon 9 (2023) e16448. [View]
Pubchem:
3034396
Cas:
4098-40-2
Gnps:
CCMSLIB00011429561
Zinc:
ZINC000013473305
Kegg Ligand:
C09226
Chebi:
6956
Nmrshiftdb2:
60074849
Metabolights:
MTBLC6956
Chembl:
CHEMBL299031
Bindingdb:
50474152
CPRiL:
54912
SMILES: C1CCCN(CC2)C1c(c2c34)[nH]c3cccc4
Level: 0
Mol. Weight: 398.5 g/mol
Anthelmintic
Antioxidant
Larval toxicity
Absorption
- Caco-2 (logPapp)
- -4.85
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.950
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -1.86
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.960
- Plasma Protein Binding
- 52.5
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 10.530
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.780
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.860
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 5.910
- Micronucleos
- Toxic
- NR-AhR
- Toxic
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -30.920
- Rat (Acute)
- 2.670
- Rat (Chronic Oral)
- 2.100
- Fathead Minnow
- 4.440
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 448.350
- Hydration Free Energy
- -4.110
- Log(D) at pH=7.4
- 3.720
- Log(P)
- 3.8
- Log S
- -3.9
- Log(Vapor Pressure)
- -8.1
- Melting Point
- 154.75
- pKa Acid
- 10.59
- pKa Basic
- 7.16
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.8867 |
| clade A/E 93TH057 HIV-1 gp120 core | A0A0M3KKW9 | A0A0M3KKW9_9HIV1 | Human immunodeficiency virus 1 | 3 | 0.8372 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7889 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7744 |
| Carbonic anhydrase 12 | O43570 | CAH12_HUMAN | Homo sapiens | 3 | 0.7656 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7601 |
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 2 | 0.7553 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 3 | 0.7487 |
| 3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 3 | 0.7486 |
| Pteridine reductase, putative | Q581W1 | Q581W1_TRYB2 | Trypanosoma brucei brucei | 3 | 0.7470 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 2 | 0.7440 |
| Dihydropteroate synthase | Q81VW8 | Q81VW8_BACAN | Bacillus anthracis | 3 | 0.7394 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7351 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7284 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7267 |
| 3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase | O33877 | FABA_PSEAE | Pseudomonas aeruginosa | 3 | 0.7212 |
| L-lactate dehydrogenase A chain | P13491 | LDHA_RABIT | Oryctolagus cuniculus | 2 | 0.7205 |
| Nitroreductase domain-containing protein | Q8DW21 | Q8DW21_STRMU | Streptococcus mutans serotype c | 3 | 0.7183 |
| 2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase | P47229 | BPHD_PARXL | Paraburkholderia xenovorans | 2 | 0.7129 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7104 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 2 | 0.7102 |
| Uncharacterized protein YML079W | Q03629 | YMH9_YEAST | Saccharomyces cerevisiae | 2 | 0.7077 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7074 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7062 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7060 |
| Xanthine dehydrogenase/oxidase | P22985 | XDH_RAT | Rattus norvegicus | 3 | 0.7059 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 2 | 0.7054 |
| TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase | Q6T1W8 | FDTA_ANETH | Aneurinibacillus thermoaerophilus | 3 | 0.7053 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 2 | 0.7047 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 2 | 0.7038 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7033 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 2 | 0.7008 |
| histone deacetylase | A5H660 | A5H660_SCHMA | Schistosoma mansoni | 3 | 0.7007 |