Ajmalicine; (±)-form
AlkaPlorer ID: AK283606
Synonym: None
IUPAC Name: methyl 16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate
Structure
SMILES: COC(=O)C1=COC(C)C2CN3CCC4=C(NC5=C4C=CC=C5)C3CC12
InChI: InChI=1S/C21H24N2O3/c1-12-16-10-23-8-7-14-13-5-3-4-6-18(13)22-20(14)19(23)9-15(16)17(11-26-12)21(24)25-2/h3-6,11-12,15-16,19,22H,7-10H2,1-2H3
InChIKey: GRTOGORTSDXSFK-UHFFFAOYSA-N
Reference
THE<i>MITRAGYNA</i>SPECIES OF ASIA
PubChem CID: 251561
CAS: 6870-40-2
LOTUS: LTS0058307
NPASS: NPC312870
COCONUT: CNP0266139.11
Source
| Species | Genus | Family | Order | Class | Phylum | Kingdom | Domain |
|---|---|---|---|---|---|---|---|
| Uncaria elliptica | Uncaria | Rubiaceae | Gentianales | Magnoliopsida | Streptophyta | Viridiplantae | Eukaryota |
| Atropa belladonna | Atropa | Solanaceae | Solanales | Magnoliopsida | Streptophyta | Viridiplantae | Eukaryota |
Properties Information
Molecule Weight: 352.434
TPSA？: 54.56
MolLogP？: 3.1788000000000016
Number of H-Donors: 1
Number of H-Acceptors: 4
RingCount: 5
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Homo sapiens | 786-0 | GI50 | 18793.17 | nM | None |
| Homo sapiens | 786-0 | GI50 | 54827.7 | nM | None |
| Homo sapiens | A498 | GI50 | 21086.28 | nM | None |
| Homo sapiens | A498 | GI50 | 74816.95 | nM | None |
| Homo sapiens | A549 | GI50 | 37583.74 | nM | None |
| Homo sapiens | A549 | GI50 | 100000.0 | nM | None |
| Homo sapiens | ACHN | GI50 | 32062.69 | nM | None |
| Homo sapiens | ACHN | GI50 | 100000.0 | nM | None |
| Homo sapiens | Bromodomain adjacent to zinc finger domain protein 2B | Potency | 89125.1 | nM | None |
| Homo sapiens | BT-549 | GI50 | 27989.81 | nM | None |
| Homo sapiens | BT-549 | GI50 | 100000.0 | nM | None |
| Homo sapiens | CAKI-1 | GI50 | 21183.61 | nM | None |
| Homo sapiens | CAKI-1 | GI50 | 100000.0 | nM | None |
| Homo sapiens | Caspase-1 | Potency | 25118.9 | nM | None |
| Homo sapiens | Caspase-7 | Potency | 25118.9 | nM | None |
| Homo sapiens | CCRF-CEM | GI50 | 20137.24 | nM | None |
| Homo sapiens | CCRF-CEM | GI50 | 50466.13 | nM | None |
| Homo sapiens | COLO 205 | GI50 | 18197.01 | nM | None |
| Homo sapiens | COLO 205 | GI50 | 100000.0 | nM | None |
| Homo sapiens | DNA-(apurinic or apyrimidinic site) lyase | Potency | 3548.1 | nM | None |
| Homo sapiens | DNA dC->dU-editing enzyme APOBEC-3F | Potency | 14125.4 | nM | None |
| Homo sapiens | DNA polymerase iota | Potency | 89125.1 | nM | None |
| Homo sapiens | DU-145 | GI50 | 33651.16 | nM | None |
| Homo sapiens | DU-145 | GI50 | 100000.0 | nM | None |
| Homo sapiens | EKVX | GI50 | 17782.79 | nM | None |
| Homo sapiens | EKVX | GI50 | 100000.0 | nM | None |
| Homo sapiens | Endoplasmic reticulum-associated amyloid beta-peptide-binding protein | Potency | 31622.8 | nM | None |
| Homo sapiens | GTP-binding nuclear protein Ran/Importin subunit beta-1/Snurportin-1 | Potency | 31622.8 | nM | None |
| Homo sapiens | HCC 2998 | GI50 | 20653.8 | nM | None |
| Homo sapiens | HCC 2998 | GI50 | 100000.0 | nM | None |
| Homo sapiens | HCT-116 | GI50 | 19010.78 | nM | None |
| Homo sapiens | HCT-116 | GI50 | 100000.0 | nM | None |
| Homo sapiens | HCT-15 | GI50 | 30060.76 | nM | None |
| Homo sapiens | HCT-15 | GI50 | 100000.0 | nM | None |
| Homo sapiens | Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 | Potency | 44668.4 | nM | None |
| Homo sapiens | HL-60 | GI50 | 17458.22 | nM | None |
| Homo sapiens | HL-60 | GI50 | 46131.76 | nM | None |
| Homo sapiens | HOP-62 | GI50 | 55080.77 | nM | None |
| Homo sapiens | HOP-62 | GI50 | 100000.0 | nM | None |
| Homo sapiens | HOP-92 | GI50 | 18323.14 | nM | None |
| Homo sapiens | HOP-92 | GI50 | 100000.0 | nM | None |
| Homo sapiens | Hs-578T | GI50 | 26001.6 | nM | None |
| Homo sapiens | Hs-578T | GI50 | 48977.88 | nM | None |
| Homo sapiens | HT-29 | GI50 | 13772.09 | nM | None |
| Homo sapiens | HT-29 | GI50 | 100000.0 | nM | None |
| Homo sapiens | Huntingtin | Potency | 11220.2 | nM | None |
| Homo sapiens | IGROV-1 | GI50 | 22130.95 | nM | None |
| Homo sapiens | IGROV-1 | GI50 | 100000.0 | nM | None |
| Homo sapiens | Importin subunit beta-1/Snurportin-1 | Potency | 100000.0 | nM | None |
| Homo sapiens | Keap1/Nrf2 | AC50 | 52000.0 | nM | None |
| Homo sapiens | Kelch-like ECH-associated protein 1 | Max_Activity_Concent | 26.0 | uM | None |
| Homo sapiens | KM12 | GI50 | 17864.88 | nM | None |
| Homo sapiens | KM12 | GI50 | 100000.0 | nM | None |
| Homo sapiens | LOX IMVI | GI50 | 18450.15 | nM | None |
| Homo sapiens | LOX IMVI | GI50 | 100000.0 | nM | None |
| Homo sapiens | Lysine-specific demethylase 4A | Potency | 79432.8 | nM | None |
| Homo sapiens | M14 | GI50 | 38370.72 | nM | None |
| Homo sapiens | M14 | GI50 | 100000.0 | nM | None |
| Homo sapiens | Malme-3M | GI50 | 14421.15 | nM | None |
| Homo sapiens | Malme-3M | GI50 | 49545.02 | nM | None |
| Homo sapiens | MCF7 | GI50 | 32062.69 | nM | None |
| Homo sapiens | MCF7 | GI50 | 100000.0 | nM | None |
| Homo sapiens | MDA-MB-231 | GI50 | 21232.44 | nM | None |
| Homo sapiens | MDA-MB-231 | GI50 | 100000.0 | nM | None |
| Homo sapiens | MDA-MB-435 | GI50 | 52119.47 | nM | None |
| Homo sapiens | MDA-MB-435 | GI50 | 100000.0 | nM | None |
| Homo sapiens | MDA-N | GI50 | 31550.05 | nM | None |
| Homo sapiens | MDA-N | GI50 | 100000.0 | nM | None |
| Homo sapiens | Menin/Histone-lysine N-methyltransferase MLL | Potency | 14125.4 | nM | None |
| Homo sapiens | MOLT-4 | GI50 | 10964.78 | nM | None |
| Homo sapiens | MOLT-4 | GI50 | 28313.92 | nM | None |
| Homo sapiens | Muscleblind-like protein 1 | Potency | 12589.3 | nM | None |
| Homo sapiens | NCI/ADR-RES | GI50 | 22646.44 | nM | None |
| Homo sapiens | NCI/ADR-RES | GI50 | 100000.0 | nM | None |
| Homo sapiens | NCI-H226 | GI50 | 3491.4 | nM | None |
| Homo sapiens | NCI-H226 | GI50 | 100000.0 | nM | None |
| Homo sapiens | NCI-H23 | GI50 | 33728.73 | nM | None |
| Homo sapiens | NCI-H23 | GI50 | 100000.0 | nM | None |
| Homo sapiens | NCI-H322M | GI50 | 46881.34 | nM | None |
| Homo sapiens | NCI-H322M | GI50 | 100000.0 | nM | None |
| Homo sapiens | NCI-H460 | GI50 | 23988.33 | nM | None |
| Homo sapiens | NCI-H460 | GI50 | 100000.0 | nM | None |
| Homo sapiens | NCI-H522 | GI50 | 23120.65 | nM | None |
| Homo sapiens | NCI-H522 | GI50 | 91201.08 | nM | None |
| Homo sapiens | OVCAR-3 | GI50 | 24210.29 | nM | None |
| Homo sapiens | OVCAR-3 | GI50 | 100000.0 | nM | None |
| Homo sapiens | OVCAR-4 | GI50 | 25409.73 | nM | None |
| Homo sapiens | OVCAR-4 | GI50 | 100000.0 | nM | None |
| Homo sapiens | OVCAR-5 | GI50 | 100000.0 | nM | None |
| Homo sapiens | OVCAR-8 | GI50 | 18620.87 | nM | None |
| Homo sapiens | OVCAR-8 | GI50 | 100000.0 | nM | None |
| Homo sapiens | PC-3 | GI50 | 23933.16 | nM | None |
| Homo sapiens | PC-3 | GI50 | 100000.0 | nM | None |
| Homo sapiens | Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 | Potency | 35481.3 | nM | None |
| Homo sapiens | Rap guanine nucleotide exchange factor 4 | Potency | 35481.3 | nM | None |
| Homo sapiens | RPMI-8226 | GI50 | 14588.14 | nM | None |
| Homo sapiens | RPMI-8226 | GI50 | 69023.98 | nM | None |
| Homo sapiens | RXF 393 | GI50 | 17298.16 | nM | None |
| Homo sapiens | RXF 393 | GI50 | 100000.0 | nM | None |
| Homo sapiens | SF-268 | GI50 | 54075.43 | nM | None |
| Homo sapiens | SF-268 | GI50 | 100000.0 | nM | None |
| Homo sapiens | SF-295 | GI50 | 30619.63 | nM | None |
| Homo sapiens | SF-295 | GI50 | 72945.75 | nM | None |
| Homo sapiens | SF-539 | GI50 | 22387.21 | nM | None |
| Homo sapiens | SF-539 | GI50 | 100000.0 | nM | None |
| Homo sapiens | SK-MEL-2 | GI50 | 19952.62 | nM | None |
| Homo sapiens | SK-MEL-2 | GI50 | 100000.0 | nM | None |
| Homo sapiens | SK-MEL-28 | GI50 | 16106.46 | nM | None |
| Homo sapiens | SK-MEL-28 | GI50 | 100000.0 | nM | None |
| Homo sapiens | SK-MEL-5 | GI50 | 22594.36 | nM | None |
| Homo sapiens | SK-MEL-5 | GI50 | 100000.0 | nM | None |
| Homo sapiens | SK-OV-3 | GI50 | 58748.94 | nM | None |
| Homo sapiens | SK-OV-3 | GI50 | 100000.0 | nM | None |
| Homo sapiens | SN12C | GI50 | 17906.06 | nM | None |
| Homo sapiens | SN12C | GI50 | 100000.0 | nM | None |
| Homo sapiens | SNB-19 | GI50 | 84527.88 | nM | None |
| Homo sapiens | SNB-19 | GI50 | 100000.0 | nM | None |
| Homo sapiens | Sphingomyelin phosphodiesterase | Potency | 31622.8 | nM | None |
| Homo sapiens | SR | GI50 | 12618.28 | nM | None |
| Homo sapiens | SR | GI50 | 27797.13 | nM | None |
| Homo sapiens | SW-620 | GI50 | 22750.97 | nM | None |
| Homo sapiens | SW-620 | GI50 | 100000.0 | nM | None |
| Homo sapiens | T47D | GI50 | 16557.7 | nM | None |
| Homo sapiens | T47D | GI50 | 100000.0 | nM | None |
| Homo sapiens | TK-10 | GI50 | 27669.42 | nM | None |
| Homo sapiens | TK-10 | GI50 | 100000.0 | nM | None |
| Homo sapiens | Tumor susceptibility gene 101 protein | Potency | 70794.6 | nM | None |
| Homo sapiens | U-251 | GI50 | 24603.68 | nM | None |
| Homo sapiens | U-251 | GI50 | 100000.0 | nM | None |
| Homo sapiens | UACC-257 | GI50 | 34197.94 | nM | None |
| Homo sapiens | UACC-257 | GI50 | 100000.0 | nM | None |
| Homo sapiens | UACC-62 | GI50 | 24378.11 | nM | None |
| Homo sapiens | UACC-62 | GI50 | 100000.0 | nM | None |
| Homo sapiens | UO-31 | GI50 | 20844.91 | nM | None |
| Homo sapiens | UO-31 | GI50 | 100000.0 | nM | None |
| Human immunodeficiency virus type 1 group M subtype B (isolate HXB2)(HIV-1) | Human immunodeficiency virus type 1 Tat protein | IC50 | 7635.0 | nM | None |
| Plasmodium falciparum | Plasmodium falciparum | Potency | 14715.7 | nM | None |
| Schistosoma japonicum | Glutathione-S-transferase | IC50 | 100000.0 | nM | None |
| Schistosoma mansoni | Thioredoxin glutathione reductase | Potency | 79432.8 | nM | None |
| Severe acute respiratory syndrome coronavirus 2 | Replicase polyprotein 1ab | Inhibition | 21.37 | % | 10.6019/CHEMBL4495564 |
| Severe acute respiratory syndrome coronavirus 2 | SARS-CoV-2 | IC50 | 19952.62 | nM | 10.6019/CHEMBL4651402 |
| Severe acute respiratory syndrome coronavirus 2 | SARS-CoV-2 | IC50 | 20000.0 | nM | 10.6019/CHEMBL4651402 |
| Severe acute respiratory syndrome coronavirus 2 | SARS-CoV-2 | Inhibition | -0.03 | % | 10.6019/CHEMBL4495565 |
| None | Unchecked | IC50 | 17950.0 | nM | None |
| None | Unchecked | Potency | 25118.9 | nM | None |