Yohimbine; 3,16,20-Triepimer
AlkaPlorer ID: AK318059
Synonym: Isorauhimbine, 3-Epirauwolscine, Isorauwolscine, Alkaloid Su 3078, 3-Epi-α-yohimbine
IUPAC Name: methyl 18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
Structure
SMILES: COC(=O)C1C(O)CCC2CN3CCC4=C(NC5=C4C=CC=C5)C3CC21
InChI: InChI=1S/C21H26N2O3/c1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-20)8-9-23(17)11-12(15)6-7-18(19)24/h2-5,12,15,17-19,22,24H,6-11H2,1H3
InChIKey: BLGXFZZNTVWLAY-UHFFFAOYSA-N
Source
Properties Information
Molecule Weight: 354.45000000000005
TPSA？: 65.56
MolLogP？: 2.647100000000001
Number of H-Donors: 2
Number of H-Acceptors: 4
RingCount: 5
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Acinetobacter baumannii | Acinetobacter baumannii | Inhibition | -5.08 | % | 10.6019/CHEMBL4296183 |
| Candida albicans | Candida albicans | Inhibition | 1.54 | % | 10.6019/CHEMBL4296183 |
| Cryptococcus neoformans | Cryptococcus neoformans | Inhibition | -9.85 | % | 10.6019/CHEMBL4296183 |
| Escherichia coli | Escherichia coli | Inhibition | 5.27 | % | 10.6019/CHEMBL4296183 |
| Giardia intestinalis | Putative fructose-1,6-bisphosphate aldolase | Potency | 8891.4 | nM | None |
| Homo sapiens | 786-0 | GI50 | 100000.0 | nM | None |
| Homo sapiens | A498 | GI50 | 100000.0 | nM | None |
| Homo sapiens | A549 | GI50 | 100000.0 | nM | None |
| Homo sapiens | ACHN | GI50 | 100000.0 | nM | None |
| Homo sapiens | Bromodomain adjacent to zinc finger domain protein 2B | Potency | 79432.8 | nM | None |
| Homo sapiens | BT-549 | GI50 | 100000.0 | nM | None |
| Homo sapiens | CAKI-1 | GI50 | 100000.0 | nM | None |
| Homo sapiens | CCRF-CEM | GI50 | 100000.0 | nM | None |
| Homo sapiens | COLO 205 | GI50 | 100000.0 | nM | None |
| Homo sapiens | DNA polymerase iota | Potency | 707.9 | nM | None |
| Homo sapiens | DU-145 | GI50 | 100000.0 | nM | None |
| Homo sapiens | EKVX | GI50 | 100000.0 | nM | None |
| Homo sapiens | Guanine nucleotide-binding protein G(s), subunit alpha | Potency | 44668.4 | nM | None |
| Homo sapiens | HCC 2998 | GI50 | 59429.22 | nM | None |
| Homo sapiens | HCT-116 | GI50 | 100000.0 | nM | None |
| Homo sapiens | HCT-15 | GI50 | 100000.0 | nM | None |
| Homo sapiens | HL-60 | GI50 | 100000.0 | nM | None |
| Homo sapiens | HOP-92 | GI50 | 100000.0 | nM | None |
| Homo sapiens | Hs-578T | GI50 | 100000.0 | nM | None |
| Homo sapiens | HT-29 | GI50 | 100000.0 | 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 | K562 | GI50 | 100000.0 | nM | None |
| Homo sapiens | KM12 | GI50 | 100000.0 | nM | None |
| Homo sapiens | LOX IMVI | GI50 | 100000.0 | nM | None |
| Homo sapiens | Lysine-specific demethylase 4D-like | Potency | 31622.8 | nM | None |
| Homo sapiens | M14 | GI50 | 100000.0 | nM | None |
| Homo sapiens | MCF7 | GI50 | 100000.0 | nM | None |
| Homo sapiens | MDA-MB-231 | GI50 | 100000.0 | nM | None |
| Homo sapiens | MDA-MB-435 | GI50 | 100000.0 | nM | None |
| Homo sapiens | MDA-N | GI50 | 100000.0 | nM | None |
| Homo sapiens | Menin/Histone-lysine N-methyltransferase MLL | Potency | 25118.9 | nM | None |
| Homo sapiens | Microtubule-associated protein tau | Potency | 39810.7 | nM | None |
| Homo sapiens | MOLT-4 | GI50 | 100000.0 | nM | None |
| Homo sapiens | NCI/ADR-RES | GI50 | 100000.0 | nM | None |
| Homo sapiens | NCI-H226 | GI50 | 100000.0 | nM | None |
| Homo sapiens | NCI-H23 | GI50 | 100000.0 | nM | None |
| Homo sapiens | NCI-H322M | GI50 | 100000.0 | nM | None |
| Homo sapiens | NCI-H460 | GI50 | 100000.0 | nM | None |
| Homo sapiens | NCI-H522 | GI50 | 100000.0 | nM | None |
| Homo sapiens | OVCAR-3 | GI50 | 100000.0 | 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 | 100000.0 | nM | None |
| Homo sapiens | PC-3 | GI50 | 100000.0 | nM | None |
| Homo sapiens | Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 | Potency | 50118.7 | nM | None |
| Homo sapiens | RPMI-8226 | GI50 | 100000.0 | nM | None |
| Homo sapiens | SF-268 | GI50 | 100000.0 | nM | None |
| Homo sapiens | SF-295 | GI50 | 100000.0 | nM | None |
| Homo sapiens | SF-539 | GI50 | 100000.0 | nM | None |
| Homo sapiens | SK-MEL-2 | GI50 | 100000.0 | nM | None |
| Homo sapiens | SK-MEL-28 | GI50 | 76032.63 | nM | None |
| Homo sapiens | SK-MEL-5 | GI50 | 100000.0 | nM | None |
| Homo sapiens | SK-OV-3 | GI50 | 100000.0 | nM | None |
| Homo sapiens | SNB-19 | GI50 | 100000.0 | nM | None |
| Homo sapiens | SNB-75 | GI50 | 100000.0 | nM | None |
| Homo sapiens | Sphingomyelin phosphodiesterase | Potency | 25118.9 | nM | None |
| Homo sapiens | SR | GI50 | 100000.0 | nM | None |
| Homo sapiens | SW-620 | GI50 | 100000.0 | nM | None |
| Homo sapiens | T47D | GI50 | 100000.0 | nM | None |
| Homo sapiens | TK-10 | GI50 | 100000.0 | nM | None |
| Homo sapiens | Tyrosyl-DNA phosphodiesterase 1 | Potency | 29092.9 | nM | None |
| Homo sapiens | U-251 | GI50 | 100000.0 | nM | None |
| Homo sapiens | UACC-257 | GI50 | 100000.0 | nM | None |
| Homo sapiens | UACC-62 | GI50 | 100000.0 | nM | None |
| Homo sapiens | UO-31 | GI50 | 100000.0 | nM | None |
| Influenza A virus | Nonstructural protein 1 | Potency | 22387.2 | nM | None |
| Klebsiella pneumoniae | Klebsiella pneumoniae | Inhibition | 13.74 | % | 10.6019/CHEMBL4296183 |
| Pseudomonas aeruginosa | Pseudomonas aeruginosa | Inhibition | 11.28 | % | 10.6019/CHEMBL4296183 |
| Schistosoma mansoni | Thioredoxin glutathione reductase | Potency | 39810.7 | nM | None |
| Staphylococcus aureus | Staphylococcus aureus | Inhibition | 7.76 | % | 10.6019/CHEMBL4296183 |
| None | NON-PROTEIN TARGET | Potency | 7.5 | nM | None |
| None | NON-PROTEIN TARGET | Potency | 472.8 | nM | None |
| None | NON-PROTEIN TARGET | Potency | 667.8 | nM | None |
| None | NON-PROTEIN TARGET | Potency | 9432.9 | nM | None |
| None | Unchecked | Potency | 12589.3 | nM | None |