Eburnamonine
AlkaPlorer ID: AK004710
Synonym: '', 'Eburnamonine', '(-)-cis-Eburnamonine', 'eburnamonine monohydrochloride', 'eburnamonine phosphate', '(+)-Eburnamonine', '(+)-cis-Eburnamonine', '(-)-Eburnamonine; Vinburnine; Vincamone', '(+)-Vincamone', '(+)-cis-Vincamone', 'Vinburnine', '(-)-Vincamone', 'cervoxan', 'd-Eburnamonine', 'l-Eburnamonine', 'vincamone'
IUPAC Name: (15S,19S)-15-ethyl-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18)-tetraen-17-one
Structure
SMILES: CC[C@@]12CCCN3CCC4=C([C@@H]31)N(C(=O)C2)C1=CC=CC=C41
InChI: InChI=1S/C19H22N2O/c1-2-19-9-5-10-20-11-8-14-13-6-3-4-7-15(13)21(16(22)12-19)17(14)18(19)20/h3-4,6-7,18H,2,5,8-12H2,1H3/t18-,19+/m1/s1
InChIKey: WYJAPUKIYAZSEM-MOPGFXCFSA-N
Reference
VIBURNINE, A MACROCYCLIC SPERMIDINE ALKALOID FROM VIBURNUM RHYTIDOPHYLLUM
PubChem CID: 71203
CAS: 13090-13-6
LOTUS: LTS0220075
SuperNatural Ⅲ: SN0423331-02
data_source: manually
Source
| Species | Genus | Family | Order | Class | Phylum | Kingdom | Domain |
|---|---|---|---|---|---|---|---|
| Kopsia pauciflora | Kopsia | Apocynaceae | Gentianales | Magnoliopsida | Streptophyta | Viridiplantae | Eukaryota |
Properties Information
Molecule Weight: 294.398
TPSA？: 25.24
MolLogP？: 3.774600000000003
Number of H-Donors: 0
Number of H-Acceptors: 3
RingCount: 5
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Electrophorus electricus | Acetylcholinesterase | Inhibition | 12.13 | % | 10.1016/j.bmc.2012.09.040 |
| Equus caballus | Cholinesterase | Inhibition | 0.04 | % | 10.1016/j.bmc.2012.09.040 |
| Homo sapiens | 786-0 | GI50 | 10069.32 | nM | None |
| Homo sapiens | A498 | GI50 | 14421.15 | nM | None |
| Homo sapiens | A549 | GI50 | 7498.94 | nM | None |
| Homo sapiens | ACHN | GI50 | 32359.37 | nM | None |
| Homo sapiens | Ataxin-2 | Potency | 8912.5 | nM | None |
| Homo sapiens | BT-549 | GI50 | 24717.24 | nM | None |
| Homo sapiens | CAKI-1 | GI50 | 100000.0 | nM | None |
| Homo sapiens | CCRF-CEM | GI50 | 1306.17 | nM | None |
| Homo sapiens | COLO 205 | GI50 | 4425.88 | nM | None |
| Homo sapiens | DNA dC->dU-editing enzyme APOBEC-3G | Potency | 7079.5 | nM | None |
| Homo sapiens | DU-145 | GI50 | 19230.92 | nM | None |
| Homo sapiens | EKVX | GI50 | 46881.34 | nM | None |
| Homo sapiens | Geminin | Potency | 12995.3 | nM | None |
| Homo sapiens | Geminin | Potency | 14581.0 | nM | None |
| Homo sapiens | Glucagon-like peptide 1 receptor | Potency | 6309.6 | nM | None |
| Homo sapiens | HCC 2998 | GI50 | 3917.42 | nM | None |
| Homo sapiens | HCT-116 | GI50 | 3863.67 | nM | None |
| Homo sapiens | HCT-15 | GI50 | 4149.54 | nM | None |
| Homo sapiens | Histone deacetylase 6 | Inhibition | -2.71 | % | 10.6019/CHEMBL4808148 |
| Homo sapiens | Histone deacetylase 6 | Inhibition | 5.53 | % | 10.6019/CHEMBL4808148 |
| Homo sapiens | HL-60 | GI50 | 2648.5 | nM | None |
| Homo sapiens | HOP-62 | GI50 | 4764.31 | nM | None |
| Homo sapiens | HOP-92 | GI50 | 80909.59 | nM | None |
| Homo sapiens | Hs-578T | GI50 | 9332.54 | nM | None |
| Homo sapiens | HT-29 | GI50 | 3564.51 | nM | None |
| Homo sapiens | IGROV-1 | GI50 | 5847.9 | nM | None |
| Homo sapiens | Isocitrate dehydrogenase [NADP] cytoplasmic | Potency | 29092.9 | nM | None |
| Homo sapiens | K562 | GI50 | 2904.02 | nM | None |
| Homo sapiens | KM12 | GI50 | 4539.42 | nM | None |
| Homo sapiens | LNCaP | IC50 | 100000.0 | nM | 10.1016/j.bmcl.2013.08.095 |
| Homo sapiens | LOX IMVI | GI50 | 10023.05 | nM | None |
| Homo sapiens | M14 | GI50 | 3971.92 | nM | None |
| Homo sapiens | Malme-3M | GI50 | 4634.47 | nM | None |
| Homo sapiens | MCF7 | GI50 | 3507.52 | nM | None |
| Homo sapiens | MDA-MB-231 | GI50 | 9354.06 | nM | None |
| Homo sapiens | MDA-MB-231 | IC50 | 41800.0 | nM | 10.1016/j.bmcl.2013.08.095 |
| Homo sapiens | MDA-MB-435 | GI50 | 1264.74 | nM | None |
| Homo sapiens | MDA-N | GI50 | 1527.57 | nM | None |
| Homo sapiens | MOLT-4 | GI50 | 12161.86 | nM | None |
| Homo sapiens | NCI/ADR-RES | GI50 | 3250.87 | nM | None |
| Homo sapiens | NCI-H226 | GI50 | 83752.93 | nM | None |
| Homo sapiens | NCI-H23 | GI50 | 13677.29 | nM | None |
| Homo sapiens | NCI-H322M | GI50 | 13243.42 | nM | None |
| Homo sapiens | NCI-H460 | GI50 | 3715.35 | nM | None |
| Homo sapiens | NCI-H522 | GI50 | 2322.74 | nM | None |
| Homo sapiens | OVCAR-3 | GI50 | 2443.43 | nM | None |
| Homo sapiens | OVCAR-4 | GI50 | 18155.16 | nM | None |
| Homo sapiens | OVCAR-5 | GI50 | 34593.94 | nM | None |
| Homo sapiens | OVCAR-8 | GI50 | 15452.54 | nM | None |
| Homo sapiens | PC-3 | GI50 | 18238.96 | nM | None |
| Homo sapiens | RPMI-8226 | GI50 | 4560.37 | nM | None |
| Homo sapiens | RPMI-8226 | IC50 | 100000.0 | nM | 10.1016/j.bmcl.2013.08.095 |
| Homo sapiens | RXF 393 | GI50 | 15595.53 | nM | None |
| Homo sapiens | SF-268 | GI50 | 11561.12 | nM | None |
| Homo sapiens | SF-295 | GI50 | 3580.96 | nM | None |
| Homo sapiens | SF-539 | GI50 | 7906.79 | nM | None |
| Homo sapiens | SK-MEL-2 | GI50 | 4920.4 | nM | None |
| Homo sapiens | SK-MEL-28 | GI50 | 36475.39 | nM | None |
| Homo sapiens | SK-MEL-5 | GI50 | 5046.61 | nM | None |
| Homo sapiens | SK-OV-3 | GI50 | 10764.65 | nM | None |
| Homo sapiens | SN12C | GI50 | 12852.87 | nM | None |
| Homo sapiens | SNB-19 | GI50 | 14454.4 | nM | None |
| Homo sapiens | SNB-75 | GI50 | 13273.94 | nM | None |
| Homo sapiens | Solute carrier organic anion transporter family member 1B1 | Inhibition | 97.38 | % | 10.1124/mol.112.084152 |
| Homo sapiens | Solute carrier organic anion transporter family member 1B3 | Inhibition | 115.26 | % | 10.1124/mol.112.084152 |
| Homo sapiens | SR | GI50 | 1309.18 | nM | None |
| Homo sapiens | SW-620 | GI50 | 3935.5 | nM | None |
| Homo sapiens | T47D | GI50 | 11508.0 | nM | None |
| Homo sapiens | TK-10 | GI50 | 12473.84 | nM | None |
| Homo sapiens | Tyrosyl-DNA phosphodiesterase 1 | Potency | 6513.1 | nM | None |
| Homo sapiens | Tyrosyl-DNA phosphodiesterase 1 | Potency | 9034.9 | nM | None |
| Homo sapiens | Tyrosyl-DNA phosphodiesterase 1 | Potency | 11374.3 | nM | None |
| Homo sapiens | U-251 | GI50 | 4875.28 | nM | None |
| Homo sapiens | U-266 | IC50 | 100000.0 | nM | 10.1016/j.bmcl.2013.08.095 |
| Homo sapiens | UACC-257 | GI50 | 15240.53 | nM | None |
| Homo sapiens | UACC-62 | GI50 | 5821.03 | nM | None |
| Homo sapiens | UO-31 | GI50 | 4753.35 | nM | None |
| Plasmodium falciparum | Plasmodium falciparum | Potency | 2332.3 | nM | None |
| Plasmodium falciparum | Plasmodium falciparum | Potency | 13115.4 | nM | None |
| Severe acute respiratory syndrome coronavirus 2 | Replicase polyprotein 1ab | Inhibition | 9.522 | % | 10.6019/CHEMBL4495564 |
| Severe acute respiratory syndrome coronavirus 2 | SARS-CoV-2 | Hit score | 0.1621 | None | 10.1101/2020.04.21.054387 |
| 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 | -34.86 | % | 10.21203/rs.3.rs-23951/v1 |
| Severe acute respiratory syndrome coronavirus 2 | SARS-CoV-2 | Inhibition | 0.27 | % | 10.6019/CHEMBL4495565 |
| None | NON-PROTEIN TARGET | IC50 | 100000.0 | nM | 10.1016/j.bmcl.2013.08.095 |
| None | Unchecked | Ac50 | 28.18 | uM | None |
| None | Unchecked | AC50 | 28183.8 | nM | None |
| None | Unchecked | IC50 | 10000.0 | nM | None |
| None | Unchecked | Potency | 3162.3 | nM | None |
| None | Unchecked | Potency | 5011.9 | nM | None |
| None | Unchecked | Potency | 6309.6 | nM | None |