Hirsutine
AlkaPlorer ID: AK001507
Synonym: None
IUPAC Name: methyl (E)-2-[(2S,3R,12bR)-3-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate
Structure
SMILES: CC[C@H]1CN2CCC3=C(NC4=CC=CC=C34)[C@H]2C[C@@H]1/C(=C\OC)C(=O)OC
InChI: InChI=1S/C22H28N2O3/c1-4-14-12-24-10-9-16-15-7-5-6-8-19(15)23-21(16)20(24)11-17(14)18(13-26-2)22(25)27-3/h5-8,13-14,17,20,23H,4,9-12H2,1-3H3/b18-13+/t14-,17-,20+/m0/s1
InChIKey: NMLUOJBSAYAYEM-AZQGJTAVSA-N
Reference
Indole Alkaloid Production in Callus Cultures of Uncaria rhyncophylla (MIQ) MIQUEL.
PubChem CID: 3037884
CAS: 7729-23-9
LOTUS: LTS0231221
NPASS: NPC111602
data_source: manually
Source
Properties Information
Molecule Weight: 368.47700000000015
TPSA？: 54.56
MolLogP？: 3.816500000000003
Number of H-Donors: 1
Number of H-Acceptors: 4
RingCount: 4
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Canis lupus familiaris | MDCK | CC50 | 23.5 | ug.mL-1 | 10.1016/S0960-894X(97)10154-8 |
| Canis lupus familiaris | MDCK | EC50 | 0.4 | ug.mL-1 | 10.1016/S0960-894X(97)10154-8 |
| Canis lupus familiaris | MDCK | EC50 | 0.57 | ug.mL-1 | 10.1016/S0960-894X(97)10154-8 |
| Canis lupus familiaris | MDCK | EC50 | 23.5 | ug.mL-1 | 10.1016/S0960-894X(97)10154-8 |
| dengue virus type 1 | dengue virus type 1 | EC50 | 1900.0 | nM | 10.1016/j.ejmech.2019.05.010 |
| Electrophorus electricus | Acetylcholinesterase | IC50 | nan | None | 10.1016/j.bmc.2012.09.040 |
| Electrophorus electricus | Acetylcholinesterase | Inhibition | 9.09 | % | 10.1016/j.bmc.2012.09.040 |
| Equus caballus | Cholinesterase | IC50 | 4970.0 | nM | 10.1016/j.bmc.2012.09.040 |
| Equus caballus | Cholinesterase | Inhibition | 87.06 | % | 10.1016/j.bmc.2012.09.040 |
| Homo sapiens | Butyrylcholinesterase | IC50 | 1970.0 | nM | 10.1016/j.bmc.2012.09.040 |
| None | Unchecked | Ratio | 41.2 | None | 10.1016/S0960-894X(97)10154-8 |
| None | Unchecked | Ratio | 58.8 | None | 10.1016/S0960-894X(97)10154-8 |