Isorhynchophylline
AlkaPlorer ID: AK003538
Synonym: None
IUPAC Name: methyl (E)-2-[(3S,6'R,7'S,8'aS)-6'-ethyl-2-oxospiro[1H-indole-3,1'-3,5,6,7,8,8a-hexahydro-2H-indolizine]-7'-yl]-3-methoxyprop-2-enoate
Structure
SMILES: CC[C@H]1CN2CC[C@@]3(C(O)=NC4=C3C=CC=C4)[C@@H]2C[C@@H]1/C(=C\OC)C(=O)OC
InChI: InChI=1S/C22H28N2O4/c1-4-14-12-24-10-9-22(17-7-5-6-8-18(17)23-21(22)26)19(24)11-15(14)16(13-27-2)20(25)28-3/h5-8,13-15,19H,4,9-12H2,1-3H3,(H,23,26)/b16-13+/t14-,15-,19-,22-/m0/s1
InChIKey: DAXYUDFNWXHGBE-VKCGGMIFSA-N
Reference
Studies of Plants containing Indole Alkaloids. (2). On the Alkaloids of Uncaria rhynchophylla MIQ
PubChem CID: 3037048
LOTUS: LTS0097426
SuperNatural Ⅲ: SN0060888-28
NPASS: NPC97380
Source
Properties Information
Molecule Weight: 384.4760000000002
TPSA？: 71.36
MolLogP？: 3.349700000000002
Number of H-Donors: 1
Number of H-Acceptors: 5
RingCount: 4
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Homo sapiens | HL-60 | IC50 | 40000.0 | nM | 10.1021/np1004938 |
| Homo sapiens | Serotonin 1a (5-HT1a) receptor | EC50 | 2000.0 | nM | 10.1021/acs.jnatprod.9b00532 |
| Homo sapiens | SW480 | IC50 | 40000.0 | nM | 10.1021/np1004938 |
| Rattus norvegicus | Aorta | IC50 | 18.41 | ug.mL-1 | 10.1021/np1004938 |
| Rattus norvegicus | Aorta | IC50 | 30.0 | ug.mL-1 | 10.1021/np1004938 |
| None | ADMET | Drug metabolism | 22.0 | % | 10.1016/j.bmc.2021.116270 |
| None | ADMET | F | 3.3 | % | 10.1016/j.bmc.2021.116270 |
| None | NON-PROTEIN TARGET | Activity | nan | None | 10.1021/np8000305 |
| None | Unchecked | IC50 | 19000.0 | nM | 10.1021/np8000305 |
| None | Unchecked | Inhibition | 30.4 | % | 10.1016/j.ejmech.2022.114566 |
| None | Unchecked | Inhibition | 33.8 | % | 10.1021/np8000305 |
| None | Unchecked | Inhibition | 42.1 | % | 10.1021/np8000305 |
| None | Unchecked | Inhibition | 76.9 | % | 10.1021/np8000305 |
| None | Unchecked | Inhibition | 95.2 | % | 10.1021/np8000305 |