Haemanthamine
AlkaPlorer ID: AK001691
Synonym: '', '(+)-Haemanthamine', '(3alpha,5alpha,11R,13beta,19alpha)-1, 2-Didehydro-3-methoxycrinan-11-ol', 'Crinamine', '(3beta,5alpha,11R,13beta,19alpha)-1,2-Didehydro-3-methoxycrinan-11-ol', 'Haemanthamine'
IUPAC Name: (1S,13S,15R,18R)-15-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.01,13.02,10.04,8]nonadeca-2,4(8),9,16-tetraen-18-ol
Structure
SMILES: CO[C@H]1C=C[C@@]23C4=CC5=C(C=C4CN(C[C@@H]2O)[C@H]3C1)OCO5
InChI: InChI=1S/C17H19NO4/c1-20-11-2-3-17-12-6-14-13(21-9-22-14)4-10(12)7-18(8-16(17)19)15(17)5-11/h2-4,6,11,15-16,19H,5,7-9H2,1H3/t11-,15-,16-,17-/m0/s1
InChIKey: YGPRSGKVLATIHT-SPOWBLRKSA-N
Reference
Further alkaloids from Brunsvigia josephinae
PubChem CID: 73620
CAS: 639-41-8
LOTUS: LTS0136441
SuperNatural Ⅲ: SN0449878-12
NPASS: NPC158148
Source
Properties Information
Molecule Weight: 301.34200000000004
TPSA？: 51.16000000000001
MolLogP？: 1.1866999999999996
Number of H-Donors: 1
Number of H-Acceptors: 5
RingCount: 5
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Electrophorus electricus | Acetylcholinesterase | IC50 | 697000.0 | nM | 10.1016/j.ejmech.2020.112792 |
| Entamoeba histolytica | Entamoeba histolytica | IC50 | 0.53 | ug.mL-1 | 10.1016/j.bmcl.2019.126642 |
| Homo sapiens | A-431 | ED50 | 6.9 | ug ml-1 | 10.1021/np50098a017 |
| Homo sapiens | HT-1080 | ED50 | 1.3 | ug ml-1 | 10.1021/np50098a017 |
| Homo sapiens | KB | ED50 | 1.0 | ug ml-1 | 10.1021/np50098a017 |
| Homo sapiens | LNCaP | ED50 | 1.5 | ug ml-1 | 10.1021/np50098a017 |
| Homo sapiens | SK-MEL-2 | ED50 | 5.0 | ug ml-1 | 10.1021/np50098a017 |
| Homo sapiens | Zinc finger protein GLI1 | IC50 | 4700.0 | nM | 10.1016/j.ejmech.2022.114867 |
| Homo sapiens | ZR-75-1 | ED50 | 0.8 | ug ml-1 | 10.1021/np50098a017 |
| Mus musculus | P388 | ED50 | 0.7 | ug ml-1 | 10.1021/np50098a017 |
| Plasmodium falciparum | Plasmodium falciparum | ED50 | 2180.0 | ug ml-1 | 10.1021/np50098a017 |
| Plasmodium falciparum | Plasmodium falciparum | ED50 | 2520.0 | ug ml-1 | 10.1021/np50098a017 |
| None | ADMET | Activity | 84.5 | % | 10.1021/np030529k |
| None | ADMET | Activity | 100.1 | % | 10.1021/np030529k |
| None | ADMET | Activity | 100.5 | % | 10.1021/np030529k |
| None | ADMET | Activity | 100.6 | % | 10.1021/np030529k |
| None | Macrophage | IC50 | 1800.0 | nM | 10.1021/np030529k |
| None | Macrophage | Inhibition | 7.8 | % | 10.1021/np030529k |
| None | Macrophage | Inhibition | 8.1 | % | 10.1021/np030529k |
| None | Macrophage | Inhibition | 30.2 | % | 10.1021/np030529k |
| None | Macrophage | Inhibition | 65.2 | % | 10.1021/np030529k |
| None | Macrophage | Inhibition | 86.1 | % | 10.1021/np030529k |
| None | NON-PROTEIN TARGET | ED50 | 0.6 | ug ml-1 | 10.1021/np50098a017 |
| None | NON-PROTEIN TARGET | ED50 | 0.9 | ug ml-1 | 10.1021/np50098a017 |
| None | NON-PROTEIN TARGET | ED50 | 1.0 | ug ml-1 | 10.1021/np50098a017 |
| None | NON-PROTEIN TARGET | ED50 | 1.4 | ug ml-1 | 10.1021/np50098a017 |
| None | Unchecked | Ratio ED50 | 0.4 | None | 10.1021/np50098a017 |