ID: ALA586091
Chembl Id: CHEMBL586091
Cas Number: 82372-67-6
PubChem CID: 443689
Max Phase: Preclinical
Molecular Formula: C16H19NO4
Molecular Weight: 289.33
Molecule Type: Small molecule
Associated Items:
Synonyms: Show More⌵
Canonical SMILES: COc1cc2c(cc1O)[C@@H]1[C@H](O)[C@@H](O)C=C3CCN(C2)[C@H]31
Standard InChI: InChI=1S/C16H19NO4/c1-21-13-5-9-7-17-3-2-8-4-12(19)16(20)14(15(8)17)10(9)6-11(13)18/h4-6,12,14-16,18-20H,2-3,7H2,1H3/t12-,14-,15+,16+/m0/s1
Standard InChI Key: CKAHWDNDUGDSLE-ARLBYUKCSA-N
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| Natural Product: Yes | Oral: No | Chemical Probe: No | Parenteral: No |
| Molecule Type: Small molecule | Topical: No | First In Class: No | Black Box: No |
| Chirality: No | Availability: No | Prodrug: No |
| MESH ID | MESH Heading | EFO IDs | EFO Terms | Max Phase for Indication | References |
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| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
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| Molecular Weight: 289.33 | Molecular Weight (Monoisotopic): 289.1314 | AlogP: 0.73 | #Rotatable Bonds: 1 |
| Polar Surface Area: 73.16 | Molecular Species: NEUTRAL | HBA: 5 | HBD: 3 |
| #RO5 Violations: ┄ | HBA (Lipinski): 5 | HBD (Lipinski): 3 | #RO5 Violations (Lipinski): ┄ |
| CX Acidic pKa: 9.89 | CX Basic pKa: 7.88 | CX LogP: 0.08 | CX LogD: -0.53 |
| Aromatic Rings: 1 | Heavy Atoms: 21 | QED Weighted: 0.66 | Np Likeness Score: 2.48 |
| 1. Gabrielsen B, Monath TP, Huggins JW, Kefauver DF, Pettit GR, Groszek G, Hollingshead M, Kirsi JJ, Shannon WM, Schubert EM.. (1992) Antiviral (RNA) activity of selected Amaryllidaceae isoquinoline constituents and synthesis of related substances., 55 (11): [PMID:1336040] [10.1021/np50089a003] |
| 2. Gamo FJ, Sanz LM, Vidal J, de Cozar C, Alvarez E, Lavandera JL, Vanderwall DE, Green DV, Kumar V, Hasan S, Brown JR, Peishoff CE, Cardon LR, Garcia-Bustos JF.. (2010) Thousands of chemical starting points for antimalarial lead identification., 465 (7296): [PMID:20485427] [10.1038/nature09107] |
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| 5. McNulty J, Nair JJ, Little JR, Brennan JD, Bastida J.. (2010) Structure-activity studies on acetylcholinesterase inhibition in the lycorine series of Amaryllidaceae alkaloids., 20 (17): [PMID:20655219] [10.1016/j.bmcl.2010.06.130] |
| 6. St. Jude Leishmania screening dataset., [10.6019/CHEMBL3433997] |
| 7. Zhan G, Zhou J, Liu J, Huang J, Zhang H, Liu R, Yao G.. (2017) Acetylcholinesterase Inhibitory Alkaloids from the Whole Plants of Zephyranthes carinata., 80 (9): [PMID:28898076] [10.1021/acs.jnatprod.7b00301] |
| 8. Nair JJ, van Staden J.. (2019) Antiprotozoal alkaloid principles of the plant family Amaryllidaceae., 29 (20): [PMID:31515186] [10.1016/j.bmcl.2019.126642] |
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