ID: ALA255919
Chembl Id: CHEMBL255919
PubChem CID: 9978176
Max Phase: Preclinical
Molecular Formula: C22H22O7
Molecular Weight: 398.41
Molecule Type: Small molecule
Associated Items:
Synonyms: (1S,2S,3R)-(+)-Isopicrodeoxypodophyllotoxin | Isopicrodeoxypodophyllotoxin | isopicrodeoxypodophyllotoxin|CHEMBL255919|SCHEMBL20800078|(1S,2S,3R)-(+)-Isopicrodeoxypodophyllotoxin
Canonical SMILES: COc1cc([C@H]2c3cc4c(cc3C[C@H]3COC(=O)[C@H]32)OCO4)cc(OC)c1OC
Standard InChI: InChI=1S/C22H22O7/c1-24-17-6-12(7-18(25-2)21(17)26-3)19-14-8-16-15(28-10-29-16)5-11(14)4-13-9-27-22(23)20(13)19/h5-8,13,19-20H,4,9-10H2,1-3H3/t13-,19-,20+/m0/s1
Standard InChI Key: ZGLXUQQMLLIKAN-QTJFZDIUSA-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: 398.41 | Molecular Weight (Monoisotopic): 398.1366 | AlogP: 2.92 | #Rotatable Bonds: 4 |
| Polar Surface Area: 72.45 | Molecular Species: NEUTRAL | HBA: 7 | HBD: ┄ |
| #RO5 Violations: ┄ | HBA (Lipinski): 7 | HBD (Lipinski): ┄ | #RO5 Violations (Lipinski): ┄ |
| CX Acidic pKa: ┄ | CX Basic pKa: ┄ | CX LogP: 2.81 | CX LogD: 2.81 |
| Aromatic Rings: 2 | Heavy Atoms: 29 | QED Weighted: 0.73 | Np Likeness Score: 1.48 |
| 1. Pettit GR, Hogan F, Xu JP, Tan R, Nogawa T, Cichacz Z, Pettit RK, Du J, Ye QH, Cragg GM, Herald CL, Hoard MS, Goswami A, Searcy J, Tackett L, Doubek DL, Williams L, Hooper JN, Schmidt JM, Chapuis JC, Tackett DN, Craciunescu F.. (2008) Antineoplastic agents. 536. New sources of naturally occurring cancer cell growth inhibitors from marine organisms, terrestrial plants, and microorganisms(1a,)., 71 (3): [PMID:18327911] [10.1021/np700738k] |
| 2. Chang LC, Song LL, Park EJ, Luyengi L, Lee KJ, Farnsworth NR, Pezzuto JM, Kinghorn AD.. (2000) Bioactive constituents of Thuja occidentalis., 63 (9): [PMID:11000026] [10.1021/np0001575] |
| 3. Gensler WJ, Murthy CD, Trammell MH.. (1977) Nonenolizable podophyllotoxin derivatives., 20 (5): [PMID:853503] [10.1021/jm00215a004] |
| 4. Pettit GR, Searcy JD, Tan R, Cragg GM, Melody N, Knight JC, Chapuis JC.. (2016) Antineoplastic Agents. 585. Isolation of Bridelia ferruginea Anticancer Podophyllotoxins and Synthesis of 4-Aza-podophyllotoxin Structural Modifications., 79 (3): [PMID:26938998] [10.1021/acs.jnatprod.5b00873] |
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