ID: ALA464432
Chembl Id: CHEMBL464432
Cas Number: 40042-05-5
PubChem CID: 101204
Max Phase: Preclinical
Molecular Formula: C14H15NO7
Molecular Weight: 309.27
Molecule Type: Small molecule
Associated Items:
Synonyms: Trans-Dihydronarciclasine | trans-Dihydronarciclasine|40042-05-5|(2S,3R,4S,4aR,11bR)-2,3,4,7-tetrahydroxy-2,3,4,4a,5,11b-hexahydro-1H-[1,3]dioxolo[4,5-j]phenanthridin-6-one|NSC381837|CHEMBL464432|SCHEMBL14732745|NSC 381837|(1,3)Dioxolo(4,5-j)phenanthridin-6(2H)-one, 1,3,4,4a,5,11b-hexahydro-2,3,4,7-tetrahydroxy-, (2S-(2alpha,3beta,4beta,4abeta, 11balpha))-|[1,3]Dioxolo[4,5-j]phenanthridin-6(2H)-one, 1,3,4,4a,5,11b-hexahydro-2,3,4,7-tetrahydroxy-, (2S,3R,4S,4aR,11bR)-
Canonical SMILES: O=C1N[C@H]2[C@H](O)[C@H](O)[C@@H](O)C[C@@H]2c2cc3c(c(O)c21)OCO3
Standard InChI: InChI=1S/C14H15NO7/c16-6-1-5-4-2-7-13(22-3-21-7)11(18)8(4)14(20)15-9(5)12(19)10(6)17/h2,5-6,9-10,12,16-19H,1,3H2,(H,15,20)/t5-,6+,9-,10-,12+/m1/s1
Standard InChI Key: SBTGHBALOCEVOR-PUZXQUAOSA-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: 309.27 | Molecular Weight (Monoisotopic): 309.0849 | AlogP: -1.20 | #Rotatable Bonds: ┄ |
| Polar Surface Area: 128.48 | Molecular Species: NEUTRAL | HBA: 7 | HBD: 5 |
| #RO5 Violations: ┄ | HBA (Lipinski): 8 | HBD (Lipinski): 5 | #RO5 Violations (Lipinski): ┄ |
| CX Acidic pKa: 8.48 | CX Basic pKa: ┄ | CX LogP: -0.88 | CX LogD: -0.92 |
| Aromatic Rings: 1 | Heavy Atoms: 22 | QED Weighted: 0.41 | Np Likeness Score: 2.26 |
| 1. Pettit GR, Cragg GM, Singh SB, Duke JA, Doubek DL.. (1990) Antineoplastic agents, 162. Zephyranthes candida., 53 (1): [PMID:2348199] [10.1021/np50067a026] |
| 2. Pettit GR, Melody N.. (2005) Antineoplastic agents. 527. Synthesis of 7-deoxynarcistatin, 7-deoxy-trans-dihydronarcistatin, and trans-dihydronarcistatin 1(1)., 68 (2): [PMID:15730244] [10.1021/np0304518] |
| 3. Pettit GR, Pettit GR, Backhaus RA, Boyd MR, Meerow AW.. (1993) Antineoplastic agents, 256. Cell growth inhibitory isocarbostyrils from Hymenocallis., 56 (10): [PMID:8277308] [10.1021/np50100a004] |
| 4. 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] |
| 5. McNulty J, Thorat A, Vurgun N, Nair JJ, Makaji E, Crankshaw DJ, Holloway AC, Pandey S.. (2011) Human cytochrome P450 liability studies of trans-dihydronarciclasine: a readily available, potent, and selective cancer cell growth inhibitor., 74 (1): [PMID:21105682] [10.1021/np100657w] |
| 6. Nair JJ, Wilhelm A, Bonnet SL, van Staden J.. (2017) Antibacterial constituents of the plant family Amaryllidaceae., 27 (22): [PMID:29033234] [10.1016/j.bmcl.2017.09.052] |
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