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ID: ALA457093
PubChem CID: 44567555
Max Phase: Preclinical
Molecular Formula: C16H30N2O5
Molecular Weight: 330.43
Molecule Type: Small molecule
Associated Items:
Canonical SMILES: CCCCC[C@H](CC(=O)NO)C(=O)N[C@@H](CC(C)C)C(=O)OC
Standard InChI: InChI=1S/C16H30N2O5/c1-5-6-7-8-12(10-14(19)18-22)15(20)17-13(9-11(2)3)16(21)23-4/h11-13,22H,5-10H2,1-4H3,(H,17,20)(H,18,19)/t12-,13+/m1/s1
Standard InChI Key: DXSLXRLCHHIQGT-OLZOCXBDSA-N
Molfile:
RDKit 2D 23 22 0 0 0 0 0 0 0 0999 V2000 11.1875 0.4458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.9020 0.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4730 0.8583 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 11.1875 -0.3792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7586 0.4458 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.6164 0.4458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.3309 0.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.6164 -0.3792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.0454 0.4458 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 13.3309 1.6833 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 14.7599 0.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.4743 0.4458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.7599 1.6833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.4743 2.0958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.4743 2.9208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.1888 1.6833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.4743 -0.3792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 16.1888 0.8583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 16.9033 0.4458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.3309 -0.7917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.3309 -1.6167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.0454 -2.0292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.0454 -2.8542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11 12 1 0 1 2 1 0 11 13 1 1 6 7 1 0 13 14 1 0 1 4 2 0 14 15 1 0 6 8 1 6 14 16 1 0 12 17 2 0 7 9 1 0 12 18 1 0 3 5 1 0 18 19 1 0 7 10 2 0 8 20 1 0 1 3 1 0 20 21 1 0 9 11 1 0 21 22 1 0 2 6 1 0 22 23 1 0 M END
Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
---|
Natural Product: No | 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 |
Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
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Molecular Weight: 330.43 | Molecular Weight (Monoisotopic): 330.2155 | AlogP: 1.78 | #Rotatable Bonds: 11 |
Polar Surface Area: 104.73 | Molecular Species: NEUTRAL | HBA: 5 | HBD: 3 |
#RO5 Violations: ┄ | HBA (Lipinski): 7 | HBD (Lipinski): 3 | #RO5 Violations (Lipinski): ┄ |
CX Acidic pKa: 8.90 | CX Basic pKa: ┄ | CX LogP: 1.98 | CX LogD: 1.96 |
Aromatic Rings: ┄ | Heavy Atoms: 23 | QED Weighted: 0.23 | Np Likeness Score: 0.42 |
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6. Cai, Qian and 17 more authors. 2011-04-28 A potent and orally active antagonist (SM-406/AT-406) of multiple inhibitor of apoptosis proteins (IAPs) in clinical development for cancer treatment. [PMID:21443232] |
7. Sun, Haiying and 11 more authors. 2011-05-12 Potent bivalent Smac mimetics: effect of the linker on binding to inhibitor of apoptosis proteins (IAPs) and anticancer activity. [PMID:21462933] |
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9. Allensworth, Jennifer L JL, Sauer, Scott J SJ, Lyerly, H Kim HK, Morse, Michael A MA and Devi, Gayathri R GR. 2013-01 Smac mimetic Birinapant induces apoptosis and enhances TRAIL potency in inflammatory breast cancer cells in an IAP-dependent and TNF-α-independent mechanism. [PMID:23225169] |
10. Sheng, Rong R and 13 more authors. 2013-05-23 A potent bivalent Smac mimetic (SM-1200) achieving rapid, complete, and durable tumor regression in mice. [PMID:23651223] |
11. Donnell, Andrew F AF and 28 more authors. 2013-10-24 Benzazepinones and benzoxazepinones as antagonists of inhibitor of apoptosis proteins (IAPs) selective for the second baculovirus IAP repeat (BIR2) domain. [PMID:24083782] |
12. Kester, Robert F RF and 31 more authors. 2013-10-24 Optimization of benzodiazepinones as selective inhibitors of the X-linked inhibitor of apoptosis protein (XIAP) second baculovirus IAP repeat (BIR2) domain. [PMID:24093940] |
13. Perez, Heidi L HL and 14 more authors. 2015-02-12 Discovery of potent heterodimeric antagonists of inhibitor of apoptosis proteins (IAPs) with sustained antitumor activity. [PMID:25584393] |
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