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(3S,6S,9S,10aR)-N-Benzhydryl-9-hydroxy-6-((S)-2-(methylamino)propanamido)-5-oxodecahydropyrrolo[1,2-a]azocine-3-carboxamide

ID: ALA1242922

PubChem CID: 46930723

Max Phase: Preclinical

Molecular Formula: C28H36N4O4

Molecular Weight: 492.62

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  CN[C@@H](C)C(=O)N[C@H]1CC[C@H](O)C[C@H]2CC[C@@H](C(=O)NC(c3ccccc3)c3ccccc3)N2C1=O

Standard InChI:  InChI=1S/C28H36N4O4/c1-18(29-2)26(34)30-23-15-14-22(33)17-21-13-16-24(32(21)28(23)36)27(35)31-25(19-9-5-3-6-10-19)20-11-7-4-8-12-20/h3-12,18,21-25,29,33H,13-17H2,1-2H3,(H,30,34)(H,31,35)/t18-,21+,22-,23-,24-/m0/s1

Standard InChI Key:  YSWSPOWPCMUWGP-GXWFBMCDSA-N

Molfile:  

     RDKit          2D

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    9.1744   -5.4925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7592   -4.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7593   -6.9007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.1672   -5.4925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1664   -6.3238    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9568   -6.5816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4462   -5.9095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.2109   -7.3665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6582   -7.9790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   15.1661   -8.7581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   15.8694   -7.5108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1521   -7.1076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9014   -7.6633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4449   -7.6634    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6272   -7.7726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3129   -8.5354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1238   -7.1190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4951   -8.6446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8163   -9.1890    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5020   -9.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1625   -4.6667    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4434   -4.1456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  2  0
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  9 10  1  0
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  9 12  1  1
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  7  6  1  0
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  5 28  2  0
  6  3  1  0
  4 29  1  1
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 15 16  1  0
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  1  2  1  0
 34 35  1  0
 15 17  1  0
  7 36  1  6
  2  3  1  0
  3 37  1  6
M  END

Associated Targets(Human)

BIRC3 Tchem Baculoviral IAP repeat-containing protein 3 (320 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BIRC2 Tchem Baculoviral IAP repeat-containing protein 2 (984 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
XIAP Tchem Inhibitor of apoptosis protein 3 (3673 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Calculated Properties

Molecular Weight: 492.62Molecular Weight (Monoisotopic): 492.2737AlogP: 1.89#Rotatable Bonds: 7
Polar Surface Area: 110.77Molecular Species: BASEHBA: 5HBD: 4
#RO5 Violations: HBA (Lipinski): 8HBD (Lipinski): 4#RO5 Violations (Lipinski):
CX Acidic pKa: 12.28CX Basic pKa: 8.60CX LogP: 1.52CX LogD: 0.29
Aromatic Rings: 2Heavy Atoms: 36QED Weighted: 0.47Np Likeness Score: -0.07

References

1. Sun H, Lu J, Liu L, Yi H, Qiu S, Yang CY, Deschamps JR, Wang S..  (2010)  Nonpeptidic and potent small-molecule inhibitors of cIAP-1/2 and XIAP proteins.,  53  (17): [PMID:20684551] [10.1021/jm100487z]
2. Sato, Shinichi S, Aoyama, Hiroshi H, Miyachi, Hiroyuki H, Naito, Mikihiko M and Hashimoto, Yuichi Y.  2008-06-01  Demonstration of direct binding of cIAP1 degradation-promoting bestatin analogs to BIR3 domain: Synthesis and application of fluorescent bestatin ester analogs.  [PMID:18448338]
3. Zhang, Bin and 8 more authors.  2008-12-11  Design, synthesis, and evaluation of tricyclic, conformationally constrained small-molecule mimetics of second mitochondria-derived activator of caspases.  [PMID:19012392]
4. Sun, Wei and 9 more authors.  2009-02-12  Design, synthesis, and evaluation of potent, nonpeptidic mimetics of second mitochondria-derived activator of caspases.  [PMID:19138149]
5. Sun, Haiying and 6 more authors.  2010-05-15  Cyclopeptide Smac mimetics as antagonists of IAP proteins.  [PMID:20443226]
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]
8. Flygare, John A JA and 41 more authors.  2012-05-10  Discovery of a potent small-molecule antagonist of inhibitor of apoptosis (IAP) proteins and clinical candidate for the treatment of cancer (GDC-0152).  [PMID:22413863]
9. 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]
10. Zhang, Yong Y and 20 more authors.  2015-07-09  Dimeric Macrocyclic Antagonists of Inhibitor of Apoptosis Proteins for the Treatment of Cancer.  [PMID:26191364]
11. Baggio, Carlo C and 8 more authors.  2018-07-26  Design of Potent pan-IAP and Lys-Covalent XIAP Selective Inhibitors Using a Thermodynamics Driven Approach.  [PMID:29940121]

Source