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(S)-3-(4-(2-azidoethoxy)phenyl)-2-((S)-2-((S)-1-((S)-2-((S)-2-(methylamino)propanamido)pent-4-ynoyl)pyrrolidine-2-carboxamido)-3-phenylpropanamido)propanoic acid

ID: ALA3414575

PubChem CID: 118732794

Max Phase: Preclinical

Molecular Formula: C34H42N8O7

Molecular Weight: 674.76

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  C#CC[C@H](NC(=O)[C@H](C)NC)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](Cc1ccc(OCCN=[N+]=[N-])cc1)C(=O)O

Standard InChI:  InChI=1S/C34H42N8O7/c1-4-9-26(38-30(43)22(2)36-3)33(46)42-18-8-12-29(42)32(45)39-27(20-23-10-6-5-7-11-23)31(44)40-28(34(47)48)21-24-13-15-25(16-14-24)49-19-17-37-41-35/h1,5-7,10-11,13-16,22,26-29,36H,8-9,12,17-21H2,2-3H3,(H,38,43)(H,39,45)(H,40,44)(H,47,48)/t22-,26-,27-,28-,29-/m0/s1

Standard InChI Key:  AITUWMHJRLZLLP-WQJHFXEDSA-N

Molfile:  

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M  CHG  2  47   1  48  -1
M  END

Alternative Forms

  1. Parent:

    ALA3414575

    ---

Associated Targets(Human)

BIRC3 Tchem Baculoviral IAP repeat-containing protein 3 (320 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: 674.76Molecular Weight (Monoisotopic): 674.3176AlogP: 1.32#Rotatable Bonds: 18
Polar Surface Area: 214.93Molecular Species: ZWITTERIONHBA: 8HBD: 5
#RO5 Violations: 1HBA (Lipinski): 15HBD (Lipinski): 5#RO5 Violations (Lipinski): 2
CX Acidic pKa: -10.22CX Basic pKa: 8.60CX LogP: -1.93CX LogD: -1.18
Aromatic Rings: 2Heavy Atoms: 49QED Weighted: 0.05Np Likeness Score: -0.22

References

1. Seigal BA, Connors WH, Fraley A, Borzilleri RM, Carter PH, Emanuel SL, Fargnoli J, Kim K, Lei M, Naglich JG, Pokross ME, Posy SL, Shen H, Surti N, Talbott R, Zhang Y, Terrett NK..  (2015)  The discovery of macrocyclic XIAP antagonists from a DNA-programmed chemistry library, and their optimization to give lead compounds with in vivo antitumor activity.,  58  (6): [PMID:25695766] [10.1021/jm501892g]
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