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US8883771, 4

ID: ALA3699019

PubChem CID: 91669022

Max Phase: Preclinical

Molecular Formula: C58H86N12O8

Molecular Weight: 1079.40

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]1CN(C(=O)NCCCCCCCCNC(=O)N2CC[C@H]3CC[C@@H](C(=O)N[C@@H]4CCCc5ccccc54)N3C(=O)[C@@H](NC(=O)[C@H](C)NC)C2)CC[C@H]2CCC(C(=O)N[C@@H]3CCCc4ccccc43)N2C1=O

Standard InChI:  InChI=1S/C58H86N12O8/c1-37(59-3)51(71)65-47-35-67(33-29-41-25-27-49(69(41)55(47)75)53(73)63-45-23-15-19-39-17-9-11-21-43(39)45)57(77)61-31-13-7-5-6-8-14-32-62-58(78)68-34-30-42-26-28-50(70(42)56(76)48(36-68)66-52(72)38(2)60-4)54(74)64-46-24-16-20-40-18-10-12-22-44(40)46/h9-12,17-18,21-22,37-38,41-42,45-50,59-60H,5-8,13-16,19-20,23-36H2,1-4H3,(H,61,77)(H,62,78)(H,63,73)(H,64,74)(H,65,71)(H,66,72)/t37-,38-,41+,42+,45+,46+,47-,48-,49-,50?/m0/s1

Standard InChI Key:  QRNCIGWSIMDYBM-VXUVBMGISA-N

Molfile:  

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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: 1079.40Molecular Weight (Monoisotopic): 1078.6692AlogP: #Rotatable Bonds:
Polar Surface Area: Molecular Species: HBA: HBD:
#RO5 Violations: HBA (Lipinski): HBD (Lipinski): #RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: CX LogP: CX LogD:
Aromatic Rings: Heavy Atoms: QED Weighted: Np Likeness Score:

References

1.  (2014)  Bivalent inhibitors of IAP proteins and therapeutic methods using the same, 
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

Source(1):