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(S)-2-(1-azidonaphthalene-5-sulfonamido)ethyl 2-((2S,3R)-3-amino-2-hydroxy-4-phenylbutanamido)-4-methylpentanoate

ID: ALA454988

PubChem CID: 44576646

Max Phase: Preclinical

Molecular Formula: C28H34N6O6S

Molecular Weight: 582.68

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  CC(C)C[C@H](NC(=O)[C@@H](O)[C@H](N)Cc1ccccc1)C(=O)OCCNS(=O)(=O)c1cccc2c(N=[N+]=[N-])cccc12

Standard InChI:  InChI=1S/C28H34N6O6S/c1-18(2)16-24(32-27(36)26(35)22(29)17-19-8-4-3-5-9-19)28(37)40-15-14-31-41(38,39)25-13-7-10-20-21(25)11-6-12-23(20)33-34-30/h3-13,18,22,24,26,31,35H,14-17,29H2,1-2H3,(H,32,36)/t22-,24+,26+/m1/s1

Standard InChI Key:  PHBGCQYYFQWIRN-CWDLOFLHSA-N

Molfile:  

     RDKit          2D

 41 43  0  0  0  0  0  0  0  0999 V2000
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   -3.5157  -10.1276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7964   -9.7141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7995   -8.8830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5177   -8.4743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6526  -10.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3682   -8.8878    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0615   -9.7115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4904   -9.7102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9186   -8.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3517   -9.7098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0658  -10.1230    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7806   -9.7111    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.4900   -9.2904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1970  -10.4233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3646   -8.9987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2085   -9.6974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9175   -9.2774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9082   -8.4518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4783   -8.4703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1831   -8.0492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1697   -7.2302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4524   -6.8313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7469   -7.2576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7638   -8.0752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8774   -6.8061    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5846   -6.3846    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2950   -5.9675    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  8 10  1  1
 20 21  1  0
  2  3  1  0
 21 22  1  0
  9 11  1  1
 21 23  1  0
  5  6  2  0
 19 24  1  0
  9 12  1  0
 24 25  1  0
  6  1  1  0
 25 26  1  0
 12 13  2  0
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  1  2  2  0
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 12 14  1  0
 26 29  2  0
  4  7  1  0
 27 30  2  0
 14 15  1  0
 30 31  1  0
  3  4  2  0
 31 32  2  0
 32 34  1  0
 33 27  1  0
 15 16  1  0
  7  8  1  0
 33 34  1  0
 34 35  2  0
 16 17  2  0
 35 36  1  0
 16 18  1  0
 36 37  2  0
  8  9  1  0
 37 38  1  0
 38 33  2  0
 18 19  1  0
 35 39  1  0
  4  5  1  0
 39 40  2  0
 15 20  1  1
 40 41  2  0
M  CHG  2  40   1  41  -1
M  END

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: 582.68Molecular Weight (Monoisotopic): 582.2261AlogP: 3.06#Rotatable Bonds: 14
Polar Surface Area: 196.58Molecular Species: NEUTRALHBA: 8HBD: 4
#RO5 Violations: 1HBA (Lipinski): 12HBD (Lipinski): 5#RO5 Violations (Lipinski): 2
CX Acidic pKa: 9.89CX Basic pKa: 8.34CX LogP: 0.20CX LogD: 2.25
Aromatic Rings: 3Heavy Atoms: 41QED Weighted: 0.07Np Likeness Score: -0.45

References

1. Sato S, Aoyama H, Miyachi H, Naito M, Hashimoto Y..  (2008)  Demonstration of direct binding of cIAP1 degradation-promoting bestatin analogs to BIR3 domain: Synthesis and application of fluorescent bestatin ester analogs.,  18  (11): [PMID:18448338] [10.1016/j.bmcl.2008.04.031]
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]

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