Your company account is blocked and you cannot place orders. If you have questions, please contact your company administrator.

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

ID: ALA526858

PubChem CID: 24857831

Max Phase: Preclinical

Molecular Formula: C30H40N4O6S

Molecular Weight: 584.74

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(C)C)cccc12

Standard InChI:  InChI=1S/C30H40N4O6S/c1-20(2)18-25(33-29(36)28(35)24(31)19-21-10-6-5-7-11-21)30(37)40-17-16-32-41(38,39)27-15-9-12-22-23(27)13-8-14-26(22)34(3)4/h5-15,20,24-25,28,32,35H,16-19,31H2,1-4H3,(H,33,36)/t24-,25+,28+/m1/s1

Standard InChI Key:  TUSRJRXMLKYQTI-QQNWGBJXSA-N

Molfile:  

     RDKit          2D

 41 43  0  0  0  0  0  0  0  0999 V2000
   -4.5024   -3.2266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5037   -4.0543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7907   -4.4671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0714   -4.0537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0745   -3.2227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7927   -2.8138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3565   -4.4656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6424   -4.0524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9276   -4.4642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6432   -3.2274    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9269   -5.2892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2135   -4.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2143   -3.2261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5014   -4.4629    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2154   -4.0498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9303   -4.4616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9345   -5.2864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6478   -4.0482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3619   -4.4614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2147   -3.2248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9287   -2.8116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9281   -1.9866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6436   -3.2234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0767   -4.0494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7908   -4.4626    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5056   -4.0506    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.2150   -3.6300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9220   -4.7629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0896   -3.3383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9335   -4.0369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6425   -3.6169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6332   -2.7914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2033   -2.8099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9081   -2.3888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8947   -1.5698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1774   -1.1709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4719   -1.5972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4888   -2.4147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6024   -1.1458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3235   -1.5466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5890   -0.3209    0.0000 C   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
 26 27  1  0
  1  2  2  0
 26 28  2  0
 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  1  0
 15 20  1  1
 39 41  1  0
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: 584.74Molecular Weight (Monoisotopic): 584.2669AlogP: 2.19#Rotatable Bonds: 14
Polar Surface Area: 151.06Molecular Species: NEUTRALHBA: 8HBD: 4
#RO5 Violations: 1HBA (Lipinski): 10HBD (Lipinski): 5#RO5 Violations (Lipinski): 1
CX Acidic pKa: 9.91CX Basic pKa: 8.34CX LogP: 2.91CX LogD: 2.05
Aromatic Rings: 3Heavy Atoms: 41QED Weighted: 0.17Np Likeness Score: -0.57

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]

Source