(S)-3-((S)-2-Acetylamino-3-methyl-butyrylamino)-N-{(S)-1-[(S)-2-((S)-2-hydroxy-5-oxo-tetrahydro-furan-3-ylcarbamoyl)-piperidine-1-carbonyl]-2-methyl-propyl}-succinamic acid

ID: ALA1835322

PubChem CID: 56659923

Max Phase: Preclinical

Molecular Formula: C26H41N5O10

Molecular Weight: 583.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@H](C(=O)N[C@@H](CC(=O)O)C(=O)N[C@H](C(=O)N1CCCC[C@H]1C(=O)N[C@H]1CC(=O)OC1O)C(C)C)C(C)C

Standard InChI:  InChI=1S/C26H41N5O10/c1-12(2)20(27-14(5)32)24(38)28-15(10-18(33)34)22(36)30-21(13(3)4)25(39)31-9-7-6-8-17(31)23(37)29-16-11-19(35)41-26(16)40/h12-13,15-17,20-21,26,40H,6-11H2,1-5H3,(H,27,32)(H,28,38)(H,29,37)(H,30,36)(H,33,34)/t15-,16-,17-,20-,21-,26?/m0/s1

Standard InChI Key:  SJKUPJSYABBYEV-VCEFXLGMSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA1835322

   (3S)-3-[[(2S)-2-acetamido-3-methylbutanoyl]amino]-4-[[(2S)-1-[(2S)-2-[[(3S)-2-hydroxy-5-oxooxolan-3-yl]carbamoyl]piperidin-1-yl]-3-methyl-1-oxobutan-2-yl]amino]-4-oxobutanoic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 583.64

Molecular Weight (Monoisotopic): 583.2853

AlogP: -1.62

#Rotatable Bonds: 12

Polar Surface Area: 220.54

Molecular Species: ACID

HBA: 9

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 15

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 4.26

CX Basic pKa: ┄

CX LogP: -1.72

CX LogD: -4.71

Aromatic Rings: ┄

Heavy Atoms: 41

QED Weighted: 0.14

Np Likeness Score: 0.14

References

1. Maillard MC, Brookfield FA, Courtney SM, Eustache FM, Gemkow MJ, Handel RK, Johnson LC, Johnson PD, Kerry MA, Krieger F, Meniconi M, Muñoz-Sanjuán I, Palfrey JJ, Park H, Schaertl S, Taylor MG, Weddell D, Dominguez C..  (2011)  Exploiting differences in caspase-2 and -3 S₂ subsites for selectivity: structure-based design, solid-phase synthesis and in vitro activity of novel substrate-based caspase-2 inhibitors.,  19  (19): [PMID:21903398] [10.1016/j.bmc.2011.08.020]

2. Chen, Yi-Hua YH and 9 more authors.  2006-03-09  Design, synthesis, and biological evaluation of isoquinoline-1,3,4-trione derivatives as potent caspase-3 inhibitors.  [PMID:16509578]

3. Maillard, Michel C MC and 17 more authors.  2011-10-01  Exploiting differences in caspase-2 and -3 S₂ subsites for selectivity: structure-based design, solid-phase synthesis and in vitro activity of novel substrate-based caspase-2 inhibitors.  [PMID:21903398]

Source

Source(1):

• Scientific Literature