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R/S-(S)-3-((S)-2-Acetylamino-3-methyl-butyrylamino)-N-{(S)-1-[1-((S)-2-hydroxy-5-oxo-tetrahydro-furan-3-ylcarbamoyl)-6-methyl-3,4-dihydro-1H-isoquinoline-2-carbonyl]-2-methyl-propyl}-succinamic acid ID: ALA1835399
PubChem CID: 56680385
Max Phase: Preclinical
Molecular Formula: C31H43N5O10
Molecular Weight: 645.71
Molecule Type: Small molecule
This compound is available for customization.
Associated Items:
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)N1CCc2cc(C)ccc2C1C(=O)N[C@H]1CC(=O)OC1O)C(C)C)C(C)C
Standard InChI: InChI=1S/C31H43N5O10/c1-14(2)24(32-17(6)37)28(42)33-20(12-22(38)39)27(41)35-25(15(3)4)30(44)36-10-9-18-11-16(5)7-8-19(18)26(36)29(43)34-21-13-23(40)46-31(21)45/h7-8,11,14-15,20-21,24-26,31,45H,9-10,12-13H2,1-6H3,(H,32,37)(H,33,42)(H,34,43)(H,35,41)(H,38,39)/t20-,21-,24-,25-,26?,31?/m0/s1
Standard InChI Key: MGIHOMZITTVQKS-QYKDOZOMSA-N
Molfile:
RDKit 2D
46 48 0 0 0 0 0 0 0 0999 V2000
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16.1784 -3.6828 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
15.3516 -3.6841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
15.0992 -4.4740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
14.8616 -3.0129 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
17.2140 -4.7235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
15.7633 -5.7870 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
15.0602 -6.2211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
14.3876 -7.4864 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
7.2401 -7.5767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
7.9489 -7.1563 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
6.5235 -7.1723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
7.2500 -8.4017 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
8.6696 -7.5608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
9.3805 -7.1403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
8.6795 -8.3857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
7.9686 -8.8062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
9.4003 -8.7901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
10.0991 -7.5448 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
9.3706 -6.3153 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
10.8058 -7.1243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
11.5266 -7.5287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
10.7960 -6.2994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
11.5365 -8.3536 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
11.5110 -5.8789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
12.2330 -6.2849 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
11.5023 -5.0556 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
12.2354 -7.1083 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
12.9561 -7.5127 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
13.6648 -7.0924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
12.9660 -8.3376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
12.2551 -8.7581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
13.6805 -8.7421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
13.6649 -6.2674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
14.4126 -8.3105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
15.0888 -7.0454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
14.3369 -5.8320 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
15.1421 -8.6952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
15.8186 -7.4383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
15.8403 -8.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
16.5646 -8.6512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
17.2637 -8.2222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
17.2400 -7.3958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
16.5151 -7.0103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
17.9893 -8.6148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1 2 1 0
2 3 1 0
3 4 1 0
4 5 1 0
1 5 1 0
4 6 2 0
2 7 1 0
1 8 1 1
11 12 1 0
11 13 1 0
11 14 2 0
12 15 1 0
15 16 1 0
15 17 1 6
17 18 1 0
17 19 1 0
16 20 1 0
16 21 2 0
20 22 1 0
22 23 1 0
22 24 1 1
23 25 2 0
24 26 1 0
26 27 1 0
26 28 2 0
23 29 1 0
29 30 1 0
30 31 1 0
30 32 1 6
32 33 1 0
32 34 1 0
31 10 1 0
31 35 2 0
10 36 1 0
10 37 1 0
36 39 1 0
40 37 1 0
37 9 1 0
9 8 1 0
9 38 2 0
41 39 1 0
40 41 2 0
41 42 1 0
42 43 2 0
43 44 1 0
44 45 2 0
45 40 1 0
43 46 1 0
M END Associated Targets(Human) Molecule Features Natural Product: NoOral: NoChemical Probe: NoParenteral: NoMolecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: NoChirality: NoAvailability: NoProdrug: No
Drug Indications MESH ID MESH Heading EFO IDs EFO Terms Max Phase for Indication References
Mechanisms of Action Mechanism of Action Action Type target ID Target Name Target Type Target Organism Binding Site Name References
Calculated Properties Molecular Weight: 645.71Molecular Weight (Monoisotopic): 645.3010AlogP: -0.57#Rotatable Bonds: 12Polar Surface Area: 220.54Molecular Species: ACIDHBA: 9HBD: 6#RO5 Violations: 2HBA (Lipinski): 15HBD (Lipinski): 6#RO5 Violations (Lipinski): 3CX Acidic pKa: 4.27CX Basic pKa: ┄CX LogP: -0.29CX LogD: -3.28Aromatic Rings: 1Heavy Atoms: 46QED Weighted: 0.16Np Likeness Score: 0.24
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 ]
