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R/S-(S)-3-((S)-2-Acetylamino-3-methyl-butyrylamino)-N-{(S)-1-[7-hydroxy-1-((S)-2-hydroxy-5-oxo-tetrahydro-furan-3-ylcarbamoyl)-3,4-dihydro-1H-isoquinoline-2-carbonyl]-2-methyl-propyl}-succinamic acid ID: ALA1835402
PubChem CID: 56683723
Max Phase: Preclinical
Molecular Formula: C30H41N5O11
Molecular Weight: 647.68
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)N1CCc2ccc(O)cc2C1C(=O)N[C@H]1CC(=O)OC1O)C(C)C)C(C)C
Standard InChI: InChI=1S/C30H41N5O11/c1-13(2)23(31-15(5)36)27(42)32-19(11-21(38)39)26(41)34-24(14(3)4)29(44)35-9-8-16-6-7-17(37)10-18(16)25(35)28(43)33-20-12-22(40)46-30(20)45/h6-7,10,13-14,19-20,23-25,30,37,45H,8-9,11-12H2,1-5H3,(H,31,36)(H,32,42)(H,33,43)(H,34,41)(H,38,39)/t19-,20-,23-,24-,25?,30?/m0/s1
Standard InChI Key: QUNGAOXLQCNBLP-ZOGZNBLASA-N
Molfile:
RDKit 2D
46 48 0 0 0 0 0 0 0 0999 V2000
15.4083 -11.4141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
16.0757 -10.9265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
15.8201 -10.1370 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
14.9933 -10.1382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
14.7409 -10.9282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
14.5033 -9.4671 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
16.8556 -11.1777 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
15.4050 -12.2411 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
14.7019 -12.6752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
14.0293 -13.9405 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
6.8818 -14.0309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
7.5905 -13.6105 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
6.1652 -13.6265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.8917 -14.8558 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
8.3113 -14.0149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
9.0222 -13.5944 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
8.3212 -14.8398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
7.6103 -15.2603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
9.0420 -15.2443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
9.7408 -13.9989 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
9.0123 -12.7695 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
10.4475 -13.5784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
11.1683 -13.9829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
10.4376 -12.7535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
11.1782 -14.8078 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
11.1527 -12.3330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
11.8747 -12.7391 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
11.1440 -11.5098 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
11.8770 -13.5625 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
12.5978 -13.9669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
13.3064 -13.5465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
12.6077 -14.7918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
11.8968 -15.2123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
13.3221 -15.1963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
13.3066 -12.7215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
14.0543 -14.7647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
14.7305 -13.4996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
13.9786 -12.2861 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
14.7837 -15.1494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
15.4603 -13.8924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
15.4820 -14.7142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
16.2062 -15.1053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
16.9054 -14.6764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
16.8817 -13.8500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
16.1567 -13.4645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
17.5827 -13.4150 0.0000 O 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
44 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: 647.68Molecular Weight (Monoisotopic): 647.2803AlogP: -1.17#Rotatable Bonds: 12Polar Surface Area: 240.77Molecular Species: ACIDHBA: 10HBD: 7#RO5 Violations: 2HBA (Lipinski): 16HBD (Lipinski): 7#RO5 Violations (Lipinski): 3CX Acidic pKa: 4.25CX Basic pKa: ┄CX LogP: -1.11CX LogD: -4.11Aromatic Rings: 1Heavy Atoms: 46QED Weighted: 0.13Np Likeness Score: 0.41
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 ]
