(R)-3-((2S,3S)-3-((S)-2-((S)-2-acetamido-5-amino-5-oxopentanamido)-3-methylbutanamido)-2-hydroxy-4-phenylbutanoyl)-N-((S)-1-((S)-1-amino-4-(methylthio)-1-oxobutan-2-ylamino)-3-methyl-1-oxobutan-2-yl)-5,5-dimethylthiazolidine-4-carboxamide

ID: ALA233649

Chembl Id: CHEMBL233649

PubChem CID: 44430647

Max Phase: Preclinical

Molecular Formula: C38H60N8O9S2

Molecular Weight: 837.08

Molecule Type: Small molecule

Names and Identifiers

Synonyms: KNI-10127 | CHEMBL233649|KNI-10127|BDBM50371711

Canonical SMILES:  CSCC[C@H](NC(=O)[C@@H](NC(=O)[C@H]1N(C(=O)[C@@H](O)[C@H](Cc2ccccc2)NC(=O)[C@@H](NC(=O)[C@H](CCC(N)=O)NC(C)=O)C(C)C)CSC1(C)C)C(C)C)C(N)=O

Standard InChI:  InChI=1S/C38H60N8O9S2/c1-20(2)28(44-33(51)25(41-22(5)47)14-15-27(39)48)35(53)43-26(18-23-12-10-9-11-13-23)30(49)37(55)46-19-57-38(6,7)31(46)36(54)45-29(21(3)4)34(52)42-24(32(40)50)16-17-56-8/h9-13,20-21,24-26,28-31,49H,14-19H2,1-8H3,(H2,39,48)(H2,40,50)(H,41,47)(H,42,52)(H,43,53)(H,44,51)(H,45,54)/t24-,25-,26-,28-,29-,30-,31+/m0/s1

Standard InChI Key:  LXYGCMDJKMGFGW-BJFASDGLSA-N

Alternative Forms

1. Parent:

   

   ALA233649

   (2S)-2-acetamido-N-[(2S)-1-[[(2S,3S)-4-[(4R)-4-[[(2S)-1-[[(2S)-1-amino-4-methylsulfanyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]carbamoyl]-5,5-dimethyl-1,3-thiazolidin-3-yl]-3-hydroxy-4-oxo-1-phenylbutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]pentan

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: 837.08

Molecular Weight (Monoisotopic): 836.3925

AlogP: -0.47

#Rotatable Bonds: 22

Polar Surface Area: 272.22

Molecular Species: NEUTRAL

HBA: 11

HBD: 8

#RO5 Violations: 3

HBA (Lipinski): 17

HBD (Lipinski): 10

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.67

CX Basic pKa: ┄

CX LogP: -1.18

CX LogD: -1.18

Aromatic Rings: 1

Heavy Atoms: 57

QED Weighted: 0.07

Np Likeness Score: 0.12

References

1. Kimura T, Nguyen JT, Maegawa H, Nishiyama K, Arii Y, Matsui Y, Hayashi Y, Kiso Y..  (2007)  Chipping at large, potent human T-cell leukemia virus type 1 protease inhibitors to uncover smaller, equipotent inhibitors.,  17  (12): [PMID:17448657] [10.1016/j.bmcl.2007.04.019]

2. Nguyen JT, Zhang M, Kumada HO, Itami A, Nishiyama K, Kimura T, Cheng M, Hayashi Y, Kiso Y..  (2008)  Truncation and non-natural amino acid substitution studies on HTLV-I protease hexapeptidic inhibitors.,  18  (1): [PMID:18006315] [10.1016/j.bmcl.2007.10.066]

Source

Source(1):

• Scientific Literature