(R)-3-((2S,3S)-3-((S)-3,3-dimethyl-2-((S)-2-(3-methylbutanamido)-2-phenylacetamido)butanamido)-2-hydroxy-4-phenylbutanoyl)-N-isobutyl-5,5-dimethylthiazolidine-4-carboxamide

ID: ALA499480

Chembl Id: CHEMBL499480

PubChem CID: 44593406

Max Phase: Preclinical

Molecular Formula: C39H57N5O6S

Molecular Weight: 723.98

Molecule Type: Small molecule

Names and Identifiers

Synonyms: KNI-10573 | CHEMBL499480|KNI-10573|BDBM50242970|(R)-3-((2S,3S)-3-((S)-3,3-dimethyl-2-((S)-2-(3-methylbutanamido)-2-phenylacetamido)butanamido)-2-hydroxy-4-phenylbutanoyl)-N-isobutyl-5,5-dimethylthiazolidine-4-carboxamide|(R)-N-Isobutyl-3-{{(2S,3S)-3-{(2S)-2-[(2S)-2-(3-methyl)butanoylamino-2-phenyl]acetylamino-3,3-dimethyl}-butanoylamino-2-hydroxy-4-phenyl}}butanoyl-5,5-dimethyl-1,3-thiazolidine-4-carboxamide

Canonical SMILES:  CC(C)CNC(=O)[C@H]1N(C(=O)[C@@H](O)[C@H](Cc2ccccc2)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CC(C)C)c2ccccc2)C(C)(C)C)CSC1(C)C

Standard InChI:  InChI=1S/C39H57N5O6S/c1-24(2)20-29(45)42-30(27-18-14-11-15-19-27)34(47)43-32(38(5,6)7)35(48)41-28(21-26-16-12-10-13-17-26)31(46)37(50)44-23-51-39(8,9)33(44)36(49)40-22-25(3)4/h10-19,24-25,28,30-33,46H,20-23H2,1-9H3,(H,40,49)(H,41,48)(H,42,45)(H,43,47)/t28-,30-,31-,32+,33+/m0/s1

Standard InChI Key:  RAPPOLGHPMJHJX-VYIXFUBHSA-N

Alternative Forms

1. Parent:

   

   ALA499480

   (R)-3-((2S,3S)-3-((S)-3,3-dimethyl-2-((S)-2-(3-methylbutanamido)-2-phenylacetamido)butanamido)-2-hydroxy-4-phenylbutanoyl)-N-isobutyl-5,5-dimethylthiazolidine-4-carboxamide

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: 723.98

Molecular Weight (Monoisotopic): 723.4030

AlogP: 3.96

#Rotatable Bonds: 15

Polar Surface Area: 156.94

Molecular Species: NEUTRAL

HBA: 7

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.82

CX Basic pKa: ┄

CX LogP: 4.16

CX LogD: 4.16

Aromatic Rings: 2

Heavy Atoms: 51

QED Weighted: 0.19

Np Likeness Score: 0.28

References

1. Zhang M, Nguyen JT, Kumada HO, Kimura T, Cheng M, Hayashi Y, Kiso Y..  (2008)  Locking the two ends of tetrapeptidic HTLV-I protease inhibitors inside the enzyme.,  16  (14): [PMID:18558491] [10.1016/j.bmc.2008.05.052]

2. Zhang M, Nguyen JT, Kumada HO, Kimura T, Cheng M, Hayashi Y, Kiso Y..  (2008)  Synthesis and activity of tetrapeptidic HTLV-I protease inhibitors possessing different P3-cap moieties.,  16  (10): [PMID:18400502] [10.1016/j.bmc.2008.03.055]

Source

Source(1):

• Scientific Literature