(R)-3-[(2S,3S)-2-Hydroxy-3-(3-hydroxy-2-methyl-benzoylamino)-4-phenyl-butyryl]-5,5-dimethyl-thiazolidine-4-carboxylic acid 2-methyl-benzylamide

ID: ALA300891

Cas Number: 186538-00-1

PubChem CID: 446837

Max Phase: Preclinical

Molecular Formula: C32H37N3O5S

Molecular Weight: 575.73

Molecule Type: Small molecule

Names and Identifiers

Synonyms: KNI-764 | JE-2147|186538-00-1|KNI-764|AG1776|AG 1776|CHEMBL300891|(4r)-3-{(2s,3s)-2-Hydroxy-3-[(3-Hydroxy-2-Methylbenzoyl)amino]-4-Phenylbutanoyl}-5,5-Dimethyl-N-(2-Methylbenzyl)-1,3-Thiazolidine-4-Carboxamide|(R)-3-((2S,3S)-2-Hydroxy-3-(3-hydroxy-2-methylbenzamido)-4-phenylbutanoyl)-5,5-dimethyl-N-(2-methylbenzyl)thiazolidine-4-carboxamide|(4R)-3-[(2S,3S)-2-hydroxy-3-[(3-hydroxy-2-methyl-benzoyl)amino]-4-phenyl-butanoyl]-5,5-dimethyl-N-[(2-methylphenyl)methyl]thiazolidine-4-carboxamide|1msn|4-TShow More⌵

Canonical SMILES:  Cc1ccccc1CNC(=O)[C@H]1N(C(=O)[C@@H](O)[C@H](Cc2ccccc2)NC(=O)c2cccc(O)c2C)CSC1(C)C

Standard InChI:  InChI=1S/C32H37N3O5S/c1-20-11-8-9-14-23(20)18-33-30(39)28-32(3,4)41-19-35(28)31(40)27(37)25(17-22-12-6-5-7-13-22)34-29(38)24-15-10-16-26(36)21(24)2/h5-16,25,27-28,36-37H,17-19H2,1-4H3,(H,33,39)(H,34,38)/t25-,27-,28+/m0/s1

Standard InChI Key:  CUFQBQOBLVLKRF-RZDMPUFOSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA300891

   (4r)-3-{(2s,3s)-2-Hydroxy-3-[(3-Hydroxy-2-Methylbenzoyl)amino]-4-Phenylbutanoyl}-5,5-Dimethyl-N-(2-Methylbenzyl)-1,3-Thiazolidine-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: 575.73

Molecular Weight (Monoisotopic): 575.2454

AlogP: 3.71

#Rotatable Bonds: 9

Polar Surface Area: 118.97

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.28

CX Basic pKa: ┄

CX LogP: 4.23

CX LogD: 4.22

Aromatic Rings: 3

Heavy Atoms: 41

QED Weighted: 0.31

Np Likeness Score: -0.05

References

1. Mimoto T, Kato R, Takaku H, Nojima S, Terashima K, Misawa S, Fukazawa T, Ueno T, Sato H, Shintani M, Kiso Y, Hayashi H..  (1999)  Structure-activity relationship of small-sized HIV protease inhibitors containing allophenylnorstatine.,  42  (10): [PMID:10346931] [10.1021/jm980637h]

2. Mimoto T, Nojima S, Terashima K, Takaku H, Shintani M, Hayashi H..  (2008)  Structure-activity relationships of novel HIV-1 protease inhibitors containing the 3-amino-2-chlorobenzoyl-allophenylnorstatine structure.,  16  (3): [PMID:17981045] [10.1016/j.bmc.2007.10.062]

3. Orrling KM, Marzahn MR, Gutiérrez-de-Terán H, Aqvist J, Dunn BM, Larhed M..  (2009)  alpha-Substituted norstatines as the transition-state mimic in inhibitors of multiple digestive vacuole malaria aspartic proteases.,  17  (16): [PMID:19635672] [10.1016/j.bmc.2009.06.065]

4. Hidaka K, Kimura T, Abdel-Rahman HM, Nguyen JT, McDaniel KF, Kohlbrenner WE, Molla A, Adachi M, Tamada T, Kuroki R, Katsuki N, Tanaka Y, Matsumoto H, Wang J, Hayashi Y, Kempf DJ, Kiso Y..  (2009)  Small-sized human immunodeficiency virus type-1 protease inhibitors containing allophenylnorstatine to explore the S2' pocket.,  52  (23): [PMID:19954246] [10.1021/jm9005115]

5. Hidaka K, Kimura T, Sankaranarayanan R, Wang J, McDaniel KF, Kempf DJ, Kameoka M, Adachi M, Kuroki R, Nguyen JT, Hayashi Y, Kiso Y..  (2018)  Identification of Highly Potent Human Immunodeficiency Virus Type-1 Protease Inhibitors against Lopinavir and Darunavir Resistant Viruses from Allophenylnorstatine-Based Peptidomimetics with P2 Tetrahydrofuranylglycine.,  61  (12): [PMID:29852069] [10.1021/acs.jmedchem.7b01709]

6. Kashif Khan R, Meanwell NA, Hager HH..  (2022)  Pseudoprolines as stereoelectronically tunable proline isosteres.,  75  [PMID:36096342] [10.1016/j.bmcl.2022.128983]

Source

Source(1):

• Scientific Literature