(2-Methyl-1-{(S)-oxo-[(S)-2-((S)-3,3,3-trifluoro-1-isopropyl-2-oxo-propylcarbamoyl)-pyrrolidin-1-yl]-methyl}-propyl)-carbamic acid methyl ester

ID: ALA79463

Chembl Id: CHEMBL79463

Cas Number: 182073-77-4

PubChem CID: 9910174

Max Phase: Preclinical

Molecular Formula: C18H28F3N3O5

Molecular Weight: 423.43

Molecule Type: Protein

Names and Identifiers

Synonyms: ZD-8321 | 182073-77-4|ZD8321|ZD-8321|T7FIA2S66D|N-(Methoxycarbonyl)-L-valyl-N-((1S)-3,3,3-trifluoro-1-(1-methylethyl)-2-oxopropyl)-L-prolinamide|UNII-T7FIA2S66D|CHEMBL79463|ZD 8321|L-Prolinamide, N-(methoxycarbonyl)-L-valyl-N-((1S)-3,3,3-trifluoro-1-(1-methylethyl)-2-oxopropyl)-|1-(2-methoxycarbonyl-3-methylbutyryl)-N-(2-methyl-1-(trifluoroacetyl)propyl)pyrrolidine-2-carboxamide|methyl ((S)-3-methyl-1-oxo-1-((S)-2-(((S)-1,1,1-trifluoro-4-methyl-2-oxopentan-3-yl)carbamoyl)pyrrolidin-1-yl)butan-2-Show More⌵

Canonical SMILES:  COC(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)C(F)(F)F)C(C)C)C(C)C

Standard InChI:  InChI=1S/C18H28F3N3O5/c1-9(2)12(14(25)18(19,20)21)22-15(26)11-7-6-8-24(11)16(27)13(10(3)4)23-17(28)29-5/h9-13H,6-8H2,1-5H3,(H,22,26)(H,23,28)/t11-,12-,13-/m0/s1

Standard InChI Key:  ZYLBZJKJNAYAFU-AVGNSLFASA-N

Alternative Forms

1. Parent:

   

   ALA79463

   N-(Methoxycarbonyl)-L-valyl-N-((1S)-3,3,3-trifluoro-1-(1-methylethyl)-2-oxopropyl)-L-prolinamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Protein

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 423.43

Molecular Weight (Monoisotopic): 423.1981

AlogP: 1.63

#Rotatable Bonds: 7

Polar Surface Area: 104.81

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.00

CX Basic pKa: ┄

CX LogP: 2.30

CX LogD: 2.30

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.65

Np Likeness Score: -0.60

References

1. Macdonald SJ, Dowle MD, Harrison LA, Spooner JE, Shah P, Johnson MR, Inglis GG, Clarke GD, Belton DJ, Smith RA, Molloy CR, Dixon M, Murkitt G, Godward RE, Skarzynski T, Singh OM, Kumar KA, Hodgson ST, McDonald E, Hardy GW, Finch H, Humphreys DC, Fleetwood G..  (2001)  Intracellular inhibition of human neutrophil elastase by orally active pyrrolidine-trans-lactams.,  11  (2): [PMID:11206469] [10.1016/s0960-894x(00)00632-6]

2. Veale CA, Bernstein PR, Bohnert CM, Brown FJ, Bryant C, Damewood JR, Earley R, Feeney SW, Edwards PD, Gomes B, Hulsizer JM, Kosmider BJ, Krell RD, Moore G, Salcedo TW, Shaw A, Silberstein DS, Steelman GB, Stein M, Strimpler A, Thomas RM, Vacek EP, Williams JC, Wolanin DJ, Woolson S..  (1997)  Orally active trifluoromethyl ketone inhibitors of human leukocyte elastase.,  40  (20): [PMID:9379436] [10.1021/jm970250z]

3. Leung D, Abbenante G, Fairlie DP..  (2000)  Protease inhibitors: current status and future prospects.,  43  (3): [PMID:10669559] [10.1021/jm990412m]

4. Plescia J, Moitessier N..  (2020)  Design and discovery of boronic acid drugs.,  195  [PMID:32302879] [10.1016/j.ejmech.2020.112270]

Source

Source(1):

• Scientific Literature