(R)-N-((R)-1-amino-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl)-1-((R)-2-((R)-4-methyl-2-(2,2,2-trifluoroacetamido)pentanamido)-4-(methylthio)butanoyl)pyrrolidine-2-carboxamide

ID: ALA2023560

Chembl Id: CHEMBL2023560

PubChem CID: 56963905

Max Phase: Preclinical

Molecular Formula: C24H36F3N7O5S

Molecular Weight: 591.66

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CSCC[C@@H](NC(=O)[C@@H](CC(C)C)NC(=O)C(F)(F)F)C(=O)N1CCC[C@@H]1C(=O)N[C@H](Cc1cnc[nH]1)C(N)=O

Standard InChI:  InChI=1S/C24H36F3N7O5S/c1-13(2)9-17(33-23(39)24(25,26)27)20(36)31-15(6-8-40-3)22(38)34-7-4-5-18(34)21(37)32-16(19(28)35)10-14-11-29-12-30-14/h11-13,15-18H,4-10H2,1-3H3,(H2,28,35)(H,29,30)(H,31,36)(H,32,37)(H,33,39)/t15-,16-,17-,18-/m1/s1

Standard InChI Key:  MEIDFYXKGOBTGS-BRSBDYLESA-N

Alternative Forms

1. Parent:

   

   ALA2023560

   Tfa-D-Leu-D-Met-D-Pro-D-His-NH2

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: 591.66

Molecular Weight (Monoisotopic): 591.2451

AlogP: 0.24

#Rotatable Bonds: 14

Polar Surface Area: 179.38

Molecular Species: NEUTRAL

HBA: 7

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 7.31

CX Basic pKa: 6.64

CX LogP: -0.92

CX LogD: -0.99

Aromatic Rings: 1

Heavy Atoms: 40

QED Weighted: 0.21

Np Likeness Score: -0.68

References

1. Sandomenico A, Russo A, Palmieri G, Bergamo P, Gogliettino M, Falcigno L, Ruvo M..  (2012)  Small peptide inhibitors of acetyl-peptide hydrolase having an uncommon mechanism of inhibition and a stable bent conformation.,  55  (5): [PMID:22309188] [10.1021/jm2013375]

Source

Source(1):

• Scientific Literature