(2S,4R)-1-((S)-2-(1-cyanocyclopropanecarboxamido)-3,3-dimethylbutanoyl)-4-hydroxy-N-((S)-3-(methylamino)-1-(4-(4-methylthiazol-5-yl)phenyl)-3-oxopropyl)pyrrolidine-2-carboxamide

ID: ALA5277721

Max Phase: Preclinical

Molecular Formula: C30H38N6O5S

Molecular Weight: 594.74

Names and Identifiers

Canonical SMILES:  CNC(=O)C[C@H](NC(=O)[C@@H]1C[C@@H](O)CN1C(=O)[C@@H](NC(=O)C1(C#N)CC1)C(C)(C)C)c1ccc(-c2scnc2C)cc1

Standard InChI:  InChI=1S/C30H38N6O5S/c1-17-24(42-16-33-17)19-8-6-18(7-9-19)21(13-23(38)32-5)34-26(39)22-12-20(37)14-36(22)27(40)25(29(2,3)4)35-28(41)30(15-31)10-11-30/h6-9,16,20-22,25,37H,10-14H2,1-5H3,(H,32,38)(H,34,39)(H,35,41)/t20-,21+,22+,25-/m1/s1

Standard InChI Key:  TXOUIGUFBKWBLO-HXKBJWFLSA-N

Molfile:  

 
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M  END

Alternative Forms

1. Parent:

   

   ALA5277721

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 594.74

Molecular Weight (Monoisotopic): 594.2624

AlogP: 2.21

#Rotatable Bonds: 9

Polar Surface Area: 164.52

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.43

CX Basic pKa: 2.65

CX LogP: 0.45

CX LogD: 0.45

Aromatic Rings: 2

Heavy Atoms: 42

QED Weighted: 0.35

Np Likeness Score: -0.54

References

1. Han X, Wang C, Qin C, Xiang W, Fernandez-Salas E, Yang CY, Wang M, Zhao L, Xu T, Chinnaswamy K, Delproposto J, Stuckey J, Wang S..  (2019)  Discovery of ARD-69 as a Highly Potent Proteolysis Targeting Chimera (PROTAC) Degrader of Androgen Receptor (AR) for the Treatment of Prostate Cancer.,  62  (2): [PMID:30629437] [10.1021/acs.jmedchem.8b01631]

Source

Source(1):

• Scientific Literature