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

ID: ALA5285978

Max Phase: Preclinical

Molecular Formula: C27H37N5O5S

Molecular Weight: 543.69

Names and Identifiers

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

Standard InChI:  InChI=1S/C27H37N5O5S/c1-15-23(38-14-29-15)18-9-7-17(8-10-18)20(12-22(35)28-6)31-25(36)21-11-19(34)13-32(21)26(37)24(27(3,4)5)30-16(2)33/h7-10,14,19-21,24,34H,11-13H2,1-6H3,(H,28,35)(H,30,33)(H,31,36)/t19-,20+,21+,24-/m1/s1

Standard InChI Key:  DHJHMRSRAVXNPQ-MDAIXWLXSA-N

Molfile:  

 
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M  END

Alternative Forms

1. Parent:

   

   ALA5285978

   ---

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: 543.69

Molecular Weight (Monoisotopic): 543.2515

AlogP: 1.92

#Rotatable Bonds: 8

Polar Surface Area: 140.73

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.41

CX Basic pKa: 2.65

CX LogP: -0.14

CX LogD: -0.14

Aromatic Rings: 2

Heavy Atoms: 38

QED Weighted: 0.40

Np Likeness Score: -0.47

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