5-(8-Oxo-5-(6-(piperidin-4-yloxy)pyridin-3-yl)-6-thioxo-5,7-diazaspiro[3.4]octan-7-yl)-3-(trifluoromethyl)-picolinonitrile

ID: ALA4858811

Chembl Id: CHEMBL4858811

PubChem CID: 130229812

Max Phase: Phase

Molecular Formula: C23H21F3N6O2S

Molecular Weight: 502.52

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Trc 253 | Trc-253 | TRC253

Canonical SMILES:  N#Cc1ncc(N2C(=O)C3(CCC3)N(c3ccc(OC4CCNCC4)nc3)C2=S)cc1C(F)(F)F

Standard InChI:  InChI=1S/C23H21F3N6O2S/c24-23(25,26)17-10-15(13-29-18(17)11-27)31-20(33)22(6-1-7-22)32(21(31)35)14-2-3-19(30-12-14)34-16-4-8-28-9-5-16/h2-3,10,12-13,16,28H,1,4-9H2

Standard InChI Key:  OUEHJEYKNYQVRC-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA4858811

   TRC-253

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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 502.52

Molecular Weight (Monoisotopic): 502.1399

AlogP: 3.56

#Rotatable Bonds: 4

Polar Surface Area: 94.38

Molecular Species: BASE

HBA: 7

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa:

CX Basic pKa: 9.82

CX LogP: 3.11

CX LogD: 0.74

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.63

Np Likeness Score: -0.88

References

1. Zhang Z, Connolly PJ, Lim HK, Pande V, Meerpoel L, Teleha C, Branch JR, Ondrus J, Hickson I, Bush T, Luistro L, Packman K, Bischoff JR, Ibrahim S, Parrett C, Chong Y, Gottardis MM, Bignan G..  (2021)  Discovery of JNJ-63576253: A Clinical Stage Androgen Receptor Antagonist for F877L Mutant and Wild-Type Castration-Resistant Prostate Cancer (mCRPC).,  64  (2.0): [PMID:33470111] [10.1021/acs.jmedchem.0c01563]

2. Unpublished dataset, 

3. Xiang W, Wang S..  (2022)  Therapeutic Strategies to Target the Androgen Receptor.,  65  (13.0): [PMID:35786895] [10.1021/acs.jmedchem.2c00716]

Source

Source(2):

• Scientific Literature
• Clinical Candidates