ID: ALA3590405

Max Phase: Preclinical

Molecular Formula: C27H34N4O4S

Molecular Weight: 510.66

Molecule Type: Small molecule

Representations

Canonical SMILES:  Cc1cncc(-c2ccc(N[C@@H]3CCNC[C@H]3OCC3CCS(=O)(=O)CC3)c3[nH]c(=O)c(C)cc23)c1

Standard InChI:  InChI=1S/C27H34N4O4S/c1-17-11-20(14-29-13-17)21-3-4-24(26-22(21)12-18(2)27(32)31-26)30-23-5-8-28-15-25(23)35-16-19-6-9-36(33,34)10-7-19/h3-4,11-14,19,23,25,28,30H,5-10,15-16H2,1-2H3,(H,31,32)/t23-,25-/m1/s1

Standard InChI Key:  KXXIBIBXJMYWNL-ILBGXUMGSA-N

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

Properties

Molecular Weight: 510.66

Molecular Weight (Monoisotopic): 510.2301

AlogP: 3.19

#Rotatable Bonds: 6

Polar Surface Area: 113.18

Molecular Species: BASE

HBA: 7

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.37

CX Basic pKa: 9.07

CX LogP: 1.31

CX LogD: -0.36

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.47

Np Likeness Score: -0.67

References

1. Bamborough P, Chung CW, Furze RC, Grandi P, Michon AM, Sheppard RJ, Barnett H, Diallo H, Dixon DP, Douault C, Jones EJ, Karamshi B, Mitchell DJ, Prinjha RK, Rau C, Watson RJ, Werner T, Demont EH..  (2015)  Structure-Based Optimization of Naphthyridones into Potent ATAD2 Bromodomain Inhibitors.,  58  (15): [PMID:26230603] [10.1021/acs.jmedchem.5b00773]

2. Bamborough P, Chung CW, Furze RC, Grandi P, Michon AM, Sheppard RJ, Barnett H, Diallo H, Dixon DP, Douault C, Jones EJ, Karamshi B, Mitchell DJ, Prinjha RK, Rau C, Watson RJ, Werner T, Demont EH..  (2015)  Structure-Based Optimization of Naphthyridones into Potent ATAD2 Bromodomain Inhibitors.,  58  (15): [PMID:26230603] [10.1021/acs.jmedchem.5b00773]

3. Bamborough P, Chung CW, Furze RC, Grandi P, Michon AM, Watson RJ, Mitchell DJ, Barnett H, Prinjha RK, Rau C, Sheppard RJ, Werner T, Demont EH..  (2018)  Aiming to Miss a Moving Target: Bromo and Extra Terminal Domain (BET) Selectivity in Constrained ATAD2 Inhibitors.,  61  (18): [PMID:30226378] [10.1021/acs.jmedchem.8b00862]

4. Lloyd JT,McLaughlin K,Lubula MY,Gay JC,Dest A,Gao C,Phillips M,Tonelli M,Cornilescu G,Marunde MR,Evans CM,Boyson SP,Carlson S,Keogh MC,Markley JL,Frietze S,Glass KC.  (2020)  Structural Insights into the Recognition of Mono- and Diacetylated Histones by the ATAD2B Bromodomain.,  63  (21.0): [PMID:33084328] [10.1021/acs.jmedchem.0c01178]

Source

Source(1):

• Scientific Literature