6-((1S,2S)-1-(dimethylamino)-1-(4-(phenylsulfonyl)phenyl)propan-2-ylamino)-2,4-dimethyl-1,2,4-triazine-3,5(2H,4H)-dione

ID: ALA4088595

PubChem CID: 132153759

Max Phase: Preclinical

Molecular Formula: C22H27N5O4S

Molecular Weight: 457.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](Nc1nn(C)c(=O)n(C)c1=O)[C@H](c1ccc(S(=O)(=O)c2ccccc2)cc1)N(C)C

Standard InChI:  InChI=1S/C22H27N5O4S/c1-15(23-20-21(28)26(4)22(29)27(5)24-20)19(25(2)3)16-11-13-18(14-12-16)32(30,31)17-9-7-6-8-10-17/h6-15,19H,1-5H3,(H,23,24)/t15-,19+/m0/s1

Standard InChI Key:  LIBRBDZWCDLREN-HNAYVOBHSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
   15.8816  -22.0559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4771  -21.3502    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.0681  -22.0533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7338  -17.2789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7379  -16.4638    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0380  -16.0550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3295  -16.4568    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3254  -17.2718    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0298  -17.6852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0432  -15.2379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0269  -18.5023    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3177  -18.9084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3147  -19.7256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6115  -18.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6056  -20.1316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0210  -20.1367    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0180  -20.9539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7302  -19.7307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6244  -16.0437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9019  -19.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1932  -20.1255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1898  -20.9435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9010  -21.3545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6068  -20.9468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4405  -17.6893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4477  -16.0588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7744  -20.9403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7779  -20.1249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0720  -19.7148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3623  -20.1218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3631  -20.9432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0696  -21.3497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  1  0
  4  9  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  6 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  6
 13 15  1  1
 13 16  1  0
 16 17  1  0
 16 18  1  0
  7 19  1  0
 15 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 15  1  0
  4 25  2  0
  5 26  1  0
 22  2  1  0
  2 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4088595

   ---

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: 457.56

Molecular Weight (Monoisotopic): 457.1784

AlogP: 1.42

#Rotatable Bonds: 7

Polar Surface Area: 106.30

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.17

CX LogP: 2.19

CX LogD: 2.16

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.57

Np Likeness Score: -0.99

References

1. Humphreys PG, Bamborough P, Chung CW, Craggs PD, Gordon L, Grandi P, Hayhow TG, Hussain J, Jones KL, Lindon M, Michon AM, Renaux JF, Suckling CJ, Tough DF, Prinjha RK..  (2017)  Discovery of a Potent, Cell Penetrant, and Selective p300/CBP-Associated Factor (PCAF)/General Control Nonderepressible 5 (GCN5) Bromodomain Chemical Probe.,  60  (2): [PMID:28002667] [10.1021/acs.jmedchem.6b01566]

2. Moustakim M, Clark PGK, Hay DA, Dixon DJ, Brennan PE..  (2016)  Chemical probes and inhibitors of bromodomains outside the BET family.,  7  (12): [PMID:29170712] [10.1039/C6MD00373G]

3. Huang L, Li H, Li L, Niu L, Seupel R, Wu C, Cheng W, Chen C, Ding B, Brennan PE, Yang S..  (2019)  Discovery of Pyrrolo[3,2- d]pyrimidin-4-one Derivatives as a New Class of Potent and Cell-Active Inhibitors of P300/CBP-Associated Factor Bromodomain.,  62  (9): [PMID:30998845] [10.1021/acs.jmedchem.9b00096]

Source

Source(1):

• Scientific Literature