3-(6-But-2-enyl-7-oxo-1H-pyrrolo[2,3-c]pyridin-4-yl)-N,N-dimethyl-benzamide

ID: ALA4519632

PubChem CID: 121335190

Max Phase: Preclinical

Molecular Formula: C20H21N3O2

Molecular Weight: 335.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C/C=C/Cn1cc(-c2cccc(C(=O)N(C)C)c2)c2cc[nH]c2c1=O

Standard InChI:  InChI=1S/C20H21N3O2/c1-4-5-11-23-13-17(16-9-10-21-18(16)20(23)25)14-7-6-8-15(12-14)19(24)22(2)3/h4-10,12-13,21H,11H2,1-3H3/b5-4+

Standard InChI Key:  RJEMCUZKQLRUIS-SNAWJCMRSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   11.8699   -2.9964    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8699   -3.8136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5752   -4.2180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5752   -2.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2805   -2.9964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2804   -3.8146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0586   -4.0675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5396   -3.4055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0586   -2.7436    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1610   -2.5898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5752   -1.7665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5745   -5.0348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8650   -5.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8642   -6.2588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5722   -6.6686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2825   -6.2560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2798   -5.4409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1561   -6.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4488   -6.2574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1553   -7.4839    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4471   -7.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8625   -7.8932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4545   -3.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7456   -2.5940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0391   -3.0047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  2  0
  3  6  1  0
  5  4  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
  1 10  1  0
  4 11  2  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  3 12  1  0
 14 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 10 23  1  0
 23 24  2  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4519632

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 335.41

Molecular Weight (Monoisotopic): 335.1634

AlogP: 3.27

#Rotatable Bonds: 4

Polar Surface Area: 58.10

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.62

CX Basic pKa: ┄

CX LogP: 2.40

CX LogD: 2.40

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.74

Np Likeness Score: -0.77

References

1. Crawford TD, Tsui V, Flynn EM, Wang S, Taylor AM, Côté A, Audia JE, Beresini MH, Burdick DJ, Cummings R, Dakin LA, Duplessis M, Good AC, Hewitt MC, Huang HR, Jayaram H, Kiefer JR, Jiang Y, Murray J, Nasveschuk CG, Pardo E, Poy F, Romero FA, Tang Y, Wang J, Xu Z, Zawadzke LE, Zhu X, Albrecht BK, Magnuson SR, Bellon S, Cochran AG..  (2016)  Diving into the Water: Inducible Binding Conformations for BRD4, TAF1(2), BRD9, and CECR2 Bromodomains.,  59  (11): [PMID:27219867] [10.1021/acs.jmedchem.6b00264]

2. Crawford TD, Vartanian S, Côté A, Bellon S, Duplessis M, Flynn EM, Hewitt M, Huang HR, Kiefer JR, Murray J, Nasveschuk CG, Pardo E, Romero FA, Sandy P, Tang Y, Taylor AM, Tsui V, Wang J, Wang S, Zawadzke L, Albrecht BK, Magnuson SR, Cochran AG, Stokoe D..  (2017)  Inhibition of bromodomain-containing protein 9 for the prevention of epigenetically-defined drug resistance.,  27  (15): [PMID:28606761] [10.1016/j.bmcl.2017.05.063]

Source

Source(1):

• Scientific Literature