(1R,5S)-3-Methyl-11-(6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridine-4-carbonyl)-2,3,5,6-tetrahydro-1,5-epiminobenzo[d]azocin-4(1H)-one

ID: ALA5090538

PubChem CID: 166631754

Max Phase: Preclinical

Molecular Formula: C21H20N4O3

Molecular Weight: 376.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN1C[C@H]2c3ccccc3C[C@@H](C1=O)N2C(=O)c1cn(C)c(=O)c2[nH]ccc12

Standard InChI:  InChI=1S/C21H20N4O3/c1-23-10-15(14-7-8-22-18(14)21(23)28)19(26)25-16-9-12-5-3-4-6-13(12)17(25)11-24(2)20(16)27/h3-8,10,16-17,22H,9,11H2,1-2H3/t16-,17-/m0/s1

Standard InChI Key:  MBYZHHIVMFYGJA-IRXDYDNUSA-N

Molfile:  

 
     RDKit          2D

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   -1.3901    1.8081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6783    0.5712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3883    0.1594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1046    0.5676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976   -0.0091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7270   -0.0091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3076    0.5712    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3076    1.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7270    1.9768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0977    1.9768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4700    1.0268    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9800    0.0839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8048    0.0610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5676   -0.6301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9406    2.7736    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0222    1.8088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8121   -0.4216    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1046    0.3577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9801   -1.3447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5676   -2.0592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2573   -2.0592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6699   -1.3446    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2571   -0.6301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8015   -1.5300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8823   -2.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1225   -2.6635    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4948   -1.3446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6699   -2.7736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  3  2  1  0
  4  3  2  0
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  1  6  1  0
  6  5  2  0
  4  7  1  0
  7  8  1  0
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  9 10  1  0
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  3 12  1  0
 11 12  1  0
 11 13  1  0
  7 13  1  0
 13 14  1  0
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 14 16  1  0
 11 17  1  6
 10 18  2  0
  7 19  1  6
  9 20  1  0
 21 16  1  0
 22 21  2  0
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 24 23  1  0
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 16 25  2  0
 21 26  1  0
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 28 27  1  0
 22 28  1  0
 24 29  1  0
 23 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5090538

   ---

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: 376.42

Molecular Weight (Monoisotopic): 376.1535

AlogP: 1.45

#Rotatable Bonds: 1

Polar Surface Area: 78.41

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.72

CX Basic pKa: ┄

CX LogP: 0.66

CX LogD: 0.66

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.70

Np Likeness Score: -0.27

References

1. Winter-Holt JJ, Bardelle C, Chiarparin E, Dale IL, Davey PRJ, Davies NL, Denz C, Fillery SM, Guérot CM, Han F, Hughes SJ, Kulkarni M, Liu Z, Milbradt A, Moss TA, Niu H, Patel J, Rabow AA, Schimpl M, Shi J, Sun D, Yang D, Guichard S..  (2022)  Discovery of a Potent and Selective ATAD2 Bromodomain Inhibitor with Antiproliferative Activity in Breast Cancer Models.,  65  (4.0): [PMID:35133824] [10.1021/acs.jmedchem.1c01871]

Source

Source(1):

• Scientific Literature