(S)-N7-methyl-N5-((1S,2S)-2-methylcyclopropyl)-3-phenyl-2,3-dihydrobenzofuran-5,7-dicarboxamide

ID: ALA4878167

PubChem CID: 155119558

Max Phase: Preclinical

Molecular Formula: C21H22N2O3

Molecular Weight: 350.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CNC(=O)c1cc(C(=O)N[C@H]2C[C@@H]2C)cc2c1OC[C@H]2c1ccccc1

Standard InChI:  InChI=1S/C21H22N2O3/c1-12-8-18(12)23-20(24)14-9-15-17(13-6-4-3-5-7-13)11-26-19(15)16(10-14)21(25)22-2/h3-7,9-10,12,17-18H,8,11H2,1-2H3,(H,22,25)(H,23,24)/t12-,17-,18-/m0/s1

Standard InChI Key:  SIPDBILHILZUAG-IGNZVWTISA-N

Molfile:  

 
     RDKit          2D

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   14.5636  -20.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5606  -19.7734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8452  -19.3642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8428  -18.5391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5561  -18.1244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1270  -18.1288    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1245  -17.3037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2787  -21.0154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2800  -21.8405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9926  -20.6017    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1322  -20.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1334  -19.7801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3497  -19.5241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8640  -20.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3477  -20.8580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0915  -21.6423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2854  -21.8110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0291  -22.5945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5806  -23.2094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3916  -23.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6440  -22.2523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7078  -21.0132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1229  -21.7239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5344  -21.0086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1257  -22.5489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0
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  4 13  1  0
  4  5  1  0
  5  6  2  0
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 21 22  2  0
 22 17  1  0
 23 11  1  1
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 23 25  1  0
 24 26  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4878167

   ---

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: 350.42

Molecular Weight (Monoisotopic): 350.1630

AlogP: 2.71

#Rotatable Bonds: 4

Polar Surface Area: 67.43

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.41

CX Basic pKa: ┄

CX LogP: 2.33

CX LogD: 2.33

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.89

Np Likeness Score: 0.10

References

1. Lucas SCC, Atkinson SJ, Chung CW, Davis R, Gordon L, Grandi P, Gray JJR, Grimes T, Phillipou A, Preston AG, Prinjha RK, Rioja I, Taylor S, Tomkinson NCO, Wall I, Watson RJ, Woolven J, Demont EH..  (2021)  Optimization of a Series of 2,3-Dihydrobenzofurans as Highly Potent, Second Bromodomain (BD2)-Selective, Bromo and Extra-Terminal Domain (BET) Inhibitors.,  64  (15.0): [PMID:34260229] [10.1021/acs.jmedchem.1c00344]

Source

Source(1):

• Scientific Literature