isopropyl ((2S,4R)-1-acetyl-2-methyl-6-(1H-pyrrol-2-yl)-1,2,3,4-tetrahydroquinolin-4-yl)carbamate

ID: ALA4202664

PubChem CID: 135141503

Max Phase: Preclinical

Molecular Formula: C20H25N3O3

Molecular Weight: 355.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N1c2ccc(-c3ccc[nH]3)cc2[C@H](NC(=O)OC(C)C)C[C@@H]1C

Standard InChI:  InChI=1S/C20H25N3O3/c1-12(2)26-20(25)22-18-10-13(3)23(14(4)24)19-8-7-15(11-16(18)19)17-6-5-9-21-17/h5-9,11-13,18,21H,10H2,1-4H3,(H,22,25)/t13-,18+/m0/s1

Standard InChI Key:  FVBZXKOSEIRNSU-SCLBCKFNSA-N

Molfile:  

     RDKit          2D

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   11.0639  -11.6460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7730  -12.0546    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0639  -10.8288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3590  -12.0546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7730  -14.5062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0639  -14.0976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0639  -13.2804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7730  -12.8718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4821  -13.2804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1871  -12.8718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8962  -13.2804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8962  -14.0976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1871  -14.5062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4821  -14.0976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3525  -13.2021    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6053  -12.8718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6893  -12.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4877  -11.8865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8963  -12.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3590  -14.5062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7730  -15.3234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0639  -15.7320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4821  -15.7320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6499  -11.6460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9408  -12.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6499  -10.8288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  1  4  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
  5 14  1  0
  9 14  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 15 19  1  0
 11 16  1  0
  6 20  1  1
 21 22  2  0
 21 23  1  0
  5 21  1  0
  8  2  1  1
 24 25  1  0
 24 26  1  0
  4 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4202664

   ---

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: 355.44

Molecular Weight (Monoisotopic): 355.1896

AlogP: 4.00

#Rotatable Bonds: 3

Polar Surface Area: 74.43

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.42

CX LogD: 2.42

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.87

Np Likeness Score: -0.52

References

1. Shadrick WR, Slavish PJ, Chai SC, Waddell B, Connelly M, Low JA, Tallant C, Young BM, Bharatham N, Knapp S, Boyd VA, Morfouace M, Roussel MF, Chen T, Lee RE, Kiplin Guy R, Shelat AA, Potter PM..  (2018)  Exploiting a water network to achieve enthalpy-driven, bromodomain-selective BET inhibitors.,  26  (1): [PMID:29170024] [10.1016/j.bmc.2017.10.042]

Source

Source(1):

• Scientific Literature