Isopropyl ((2S,4R)-1-acetyl-2-methyl-6-(thiophen-2-yl)-1,2,3,4-tetrahydroquinolin-4-yl)carbamate

ID: ALA4205876

PubChem CID: 135141500

Max Phase: Preclinical

Molecular Formula: C20H24N2O3S

Molecular Weight: 372.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N1c2ccc(-c3cccs3)cc2[C@H](NC(=O)OC(C)C)C[C@@H]1C

Standard InChI:  InChI=1S/C20H24N2O3S/c1-12(2)25-20(24)21-17-10-13(3)22(14(4)23)18-8-7-15(11-16(17)18)19-6-5-9-26-19/h5-9,11-13,17H,10H2,1-4H3,(H,21,24)/t13-,17+/m0/s1

Standard InChI Key:  CMAUHLPZEGZJFI-SUMWQHHRSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   11.6500  -13.1600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3591  -13.5686    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6500  -12.3428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9450  -13.5686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3591  -16.0201    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6500  -15.6115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6500  -14.7944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3591  -14.3858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0682  -14.7944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7731  -14.3858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4822  -14.7944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4822  -15.6115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7731  -16.0201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0682  -15.6115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1913  -14.3858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2753  -13.5712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0737  -13.4005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4823  -14.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9386  -14.7160    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.9450  -16.0201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3591  -16.8373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6500  -17.2459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0682  -17.2459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2359  -13.1600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5269  -13.5686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2359  -12.3428    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  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 15 19  1  0
 11 15  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:

   

   ALA4205876

   ---

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: 372.49

Molecular Weight (Monoisotopic): 372.1508

AlogP: 4.74

#Rotatable Bonds: 3

Polar Surface Area: 58.64

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.20

CX LogD: 3.20

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.85

Np Likeness Score: -0.98

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