[(S)-1-((S)-1-Benzylcarbamoyl-ethylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester

ID: ALA312437

PubChem CID: 44318086

Max Phase: Preclinical

Molecular Formula: C18H27N3O4

Molecular Weight: 349.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@@H](C)C(=O)NCc1ccccc1

Standard InChI:  InChI=1S/C18H27N3O4/c1-12(15(22)19-11-14-9-7-6-8-10-14)20-16(23)13(2)21-17(24)25-18(3,4)5/h6-10,12-13H,11H2,1-5H3,(H,19,22)(H,20,23)(H,21,24)/t12-,13-/m0/s1

Standard InChI Key:  SSUGNUAZQHRGDK-STQMWFEESA-N

Molfile:  

     RDKit          2D

 25 25  0  0  1  0  0  0  0  0999 V2000
   -1.9458   -1.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2292   -1.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9042   -1.4500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3167   -1.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1875   -2.0792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0792   -1.6375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5208   -1.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6542   -1.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6125   -2.2292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0333   -0.9250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3167   -2.7542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2375   -0.4792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3625   -1.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7417   -1.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5000   -1.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6083   -0.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7417   -2.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0333   -2.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4500   -1.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0708   -2.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5792   -2.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1542   -1.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9125   -1.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3292   -2.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0042   -2.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  7  1  0
  3  2  1  0
  4  8  1  0
  5  1  1  0
  6  4  1  0
  7  5  1  0
  8  3  1  0
  9  1  1  0
 10  1  2  0
 11  2  2  0
 12  4  2  0
 13  9  1  0
 14  6  1  0
 15 14  1  0
  7 16  1  1
  8 17  1  6
 18 13  1  0
 19 13  1  0
 20 13  1  0
 21 15  2  0
 22 15  1  0
 23 22  2  0
 24 21  1  0
 25 23  1  0
 24 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA312437

   tert-butyl N-[(2S)-1-[[(2S)-1-(benzylamino)-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]carbamate

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: 349.43

Molecular Weight (Monoisotopic): 349.2002

AlogP: 1.72

#Rotatable Bonds: 6

Polar Surface Area: 96.53

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.61

CX Basic pKa: ┄

CX LogP: 1.52

CX LogD: 1.52

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.73

Np Likeness Score: -0.90

References

1. Shuttleworth SJ, Nasturica D, Gervais C, Siddiqui MA, Rando RF, Lee N..  (2000)  Parallel synthesis of isatin-based serine protease inhibitors.,  10  (22): [PMID:11086715] [10.1016/s0960-894x(00)00523-0]

Source

Source(1):

• Scientific Literature