N-(tert-butoxycarbonyl)-phenylalanyl-glycine-methylketone

ID: ALA200181

PubChem CID: 11551502

Max Phase: Preclinical

Molecular Formula: C17H24N2O4

Molecular Weight: 320.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)CNC(=O)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C

Standard InChI:  InChI=1S/C17H24N2O4/c1-12(20)11-18-15(21)14(10-13-8-6-5-7-9-13)19-16(22)23-17(2,3)4/h5-9,14H,10-11H2,1-4H3,(H,18,21)(H,19,22)/t14-/m0/s1

Standard InChI Key:  PFTNGMXDAPTVQN-AWEZNQCLSA-N

Molfile:  

     RDKit          2D

 23 23  0  0  1  0  0  0  0  0999 V2000
   -4.0333   -7.2417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3189   -6.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6044   -7.2417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3189   -6.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8899   -6.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1754   -7.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4610   -6.8292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1754   -8.0667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2535   -7.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0333   -8.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8899   -6.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1754   -5.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4612   -6.0067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2528   -5.5949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2532   -4.7690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4663   -4.3567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1773   -4.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0375   -8.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2083   -8.0687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8583   -8.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2535   -8.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4610   -8.4792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9680   -8.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0
  1  2  1  0
 12 13  2  0
  6  7  1  0
 13 14  1  0
  2  4  2  0
 14 15  2  0
  6  8  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  7  9  1  0
 10 18  1  0
  3  5  1  0
 10 19  1  0
  1 10  1  0
 10 20  1  0
  2  3  1  0
  9 21  1  0
  5 11  1  1
 21 22  2  0
  5  6  1  0
 21 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA200181

   tert-butyl N-[(1S)-1-[(2-oxopropyl)carbamoyl]-2-phenylethyl]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: 320.39

Molecular Weight (Monoisotopic): 320.1736

AlogP: 1.83

#Rotatable Bonds: 6

Polar Surface Area: 84.50

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.06

CX Basic pKa: ┄

CX LogP: 1.79

CX LogD: 1.79

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.84

Np Likeness Score: -0.49

References

1. Löser R, Schilling K, Dimmig E, Gütschow M..  (2005)  Interaction of papain-like cysteine proteases with dipeptide-derived nitriles.,  48  (24): [PMID:16302809] [10.1021/jm050686b]

Source

Source(1):

• Scientific Literature