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

ID: ALA200521

PubChem CID: 11702249

Max Phase: Preclinical

Molecular Formula: C16H22N2O4

Molecular Weight: 306.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)C(=O)NCC=O

Standard InChI:  InChI=1S/C16H22N2O4/c1-16(2,3)22-15(21)18-13(14(20)17-9-10-19)11-12-7-5-4-6-8-12/h4-8,10,13H,9,11H2,1-3H3,(H,17,20)(H,18,21)/t13-/m0/s1

Standard InChI Key:  WFIHUJGSDBPSIV-ZDUSSCGKSA-N

Molfile:  

     RDKit          2D

 22 22  0  0  1  0  0  0  0  0999 V2000
    7.7375    0.7833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4520    1.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1664    0.7833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4520    2.0208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8809    1.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5954    0.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3099    1.1958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5954   -0.0417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0243    0.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7375   -0.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8809    2.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5954    2.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3096    2.0183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0236    2.4301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0240    3.2560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3046    3.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5935    3.2541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7333   -0.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5625   -0.0438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9125   -0.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0243   -0.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7388   -0.4542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  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
M  END

Alternative Forms

1. Parent:

   

   ALA200521

   tert-butyl N-[(1S)-1-[(2-oxoethyl)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: 306.36

Molecular Weight (Monoisotopic): 306.1580

AlogP: 1.44

#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: 13.07

CX Basic pKa: ┄

CX LogP: 1.31

CX LogD: 1.31

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.78

Np Likeness Score: -0.40

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