N-(tert-butoxycarbonyl)-phenylalanyl-allylamide

ID: ALA197975

PubChem CID: 14308232

Max Phase: Preclinical

Molecular Formula: C17H24N2O3

Molecular Weight: 304.39

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H24N2O3/c1-5-11-18-15(20)14(12-13-9-7-6-8-10-13)19-16(21)22-17(2,3)4/h5-10,14H,1,11-12H2,2-4H3,(H,18,20)(H,19,21)/t14-/m0/s1

Standard InChI Key:  CGOKANXAZNFJJW-AWEZNQCLSA-N

Molfile:  

     RDKit          2D

 22 22  0  0  1  0  0  0  0  0999 V2000
   -4.5583  -14.1708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8439  -13.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1294  -14.1708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8439  -12.9333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4149  -13.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7004  -14.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9860  -13.7583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7004  -14.9958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2715  -14.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5583  -14.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4149  -12.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7004  -12.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9862  -12.9359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2722  -12.5241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2718  -11.6982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9913  -11.2859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7023  -11.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5625  -15.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7333  -14.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3833  -14.9937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4430  -13.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1574  -14.1708    0.0000 C   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:

   

   ALA197975

   tert-butyl N-[(1S)-2-phenyl-1-(prop-2-en-1-ylcarbamoyl)ethyl]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: 304.39

Molecular Weight (Monoisotopic): 304.1787

AlogP: 2.42

#Rotatable Bonds: 6

Polar Surface Area: 67.43

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.77

CX Basic pKa: ┄

CX LogP: 2.72

CX LogD: 2.72

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.79

Np Likeness Score: -0.69

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