N-(tert-butoxycarbonyl)-phenylalanyl-propargylamide

ID: ALA200150

PubChem CID: 11673861

Max Phase: Preclinical

Molecular Formula: C17H22N2O3

Molecular Weight: 302.37

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/C17H22N2O3/c1-5-11-18-15(20)14(12-13-9-7-6-8-10-13)19-16(21)22-17(2,3)4/h1,6-10,14H,11-12H2,2-4H3,(H,18,20)(H,19,21)/t14-/m0/s1

Standard InChI Key:  GHEXEERTZYTTDD-AWEZNQCLSA-N

Molfile:  

     RDKit          2D

 22 22  0  0  1  0  0  0  0  0999 V2000
    8.2750   -6.8667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9895   -6.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7039   -6.8667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9895   -5.6292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4184   -6.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1329   -6.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8474   -6.4542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1329   -7.6917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5618   -6.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2750   -7.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4184   -5.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1329   -5.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8471   -5.6317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5611   -5.2199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5615   -4.3940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8421   -3.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1310   -4.3959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2708   -8.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1000   -7.6937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4500   -7.6896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2763   -6.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9875   -6.0375    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  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA200150

   tert-butyl N-[(1S)-2-phenyl-1-(prop-2-yn-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: 302.37

Molecular Weight (Monoisotopic): 302.1630

AlogP: 1.87

#Rotatable Bonds: 5

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: 12.93

CX Basic pKa: ┄

CX LogP: 2.21

CX LogD: 2.21

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.82

Np Likeness Score: -0.89

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