benzyl(S)-1-((S)-4-diazo-3-oxobutan-2-ylamino)-1-oxo-3-phenylpropan-2-ylcarbamate

ID: ALA2179950

Cas Number: 71732-53-1

PubChem CID: 155664

Max Phase: Preclinical

Molecular Formula: C21H22N4O4

Molecular Weight: 394.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)OCc1ccccc1)C(=O)C=[N+]=[N-]

Standard InChI:  InChI=1S/C21H22N4O4/c1-15(19(26)13-23-22)24-20(27)18(12-16-8-4-2-5-9-16)25-21(28)29-14-17-10-6-3-7-11-17/h2-11,13,15,18H,12,14H2,1H3,(H,24,27)(H,25,28)/t15-,18-/m0/s1

Standard InChI Key:  QMPATRQNERZOMF-YJBOKZPZSA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
    1.2902   -3.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2891   -4.5980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0038   -5.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7203   -4.5976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7175   -3.7671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0020   -3.3579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4303   -3.3519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1464   -3.7617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8592   -3.3465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5753   -3.7563    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8561   -2.5215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2881   -3.3412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0042   -3.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7170   -3.3357    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0073   -4.5759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4331   -3.7456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1459   -3.3304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8620   -3.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1429   -2.5054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2851   -2.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9979   -2.1009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7116   -2.5152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4239   -2.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4213   -1.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7002   -0.8652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9907   -1.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4362   -4.5706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5749   -3.3250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2873   -2.9083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 12 10  1  1
 12 13  1  0
 13 14  1  0
 13 15  2  0
 16 14  1  6
 16 17  1  0
 17 18  1  0
 17 19  2  0
 12 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 16 27  1  0
 18 28  2  0
 28 29  2  0
M  CHG  2  28   1  29  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2179950

   Z-Phe-Ala-Diazomethylketone

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: 394.43

Molecular Weight (Monoisotopic): 394.1641

AlogP: 1.90

#Rotatable Bonds: 9

Polar Surface Area: 120.90

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.97

CX Basic pKa: ┄

CX LogP: 1.61

CX LogD: 1.61

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.38

Np Likeness Score: -0.05

References

1. Viswanathan K, Hoover DJ, Hwang J, Wisniewski ML, Ikonne US, Bahr BA, Wright DL..  (2012)  Nonpeptidic lysosomal modulators derived from z-phe-ala-diazomethylketone for treating protein accumulation diseases.,  3  (11): [PMID:24900408] [10.1021/ml300197h]

2. Ettari R, Tamborini L, Angelo IC, Micale N, Pinto A, De Micheli C, Conti P..  (2013)  Inhibition of rhodesain as a novel therapeutic modality for human African trypanosomiasis.,  56  (14): [PMID:23611656] [10.1021/jm301424d]

Source

Source(1):

• Scientific Literature