benzyl(2S,3R)-4-(N-benzyl-2-diazoacetamido)-3-hydroxy-1-phenylbutan-2-ylcarbamate

ID: ALA2179952

PubChem CID: 86635877

Max Phase: Preclinical

Molecular Formula: C27H28N4O4

Molecular Weight: 472.55

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C27H28N4O4/c28-29-17-26(33)31(18-22-12-6-2-7-13-22)19-25(32)24(16-21-10-4-1-5-11-21)30-27(34)35-20-23-14-8-3-9-15-23/h1-15,17,24-25,32H,16,18-20H2,(H,30,34)/t24-,25+/m0/s1

Standard InChI Key:  YELDMMOUQWGLJX-LOSJGSFVSA-N

Molfile:  

     RDKit          2D

 35 37  0  0  0  0  0  0  0  0999 V2000
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    0.9015  -11.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6164  -12.2109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3328  -11.7975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3299  -10.9670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6146  -10.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0428  -10.5518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4686   -9.7214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.6166  -10.9509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6197  -11.7758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.0456  -10.9454    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7584  -10.5303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4745  -10.9401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7553   -9.7053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0486  -11.7704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7647  -12.1802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7627  -13.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4778  -13.4147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1917  -12.9995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1859  -12.1703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4702  -11.7642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1873  -10.5248    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8998  -10.1082    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
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 12 13  1  0
 13 14  1  1
 12 15  1  1
 15 16  1  0
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 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 13 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 23 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 28  1  0
 25 34  2  0
 34 35  2  0
M  CHG  2  34   1  35  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2179952

   (2R,3S)-3-Cbz amino-2-hydroxy-4-phenyl-1-(N-benzyl-2-diazo-ethanamido) butane

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: 472.55

Molecular Weight (Monoisotopic): 472.2111

AlogP: 3.21

#Rotatable Bonds: 11

Polar Surface Area: 115.27

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.87

CX Basic pKa: ┄

CX LogP: 2.53

CX LogD: 2.53

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.25

Np Likeness Score: -0.18

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]

Source

Source(1):

• Scientific Literature