(S)-Isopropyl 6-Diazo-5-oxo-2-((((2-(pivaloyloxy)propan-2-yl)-oxy)carbonyl)amino)hexanoate

ID: ALA4071629

PubChem CID: 137033605

Max Phase: Preclinical

Molecular Formula: C18H29N3O7

Molecular Weight: 399.44

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H29N3O7/c1-11(2)26-14(23)13(9-8-12(22)10-20-19)21-16(25)28-18(6,7)27-15(24)17(3,4)5/h10-11,13H,8-9H2,1-7H3,(H,21,25)/t13-/m0/s1

Standard InChI Key:  WDCPKJRGPUFUJJ-ZDUSSCGKSA-N

Molfile:  

     RDKit          2D

 28 27  0  0  0  0  0  0  0  0999 V2000
    8.4209   -6.8584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8376   -7.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2499   -6.8558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9834   -7.9917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6979   -7.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4124   -7.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1268   -7.5792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4124   -8.8167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6979   -6.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4124   -6.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4124   -5.5168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1268   -5.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6979   -5.1042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8413   -5.5168    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5459   -5.9278    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2690   -7.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5545   -7.9917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2690   -6.7542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1255   -7.9917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4110   -7.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6965   -7.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4110   -6.7542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9821   -7.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6965   -8.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9792   -8.3959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8413   -7.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5558   -7.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8413   -8.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  5  9  1  1
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 12 14  2  0
 14 15  2  0
  4 16  1  0
 16 17  1  0
 16 18  2  0
 17  2  1  0
  2 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 21 23  1  0
 21 24  1  0
 21 25  1  0
  7 26  1  0
 26 27  1  0
 26 28  1  0
M  CHG  2  14   1  15  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4071629

   ---

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: 399.44

Molecular Weight (Monoisotopic): 399.2006

AlogP: 2.01

#Rotatable Bonds: 9

Polar Surface Area: 144.40

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.99

CX Basic pKa: ┄

CX LogP: 1.47

CX LogD: 1.47

Aromatic Rings: ┄

Heavy Atoms: 28

QED Weighted: 0.21

Np Likeness Score: 0.02

References

1. Nedelcovych MT, Tenora L, Kim BH, Kelschenbach J, Chao W, Hadas E, Jančařík A, Prchalová E, Zimmermann SC, Dash RP, Gadiano AJ, Garrett C, Furtmüller G, Oh B, Brandacher G, Alt J, Majer P, Volsky DJ, Rais R, Slusher BS..  (2017)  N-(Pivaloyloxy)alkoxy-carbonyl Prodrugs of the Glutamine Antagonist 6-Diazo-5-oxo-l-norleucine (DON) as a Potential Treatment for HIV Associated Neurocognitive Disorders.,  60  (16): [PMID:28759224] [10.1021/acs.jmedchem.7b00966]

Source

Source(1):

• Scientific Literature