(2S)-Isopropyl 6-Diazo-5-oxo-2-(((phenyl(pivaloyloxy)methoxy)carbonyl)amino)hexanoate

ID: ALA4085730

PubChem CID: 137033613

Max Phase: Preclinical

Molecular Formula: C22H29N3O7

Molecular Weight: 447.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)OC(=O)[C@H](CCC(=O)C=[N+]=[N-])NC(=O)OC(OC(=O)C(C)(C)C)c1ccccc1

Standard InChI:  InChI=1S/C22H29N3O7/c1-14(2)30-18(27)17(12-11-16(26)13-24-23)25-21(29)32-19(15-9-7-6-8-10-15)31-20(28)22(3,4)5/h6-10,13-14,17,19H,11-12H2,1-5H3,(H,25,29)/t17-,19?/m0/s1

Standard InChI Key:  QQIBFRQTTLIECS-KKFHFHRHSA-N

Molfile:  

     RDKit          2D

 32 32  0  0  0  0  0  0  0  0999 V2000
   11.0167   -7.6501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7312   -7.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4457   -7.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1601   -7.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4457   -8.4751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7312   -6.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4457   -6.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4457   -5.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1601   -4.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7312   -4.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8746   -5.1750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5792   -5.5861    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3023   -7.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5878   -7.6501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3023   -6.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8733   -7.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1589   -7.6501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4444   -7.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7298   -7.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4444   -6.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0154   -7.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7298   -8.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0125   -8.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8746   -7.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5891   -7.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8746   -8.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8733   -6.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5913   -6.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5916   -5.1798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8767   -4.7664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1598   -5.1834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1630   -6.0063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  2  6  1  1
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  9 11  2  0
 11 12  2  0
  1 13  1  0
 13 14  1  0
 13 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 19 21  1  0
 19 22  1  0
 19 23  1  0
  4 24  1  0
 24 25  1  0
 24 26  1  0
 16 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
M  CHG  2  11   1  12  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4085730

   ---

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: 447.49

Molecular Weight (Monoisotopic): 447.2006

AlogP: 2.97

#Rotatable Bonds: 10

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: 2.94

CX LogD: 2.93

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.19

Np Likeness Score: 0.03

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