(2S,3S)-2-[[(1S)-1-[3-[(1R)-1-amino-2-hydroxy-ethyl]-1,2,4-oxadiazol-5-yl]-4-oxo-4-(propylamino)butyl]carbamoylamino]-3-hydroxy-butanoic acid

ID: ALA5287411

Max Phase: Preclinical

Molecular Formula: C16H28N6O7

Molecular Weight: 416.44

Names and Identifiers

Canonical SMILES:  CCCNC(=O)CC[C@H](NC(=O)N[C@H](C(=O)O)[C@H](C)O)c1nc([C@@H](N)CO)no1

Standard InChI:  InChI=1S/C16H28N6O7/c1-3-6-18-11(25)5-4-10(14-21-13(22-29-14)9(17)7-23)19-16(28)20-12(8(2)24)15(26)27/h8-10,12,23-24H,3-7,17H2,1-2H3,(H,18,25)(H,26,27)(H2,19,20,28)/t8-,9-,10-,12-/m0/s1

Standard InChI Key:  YZLYUYDWVJSYRO-GMOBBJLQSA-N

Molfile:  

 
     RDKit          2D

 29 29  0  0  0  0  0  0  0  0999 V2000
   -3.6352   -0.0794    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9207    0.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2060   -0.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4525    0.2558    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9005   -0.3571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3129   -1.0714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1198   -0.8999    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0758   -0.3571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3365    0.3571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0758    1.0713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3365    1.7855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3365   -1.0713    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1612   -1.0713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5736   -1.7855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3983   -1.7855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8107   -2.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6354   -2.4998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3983   -3.2140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8107   -1.0713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3983   -0.3571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6354   -1.0713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5736   -0.3571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9207    1.1582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6354    1.5708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0758    2.4998    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1612    1.7855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9005    2.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3129    3.2140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1376    3.2140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  0
  4  3  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  3  2  0
  5  8  1  0
  8  9  1  6
  9 10  1  0
 10 11  1  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 15 14  1  1
 15 16  1  0
 16 17  1  0
 16 18  2  0
 15 19  1  0
 19 20  1  0
 19 21  1  6
 13 22  2  0
  2 23  1  1
 23 24  1  0
 11 25  1  0
 11 26  2  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5287411

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 416.44

Molecular Weight (Monoisotopic): 416.2019

AlogP: -1.46

#Rotatable Bonds: 12

Polar Surface Area: 212.93

Molecular Species: ACID

HBA: 9

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.50

CX Basic pKa: 6.97

CX LogP: -4.60

CX LogD: -5.07

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.21

Np Likeness Score: -0.79

References

1. Wu C, Cao X, Zhang X..  (2021)  VISTA inhibitors in cancer immunotherapy: a short perspective on recent progresses.,  12  (10.0): [PMID:34778768] [10.1039/D1MD00185J]

Source

Source(1):

• Scientific Literature