(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-2-amino-3-carboxy-propanoyl]amino]hexanoyl]amino]hexanoic acid

ID: ALA5287949

Max Phase: Preclinical

Molecular Formula: C16H31N5O6

Molecular Weight: 389.45

Names and Identifiers

Canonical SMILES:  NCCCC[C@H](NC(=O)[C@H](CCCCN)NC(=O)[C@@H](N)CC(=O)O)C(=O)O

Standard InChI:  InChI=1S/C16H31N5O6/c17-7-3-1-5-11(20-14(24)10(19)9-13(22)23)15(25)21-12(16(26)27)6-2-4-8-18/h10-12H,1-9,17-19H2,(H,20,24)(H,21,25)(H,22,23)(H,26,27)/t10-,11-,12-/m0/s1

Standard InChI Key:  NVFSJIXJZCDICF-SRVKXCTJSA-N

Molfile:  

 
     RDKit          2D

 27 26  0  0  0  0  0  0  0  0999 V2000
   -3.0851   -0.2003    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3639    0.2003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6827   -0.2003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0016    0.2003    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3205   -0.2003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3606    0.2003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0417   -0.2003    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7228    0.2003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4040   -0.2003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0851    0.2003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4040   -1.0016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7228    1.0016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4040    1.4023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4040    2.1635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0851    2.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0851    3.3656    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3606    1.0016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3205   -1.0016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3606   -1.4023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3606   -2.1636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0417   -2.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0417   -3.3656    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6827   -1.0016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3639    1.0016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6827    1.4023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6827    2.1635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0016    1.0016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
  8 12  1  1
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  6 17  2  0
  5 18  1  6
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
  3 23  2  0
  2 24  1  1
 24 25  1  0
 25 26  2  0
 25 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5287949

   ---

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: 389.45

Molecular Weight (Monoisotopic): 389.2274

AlogP: -1.90

#Rotatable Bonds: 15

Polar Surface Area: 210.86

Molecular Species: ZWITTERION

HBA: 7

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 10

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.39

CX Basic pKa: 13.78

CX LogP: -7.19

CX LogD: -7.96

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.16

Np Likeness Score: 0.55

References

1. Mou Y, Wen S, Li YX, Gao XX, Zhang X, Jiang ZY..  (2020)  Recent progress in Keap1-Nrf2 protein-protein interaction inhibitors.,  202  [PMID:32668381] [10.1016/j.ejmech.2020.112532]

Source

Source(1):

• Scientific Literature