(2S,3S,Z)-N'-benzylidene-2-(1,3-dioxoisoindolin-2-yl)-3-methylpentanehydrazide

ID: ALA3580856

PubChem CID: 122178479

Max Phase: Preclinical

Molecular Formula: C21H21N3O3

Molecular Weight: 363.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@H](C)[C@@H](C(=O)N/N=C\c1ccccc1)N1C(=O)c2ccccc2C1=O

Standard InChI:  InChI=1S/C21H21N3O3/c1-3-14(2)18(19(25)23-22-13-15-9-5-4-6-10-15)24-20(26)16-11-7-8-12-17(16)21(24)27/h4-14,18H,3H2,1-2H3,(H,23,25)/b22-13-/t14-,18-/m0/s1

Standard InChI Key:  YXGPRAKCMVWTTC-AHXWOFLFSA-N

Molfile:  

     RDKit          2D

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   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0872    0.0382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0825    2.3453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0907   -2.3426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8208    1.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2072    2.3788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8520   -1.2531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3215    1.3677    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0552    2.6770    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5559    2.6972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3246    1.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8245    1.4262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5901    0.1363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8558   -1.1717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3559   -1.1898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5903    0.1001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1168   -2.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7283   -3.5941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0519   -1.2394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  5  1  0
  8 10  1  0
  9 11  2  0
  7 12  2  0
 10 13  1  6
 13 14  2  0
 10 15  1  0
 13 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 15 25  1  0
 25 26  1  0
 15 27  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA3580856

   ---

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: 363.42

Molecular Weight (Monoisotopic): 363.1583

AlogP: 2.85

#Rotatable Bonds: 6

Polar Surface Area: 78.84

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.61

CX Basic pKa: 1.73

CX LogP: 3.63

CX LogD: 3.63

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.49

Np Likeness Score: -0.99

References

1. Coelho LCD, Cardoso MVdO, Moreira DRM, Gomes PATdM, Cavalcanti SMT, Oliveira AR, Filho GBdO, Siqueira LRPd, Barbosa MdO, Borba EFdO, Silva TGd, Kaskow B, Karimi M, Abraham LJ, Leite ACL.  (2014)  Novel phthalimide derivatives with TNF- and IL-1 expression inhibitory and apoptotic inducing properties,  5  (6): [10.1039/C4MD00070F]

Source

Source(1):

• Scientific Literature