(R)-N-(1-(benzylamino)-8-(hydroxyamino)-1,8-dioxooctan-2-yl)-4-(dimethylamino)benzamide

ID: ALA2096849

PubChem CID: 16098510

Max Phase: Preclinical

Molecular Formula: C24H32N4O4

Molecular Weight: 440.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)c1ccc(C(=O)N[C@H](CCCCCC(=O)NO)C(=O)NCc2ccccc2)cc1

Standard InChI:  InChI=1S/C24H32N4O4/c1-28(2)20-15-13-19(14-16-20)23(30)26-21(11-7-4-8-12-22(29)27-32)24(31)25-17-18-9-5-3-6-10-18/h3,5-6,9-10,13-16,21,32H,4,7-8,11-12,17H2,1-2H3,(H,25,31)(H,26,30)(H,27,29)/t21-/m1/s1

Standard InChI Key:  QQZGICVGLPMNFI-OAQYLSRUSA-N

Molfile:  

     RDKit          2D

 32 33  0  0  0  0  0  0  0  0999 V2000
    4.5917    0.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3061    0.5083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8772    0.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5917   -0.7292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0206    0.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7351    0.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4496    0.0958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7351    1.3333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0206   -0.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7351   -1.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1640   -1.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8785   -0.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5930   -1.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3074   -0.7292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5930   -1.9667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0219   -1.1417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8780    1.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1644    1.7468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4489    1.3343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4516    0.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1658    0.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7339    1.7458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7328    2.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0200    1.3324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4496   -0.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1640    0.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1640    1.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8816    1.7426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8819    2.5669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1669    2.9802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4501    2.5633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4532    1.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 14 16  1  0
  3 17  2  0
  5  9  1  1
 17 18  1  0
  2  5  1  0
 18 19  2  0
  9 10  1  0
 19 20  1  0
 10 25  1  0
 20 21  2  0
 21  3  1  0
  1  3  1  0
 19 22  1  0
 25 11  1  0
 22 23  1  0
  5  6  1  0
 22 24  1  0
 11 12  1  0
  1  2  1  0
  7 26  1  0
 12 13  1  0
 26 27  1  0
  6  7  1  0
 27 28  2  0
 13 14  1  0
 28 29  1  0
  1  4  2  0
 29 30  2  0
 13 15  2  0
 30 31  1  0
  6  8  2  0
 31 32  2  0
 32 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2096849

   (2R)-N-benzyl-2-[[4-(dimethylamino)benzoyl]amino]-N'-hydroxyoctanediamide

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: 440.54

Molecular Weight (Monoisotopic): 440.2424

AlogP: 2.62

#Rotatable Bonds: 12

Polar Surface Area: 110.77

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.91

CX Basic pKa: 3.48

CX LogP: 2.51

CX LogD: 2.50

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.23

Np Likeness Score: -0.68

References

1. Kahnberg P, Lucke AJ, Glenn MP, Boyle GM, Tyndall JD, Parsons PG, Fairlie DP..  (2006)  Design, synthesis, potency, and cytoselectivity of anticancer agents derived by parallel synthesis from alpha-aminosuberic acid.,  49  (26): [PMID:17181145] [10.1021/jm050214x]

Source

Source(1):

• Scientific Literature