4,5-dihydroxy-N-(6-(hydroxyamino)-6-oxohexyl)-9,10-dioxo-4a,8a,9,9a,10,10a-hexahydroanthracene-2-carboxamide

ID: ALA5268257

Max Phase: Preclinical

Molecular Formula: C21H24N2O7

Molecular Weight: 416.43

Names and Identifiers

Canonical SMILES:  O=C(CCCCCNC(=O)C1=CC2C(=O)C3C=CC=C(O)C3C(=O)C2C(O)=C1)NO

Standard InChI:  InChI=1S/C21H24N2O7/c24-14-6-4-5-12-17(14)20(28)18-13(19(12)27)9-11(10-15(18)25)21(29)22-8-3-1-2-7-16(26)23-30/h4-6,9-10,12-13,17-18,24-25,30H,1-3,7-8H2,(H,22,29)(H,23,26)

Standard InChI Key:  ALJZJKPKINLHPS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   -5.7157    0.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0011    0.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2893    0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2893   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9994   -0.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7157   -0.4162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5746    0.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8599    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8599   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5746   -0.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1472    0.8234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4306    0.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4306   -0.4100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1422   -0.8266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5746    1.6503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5746   -1.6503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1472    1.6486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0011    1.6497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7159   -0.8226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0012   -0.4100    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7159   -1.6478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7132   -0.8226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4279   -0.4100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1426   -0.8226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8571   -0.4100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5718   -0.8226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2865   -0.4100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0011   -0.8226    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2865    0.4151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7157   -0.4100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  1  0
  5  4  1  0
  6  5  2  0
  1  6  1  0
  3  7  1  0
  8  7  1  0
  9  8  1  0
 10  9  1  0
  4 10  1  0
  8 11  1  0
 12 11  2  0
 13 12  1  0
 14 13  2  0
  9 14  1  0
  7 15  2  0
 10 16  2  0
 11 17  1  0
  2 18  1  0
 13 19  1  0
 19 20  1  0
 19 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
 28 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5268257

   ---

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: 416.43

Molecular Weight (Monoisotopic): 416.1584

AlogP: 1.18

#Rotatable Bonds: 7

Polar Surface Area: 153.03

Molecular Species: NEUTRAL

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.42

CX Basic pKa: ┄

CX LogP: -0.52

CX LogD: -0.85

Aromatic Rings: ┄

Heavy Atoms: 30

QED Weighted: 0.24

Np Likeness Score: 0.80

References

1. Liu W, Liang Y, Si X..  (2020)  Hydroxamic acid hybrids as the potential anticancer agents: An Overview.,  205  [PMID:32791404] [10.1016/j.ejmech.2020.112679]

Source

Source(1):

• Scientific Literature