Amsacrine

ID: ALA4575796

PubChem CID: 155563816

Max Phase: Preclinical

Molecular Formula: C21H18N2O3S

Molecular Weight: 378.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(S(C)(=O)=O)ccc1Nc1c2ccccc2nc2ccccc12

Standard InChI:  InChI=1S/C21H18N2O3S/c1-26-20-13-14(27(2,24)25)11-12-19(20)23-21-15-7-3-5-9-17(15)22-18-10-6-4-8-16(18)21/h3-13H,1-2H3,(H,22,23)

Standard InChI Key:  NHUIFDIHYWSPOK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   32.6546   -6.8099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.0674   -7.5198    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   33.4758   -6.8074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.1339  -10.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1328  -11.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8408  -11.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8390   -9.9876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6763  -11.6137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3856  -11.1991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3780  -10.3742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6651   -9.9720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9640  -11.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9610  -10.3897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2522   -9.9850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5459  -10.3973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5528  -11.2185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2623  -11.6194    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.2482   -9.1678    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.9539   -8.7558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6616   -9.1627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3668   -8.7514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3633   -7.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6487   -7.5283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9464   -7.9420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2350   -7.5398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.5310   -7.9547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7787   -7.9246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6 16  2  0
 15  7  2  0
  7  4  1  0
 12  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 13  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 12  2  0
 14 18  1  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
 24 25  1  0
 25 26  1  0
 22  2  1  0
  2 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4575796

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 378.45

Molecular Weight (Monoisotopic): 378.1038

AlogP: 4.54

#Rotatable Bonds: 4

Polar Surface Area: 68.29

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.43

CX LogP: 3.63

CX LogD: 2.65

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.53

Np Likeness Score: -1.08

References

1. Hu W, Huang XS, Wu JF, Yang L, Zheng YT, Shen YM, Li ZY, Li X..  (2018)  Discovery of Novel Topoisomerase II Inhibitors by Medicinal Chemistry Approaches.,  61  (20): [PMID:29870668] [10.1021/acs.jmedchem.7b01202]

Source

Source(1):

• Scientific Literature