(R/S)-5-((1-(2-Hydroxy-3-(9-oxoacridin-10(9H)-yl)propyl)-1H-indol-3-yl)methylene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione

ID: ALA4544130

PubChem CID: 155552635

Max Phase: Preclinical

Molecular Formula: C31H26N4O5

Molecular Weight: 534.57

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN1C(=O)C(=Cc2cn(CC(O)Cn3c4ccccc4c(=O)c4ccccc43)c3ccccc23)C(=O)N(C)C1=O

Standard InChI:  InChI=1S/C31H26N4O5/c1-32-29(38)24(30(39)33(2)31(32)40)15-19-16-34(25-12-6-3-9-21(19)25)17-20(36)18-35-26-13-7-4-10-22(26)28(37)23-11-5-8-14-27(23)35/h3-16,20,36H,17-18H2,1-2H3

Standard InChI Key:  GAZPMMMRETXIIJ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 40 45  0  0  0  0  0  0  0  0999 V2000
   17.2516  -17.4411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2365  -16.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5136  -16.2152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5481  -17.8679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8247  -17.4729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8095  -16.6399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0845  -16.2388    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1150  -17.9048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3854  -17.4992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3703  -16.6704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6462  -16.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9367  -16.6989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9557  -17.5308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6804  -17.9266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1312  -18.7296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0687  -15.4140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7752  -14.9880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4975  -15.3868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7595  -14.1631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4660  -13.7370    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2241  -14.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7643  -13.4295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5346  -12.9100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3351  -12.7269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5752  -11.9436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0159  -11.3429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2134  -11.5305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9770  -12.3134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5865  -13.4978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9384  -14.2439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4667  -14.9190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8153  -15.6628    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6375  -15.7354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1099  -15.0577    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7601  -14.3076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2299  -13.6295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6448  -14.8485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3427  -16.3389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9319  -15.1288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9867  -16.4828    0.0000 O   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
  5  8  1  0
  6  7  1  0
  7 10  1  0
  9  8  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  8 15  2  0
  7 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 24  1  0
 23 20  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 22 29  1  0
 29 30  2  0
 30 31  1  0
 30 35  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  2  0
 31 37  2  0
 32 38  1  0
 34 39  1  0
 33 40  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4544130

   ---

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: 534.57

Molecular Weight (Monoisotopic): 534.1903

AlogP: 3.60

#Rotatable Bonds: 5

Polar Surface Area: 104.85

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.87

CX LogD: 3.87

Aromatic Rings: 5

Heavy Atoms: 40

QED Weighted: 0.21

Np Likeness Score: -0.82

References

1. Singh H, Kaur M, Kaur H, Sharma I, Bhandari A, Kaur G, Singh P..  (2019)  Structural tuning of acridones for developing anticancer agents targeting dihydrofolate reductase.,  29  (19): [PMID:31447082] [10.1016/j.bmcl.2019.126631]

Source

Source(1):

• Scientific Literature