6'-chloro-5H-spiro[benzo[h]tetrazolo[5,1-b]quinazoline-7,3'-indoline]-2',5,6(9H)-trione

ID: ALA4533309

PubChem CID: 155547198

Max Phase: Preclinical

Molecular Formula: C19H9ClN6O3

Molecular Weight: 404.77

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1C(=O)c2ccccc2C2=C1C1(C(=O)Nc3cc(Cl)ccc31)N1NN=NC1=N2

Standard InChI:  InChI=1S/C19H9ClN6O3/c20-8-5-6-11-12(7-8)21-17(29)19(11)13-14(22-18-23-24-25-26(18)19)9-3-1-2-4-10(9)15(27)16(13)28/h1-7H,(H,21,29)(H,22,23,25)

Standard InChI Key:  JBSHCAMHYGUVSA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 34  0  0  0  0  0  0  0  0999 V2000
   25.2502  -10.6301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2332   -9.7488    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.4218   -9.8352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7020   -9.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7003  -10.2114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4093  -10.6202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4066   -8.9827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1164   -9.3859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1146  -10.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5410   -9.3890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8262   -8.9738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5392  -10.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8218  -10.6221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8141  -11.4405    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.2387  -11.4554    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.5225  -11.8634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6881  -12.6708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.5041  -12.7636    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.8494  -12.0152    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.5649  -10.4938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9580  -11.0358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1228  -11.8271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8938  -12.0780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5002  -11.5326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3307  -10.7444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8262   -8.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5346   -8.5687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8756   -9.2283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.2772  -11.7857    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1 21  1  0
 20  2  1  0
  2  3  1  0
  3  1  1  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  8 11  1  0
  9 13  1  0
 12 10  1  0
 10 11  1  0
 12 13  2  0
 12  1  1  0
 13 14  1  0
 14 16  2  0
 15  1  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 15  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 11 26  2  0
 10 27  2  0
  3 28  2  0
 24 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4533309

   ---

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: 404.77

Molecular Weight (Monoisotopic): 404.0425

AlogP: 2.22

#Rotatable Bonds: ┄

Polar Surface Area: 115.59

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.07

CX Basic pKa: ┄

CX LogP: 2.51

CX LogD: 2.51

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.65

Np Likeness Score: -0.24

References

1. da Silva Júnior EN, Jardim GAM, Jacob C, Dhawa U, Ackermann L, de Castro SL..  (2019)  Synthesis of quinones with highlighted biological applications: A critical update on the strategies towards bioactive compounds with emphasis on lapachones.,  179  [PMID:31306817] [10.1016/j.ejmech.2019.06.056]

Source

Source(1):

• Scientific Literature