1-benzyl-11-(4-methoxyphenyl)-4-methyl-8-nitro-1,2,3,4,11,11a-hexahydro-10H-benzo[e]pyrazino[2,3-b][1,4]diazepin-10-one

ID: ALA5077889

PubChem CID: 166628668

Max Phase: Preclinical

Molecular Formula: C26H25N5O4

Molecular Weight: 471.52

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(N2C(=O)c3cc([N+](=O)[O-])ccc3N=C3C2N(Cc2ccccc2)CCN3C)cc1

Standard InChI:  InChI=1S/C26H25N5O4/c1-28-14-15-29(17-18-6-4-3-5-7-18)25-24(28)27-23-13-10-20(31(33)34)16-22(23)26(32)30(25)19-8-11-21(35-2)12-9-19/h3-13,16,25H,14-15,17H2,1-2H3

Standard InChI Key:  QPOMCXYMUSFBQT-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 35 39  0  0  0  0  0  0  0  0999 V2000
   27.9977  -14.8662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9966  -15.6858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7046  -16.0947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7028  -14.4574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4162  -15.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4114  -14.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0524  -14.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0662  -16.1925    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.8569  -14.5143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.2182  -15.2537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8656  -16.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3370  -16.6817    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.1632  -16.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5158  -15.8630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0422  -15.1798    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.2892  -14.4581    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.5816  -14.8668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2890  -13.6409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.8617  -13.5471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.9886  -17.4209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3567  -13.8733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1668  -13.9890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6701  -13.3461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3645  -12.5873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5508  -12.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0511  -13.1190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8671  -11.9429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.6765  -12.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3885  -14.4397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2027  -14.3695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6681  -15.0393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4816  -14.9696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8287  -14.2288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3562  -13.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5444  -13.6299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  5  2  0
  6  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  5  8  1  0
  7  9  1  0
  8 11  2  0
  9 10  1  0
 10 11  1  0
 10 15  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 16 17  2  0
 16 18  1  0
  1 16  1  0
  7 19  2  0
 12 20  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
  9 21  1  0
 24 27  1  0
 27 28  1  0
 15 29  1  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 30  1  0
M  CHG  2  16   1  18  -1
M  END

Alternative Forms

1. Parent:

   

   ALA5077889

   ---

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: 471.52

Molecular Weight (Monoisotopic): 471.1907

AlogP: 4.07

#Rotatable Bonds: 5

Polar Surface Area: 91.52

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.00

CX LogP: 4.04

CX LogD: 4.04

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.41

Np Likeness Score: -0.89

References

1. Ryan MC, Kim E, Cao X, Reichard W, Ogorek TJ, Das P, Jonsson CB, Baudry J, Chung D, Golden JE..  (2022)  Piperazinobenzodiazepinones: New Encephalitic Alphavirus Inhibitors via Ring Expansion of 2-Dichloromethylquinazolinones.,  13  (4.0): [PMID:35450382] [10.1021/acsmedchemlett.1c00539]

Source

Source(1):

• Scientific Literature