1-cyclohexyl-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: ALA5087708

PubChem CID: 166634285

Max Phase: Preclinical

Molecular Formula: C25H29N5O4

Molecular Weight: 463.54

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(N2C(=O)c3cc([N+](=O)[O-])ccc3N=C3C2N(C2CCCCC2)CCN3C)cc1

Standard InChI:  InChI=1S/C25H29N5O4/c1-27-14-15-28(17-6-4-3-5-7-17)24-23(27)26-22-13-10-19(30(32)33)16-21(22)25(31)29(24)18-8-11-20(34-2)12-9-18/h8-13,16-17,24H,3-7,14-15H2,1-2H3

Standard InChI Key:  LUWMLIOCVDQCIE-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
   14.7576  -14.9735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7564  -15.7931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4645  -16.2020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4627  -14.5647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1761  -15.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1713  -14.9699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8123  -14.4490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8261  -16.2998    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6167  -14.6216    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9781  -15.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6255  -16.1119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0968  -16.7890    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9231  -16.7212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2757  -15.9703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8021  -15.2871    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0490  -14.5654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3414  -14.9741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0489  -13.7482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6216  -13.6544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7485  -17.5282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8255  -13.8262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6205  -13.6117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8294  -12.8171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2446  -12.2376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4480  -12.4582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2428  -13.2524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2040  -14.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0242  -14.5663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4260  -13.8565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0122  -13.1490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1920  -13.1560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7857  -13.8703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4510  -11.4469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2390  -11.2303    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
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 16 17  2  0
 16 18  1  0
  1 16  1  0
  7 19  2  0
 12 20  1  0
  9 21  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
 15 27  1  0
 27 28  1  0
 27 32  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 24 33  1  0
 33 34  1  0
M  CHG  2  16   1  18  -1
M  END

Alternative Forms

1. Parent:

   

   ALA5087708

   ---

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: 463.54

Molecular Weight (Monoisotopic): 463.2220

AlogP: 4.20

#Rotatable Bonds: 4

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: 4.62

CX LogP: 4.12

CX LogD: 4.11

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.50

Np Likeness Score: -0.75

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