1,4-dimethyl-7-nitro-11-phenyl-1,2,3,4,11,11a-hexahydro-10H-benzo[e]pyrazino[2,3-b][1,4]diazepin-10-one

ID: ALA5077885

PubChem CID: 166628664

Max Phase: Preclinical

Molecular Formula: C19H19N5O3

Molecular Weight: 365.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN1CCN(C)C2C1=Nc1cc([N+](=O)[O-])ccc1C(=O)N2c1ccccc1

Standard InChI:  InChI=1S/C19H19N5O3/c1-21-10-11-22(2)18-17(21)20-16-12-14(24(26)27)8-9-15(16)19(25)23(18)13-6-4-3-5-7-13/h3-9,12,18H,10-11H2,1-2H3

Standard InChI Key:  TXHGMLZJKOBZBV-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    3.9814  -25.1348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9802  -25.9543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6883  -26.3633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6865  -24.7259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3999  -25.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3951  -25.1312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0361  -24.6103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0499  -26.4611    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8405  -24.7829    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2019  -25.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8493  -26.2732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3207  -26.9502    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1469  -26.8825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4995  -26.1316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0259  -25.4484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3404  -24.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1505  -24.2575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6538  -23.6146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3482  -22.8558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5344  -22.7436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0347  -23.3876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8454  -23.8156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9723  -27.6895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3722  -24.7082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2703  -26.3661    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2696  -27.1833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5629  -25.9570    0.0000 O   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
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  9 10  1  0
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  7 22  2  0
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  2 25  1  0
M  CHG  2  25   1  27  -1
M  END

Alternative Forms

1. Parent:

   

   ALA5077885

   ---

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: 365.39

Molecular Weight (Monoisotopic): 365.1488

AlogP: 2.49

#Rotatable Bonds: 2

Polar Surface Area: 82.29

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.59

CX LogP: 2.47

CX LogD: 2.47

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.60

Np Likeness Score: -0.72

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