6-bromo-11-(3-fluoro-4-methoxyphenyl)-1,4-dimethyl-10-oxo-2,3,4,10,11,11ahexahydro-1H-benzo[e]pyrazino[2,3-b][1,4]diazepine-8-carbonitrile

ID: ALA5080705

PubChem CID: 166629980

Max Phase: Preclinical

Molecular Formula: C21H19BrFN5O2

Molecular Weight: 472.32

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(N2C(=O)c3cc(C#N)cc(Br)c3N=C3C2N(C)CCN3C)cc1F

Standard InChI:  InChI=1S/C21H19BrFN5O2/c1-26-6-7-27(2)20-19(26)25-18-14(8-12(11-24)9-15(18)22)21(29)28(20)13-4-5-17(30-3)16(23)10-13/h4-5,8-10,20H,6-7H2,1-3H3

Standard InChI Key:  PBJMGLXTOARERF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
    3.9112   -4.6637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9100   -5.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6181   -5.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6163   -4.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3297   -5.4804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3249   -4.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9659   -4.1392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9797   -5.9900    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7704   -4.3118    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1317   -5.0512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7791   -5.8021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2505   -6.4792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0767   -6.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4293   -5.6605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9557   -4.9773    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2702   -3.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0803   -3.7864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5836   -3.1436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2780   -2.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4643   -2.2726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9646   -2.9165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7752   -3.3446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9021   -7.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3020   -4.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2039   -4.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4961   -3.8474    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7806   -1.7404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5900   -1.8535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1559   -1.5158    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184   -6.7094    0.0000 Br  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
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
  9 16  1  0
  7 22  2  0
 12 23  1  0
 15 24  1  0
 25 26  3  0
  1 25  1  0
 19 27  1  0
 27 28  1  0
 20 29  1  0
  3 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5080705

   ---

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: 472.32

Molecular Weight (Monoisotopic): 471.0706

AlogP: 3.36

#Rotatable Bonds: 2

Polar Surface Area: 72.17

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.25

CX LogP: 3.14

CX LogD: 3.14

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.67

Np Likeness Score: -1.10

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