5-bromocytisine

ID: ALA1084012

Cas Number: 207390-16-7

PubChem CID: 15519736

Max Phase: Preclinical

Molecular Formula: C11H13BrN2O

Molecular Weight: 269.14

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 5-Bromocytisine | 5-bromocytisine|CHEMBL1084012|DTXSID101126759|BDBM50482167|207390-16-7|(1R,5S)-11-Bromo-1,2,3,4,5,6-hexahydro-1,5-methano-8H-pyrido[1,2-a][1,5]diazocin-8-one

Canonical SMILES:  O=c1ccc(Br)c2n1C[C@@H]1CNC[C@H]2C1

Standard InChI:  InChI=1S/C11H13BrN2O/c12-9-1-2-10(15)14-6-7-3-8(11(9)14)5-13-4-7/h1-2,7-8,13H,3-6H2/t7-,8+/m0/s1

Standard InChI Key:  QGUJDQNVLMZXLT-JGVFFNPUSA-N

Molfile:  

     RDKit          2D

 17 19  0  0  0  0  0  0  0  0999 V2000
   -2.2849  -12.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2849  -13.2146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5701  -13.6265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8553  -13.2146    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8553  -12.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5701  -11.9748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5701  -14.4543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1363  -13.6265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5597  -11.5702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5785  -12.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2745  -12.8099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5701  -11.1468    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.2729  -11.9849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1363  -11.9748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7197  -11.3914    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5785  -13.2146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5785  -14.0396    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  3  7  2  0
  4  8  1  0
  8 16  1  0
  5 14  1  0
 14  9  1  0
 16 10  1  0
 14 10  1  0
 16 11  1  0
  6 12  1  0
  9 13  1  0
 11 13  1  0
 14 15  1  6
 16 17  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1084012

   5-Bromocytisine

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 269.14

Molecular Weight (Monoisotopic): 268.0211

AlogP: 1.32

#Rotatable Bonds: ┄

Polar Surface Area: 34.03

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.82

CX LogP: 0.39

CX LogD: -1.97

Aromatic Rings: 1

Heavy Atoms: 15

QED Weighted: 0.77

Np Likeness Score: -0.25

References

1. Abin-Carriquiry JA, Zunini MP, Cassels BK, Wonnacott S, Dajas F..  (2010)  In silico characterization of cytisinoids docked into an acetylcholine binding protein.,  20  (12): [PMID:20493692] [10.1016/j.bmcl.2010.04.092]

Source

Source(1):

• Scientific Literature