Quinapyramine sulfate

ID: ALA1650565

PubChem CID: 136141534

Max Phase: Preclinical

Molecular Formula: C17H22N6O4S

Molecular Weight: 309.40

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Quinapyramine Sulfate

Canonical SMILES:  Cc1cc(=N)c2ccc(Nc3cc(C)[n+](C)c(N)n3)cc2n1C.O=S(=O)([O-])O

Standard InChI:  InChI=1S/C17H20N6.H2O4S/c1-10-7-14(18)13-6-5-12(9-15(13)22(10)3)20-16-8-11(2)23(4)17(19)21-16;1-5(2,3)4/h5-9H,1-4H3,(H3,18,19,20,21);(H2,1,2,3,4)

Standard InChI Key:  LYZSIPLTVVBMHP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
    2.2812   -0.6875    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.2812   -1.5125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2812    0.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4562   -0.6875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1062   -0.6875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9668   -2.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9668   -3.8111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2528   -4.2234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2528   -2.5651    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5341   -2.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5331   -3.8111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8186   -4.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1005   -3.8093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1014   -2.9801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8206   -2.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6819   -2.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2540   -1.7406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2542   -5.0479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3875   -2.5678    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3266   -2.9798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3228   -3.8032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0361   -4.2153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7511   -3.8027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7482   -2.9740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0343   -2.5657    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4607   -2.5590    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4657   -4.2138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0359   -5.0398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1  3  2  0
  1  4  1  0
  1  5  1  0
  6 16  1  0
  9 17  1  0
  6  7  2  0
  8 18  2  0
  6  9  1  0
 14 19  1  0
  7  8  1  0
 19 20  1  0
  8 11  1  0
 20 21  2  0
 10  9  1  0
 21 22  1  0
 10 15  1  0
 22 23  2  0
 11 12  1  0
 23 24  1  0
 12 13  2  0
 24 25  2  0
 25 20  1  0
 13 14  1  0
 24 26  1  0
 14 15  2  0
 23 27  1  0
 10 11  2  0
 22 28  1  0
M  CHG  2   4  -1  23   1
M  END

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: 309.40

Molecular Weight (Monoisotopic): 309.1822

AlogP: 1.82

#Rotatable Bonds: 2

Polar Surface Area: 83.60

Molecular Species: BASE

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.97

CX LogP: -2.80

CX LogD: -4.38

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.63

Np Likeness Score: -0.73

References

1. Gillingwater K, Kumar A, Anbazhagan M, Boykin DW, Tidwell RR, Brun R..  (2009)  In vivo investigations of selected diamidine compounds against Trypanosoma evansi using a mouse model.,  53  (12): [PMID:19786604] [10.1128/aac.00422-09]

Source

Source(1):

• Scientific Literature