5-(3-(hydroxycarbamoyl)-2-(hydroxymethyl)pentyl)-3-(2-(hydroxyimino)-2-(4-nitrophenyl)ethyl)-1-methyl-1H-imidazol-3-ium bromide

ID: ALA3275313

PubChem CID: 90679007

Max Phase: Preclinical

Molecular Formula: C19H26BrN5O6

Molecular Weight: 420.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(C(=O)NO)C(CO)Cc1c[n+](C/C(=N\O)c2ccc([N+](=O)[O-])cc2)cn1C.[Br-]

Standard InChI:  InChI=1S/C19H25N5O6.BrH/c1-3-17(19(26)21-28)14(11-25)8-16-9-23(12-22(16)2)10-18(20-27)13-4-6-15(7-5-13)24(29)30;/h4-7,9,12,14,17,25H,3,8,10-11H2,1-2H3,(H2-,21,26,27,28);1H/b20-18+;

Standard InChI Key:  JCNHDTHHWSGFEH-KPJFUTMLSA-N

Molfile:  

     RDKit          2D

 31 31  0  0  0  0  0  0  0  0999 V2000
   22.4225  -31.2017    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   18.8077  -30.6612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6249  -30.6612    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8793  -29.8845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2163  -29.4024    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5576  -29.8845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7803  -29.6323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1733  -30.1794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1045  -31.3229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7713  -32.0690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2151  -28.5852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2508  -32.7307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9130  -33.4740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3918  -34.1353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2055  -34.0512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5381  -33.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0572  -32.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9584  -32.1535    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.6860  -34.7122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3959  -29.9272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3435  -30.9787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7365  -31.5257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7889  -30.4743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0116  -30.2221    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9592  -31.2736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2257  -29.1280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8327  -28.5809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4045  -30.7692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4789  -31.4918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5006  -34.6289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3556  -35.4610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  2  2  0
  6  7  1  0
  7  8  1  0
  3  9  1  0
  9 10  1  0
  5 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 10 18  2  0
 15 19  1  0
  8 20  1  0
  8 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  1  0
 23 25  2  0
 20 26  1  0
 26 27  1  0
 24 28  1  0
 18 29  1  0
 19 30  2  0
 19 31  1  0
M  CHG  4   1  -1   3   1  19   1  31  -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: 420.45

Molecular Weight (Monoisotopic): 420.1878

AlogP: 0.78

#Rotatable Bonds: 10

Polar Surface Area: 154.10

Molecular Species: ACID

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.36

CX Basic pKa: 0.14

CX LogP: -2.89

CX LogD: -3.74

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.11

Np Likeness Score: -0.19

References

1. Ben-Bassat AA, Lavie D..  (1976)  Quaternary pilocarpine derivatives as potential acetylcholine antagonists. 2. Alterations in the lactone and imidazole moieties.,  19  (7): [PMID:940111] [10.1021/jm00229a014]

Source

Source(1):

• Scientific Literature