16-(1-methyl-5-nitro-1H-imidazol-2-ylthio)hexadecanoic acid

ID: ALA3274669

PubChem CID: 12381540

Max Phase: Preclinical

Molecular Formula: C20H35N3O4S

Molecular Weight: 413.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1c([N+](=O)[O-])cnc1SCCCCCCCCCCCCCCCC(=O)O

Standard InChI:  InChI=1S/C20H35N3O4S/c1-22-18(23(26)27)17-21-20(22)28-16-14-12-10-8-6-4-2-3-5-7-9-11-13-15-19(24)25/h17H,2-16H2,1H3,(H,24,25)

Standard InChI Key:  ZAWNJYXFXCZYAX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 28  0  0  0  0  0  0  0  0999 V2000
    3.0907   -5.8584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4827   -6.5767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2863   -6.4272    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3898   -5.6162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6499   -5.2697    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8804   -6.9925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1105   -5.2233    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.8080   -5.6491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5255   -5.2579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2230   -5.6837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9405   -5.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6380   -5.7183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3555   -5.3271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0530   -5.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7705   -5.3617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4680   -5.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1854   -5.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8830   -5.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6004   -5.4309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1330   -7.3187    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5968   -7.9916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3184   -7.3840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2979   -5.8567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0154   -5.4655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7129   -5.8913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4304   -5.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1279   -5.9259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4504   -4.6832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  1  2  2  0
  3  4  1  0
  4  5  2  0
  5  1  1  0
  3  6  1  0
  4  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 20 21  2  0
 20 22  1  0
  2 20  1  0
 19 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
M  CHG  2  20   1  22  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3274669

   16-(1-Methyl-5-nitroimidazol-2-yl)sulfanylhexadecanoic acid

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: 413.58

Molecular Weight (Monoisotopic): 413.2348

AlogP: 5.97

#Rotatable Bonds: 18

Polar Surface Area: 98.26

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.95

CX Basic pKa: 1.06

CX LogP: 6.65

CX LogD: 4.24

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.14

Np Likeness Score: -0.81

References

1. Tweit RC, Muir RD, Ziecina S..  (1977)  Nitroimidazoles with antibacterial activity against Neisseria gonorrhoeae.,  20  (12): [PMID:412966] [10.1021/jm00222a036]

Source

Source(1):

• Scientific Literature