{8-[5-Methoxycarbonyl-2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3-carbonyloxy]-octyl}-trimethyl-ammonium

ID: ALA3350227

PubChem CID: 10699201

Max Phase: Preclinical

Molecular Formula: C27H40IN3O6

Molecular Weight: 502.63

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCCCCCC[N+](C)(C)C)[C@H]1c1cccc([N+](=O)[O-])c1.[I-]

Standard InChI:  InChI=1S/C27H39N3O6.HI/c1-19-23(26(31)35-6)25(21-14-13-15-22(18-21)29(33)34)24(20(2)28-19)27(32)36-17-12-10-8-7-9-11-16-30(3,4)5;/h13-15,18,25H,7-12,16-17H2,1-6H3;1H/t25-;/m0./s1

Standard InChI Key:  XKIUNKMRICVREO-UQIIZPHYSA-N

Molfile:  

     RDKit          2D

 37 37  0  0  0  0  0  0  0  0999 V2000
    7.8329   -2.5094    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    2.5428   -4.0501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1148   -4.0501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8288   -3.6367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8288   -5.2901    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5428   -4.8768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1148   -4.8768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2484   -1.1524    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8288   -2.8058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5344   -1.5699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5428   -2.3924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9707   -1.5657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2442   -0.3257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4007   -3.6367    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2609   -2.8100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1148   -2.3967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8163   -1.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6867   -4.0501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1023   -1.5825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3965   -2.8100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6137   -4.4342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1147   -4.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6889   -3.6450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0354   -3.6450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9728   -3.6367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4029   -4.0626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2588   -4.0501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1169   -3.6492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8308   -4.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5448   -3.6450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
  4  2  1  0
  5  6  1  0
  6  2  2  0
  7  5  1  0
  8 12  1  0
  4  9  1  6
 10  3  1  0
 11  2  1  0
 12 13  2  0
 13  9  1  0
 14  8  1  0
 15  8  2  0
 16 25  1  0
 17 11  2  0
 18 10  2  0
 19 10  1  0
 20 11  1  0
 21  6  1  0
 22  7  1  0
 23  9  2  0
 24 26  2  0
 25 32  1  0
 26 23  1  0
 27 16  1  0
 28 16  1  0
 29 16  1  0
 30 20  1  0
 31 19  1  0
 32 34  1  0
 33 30  1  0
 34 37  1  0
 35 33  1  0
 36 35  1  0
 37 36  1  0
  7  3  2  0
 12 24  1  0
M  CHG  4   1  -1   8   1  14  -1  16   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: 502.63

Molecular Weight (Monoisotopic): 502.2912

AlogP: 4.59

#Rotatable Bonds: 13

Polar Surface Area: 107.77

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 0.03

CX LogD: 0.03

Aromatic Rings: 1

Heavy Atoms: 36

QED Weighted: 0.14

Np Likeness Score: -0.42

References

1. Peri R, Padmanabhan S, Rutledge A, Singh S, Triggle DJ..  (2000)  Permanently charged chiral 1,4-dihydropyridines: molecular probes of L-type calcium channels. Synthesis and pharmacological characterization of methyl(omega-trimethylalkylammonium) 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate iodide, calcium channel antagonists.,  43  (15): [PMID:10956198] [10.1021/jm000028l]

Source

Source(1):

• Scientific Literature