Ethyl 6-methyl-4-(3-nitrophenyl)-2-oxo-3-[2-(2-{phenylcarbamothioyl}hydrazinylcarbonyl)ethyl]-1,2,3,4-tetrahydropyrimidine-5-carboxylate

ID: ALA4095935

PubChem CID: 137654095

Max Phase: Preclinical

Molecular Formula: C24H26N6O6S

Molecular Weight: 526.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C1=C(C)NC(=O)N(CCC(=O)NNC(=S)Nc2ccccc2)C1c1cccc([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C24H26N6O6S/c1-3-36-22(32)20-15(2)25-24(33)29(21(20)16-8-7-11-18(14-16)30(34)35)13-12-19(31)27-28-23(37)26-17-9-5-4-6-10-17/h4-11,14,21H,3,12-13H2,1-2H3,(H,25,33)(H,27,31)(H2,26,28,37)

Standard InChI Key:  PEJKSINMXNHPTQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 37 39  0  0  0  0  0  0  0  0999 V2000
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   11.7121   -7.7518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0087   -7.3263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2848   -7.7257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2685   -8.5504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9719   -8.9759    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5773   -7.3003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8577   -7.6954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   13.8794   -6.5578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5707   -7.8122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2944   -7.4087    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9978   -7.8383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   18.1161   -9.1187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4129   -8.6892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4033   -9.0061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0251   -6.5015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7447   -6.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7611   -5.2773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0578   -4.8519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.4849   -4.8822    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5013   -4.0574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1882   -5.3076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5447   -8.9498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.9025   -5.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  1  6  1  0
  7  8  2  0
  7  9  1  0
  4  7  1  0
 10 11  1  0
 12 13  2  0
 14 15  1  0
 12 14  1  0
 16 17  1  0
 16 18  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 19 24  2  0
 17 19  1  0
 15 16  1  0
 11 12  1  0
  2 10  1  0
  1 25  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 26 31  2  0
 32 33  2  0
 32 34  1  0
 28 32  1  0
  3 26  1  0
  5 35  1  0
 36 37  1  0
  9 36  1  0
M  CHG  2  32   1  34  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4095935

   ---

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: 526.58

Molecular Weight (Monoisotopic): 526.1635

AlogP: 2.91

#Rotatable Bonds: 8

Polar Surface Area: 154.94

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.83

CX Basic pKa: ┄

CX LogP: 2.52

CX LogD: 2.52

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.18

Np Likeness Score: -1.84

References

1. Teleb M, Zhang FX, Huang J, Gadotti VM, Farghaly AM, AboulWafa OM, Zamponi GW, Fahmy H..  (2017)  Synthesis and biological evaluation of novel N3-substituted dihydropyrimidine derivatives as T-type calcium channel blockers and their efficacy as analgesics in mouse models of inflammatory pain.,  25  (6): [PMID:28233679] [10.1016/j.bmc.2017.02.015]

Source

Source(1):

• Scientific Literature