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

ID: ALA4098145

PubChem CID: 137659471

Max Phase: Preclinical

Molecular Formula: C25H26FN5O6

Molecular Weight: 511.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C1=C(C)NC(=O)N(CCC(=O)N/N=C(/C)c2ccc(F)cc2)C1c1cccc([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C25H26FN5O6/c1-4-37-24(33)22-16(3)27-25(34)30(23(22)18-6-5-7-20(14-18)31(35)36)13-12-21(32)29-28-15(2)17-8-10-19(26)11-9-17/h5-11,14,23H,4,12-13H2,1-3H3,(H,27,34)(H,29,32)/b28-15-

Standard InChI Key:  BBRIZAZCMQHBCL-MBTHVWNTSA-N

Molfile:  

     RDKit          2D

 37 39  0  0  0  0  0  0  0  0999 V2000
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   10.8162   -7.1017    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1094   -6.6931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3980   -7.0976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3974   -7.9148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1000   -8.3275    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6913   -6.6849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9840   -7.0936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   10.8221   -4.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1195   -4.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4081   -4.6461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4033   -5.4633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.9375   -6.7013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9423   -5.8841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6442   -7.1140    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3557   -6.7095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0624   -7.1181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7697   -6.7136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0577   -7.9352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.3456   -9.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0523   -9.5696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7596   -9.1651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7644   -8.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0476  -10.3868    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.9893   -5.4592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9940   -4.6420    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
  1 10  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 11 16  2  0
 17 18  2  0
 17 19  1  0
 13 17  1  0
  3 11  1  0
  5 20  1  0
 21 22  1  0
 23 24  2  0
 25 26  1  0
 23 25  1  0
 27 28  1  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 29 34  2  0
 32 35  1  0
 27 29  1  0
 26 27  2  0
 22 23  1  0
  2 21  1  0
 36 37  1  0
  9 36  1  0
M  CHG  2  17   1  19  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4098145

   ---

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: 511.51

Molecular Weight (Monoisotopic): 511.1867

AlogP: 3.57

#Rotatable Bonds: 9

Polar Surface Area: 143.24

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.74

CX Basic pKa: 0.97

CX LogP: 2.44

CX LogD: 2.44

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.23

Np Likeness Score: -1.74

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