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

ID: ALA4069634

PubChem CID: 137639831

Max Phase: Preclinical

Molecular Formula: C24H24N6O5S

Molecular Weight: 508.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C1=C(C)NC(=O)N(CCc2nnc(Nc3ccccc3)s2)C1c1cccc([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C24H24N6O5S/c1-3-35-22(31)20-15(2)25-24(32)29(21(20)16-8-7-11-18(14-16)30(33)34)13-12-19-27-28-23(36-19)26-17-9-5-4-6-10-17/h4-11,14,21H,3,12-13H2,1-2H3,(H,25,32)(H,26,28)

Standard InChI Key:  JCPUIMRWUPQSRO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 36 39  0  0  0  0  0  0  0  0999 V2000
    9.9627   -8.7191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9632   -7.9019    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2545   -7.4928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5492   -7.9009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5486   -8.7181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2533   -9.1272    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8404   -7.4918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1351   -7.8999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8410   -6.6746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6726   -7.4938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3773   -7.9029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1713   -6.6804    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.0867   -7.4948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8337   -7.8256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3820   -7.2196    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9739   -6.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3047   -5.7673    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   14.5990   -6.3433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4095   -6.2557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7444   -5.5128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2647   -4.8492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4501   -4.9326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6715   -9.1282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2550   -6.6756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9644   -6.2675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9650   -5.4503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2562   -5.0412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5510   -5.4493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5504   -6.2665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6744   -5.0423    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6750   -4.2251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3791   -5.4514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8392   -9.1262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1322   -6.2655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1328   -5.4483    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  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 12 16  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 18 23  2  0
 17 18  1  0
 16 17  1  0
 11 13  1  0
  2 10  1  0
  1 24  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 25 30  2  0
 31 32  2  0
 31 33  1  0
 27 31  1  0
  3 25  1  0
  5 34  1  0
 35 36  1  0
  9 35  1  0
M  CHG  2  31   1  33  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4069634

   ---

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: 508.56

Molecular Weight (Monoisotopic): 508.1529

AlogP: 4.34

#Rotatable Bonds: 9

Polar Surface Area: 139.59

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.01

CX Basic pKa: ┄

CX LogP: 3.34

CX LogD: 3.34

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.25

Np Likeness Score: -1.82

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