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

ID: ALA4089516

PubChem CID: 137642142

Max Phase: Preclinical

Molecular Formula: C26H27N5O6

Molecular Weight: 505.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C1=C(C)NC(=O)N(CCC(=O)N/N=C\C=C\c2ccccc2)C1c1cccc([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C26H27N5O6/c1-3-37-25(33)23-18(2)28-26(34)30(24(23)20-12-7-13-21(17-20)31(35)36)16-14-22(32)29-27-15-8-11-19-9-5-4-6-10-19/h4-13,15,17,24H,3,14,16H2,1-2H3,(H,28,34)(H,29,32)/b11-8+,27-15-

Standard InChI Key:  HGECWWLNFZXVLD-FOLKEUSFSA-N

Molfile:  

     RDKit          2D

 37 39  0  0  0  0  0  0  0  0999 V2000
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    9.9608   -6.1314    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2507   -5.7319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5468   -6.1453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5531   -6.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2632   -7.3662    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8367   -5.7416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1287   -6.1551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8263   -4.9245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   12.0724   -4.8870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7929   -6.1078    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4967   -5.6944    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2068   -6.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.9461   -9.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6500   -9.3528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6437   -8.5357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6772   -7.3523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2444   -4.9147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9483   -4.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9420   -3.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2319   -3.2804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5239   -3.6939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5343   -4.5110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6459   -3.2666    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6396   -2.4494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3560   -3.6703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8492   -7.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1162   -4.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1099   -3.7036    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
 17 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
 18 19  1  0
 15 16  2  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:

   

   ALA4089516

   ---

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: 505.53

Molecular Weight (Monoisotopic): 505.1961

AlogP: 3.70

#Rotatable Bonds: 10

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: 11.80

CX Basic pKa: 1.90

CX LogP: 2.74

CX LogD: 2.74

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.22

Np Likeness Score: -1.35

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