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

ID: ALA4092868

PubChem CID: 137653725

Max Phase: Preclinical

Molecular Formula: C23H29N5O8

Molecular Weight: 503.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C/C(C)=N\NC(=O)CCN1C(=O)NC(C)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C23H29N5O8/c1-5-35-19(30)12-14(3)25-26-18(29)10-11-27-21(16-8-7-9-17(13-16)28(33)34)20(22(31)36-6-2)15(4)24-23(27)32/h7-9,13,21H,5-6,10-12H2,1-4H3,(H,24,32)(H,26,29)/b25-14-

Standard InChI Key:  AMEMCYRSYUHAEH-QFEZKATASA-N

Molfile:  

     RDKit          2D

 36 37  0  0  0  0  0  0  0  0999 V2000
   10.8136   -7.7808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8226   -6.9637    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1201   -6.5480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4086   -6.9493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3997   -7.7664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1022   -8.1822    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7061   -6.5336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9906   -6.9349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7151   -5.7164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5161   -8.2007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1290   -5.7308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8405   -5.3295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8494   -4.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1469   -4.0966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4355   -4.4980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4265   -5.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5609   -4.1110    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2633   -4.5309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5698   -3.2939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6882   -8.1678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5340   -6.5623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2406   -6.9822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9521   -6.5809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9610   -5.7637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6546   -6.9966    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3660   -6.5953    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7799   -6.6097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0685   -7.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0595   -7.8281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7620   -8.2439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4776   -7.8425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7572   -9.0610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4597   -9.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4508  -10.2939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0085   -5.3007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0174   -4.4836    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
 28 29  1  0
 29 30  1  0
 30 31  2  0
 33 34  1  0
 32 33  1  0
 30 32  1  0
 26 28  2  0
 22 23  1  0
  2 21  1  0
 35 36  1  0
  9 35  1  0
M  CHG  2  17   1  19  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4092868

   ---

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: 503.51

Molecular Weight (Monoisotopic): 503.2016

AlogP: 2.33

#Rotatable Bonds: 11

Polar Surface Area: 169.54

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.80

CX Basic pKa: 0.90

CX LogP: 1.27

CX LogD: 1.27

Aromatic Rings: 1

Heavy Atoms: 36

QED Weighted: 0.20

Np Likeness Score: -1.37

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