rac-Ethyl 4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

ID: ALA4458540

PubChem CID: 3103260

Max Phase: Preclinical

Molecular Formula: C14H15N3O5S

Molecular Weight: 337.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)C1=C(C)NC(=S)NC1c1ccc(O)c([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C14H15N3O5S/c1-3-22-13(19)11-7(2)15-14(23)16-12(11)8-4-5-10(18)9(6-8)17(20)21/h4-6,12,18H,3H2,1-2H3,(H2,15,16,23)

Standard InChI Key:  XULFDOQRTWOEIJ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   22.3201  -17.8544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3201  -18.6716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0253  -19.0761    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.7306  -18.6716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7306  -17.8544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.0253  -17.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4377  -19.0812    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   21.6129  -19.0812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0253  -16.6245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7351  -16.2173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7354  -15.4009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0272  -14.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3172  -15.4045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3203  -16.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6112  -17.4479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6088  -16.6307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9046  -17.8585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1957  -17.4520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4892  -17.8627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0261  -14.1743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4461  -14.9905    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.4465  -14.1733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1536  -15.3995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  4  7  2  0
  2  8  1  0
  6  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  1 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 12 20  1  0
 21 22  2  0
 21 23  1  0
 11 21  1  0
M  CHG  2  21   1  23  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4458540

   Ethyl 4-(4-hydroxy-3-nitrophenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 337.36

Molecular Weight (Monoisotopic): 337.0732

AlogP: 1.66

#Rotatable Bonds: 4

Polar Surface Area: 113.73

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.72

CX Basic pKa: ┄

CX LogP: 1.77

CX LogD: 1.03

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.33

Np Likeness Score: -1.20

References

1. González-Hernández E, Aparicio R, Garayoa M, Montero MJ, Sevilla MÁ, Pérez-Melero C..  (2019)  Dihydropyrimidine-2-thiones as Eg5 inhibitors and L-type calcium channel blockers: potential antitumour dual agents.,  10  (9): [PMID:31673316] [10.1039/C9MD00108E]

Source

Source(1):

• Scientific Literature