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

ID: ALA4585154

PubChem CID: 3097578

Max Phase: Preclinical

Molecular Formula: C15H18N2O4S

Molecular Weight: 322.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)C1=C(C)NC(=S)NC1c1ccc(OC)c(O)c1

Standard InChI:  InChI=1S/C15H18N2O4S/c1-4-21-14(19)12-8(2)16-15(22)17-13(12)9-5-6-11(20-3)10(18)7-9/h5-7,13,18H,4H2,1-3H3,(H2,16,17,22)

Standard InChI Key:  NJICFSFGSZPETL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    6.7563  -25.0193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7563  -25.8365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4616  -26.2409    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1668  -25.8365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1668  -25.0193    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4616  -24.6065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8739  -26.2461    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.0492  -26.2461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4616  -23.7893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1713  -23.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1717  -22.5658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4634  -22.1563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7534  -22.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7565  -23.3844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474  -24.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0450  -23.7956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3409  -25.0234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6320  -24.6169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9255  -25.0276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8796  -22.1575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4623  -21.3392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1695  -20.9296    0.0000 C   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
 11 20  1  0
 12 21  1  0
 21 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4585154

   ethyl 4-(3-hydroxy-4-methoxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-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: 322.39

Molecular Weight (Monoisotopic): 322.0987

AlogP: 1.76

#Rotatable Bonds: 4

Polar Surface Area: 79.82

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.79

CX Basic pKa: ┄

CX LogP: 1.67

CX LogD: 1.67

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.58

Np Likeness Score: -0.63

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