(+/-)-Isobutyl 4-(furan-3-yl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

ID: ALA4776203

PubChem CID: 162643714

Max Phase: Preclinical

Molecular Formula: C14H18N2O3S

Molecular Weight: 294.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1=C(C(=O)OCC(C)C)C(c2ccoc2)NC(=S)N1

Standard InChI:  InChI=1S/C14H18N2O3S/c1-8(2)6-19-13(17)11-9(3)15-14(20)16-12(11)10-4-5-18-7-10/h4-5,7-8,12H,6H2,1-3H3,(H2,15,16,20)

Standard InChI Key:  XPHPFTCZJSCGOJ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
    9.5752   -8.5067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5752   -9.3317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2461   -8.0192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9911   -7.2346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1661   -7.2346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9113   -8.0192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0043   -9.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2899  -10.5728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0043  -10.9853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7188   -9.7478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5754  -10.9853    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2899   -9.7478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8609  -10.5728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0043   -8.5103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1464  -10.9853    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.8609   -9.7478    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4333   -9.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1410   -9.7439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1410  -10.5611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8487   -9.3354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  1  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  1  2  0
  8 12  2  0
 13 11  1  0
 10 17  1  0
  7 14  2  0
  7 10  1  0
 11  8  1  0
  2 16  1  0
  2 12  1  0
 13 15  2  0
 16 13  1  0
 12  7  1  0
  8  9  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4776203

   ---

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: 294.38

Molecular Weight (Monoisotopic): 294.1038

AlogP: 2.27

#Rotatable Bonds: 4

Polar Surface Area: 63.50

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.88

CX Basic pKa: ┄

CX LogP: 2.16

CX LogD: 2.16

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.66

Np Likeness Score: -0.53

References

1. Majellaro M,Jespers W,Crespo A,Núñez MJ,Novio S,Azuaje J,Prieto-Díaz R,Gioé C,Alispahic B,Brea J,Loza MI,Freire-Garabal M,Garcia-Santiago C,Rodríguez-García C,García-Mera X,Caamaño O,Fernandez-Masaguer C,Sardina JF,Stefanachi A,El Maatougui A,Mallo-Abreu A,Åqvist J,Gutiérrez-de-Terán H,Sotelo E.  (2021)  3,4-Dihydropyrimidin-2(1H)-ones as Antagonists of the Human A Adenosine Receptor: Optimization, Structure-Activity Relationship Studies, and Enantiospecific Recognition.,  64  (1.0): [PMID:33372800] [10.1021/acs.jmedchem.0c01431]

Source

Source(1):

• Scientific Literature