N-(4-chlorobenzyl)-5,6-dihydroxy-2-(thiophen-2-yl)pyrimidine-4-carboxamide

ID: ALA232444

Chembl Id: CHEMBL232444

PubChem CID: 135601984

Max Phase: Preclinical

Molecular Formula: C16H12ClN3O3S

Molecular Weight: 361.81

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCc1ccc(Cl)cc1)c1nc(-c2cccs2)nc(O)c1O

Standard InChI:  InChI=1S/C16H12ClN3O3S/c17-10-5-3-9(4-6-10)8-18-15(22)12-13(21)16(23)20-14(19-12)11-2-1-7-24-11/h1-7,21H,8H2,(H,18,22)(H,19,20,23)

Standard InChI Key:  FSFOUSUJEBSBEN-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA232444

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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: 361.81

Molecular Weight (Monoisotopic): 361.0288

AlogP: 3.20

#Rotatable Bonds: 4

Polar Surface Area: 95.34

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.40

CX Basic pKa: ┄

CX LogP: 4.45

CX LogD: 4.16

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.66

Np Likeness Score: -1.79

References

1. Petrocchi A, Koch U, Matassa VG, Pacini B, Stillmock KA, Summa V..  (2007)  From dihydroxypyrimidine carboxylic acids to carboxamide HIV-1 integrase inhibitors: SAR around the amide moiety.,  17  (2): [PMID:17107799] [10.1016/j.bmcl.2006.10.054]

2. de Melo EB, Ferreira MM..  (2009)  Multivariate QSAR study of 4,5-dihydroxypyrimidine carboxamides as HIV-1 integrase inhibitors.,  44  (9): [PMID:19327872] [10.1016/j.ejmech.2009.03.001]

3. He T, Edwards TC, Xie J, Aihara H, Geraghty RJ, Wang Z..  (2022)  4,5-Dihydroxypyrimidine Methyl Carboxylates, Carboxylic Acids, and Carboxamides as Inhibitors of Human Cytomegalovirus pUL89 Endonuclease.,  65  (7.0): [PMID:35377638] [10.1021/acs.jmedchem.2c00203]

Source

Source(1):

• Scientific Literature