5,6-dihydroxy-2-thiophen-2-yl-pyrimidine-4-carboxylic acid 4-methyl-benzylamide

ID: ALA277754

Chembl Id: CHEMBL277754

PubChem CID: 135601762

Max Phase: Preclinical

Molecular Formula: C17H15N3O3S

Molecular Weight: 341.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(CNC(=O)c2nc(-c3cccs3)nc(O)c2O)cc1

Standard InChI:  InChI=1S/C17H15N3O3S/c1-10-4-6-11(7-5-10)9-18-16(22)13-14(21)17(23)20-15(19-13)12-3-2-8-24-12/h2-8,21H,9H2,1H3,(H,18,22)(H,19,20,23)

Standard InChI Key:  BHSASERQYVVBSX-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA277754

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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: 341.39

Molecular Weight (Monoisotopic): 341.0834

AlogP: 2.85

#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: 4.38

CX LogD: 4.09

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.68

Np Likeness Score: -1.67

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