ID: ALA377582

Max Phase: Preclinical

Molecular Formula: C28H27N3O4

Molecular Weight: 469.54

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=c1ccn([C@H]2C[C@H](O)[C@@H](CNC(c3ccccc3)(c3ccccc3)c3ccccc3)O2)c(=O)[nH]1

Standard InChI:  InChI=1S/C28H27N3O4/c32-23-18-26(31-17-16-25(33)30-27(31)34)35-24(23)19-29-28(20-10-4-1-5-11-20,21-12-6-2-7-13-21)22-14-8-3-9-15-22/h1-17,23-24,26,29,32H,18-19H2,(H,30,33,34)/t23-,24+,26+/m0/s1

Standard InChI Key:  TUZNCXRMWDUVNX-BFLUCZKCSA-N

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

Properties

Molecular Weight: 469.54

Molecular Weight (Monoisotopic): 469.2002

AlogP: 2.77

#Rotatable Bonds: 7

Polar Surface Area: 96.35

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.71

CX Basic pKa: 7.45

CX LogP: 3.97

CX LogD: 3.64

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.36

Np Likeness Score: 0.31

References

1. Nguyen C, Ruda GF, Schipani A, Kasinathan G, Leal I, Musso-Buendia A, Kaiser M, Brun R, Ruiz-Pérez LM, Sahlberg BL, Johansson NG, Gonzalez-Pacanowska D, Gilbert IH..  (2006)  Acyclic nucleoside analogues as inhibitors of Plasmodium falciparum dUTPase.,  49  (14): [PMID:16821778] [10.1021/jm060126s]

2. McCarthy O, Musso-Buendia A, Kaiser M, Brun R, Ruiz-Perez LM, Johansson NG, Pacanowska DG, Gilbert IH..  (2009)  Design, synthesis and evaluation of novel uracil acetamide derivatives as potential inhibitors of Plasmodium falciparum dUTP nucleotidohydrolase.,  44  (2): [PMID:18619713] [10.1016/j.ejmech.2008.05.018]

3. Baragaña B, McCarthy O, Sánchez P, Bosch-Navarrete C, Kaiser M, Brun R, Whittingham JL, Roberts SM, Zhou XX, Wilson KS, Johansson NG, González-Pacanowska D, Gilbert IH..  (2011)  β-Branched acyclic nucleoside analogues as inhibitors of Plasmodium falciparum dUTPase.,  19  (7): [PMID:21411327] [10.1016/j.bmc.2011.02.012]

4. Recio E, Musso-Buendía A, Vidal AE, Ruda GF, Kasinathan G, Nguyen C, Ruiz-Pérez LM, Gilbert IH, González-Pacanowska D..  (2011)  Site-directed mutagenesis provides insights into the selective binding of trityl derivatives to Plasmodium falciparum dUTPase.,  46  (8): [PMID:21600680] [10.1016/j.ejmech.2011.04.052]

5. Hampton SE, Schipani A, Bosch-Navarrete C, Recio E, Kaiser M, Kahnberg P, González-Pacanowska D, Johansson NG, Gilbert IH..  (2013)  Investigation of acyclic uridine amide and 5'-amido nucleoside analogues as potential inhibitors of the Plasmodium falciparum dUTPase.,  21  (18): [PMID:23916149] [10.1016/j.bmc.2013.07.004]

Source

Source(1):

• Scientific Literature