ID: ALA211120

Max Phase: Preclinical

Molecular Formula: C29H31N3O2

Molecular Weight: 453.59

Molecule Type: Small molecule

Representations

Synonyms (1): 1-(6-Tritylaminohexyl)Uracil
Synonyms from Alternative Forms(1):

Canonical SMILES:  O=c1ccn(CCCCCCNC(c2ccccc2)(c2ccccc2)c2ccccc2)c(=O)[nH]1

Standard InChI:  InChI=1S/C29H31N3O2/c33-27-20-23-32(28(34)31-27)22-13-2-1-12-21-30-29(24-14-6-3-7-15-24,25-16-8-4-9-17-25)26-18-10-5-11-19-26/h3-11,14-20,23,30H,1-2,12-13,21-22H2,(H,31,33,34)

Standard InChI Key:  VSXSPOQXSWUNCD-UHFFFAOYSA-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: 453.59

Molecular Weight (Monoisotopic): 453.2416

AlogP: 4.68

#Rotatable Bonds: 11

Polar Surface Area: 66.89

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 10.07

CX Basic pKa: 8.48

CX LogP: 5.47

CX LogD: 4.50

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.26

Np Likeness Score: -0.49

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. 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]

4. 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