Octanoic acid 2-[5-((E)-2-bromo-vinyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yl ester

ID: ALA238635

Chembl Id: CHEMBL238635

PubChem CID: 6476766

Max Phase: Preclinical

Molecular Formula: C19H27BrN2O7

Molecular Weight: 475.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCC(=O)O[C@H]1[C@H](O)[C@@H](CO)O[C@H]1n1cc(/C=C/Br)c(=O)[nH]c1=O

Standard InChI:  InChI=1S/C19H27BrN2O7/c1-2-3-4-5-6-7-14(24)29-16-15(25)13(11-23)28-18(16)22-10-12(8-9-20)17(26)21-19(22)27/h8-10,13,15-16,18,23,25H,2-7,11H2,1H3,(H,21,26,27)/b9-8+/t13-,15-,16+,18-/m1/s1

Standard InChI Key:  RDRKUMOEJLAQLK-OLQWOGRFSA-N

Alternative Forms

1. Parent:

   

   ALA238635

   Octanoic acid 2-[5-((E)-2-bromo-vinyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yl ester

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: 475.34

Molecular Weight (Monoisotopic): 474.1002

AlogP: 1.43

#Rotatable Bonds: 10

Polar Surface Area: 130.85

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.74

CX Basic pKa: ┄

CX LogP: 1.97

CX LogD: 1.97

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.34

Np Likeness Score: 1.22

References

1. Manfredini S, Baraldi PG, Durini E, Porcu L, Angusti A, Vertuani S, Solaroli N, De Clercq E, Karlsson A, Balzarini J..  (2001)  Design, synthesis and enzymatic activity of highly selective human mitochondrial thymidine kinase inhibitors.,  11  (10): [PMID:11392548] [10.1016/s0960-894x(01)00207-4]

2. Ciliberti N, Manfredini S, Angusti A, Durini E, Solaroli N, Vertuani S, Buzzoni L, Bonache MC, Ben-Shalom E, Karlsson A, Saada A, Balzarini J..  (2007)  Novel selective human mitochondrial kinase inhibitors: design, synthesis and enzymatic activity.,  15  (8): [PMID:17324575] [10.1016/j.bmc.2007.01.049]

3. Van Poecke S, Negri A, Gago F, Van Daele I, Solaroli N, Karlsson A, Balzarini J, Van Calenbergh S..  (2010)  3'-[4-Aryl-(1,2,3-triazol-1-yl)]-3'-deoxythymidine analogues as potent and selective inhibitors of human mitochondrial thymidine kinase.,  53  (7): [PMID:20218622] [10.1021/jm901532h]

Source

Source(1):

• Scientific Literature