10,10-Dioxo-9,10-dihydro-10lambda*6*-thioxanthene-9-carboxylic acid [(2R,3S,5R)-5-(5-ethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl]-amide

ID: ALA42459

Chembl Id: CHEMBL42459

PubChem CID: 5275944

Max Phase: Preclinical

Molecular Formula: C25H25N3O7S

Molecular Weight: 511.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1cn([C@H]2C[C@H](O)[C@@H](CNC(=O)C3c4ccccc4S(=O)(=O)c4ccccc43)O2)c(=O)[nH]c1=O

Standard InChI:  InChI=1S/C25H25N3O7S/c1-2-14-13-28(25(32)27-23(14)30)21-11-17(29)18(35-21)12-26-24(31)22-15-7-3-5-9-19(15)36(33,34)20-10-6-4-8-16(20)22/h3-10,13,17-18,21-22,29H,2,11-12H2,1H3,(H,26,31)(H,27,30,32)/t17-,18+,21+/m0/s1

Standard InChI Key:  VJODWSHHDKRNOJ-WAOWUJCRSA-N

Alternative Forms

1. Parent:

   

   ALA42459

   N-[[(2R,3S,5R)-5-(5-ethyl-2,4-dioxo-pyrimidin-1-yl)-3-hydroxy-tetrahydrofuran-2-yl]methyl]-10,10-dioxo-9H-thioxanthene-9-carboxamide

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: 511.56

Molecular Weight (Monoisotopic): 511.1413

AlogP: 0.84

#Rotatable Bonds: 5

Polar Surface Area: 147.56

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.95

CX Basic pKa: ┄

CX LogP: 1.53

CX LogD: 1.53

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.46

Np Likeness Score: -0.25

References

1. Martin JA, Lambert RW, Merrett JH, Parkes KE, Thomas GJ, Baker SJ, Bushnell DJ, Cansfield JE, Dunsdon SJ, Freeman AC, Hopkins RA, Johns IR, Keech E, Simmonite H, Walmsley A, Wong Kai-In P, Holland M..  (2001)  Nucleoside analogues as highly potent and selective inhibitors of herpes simplex virus thymidine kinase.,  11  (13): [PMID:11425530] [10.1016/s0960-894x(01)00256-6]

Source

Source(1):

• Scientific Literature