(R,S)-PHPNECA   Click here for help

GtoPdb Ligand ID: 369

Synonyms: (R,S)-2-phenylhydroxypropynyl-NECA | 2-(3-hydroxy-3-phenyl)propyn-1-yladenosine-5'-N-ethyluronamide
Compound class: Synthetic organic
Comment: The reference for our activity data specifies that this compound is the RS-form, therefore a mixture of the (R) and (S)-isomers [1]. The conformation of these isomers is dependent on the position of the phenyl group in relation to the hydroxy group. We do not specify stereochemistry at this position in our image therefore this ligand entry represents the mixture. Note that the ChEMBL entries CHEMBL258534 and CHEMBL224874 are records of the (R) and (S)- stereoisomers of this compound respectively.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 10
Hydrogen bond donors 5
Rotatable bonds 5
Topological polar surface area 168.64
Molecular weight 438.17
XLogP 0.9
No. Lipinski's rules broken 0
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Canonical SMILES CCNC(=O)C1OC(C(C1O)O)n1cnc2c1nc(C#CC(c1ccccc1)O)nc2N
Isomeric SMILES CCNC(=O)[C@H]1O[C@H]([C@H]([C@H]1O)O)n1cnc2c1nc(C#CC(c1ccccc1)O)nc2N
InChI InChI=1S/C21H22N6O5/c1-2-23-20(31)17-15(29)16(30)21(32-17)27-10-24-14-18(22)25-13(26-19(14)27)9-8-12(28)11-6-4-3-5-7-11/h3-7,10,12,15-17,21,28-30H,2H2,1H3,(H,23,31)(H2,22,25,26)/t12?,15-,16+,17+,21-/m1/s1
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Molecular structure representations generated using Open Babel