(2R,6R) 6-hydroxynorketamine   Click here for help

GtoPdb Ligand ID: 9154

Synonyms: (2R,6R)HNK
Compound class: Synthetic organic
Comment: A recent (April 2016) report [1] shows that the metabolism of racemic ketamine to hydroxynorketamine (HNK) is essential for its antidepressant effects, and that these reside in this entry as the (2R,6R)-HNK enantiomer. In mice these actions are independent of NMDAR inhibition and lack ketamine-related side effects. The (flat) rendering of HNK is PubChem CID 133669. The (2S,6S)-HNK is represented as PubChem CID 71519584 but this showed a decreased antidepressant effect compared to (2R,6R)-HNK.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 1
Topological polar surface area 63.32
Molecular weight 239.07
XLogP 2.16
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES OC1CCCC(C1=O)(N)c1ccccc1Cl
Isomeric SMILES O[C@@H]1CCC[C@@](C1=O)(N)c1ccccc1Cl
InChI InChI=1S/C12H14ClNO2/c13-9-5-2-1-4-8(9)12(14)7-3-6-10(15)11(12)16/h1-2,4-5,10,15H,3,6-7,14H2/t10-,12-/m1/s1
InChI Key CFBVGSWSOJBYGC-ZYHUDNBSSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(2R,6R)-2-amino-2-(2-chlorophenyl)-6-hydroxycyclohexan-1-one
Synonyms Click here for help
(2R,6R)HNK
Database Links Click here for help
GtoPdb PubChem SID 315661239
PubChem CID 89504167
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