(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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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
Search Google for chemical match using the InChIKey CFBVGSWSOJBYGC-ZYHUDNBSSA-N
Search Google for chemicals with the same backbone CFBVGSWSOJBYGC
UniChem Compound Search for chemical match using the InChIKey CFBVGSWSOJBYGC-ZYHUDNBSSA-N
UniChem Connectivity Search for chemical match using the InChIKey CFBVGSWSOJBYGC-ZYHUDNBSSA-N