6-hydroxymelatonin   

GtoPdb Ligand ID: 1347

Synonyms: 6-OH-melatonin | 6-OH-MLT
Compound class: Synthetic organic
Comment: One of the metabolites of the approved drug melatonin.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 2
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 74.35
Molecular weight 248.12
XLogP 0.93
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES COc1cc2c(CCNC(=O)C)c[nH]c2cc1O
Isomeric SMILES COc1cc2c(CCNC(=O)C)c[nH]c2cc1O
InChI InChI=1S/C13H16N2O3/c1-8(16)14-4-3-9-7-15-11-6-12(17)13(18-2)5-10(9)11/h5-7,15,17H,3-4H2,1-2H3,(H,14,16)
InChI Key OMYMRCXOJJZYKE-UHFFFAOYSA-N
References
1. Beresford IJ, Browning C, Starkey SJ, Brown J, Foord SM, Coughlan J, North PC, Dubocovich ML, Hagan RM. (1998)
GR196429: a nonindolic agonist at high-affinity melatonin receptors.
J. Pharmacol. Exp. Ther., 285 (3): 1239-45. [PMID:9618428]
2. Browning C, Beresford I, Fraser N, Giles H. (2000)
Pharmacological characterization of human recombinant melatonin mt(1) and MT(2) receptors.
Br. J. Pharmacol., 129 (5): 877-86. [PMID:10696085]
3. Dubocovich ML. (1985)
Characterization of a retinal melatonin receptor.
J. Pharmacol. Exp. Ther., 234 (2): 395-401. [PMID:2991499]
4. Dubocovich ML, Masana MI, Iacob S, Sauri DM. (1997)
Melatonin receptor antagonists that differentiate between the human Mel1a and Mel1b recombinant subtypes are used to assess the pharmacological profile of the rabbit retina ML1 presynaptic heteroreceptor.
Naunyn Schmiedebergs Arch. Pharmacol., 355 (3): 365-75. [PMID:9089668]