Compound: 6beta-Naltrexol
SMILES: O1c2c(O)ccc3c2[C@@]45[C@@H]1[C@H](O)CC[C@@]4(O)[C@H](N(CC6CC6)CC5)C3
InChIKey: JLVNEHKORQFVQJ-PYIJOLGTSA-N
Synonyms: 6beta-Naltrexol, 49625-89-0, beta-Naltrexol, AIKO-150, 6beta-Hydroxynaltrexone, DTXSID80197942, J0W963M37T, .BETA.-NALTREXOL, 6.BETA.-NALTREXOL, 6.BETA.-HYDROXYNALTREXONE, Morphinan-3,6,14-triol, 17-(cyclopropylmethyl)-4,5-epoxy-, (5.alpha.,6.beta.)-, 17-(Cyclopropylmethyl)-4,5-epoxymorphinan-3,6beta,14-triol, Morphinan-3,6,14-triol, 17-(cyclopropylmethyl)-4,5-epoxy-, (5alpha,6beta)-, RefChem:544403, DTXCID40120433, 6alpha-Naltrexol, 6|A-Naltrexol, 6alpha-Hydroxynaltrexone, alpha-Naltrexol, 6b-Naltrexol, (4R,4aS,7R,7aR,12bS)-3-(cyclopropylmethyl)-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,7,9-triol, CHEMBL140278, EN 2260, Naltrexone-6-beta-ol, 6 alpha-hydroxynaltrexone, 17-(Cyclopropylmethyl)-4,5alpha-epoxymorphinan-3,6alpha,14-triol, Morphinan-3,6alpha,14-triol, 17-(cyclopropylmethyl)-4,5alpha-epoxy-, 6-alpha-naltrexol, 6b-Naltrexol (1.0 mg/mL in Methanol), Naltrexone impurity 31, 6?-NALTREXOL, UNII-J0W963M37T, 6-Naltrexol, JLVNEHKORQFVQJ-PYIJOLGTSA-N, Morphinan-3,6,14-triol, 17-(cyclopropylmethyl)-4,5-epoxy-, (5a,6ss)-; (5a,6ss)-17-(Cyclopropylmethyl)-4,5-epoxymorphinan-3,6,14-triol; 17-(Cyclopropylmethyl)-4,5a-epoxy-3,14-dihydroxymorphinan-6ss-ol; 6ss-Hydroxynaltrexone; 6ss-Naltrexol; ss-Naltrexol, 6-Beta-naltrexol hcl, N-Cyclopropylmethyl-7,8-dihydro-14-hydroxynorisomorphine, 6-|A-Naltrexol HCl, SCHEMBL679700, orb2567150, SCHEMBL29379302, CHEBI:192658, ARD159640, BDBM50001709, 6-beta-Naltrexol, 1mg/ml in Methanol, NCGC00165851-01, DA-49953, HY-108229, CS-0027591, NS00003924, G87745, Q19598102, 17-(Cyclopropylmethyl)-5alpha-4,5-epoxymorphinan-3,6beta,14-triol, 17-Cyclopropylmethyl-4,5alpha-epoxy-3,6beta,14-trihydroxymorphinan, (4R,4aS,7R,7aR,12bS)-3-(cyclopropylmethyl)-1,2,3,4,5,6,7,7a-octahydro-4aH-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,7,9-triol, (4R,4aS,7R,7aR,12bS)-3-(cyclopropylmethyl)-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzouro[3,2-e]isoquinoline-4a,7,9-triol, 17-(Cyclopropylmethyl)-4,5-epoxy-(5?,6?)-morphinan-3,6,14-triol; 6?-Hydroxynaltrexone; ?-Naltrexol;, 4-cyclopropylmethyl-(13R)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7,9,11(18)-triene-10,14,17-triol
Theoretical properties:
molecular_formula: C20H25NO4
molecular_weight: 343.4 g/mol
exact_mass: 343.17835828 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 3
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 2
heavy_atom_count: 25
topological_polar_surface_area: 73.2 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
{"pubchem": "6alpha-Naltrexol is a member of phenanthrenes.", "chebi": null, "chembl": "Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.", "wikipedia": "6\u03b2-Naltrexol, or 6\u03b2-hydroxynaltrexone (developmental code name AIKO-150), is a peripherally-selective opioid receptor antagonist related to naltrexone. It is a major active metabolite of naltrexone formed by hepatic dihydrodiol dehydrogenase enzymes. With naltrexone therapy, 6\u03b2-naltrexol is present at approximately 10- to 30-fold higher concentrations than naltrexone at steady state due to extensive first-pass metabolism of naltrexone into 6\u03b2-naltrexol. In addition to being an active metabolite of naltrexone, 6\u03b2-naltrexol was itself studied for the treatment of opioid-induced constipation. It was found to be effective and well-tolerated, and did not precipitate opioid withdrawal symptoms or interfere with opioid pain relief, but development was not further pursued.\n6\u03b2-Naltrexol binds to the opioid receptors with affinity (Ki) values of 2.12 nM for the \u03bc-opioid receptor (MOR), 7.24 nM for the \u03ba-opioid receptor (KOR), and 213 nM for the \u03b4-opioid receptor (DOR). Hence, 6\u03b2-naltrexol shows 3.5-fold selectivity for the MOR over the KOR and 100-fold selectivity for the MOR over the DOR. Relative to naltrexone, 6\u03b2-naltrexol has about half the affinity for the MOR. In contrast to naltrexone, 6\u03b2-naltrexol is a neutral antagonist of the MOR (as opposed to an inverse agonist) and can antagonize the actions of both agonists and inverse agonists at the receptor.\n6\u03b2-Naltrexol is said to have very limited capacity to cross the blood\u2013brain barrier. However, 6\u03b2-naltrexol is still able to cross into the brain and produce central opioid receptor antagonism at sufficient levels. In animal studies, 6\u03b2-naltrexol showed about 10-fold separation in potency between peripheral and central opioid antagonism, whereas naltrexone showed no separation. Because it is a MOR neutral antagonist and hence does not reduce basal MOR signaling, 6\u03b2-naltrexol shows much lower potential for producing opioid withdrawal symptoms than naltrexone at doses achieving similar central opioid blockade in animal studies. Due to the very high levels of 6\u03b2-naltrexol that occur during naltrexone therapy, 6\u03b2-naltrexol may contribute to the central opioid receptor antagonism of naltrexone."}