Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C15H16O5 |
Molecular Weight | 276.2845 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC(=O)O[C@@H](CCC2=CC=C3OCOC3=C2)C1
InChI
InChIKey=RSIWXFIBHXYNFM-NSHDSACASA-N
InChI=1S/C15H16O5/c1-17-12-7-11(20-15(16)8-12)4-2-10-3-5-13-14(6-10)19-9-18-13/h3,5-6,8,11H,2,4,7,9H2,1H3/t11-/m0/s1
Molecular Formula | C15H16O5 |
Molecular Weight | 276.2845 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Dihydromethysticin is one of the six major kavalactones found in the roots of kava plant. Dihydromethysticin was found to be very effective in producing analgesia in the tail immersion test. Dihydromethysticin kavalactone induces apoptosis in osteosarcoma cells through modulation of PI3K/Akt pathway, disruption of mitochondrial membrane potential and inducing cell cycle arrest. Dihydromethysticin was identified as a promising lung cancer chemopreventive agent. Low concentrations of the kavalactone (+)-dihydromethysticin enhanced the binding of ligands to the GABAA receptors on freeze-dried rat cortex preparations.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: WP254 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26191127 |
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Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12127912 |
2.5 µM [IC50] | ||
Target ID: CHEMBL3622 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12127912 |
0.43 µM [IC50] | ||
Target ID: CHEMBL3397 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12127912 |
13.35 µM [IC50] | ||
Target ID: CHEMBL3356 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12127912 |
14.8 µM [IC50] | ||
Target ID: CHEMBL289 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12127912 |
37.03 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Preventing | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Sources: https://www.ncbi.nlm.nih.gov/pubmed/2401103 |
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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The antinociceptive actions of kava components in mice. | 1990 Jul |
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Effects of kawain and dihydromethysticin on field potential changes in the hippocampus. | 1997 May |
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Therapeutic potential of kava in the treatment of anxiety disorders. | 2002 |
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Effects of herbal components on cDNA-expressed cytochrome P450 enzyme catalytic activity. | 2002 Aug 16 |
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Pharmacokinetics and disposition of the kavalactone kawain: interaction with kava extract and kavalactones in vivo and in vitro. | 2005 Oct |
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Methysticin and 7,8-dihydromethysticin are two major kavalactones in kava extract to induce CYP1A1. | 2011 Dec |
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Dihydromethysticin kavalactone induces apoptosis in osteosarcoma cells through modulation of PI3K/Akt pathway, disruption of mitochondrial membrane potential and inducing cell cycle arrest. | 2015 |
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Dietary Dihydromethysticin Increases Glucuronidation of 4-(Methylnitrosamino)-1-(3-Pyridyl)-1-Butanol in A/J Mice, Potentially Enhancing Its Detoxification. | 2016 Mar |
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Pilot in Vivo Structure-Activity Relationship of Dihydromethysticin in Blocking 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone-Induced O(6)-Methylguanine and Lung Tumor in A/J Mice. | 2017 Sep 28 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26744252
Rat: 1 mg/g of diet
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26191127
Dihydromethysticin induced dose-dependent as well as time-dependent antiproliferative effects against MG-63 cell growth. Cell death and apoptotic body formation was noticed followed dihydromethysticin treatment at various doses. The percentage of apoptotic cells (early apoptosis+late apoptosis) increased from 6.63% in untreated control to 23.92%, 23.81% and 93.9% in 25uM, 75uM and 100uM dihydromethysticin-treated cells respectively.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 19:42:47 GMT 2023
by
admin
on
Fri Dec 15 19:42:47 GMT 2023
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Record UNII |
FZ66MQ73GS
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Record Status |
Validated (UNII)
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Record Version |
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DSLD |
2592 (Number of products:13)
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88308
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DIHYDROMETHYSTICIN
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19902-91-1
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FZ66MQ73GS
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112159
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