Page last updated: 2024-11-12

dihydrokavain

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

dihydrokavain: inhibits binding of batrachotoxinin-A 20-alpha-benzoate to receptor site 2 of voltage-gated sodium channels [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID10220256
CHEMBL ID569329
CHEBI ID157713
SCHEMBL ID5672433
MeSH IDM0293866

Synonyms (51)

Synonym
MEGXP0_001719
nsc 112163
2h-pyran-2-one, 5,6-dihydro-4-methoxy-6-(2-phenylethyl)-, (s)-
2h-pyran-2-one, 5,6-dihydro-4-methoxy-6-phenethyl-
marindinin
ACON1_000519
ACON0_000958
kawain, dihydro-
dihydrokavain
nsc-112163
nsc112163
dihydrokawain
2h-pyran-2-one,6-dihydro-4-methoxy-6-phenethyl-
kavain, dihydro-
2h-pyran-2-one,6-dihydro-4-methoxy-6-(2-phenylethyl)-, (s)-
7,8-dihydro-kawain
587-63-3
NCGC00169002-01
BRD-K31961554-001-01-9
CHEBI:157713
(2s)-4-methoxy-2-(2-phenylethyl)-2,3-dihydropyran-6-one
(+)-dihydrokavain
CHEMBL569329
NCGC00258586-01
tox21_201033
dtxsid8033433 ,
cas-587-63-3
dtxcid501476403
unii-nw8zgw9xrz
nw8zgw9xrz ,
ccris 9371
S9446
2h-pyran-2-one, 5,6-dihydro-4-methoxy-6-(2-phenylethyl)-, (6s)-
dihydrokawain [mi]
(6s)-5,6-dihydro-4-methoxy-6-(2-phenylethyl)-2h-pyran-2-one
(s)-(+)-dihydrokawain
SCHEMBL5672433
CS-4244
AC-34187
Q-100678
HY-N0920
AKOS028109012
(s)-(+)-7,8-dihydrokavain, analytical standard
NCGC00169002-05
mfcd01694032
(s)-4-methoxy-6-phenethyl-5,6-dihydro-2h-pyran-2-one
(s)-(+)-7,8-dihydrokavain
HMS3887C05
CCG-266804
Q27285076
MS-23329

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"To examine the bioavailability of kavalactones in vitro and the possible differences in their bioavailability because of variations in either chemical structure or the method of extraction used."( Permeability studies of Kavalactones using a Caco-2 cell monolayer model.
Blanchfield, JT; Bone, KM; Lehmann, RP; Matthias, A; Penman, KG; Toth, I, 2007
)
0.34
"Caco-2 cell monolayers were used to determine the potential bioavailability of kavalactones."( Permeability studies of Kavalactones using a Caco-2 cell monolayer model.
Blanchfield, JT; Bone, KM; Lehmann, RP; Matthias, A; Penman, KG; Toth, I, 2007
)
0.34
" Not all differences in their bioavailability can be related to kavalactone structural differences as it appears that bioavailability may also be affected by co-extracted compounds."( Permeability studies of Kavalactones using a Caco-2 cell monolayer model.
Blanchfield, JT; Bone, KM; Lehmann, RP; Matthias, A; Penman, KG; Toth, I, 2007
)
0.34
" In the range 2-4mM of host, solubility of DHK was increased only two-fold, but being beta-CyD also a penetration enhancer, in vivo studies will be performed to clarify a possible role of the complex on the bioavailability of DHK."( Cyclodextrins as carriers for kavalactones in aqueous media: spectroscopic characterization of (S)-7,8-dihydrokavain and beta-cyclodextrin inclusion complex.
Bergonzi, MC; Bilia, AR; Di Bari, L; Pescitelli, G; Vincieri, FF, 2010
)
0.58
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
2-pyranonesA pyranone based on the structure of 2H-pyran-2-one and its substituted derivatives.
aromatic etherAny ether in which the oxygen is attached to at least one aryl substituent.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (13)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
SMAD family member 2Homo sapiens (human)Potency20.28830.173734.304761.8120AID1346859
SMAD family member 3Homo sapiens (human)Potency20.28830.173734.304761.8120AID1346859
AR proteinHomo sapiens (human)Potency32.90250.000221.22318,912.5098AID1259243; AID743036; AID743063
estrogen receptor 2 (ER beta)Homo sapiens (human)Potency25.32980.000657.913322,387.1992AID1259377
nuclear receptor subfamily 1, group I, member 3Homo sapiens (human)Potency39.37570.001022.650876.6163AID1224838; AID1224839; AID1224893
progesterone receptorHomo sapiens (human)Potency40.14500.000417.946075.1148AID1346795
retinoic acid nuclear receptor alpha variant 1Homo sapiens (human)Potency28.42050.003041.611522,387.1992AID1159552
retinoid X nuclear receptor alphaHomo sapiens (human)Potency45.41980.000817.505159.3239AID1159527
estrogen-related nuclear receptor alphaHomo sapiens (human)Potency80.09990.001530.607315,848.9004AID1224848
pregnane X nuclear receptorHomo sapiens (human)Potency63.62560.005428.02631,258.9301AID1346982
estrogen nuclear receptor alphaHomo sapiens (human)Potency1.43630.000229.305416,493.5996AID743075
vitamin D (1,25- dihydroxyvitamin D3) receptorHomo sapiens (human)Potency4.54200.023723.228263.5986AID743223
histone deacetylase 9 isoform 3Homo sapiens (human)Potency56.70640.037617.082361.1927AID1259364
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (29)

Assay IDTitleYearJournalArticle
AID1090307Antifungal activity against Hypocrea rufa assessed as growth inhibition at 10 ppm after 4 days relative to untreated control2006Journal of agricultural and food chemistry, Feb-08, Volume: 54, Issue:3
Herbicidal and Fungicidal Activities of Lactones in Kava (Piper methysticum).
AID1090306Herbicidal activity against Lactuca sativa cv. Great Lakes 366 (lettuce) assessed as inhibition of germination at 1 ppm relative to untreated control2006Journal of agricultural and food chemistry, Feb-08, Volume: 54, Issue:3
Herbicidal and Fungicidal Activities of Lactones in Kava (Piper methysticum).
AID1090317Herbicidal activity against Echinochloa crus-galli (barnyard grass) assessed as inhibition of shoot length at 10 ppm relative to untreated control2006Journal of agricultural and food chemistry, Feb-08, Volume: 54, Issue:3
Herbicidal and Fungicidal Activities of Lactones in Kava (Piper methysticum).
AID1090302Herbicidal activity against Lactuca sativa cv. Great Lakes 366 (lettuce) assessed as inhibition of root length at 1 ppm relative to untreated control2006Journal of agricultural and food chemistry, Feb-08, Volume: 54, Issue:3
Herbicidal and Fungicidal Activities of Lactones in Kava (Piper methysticum).
AID1090308Antifungal activity against Hypocrea rufa assessed as growth inhibition at 50 ppm after 4 days relative to untreated control2006Journal of agricultural and food chemistry, Feb-08, Volume: 54, Issue:3
Herbicidal and Fungicidal Activities of Lactones in Kava (Piper methysticum).
AID1090299Herbicidal activity against Echinochloa crus-galli (barnyard grass) assessed as inhibition of germination at 10 ppm relative to untreated control2006Journal of agricultural and food chemistry, Feb-08, Volume: 54, Issue:3
Herbicidal and Fungicidal Activities of Lactones in Kava (Piper methysticum).
AID1090301Herbicidal activity against Lactuca sativa cv. Great Lakes 366 (lettuce) assessed as inhibition of root length at 10 ppm relative to untreated control2006Journal of agricultural and food chemistry, Feb-08, Volume: 54, Issue:3
Herbicidal and Fungicidal Activities of Lactones in Kava (Piper methysticum).
AID666150Inhibition of PA endonuclease at 10 uM2011PloS one, , Volume: 6, Issue:5
Anti-influenza activity of marchantins, macrocyclic bisbibenzyls contained in liverworts.
AID1090315Herbicidal activity against Echinochloa crus-galli (barnyard grass) assessed as inhibition of root length at 10 ppm relative to untreated control2006Journal of agricultural and food chemistry, Feb-08, Volume: 54, Issue:3
Herbicidal and Fungicidal Activities of Lactones in Kava (Piper methysticum).
AID1090312Antifungal activity against Fusarium solani assessed as growth inhibition at 10 ppm after 4 days relative to untreated control2006Journal of agricultural and food chemistry, Feb-08, Volume: 54, Issue:3
Herbicidal and Fungicidal Activities of Lactones in Kava (Piper methysticum).
AID1090314Antifungal activity against Colletotrichum gloeosporioides assessed as growth inhibition at 10 ppm after 4 days relative to untreated control2006Journal of agricultural and food chemistry, Feb-08, Volume: 54, Issue:3
Herbicidal and Fungicidal Activities of Lactones in Kava (Piper methysticum).
AID1090304Herbicidal activity against Lactuca sativa cv. Great Lakes 366 (lettuce) assessed as inhibition of shoot length at 1 ppm relative to untreated control2006Journal of agricultural and food chemistry, Feb-08, Volume: 54, Issue:3
Herbicidal and Fungicidal Activities of Lactones in Kava (Piper methysticum).
AID1090298Herbicidal activity against Echinochloa crus-galli (barnyard grass) assessed as inhibition of shoot length at 1 ppm relative to untreated control2006Journal of agricultural and food chemistry, Feb-08, Volume: 54, Issue:3
Herbicidal and Fungicidal Activities of Lactones in Kava (Piper methysticum).
AID1090310Antifungal activity against Fusarium oxysporum assessed as growth inhibition at 10 ppm after 4 days relative to untreated control2006Journal of agricultural and food chemistry, Feb-08, Volume: 54, Issue:3
Herbicidal and Fungicidal Activities of Lactones in Kava (Piper methysticum).
AID1090311Antifungal activity against Fusarium solani assessed as growth inhibition at 50 ppm after 4 days relative to untreated control2006Journal of agricultural and food chemistry, Feb-08, Volume: 54, Issue:3
Herbicidal and Fungicidal Activities of Lactones in Kava (Piper methysticum).
AID666151Inhibition of PA endonuclease at 1 uM2011PloS one, , Volume: 6, Issue:5
Anti-influenza activity of marchantins, macrocyclic bisbibenzyls contained in liverworts.
AID1090309Antifungal activity against Fusarium oxysporum assessed as growth inhibition at 50 ppm after 4 days relative to untreated control2006Journal of agricultural and food chemistry, Feb-08, Volume: 54, Issue:3
Herbicidal and Fungicidal Activities of Lactones in Kava (Piper methysticum).
AID1090300Herbicidal activity against Echinochloa crus-galli (barnyard grass) assessed as inhibition of germination at 1 ppm relative to untreated control2006Journal of agricultural and food chemistry, Feb-08, Volume: 54, Issue:3
Herbicidal and Fungicidal Activities of Lactones in Kava (Piper methysticum).
AID1090303Herbicidal activity against Lactuca sativa cv. Great Lakes 366 (lettuce) assessed as inhibition of shoot length at 10 ppm relative to untreated control2006Journal of agricultural and food chemistry, Feb-08, Volume: 54, Issue:3
Herbicidal and Fungicidal Activities of Lactones in Kava (Piper methysticum).
AID1090305Herbicidal activity against Lactuca sativa cv. Great Lakes 366 (lettuce) assessed as inhibition of germination at 10 ppm relative to untreated control2006Journal of agricultural and food chemistry, Feb-08, Volume: 54, Issue:3
Herbicidal and Fungicidal Activities of Lactones in Kava (Piper methysticum).
AID447711Inhibition of TNF-alpha-induced NF-kappaB expressed in human A549 cells treated 1 hr after TNFalpha challenge measured after 6 hrs by luciferase reporter gene assay2009Bioorganic & medicinal chemistry letters, Oct-01, Volume: 19, Issue:19
Identification of methysticin as a potent and non-toxic NF-kappaB inhibitor from kava, potentially responsible for kava's chemopreventive activity.
AID447716Hepatotoxicity against mouse Hepa-1c1c7 cells after 48 hrs by celltiter blue assay2009Bioorganic & medicinal chemistry letters, Oct-01, Volume: 19, Issue:19
Identification of methysticin as a potent and non-toxic NF-kappaB inhibitor from kava, potentially responsible for kava's chemopreventive activity.
AID1090316Herbicidal activity against Echinochloa crus-galli (barnyard grass) assessed as inhibition of root length at 1 ppm relative to untreated control2006Journal of agricultural and food chemistry, Feb-08, Volume: 54, Issue:3
Herbicidal and Fungicidal Activities of Lactones in Kava (Piper methysticum).
AID1090313Antifungal activity against Colletotrichum gloeosporioides assessed as growth inhibition at 50 ppm after 4 days relative to untreated control2006Journal of agricultural and food chemistry, Feb-08, Volume: 54, Issue:3
Herbicidal and Fungicidal Activities of Lactones in Kava (Piper methysticum).
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1347160Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1347159Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (28)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (7.14)18.7374
1990's1 (3.57)18.2507
2000's12 (42.86)29.6817
2010's10 (35.71)24.3611
2020's3 (10.71)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 30.54

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index30.54 (24.57)
Research Supply Index3.40 (2.92)
Research Growth Index5.59 (4.65)
Search Engine Demand Index36.71 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (30.54)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other29 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]