Page last updated: 2024-12-11

grayanotoxin i

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

Description

grayanotoxin I: RN given refers to (3beta,6beta,14R)-isomer; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

grayanotoxin I : A tetracyclic diterpenoid that is grayanotoxane in which the pro-R hydrogen at position 14 is substituted by an acetoxy group and in which the 3beta-, 5-, 6beta-, 10-, and 16- positions are substituted by hydroxy groups. [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]

Cross-References

ID SourceID
PubMed CID9548612
CHEMBL ID3085397
CHEBI ID5542
SCHEMBL ID3229044
MeSH IDM0041440

Synonyms (35)

Synonym
asebotoxin
(14r)-3beta,5,6beta,10,16-pentahydroxygrayanotoxan-14-yl acetate
(3beta,6beta,14r)-grayanotoxane-3,5,6,10,14,16-hexol, 14-acetate
perhydro-2beta,4alpha,8alpha,11beta,11abeta-pentahydroxy-1,1,4,8-tetramethyl-7,9a-methano-9aalphah-cyclopenta(b)heptalen-12beta-yl acetate
acetylandromedol
CHEBI:5542 ,
grayanotoxane-3,5,6,10,14,16-hexol 14-acetate
rhodotoxin
andromedotoxin
gtx-i
nsc-26711
hsdb 3463
7,9a-methano-9ah-cyclopenta(b)heptalene-2,4,8,11,11a,12(1h)-hexol-, dodecahydro-1,1,4,8-tetramethyl-, 12-acetate, (2s,3as,4ar,7r,8r,9as,11r,11ar,12r)-
7,9a-methano-9ah-cyclopenta(b)heptalene-2,4,8,11,11a,12(1h)-hexol, dodecahydro-1,1,4,8-tetramethyl-, 12-acetate (2s,3as,4r,4ar,7r,8r,9as,11r,11ar,12r)-
g-i
nsc 26711
brn 2065643
perhydro-2beta,4alpha,8alpha,11beta,11abeta-pentahydroxy-1,1,4,8-tetramethyl-7,9a-methano-9aalphah-cyclopenta(b)heptalen-12beta-yl acetat
grayanotoxane-3,5,6,10,14,16-hexol, 14-acetate, (3beta,6beta,14r)-
ACON0_000384
MEGXP0_001761
ACON1_000099
grayanotoxin i
NCGC00168796-01
w4e6hc3t2b ,
unii-w4e6hc3t2b
CHEMBL3085397
grayanotoxin i [mi]
grayanotoxane-3,5,6,10,14,16-hexol, 14-acetate, (3.beta.,6.beta.,14r)-
7,9a-methano-9ah-cyclopenta(b)heptalene-2,4,8,11,11a,12(1h)- hexol-, dodecahydro-1,1,4,8-tetramethyl-, 12-acetate, (2s,3as,4ar,7r,8r,9as,11r,11ar,12r)-
SCHEMBL3229044
AKOS027326735
NCGC00168796-02
grayanotoxin i (andromedotoxin)
Q27106802

Research Excerpts

Overview

Grayanotoxin I (GTX I) is a diterpenoid extracted from the family of Ericaceae. It binds to Na(+) channels and causes persistent activation.

ExcerptReferenceRelevance
"Grayanotoxin I (GTX I) is a major toxin in leaves of Rhododendron species, where it provides a defence against insect and vertebrate herbivores. "( Grayanotoxin I variation across tissues and species of Rhododendron suggests pollinator-herbivore defence trade-offs.
Egan, PA; Farrell, IW; Fattorini, R; Rosindell, J; Stevenson, PC, 2023
)
3.8
"Grayanotoxin I (GTX I) is a diterpenoid extracted from the family of Ericaceae that binds to Na(+) channels and causes persistent activation. "( On site of action of grayanotoxin in domain 4 segment 6 of rat skeletal muscle sodium channel.
Kimura, T; Kinoshita, E; Seyama, I; Yakehiro, M; Yamaoka, K; Yuki, T, 2000
)
2.07

Toxicity

ExcerptReferenceRelevance
"Developmental toxicity potential of grayanotoxin I (GTX I), a toxic diterpenoid contained in plants of the family Ericaceae, with sodium ionophore activity, was studied in mice and chicks."( Developmental toxicity potential of grayanotoxin I in mice and chicks.
Kobayashi, T; Seyama, I; Yasuda, M, 1990
)
0.83

Bioavailability

ExcerptReferenceRelevance
"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

Dosage Studied

ExcerptRelevanceReference
" Pretreatment with propranolol shifted the dose-response curves for the inotropic effect of both grayanotoxins slightly to the right."( The effects of grayanotoxin I and alpha-dihydrograyanotoxin II on guinea-pig myocardium.
Akera, T; Brody, TM; Frank, M; Iwasa, J; Ku, DD, 1977
)
0.61
" The dose-response curve was shifted to the right in the presence of these blocking agents."( Further evidence for the involvement of Na+ channels in the release of adrenal catecholamine: the effect of scorpion venom and grayanotoxin I.
Ito, S; Nakazato, Y; Ohga, A, 1981
)
0.47
"5 G-I (3 x 10(-5) M) shifted the dose-response curves for noradrenaline (NA), acetylcholine and high-K contractions to the left in a parallel manner and slightly increased the maximal response to these agonists."( Contractions induced by grayanotoxin I in the guinea-pig vas deferens.
Ohizumi, Y, 1983
)
0.57
" A dose-response curve for each GTX analog was constructed using membrane depolarization as an index and assuming a one-to-one stoichiometry."( Structure-activity relationship for D-ring derivatives of grayanotoxin in the squid giant axon.
Baba, N; Iwasa, J; Nakajima, S; Seyama, I; Yakehiro, M; Yamamoto, S, 1993
)
0.53
" The dose-response relation for GTX-modified Na(+) channels was constructed by plotting the normalized slope conductance against GTX concentration."( An analysis of the variations in potency of grayanotoxin analogs in modifying frog sodium channels of differing subtypes.
Furue, T; Imoto, K; Mori, Y; Seyama, I; Yakehiro, M; Yamaoka, K; Yuki, T, 2000
)
0.31
" Approximately 36 h after Japanese pieris ingestion, one of the three remaining anorectic goats was dosed with intravenous lipid emulsion (ILE)."( Treatment of pieris ingestion in goats with intravenous lipid emulsion.
Bischoff, K; Smith, MC; Stump, S, 2014
)
0.4
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Occurs in Manufacturing (1 Product(s))

Product Categories

Product CategoryProducts
Weight Management1

Products

ProductBrandCategoryCompounds Matched from IngredientsDate Retrieved
Naturade VeganSmart Protein & Greens Vanilla Crème -- 22.8 ozNaturadeWeight ManagementVitamin C, Biotin, Chromium, Folate, GI, Iodine, Manganese, Molybdenum, Niacin, Pantothenic Acid, Vitamin B6, Vitamin A, Riboflavin, Selenium, Sugar, Thiamin, Vitamin B12, Vitamin B6, Vitamin D2, Vitamin K2024-11-29 10:47:42

Roles (4)

RoleDescription
phytotoxinAny toxin produced by a plant.
antihypertensive agentAny drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
neuromuscular agentA drug used for its actions on skeletal muscle.
[role 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]

Drug Classes (5)

ClassDescription
tetracyclic diterpenoidA diterpenoid with a tetracyclic skeleton.
pentolA polyol with five hydroxy groups.
tertiary alcoholA tertiary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has three other carbon atoms attached to it.
secondary alcoholA secondary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has two other carbon atoms attached to it.
acetate esterAny carboxylic ester where the carboxylic acid component is acetic acid.
[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]

Bioassays (12)

Assay IDTitleYearJournalArticle
AID1543165Analgesic activity in Kunming mouse model of acetic-acid-induced writhing assessed as inhibition of writhing numbers at 0.2 mg/kg measured for 30 mins relative to control
AID1543167Analgesic activity in Kunming mouse model of acetic-acid-induced writhing assessed as inhibition of writhing numbers at 0.04 to 0.2 mg/kg measured for 30 mins relative to control
AID381258Cytotoxicity against human 9KB cells relative to control
AID977599Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID977602Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID381254Toxicity in ip dosed mouse
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.
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.
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.
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.
AID1159550Human Phosphogluconate dehydrogenase (6PGD) Inhibitor Screening2015Nature cell biology, Nov, Volume: 17, Issue:11
6-Phosphogluconate dehydrogenase links oxidative PPP, lipogenesis and tumour growth by inhibiting LKB1-AMPK signalling.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (115)

TimeframeStudies, This Drug (%)All Drugs %
pre-199045 (39.13)18.7374
1990's17 (14.78)18.2507
2000's19 (16.52)29.6817
2010's30 (26.09)24.3611
2020's4 (3.48)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 14.97

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index14.97 (24.57)
Research Supply Index4.78 (2.92)
Research Growth Index4.57 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (14.97)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews9 (7.63%)6.00%
Case Studies17 (14.41%)4.05%
Observational1 (0.85%)0.25%
Other91 (77.12%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]