Compounds > cucurbitacin I 2-O-beta-D-glucopyranoside
Page last updated: 2024-11-11

cucurbitacin I 2-O-beta-D-glucopyranoside

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

Description

cucurbitacin I 2-O-beta-D-glucopyranoside : A triterpenoid saponin that is cucurbitacin I attached to a beta-D-glucopyranosyl residue at position 2 via a glycosidic linkage. It has been isolated from Machilus yaoshansis. [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]

FloraRankFlora DefinitionFamilyFamily Definition
Machilusgenus[no description available]LauraceaeA family of mainly aromatic evergreen plants in the order Laurales. The laurel family includes 2,200 species in 45 genera and from these are derived medicinal extracts, essential oils, camphor and other products.[MeSH]

Cross-References

ID SourceID
PubMed CID6441519
CHEMBL ID1765380
CHEBI ID68917

Synonyms (17)

Synonym
beta-glucoside de la cucurbitacine (i)
cucurbitacine-i-glucoside
19-nor-9-beta,10-alpha-lanosta-1,5,23-triene-3,11,22-trione, 2-(beta-d-glucopyranosyloxy)-9-methyl-16,20,25-trihydroxy-
NCGC00179885-01
ACON1_002046
BRD-K10934705-001-01-9
(8s,9r,10r,13r,14s,16r,17r)-17-[(e,2r)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-16-hydroxy-4,4,9,13,14-pentamethyl-2-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-8,10,12,15,16,17-hexahydro-7h-cyclopenta[a]phenanthrene-3,11-dione
chebi:68917 ,
CHEMBL1765380
29803-94-9
cucurbitacine i glucoside
(4r,9beta,16alpha,23e)-16,20,25-trihydroxy-9,10,14-trimethyl-1,11,22-trioxo-4,9-cyclo-9,10-secocholesta-2,5,23-trien-2-yl beta-d-glucopyranoside
cucurbitacin i 2-o-beta-d-glucopyranoside
NCGC00179885-03
Q27137272
compound np-002365
AKOS040735120

Research Excerpts

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
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[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
beta-D-glucosideAny D-glucoside in which the anomeric centre has beta-configuration.
cucurbitacinAny one of a class of tetracyclic triterpenoids, formally derived from the triterpene hydrocarbon cucurbitane, developed by some plants (especially those of the family Cucurbitaceaeas) as a defence mechanism against herbivores.
monosaccharide derivativeA carbohydrate derivative that is formally obtained from a monosaccharide.
triterpenoid saponinA terpene glycoside in which the terpene moiety is a triterpenoid.
tertiary alpha-hydroxy ketoneAn alpha-hydroxy ketone in which the carbonyl group and the hydroxy group are linked by a carbon bearing two organyl groups.
[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 (19)

Assay IDTitleYearJournalArticle
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.
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.
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.
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.
AID592721Cytotoxicity against rat HSC-T6 cell after 24 hrs by MTT assay2011Bioorganic & medicinal chemistry, Apr-15, Volume: 19, Issue:8
In vitro and QSAR studies of cucurbitacins on HepG2 and HSC-T6 liver cell lines.
AID592718Ratio of IC50 to EC50 for hepatoprotective activity in human HepG2 cells2011Bioorganic & medicinal chemistry, Apr-15, Volume: 19, Issue:8
In vitro and QSAR studies of cucurbitacins on HepG2 and HSC-T6 liver cell lines.
AID592722Antiproliferative activity against serum-stimulated rat HSC-T6 cells after 24 hrs by MTT assay2011Bioorganic & medicinal chemistry, Apr-15, Volume: 19, Issue:8
In vitro and QSAR studies of cucurbitacins on HepG2 and HSC-T6 liver cell lines.
AID633484Cytotoxicity against human BCG823 cells after 96 hrs by MTT assay2011Journal of natural products, Nov-28, Volume: 74, Issue:11
Cucurbitane glucosides from the root of Machilus yaoshansis.
AID592714Cytotoxicity against human HepG2 cells after 24 hrs assessed as inhibition of cell viability by MTT assay2011Bioorganic & medicinal chemistry, Apr-15, Volume: 19, Issue:8
In vitro and QSAR studies of cucurbitacins on HepG2 and HSC-T6 liver cell lines.
AID592724Hepatoprotective activity in human HepG2 cells assessed as protection against cell damage after 24 hrs by MTT assay2011Bioorganic & medicinal chemistry, Apr-15, Volume: 19, Issue:8
In vitro and QSAR studies of cucurbitacins on HepG2 and HSC-T6 liver cell lines.
AID633486Antiinflammatory activity in C57BL6J mouse peritoneal macrophages assessed as inhibition of LPS-stimulated TNFalpha secretion at 10 uM after 24 hrs by MTT assay2011Journal of natural products, Nov-28, Volume: 74, Issue:11
Cucurbitane glucosides from the root of Machilus yaoshansis.
AID592719Cytotoxicity against human HeLa cells after 24 hrs by MTT assay2011Bioorganic & medicinal chemistry, Apr-15, Volume: 19, Issue:8
In vitro and QSAR studies of cucurbitacins on HepG2 and HSC-T6 liver cell lines.
AID633485Cytotoxicity against human A549 cells after 96 hrs by MTT assay2011Journal of natural products, Nov-28, Volume: 74, Issue:11
Cucurbitane glucosides from the root of Machilus yaoshansis.
AID633482Cytotoxicity against human HCT8 cells after 96 hrs by MTT assay2011Journal of natural products, Nov-28, Volume: 74, Issue:11
Cucurbitane glucosides from the root of Machilus yaoshansis.
AID592723Ratio of IC50 to EC50 for antiproliferative activity in rat HSC-T6 cells2011Bioorganic & medicinal chemistry, Apr-15, Volume: 19, Issue:8
In vitro and QSAR studies of cucurbitacins on HepG2 and HSC-T6 liver cell lines.
AID633481Cytotoxicity against human A2780 cells after 96 hrs by MTT assay2011Journal of natural products, Nov-28, Volume: 74, Issue:11
Cucurbitane glucosides from the root of Machilus yaoshansis.
AID592715Hepatoprotective activity in human HepG2 cells assessed as inhibition of CCl4-induced toxicity after 24 hrs by MTT assay2011Bioorganic & medicinal chemistry, Apr-15, Volume: 19, Issue:8
In vitro and QSAR studies of cucurbitacins on HepG2 and HSC-T6 liver cell lines.
AID633483Cytotoxicity against human Bel7402 cells after 96 hrs by MTT assay2011Journal of natural products, Nov-28, Volume: 74, Issue:11
Cucurbitane glucosides from the root of Machilus yaoshansis.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's3 (60.00)24.3611
2020's2 (40.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.72

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 Index12.72 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.51 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.72)

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%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
phenylbutazone
Phenylbutazone: A butyl-diphenyl-pyrazolidinedione that has anti-inflammatory, antipyretic, and analgesic activities. It has been used in ANKYLOSING SPONDYLITIS; RHEUMATOID ARTHRITIS; and REACTIVE ARTHRITIS.. phenylbutazone : A member of the class of pyrazolidines that is 1,2-diphenylpyrazolidine-3,5-dione carrying a butyl group at the 4-position.		2.0610pyrazolidinesantirheumatic drug;
EC 1.1.1.184 [carbonyl reductase (NADPH)] inhibitor;
metabolite;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
peripheral nervous system drug
carbon tetrachloride
Carbon Tetrachloride: A solvent for oils, fats, lacquers, varnishes, rubber waxes, and resins, and a starting material in the manufacturing of organic compounds. Poisoning by inhalation, ingestion or skin absorption is possible and may be fatal. (Merck Index, 11th ed). tetrachloromethane : A chlorocarbon that is methane in which all the hydrogens have been replaced by chloro groups.		2.0610chlorocarbon;
chloromethanes		hepatotoxic agent;
refrigerant
oleanolic acid
[no description available]		2.0610hydroxy monocarboxylic acid;
pentacyclic triterpenoid		plant metabolite
camptothecin
NSC 100880: carboxylate (opened lactone) form of camptothecin; RN refers to (S)-isomer; structure given in first source		2.0610delta-lactone;
pyranoindolizinoquinoline;
quinoline alkaloid;
tertiary alcohol		antineoplastic agent;
EC 5.99.1.2 (DNA topoisomerase) inhibitor;
genotoxin;
plant metabolite
6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid
[no description available]		2.0610chromanol;
monocarboxylic acid;
phenols		antioxidant;
ferroptosis inhibitor;
neuroprotective agent;
radical scavenger;
Wnt signalling inhibitor
silybin
[no description available]		2.0610
quercetin
[no description available]		2.06107-hydroxyflavonol;
pentahydroxyflavone		antibacterial agent;
antineoplastic agent;
antioxidant;
Aurora kinase inhibitor;
chelator;
EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor;
geroprotector;
phytoestrogen;
plant metabolite;
protein kinase inhibitor;
radical scavenger
cucurbitacin d
cucurbitacin D: toxic constituent in edible gourd; see also records for cucurbitacins & specific cucurbitacins. cucurbitacin D : A cucurbitacin in which a lanostane skeleton is multi-substituted with hydroxy, methyl and oxo substituents, with unsaturation at positions 5 and 23.		2.0610cucurbitacin;
secondary alpha-hydroxy ketone;
tertiary alpha-hydroxy ketone
nsc 106399
cucurbitacin E: RN refers to (9beta,10alpha,16alpha,23E)-isomer; structure given in first source. cucurbitacin E : A cucurbitacin in which a lanostane skeleton is multi-substituted with hydroxy, methyl and oxo substituents, with unsaturation at positions 1, 5 and 23.		2.0610cucurbitacin;
tertiary alpha-hydroxy ketone
cucurbitacin i
cucurbitacin I: toxic constituent in edible gourd; see also records for cucurbitacins & specific cucurbitacins. cucurbitacin I : A cucurbitacin that is 9,10,14-trimethyl-4,9-cyclo-9,10-secocholesta-2,5,23-triene substituted by hydroxy groups at positions 2, 16, 20 and 25 and oxo groups at positions 1, 11 and 22.		2.0610cucurbitacin;
tertiary alpha-hydroxy ketone		antineoplastic agent;
plant metabolite
ascorbic acid
Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.		2.0610ascorbic acid;
vitamin C		coenzyme;
cofactor;
flour treatment agent;
food antioxidant;
food colour retention agent;
geroprotector;
plant metabolite;
skin lightening agent
ConditionIndicatedRelationship StrengthStudiesTrials
Cirrhosis
[description not available]		02.0610
Fibrosis
Any pathological condition where fibrous connective tissue invades any organ, usually as a consequence of inflammation or other injury.		02.0610
Congenital Zika Syndrome
[description not available]		02.2510
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.2510
Zika Virus Infection
A viral disease transmitted by the bite of AEDES mosquitoes infected with ZIKA VIRUS. Its mild DENGUE-like symptoms include fever, rash, headaches and ARTHRALGIA. The viral infection during pregnancy, in rare cases, is associated with congenital brain and ocular abnormalities, called Congenital Zika Syndrome, including MICROCEPHALY and may also lead to GUILLAIN-BARRE SYNDROME.		02.2510