Compounds > lupeol, (3alpha)-isomer
Page last updated: 2024-11-10

lupeol, (3alpha)-isomer

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

Cross-References

ID SourceID
PubMed CID5270628
CHEMBL ID459702
CHEBI ID182364
SCHEMBL ID15263404
MeSH IDM0311131

Synonyms (23)

Synonym
unii-e8sut3imrz
3-epi-epilupeol
e8sut3imrz ,
epilupeol
(1r,3ar,5ar,5br,7ar,9r,11ar,11br,13ar,13br)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol
4439-99-0
CHEBI:182364
ACON1_000037
lup-20(29)-en-3-ol, (3alpha)-
(1r,3ar,5ar,5br,7ar,9r,11ar,11br,13ar,13br)-1-isopropenyl-3a,5a,5b,8,8,11a-hexamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol
3-epilupeol
MEGXP0_001577
NCGC00168853-01
CHEMBL459702
3-epi-lupeol
lup-20(29)-en-3-ol, (3.alpha.)-
lup-20(29)-en-3.alpha.-ol
lup-20(30)-en-3.alpha.-ol
SCHEMBL15263404
NCGC00384683-01
Q27277014
DTXSID701318679
AKOS040751700

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]

Drug Classes (1)

ClassDescription
triterpenoidAny terpenoid derived from a triterpene. The term includes compounds in which the C30 skeleton of the parent triterpene has been rearranged or modified by the removal of one or more skeletal atoms (generally methyl 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 (15)

Assay IDTitleYearJournalArticle
AID1173022Induction of CYP3A4 in human HepG2 cells at 10 uM after 24 hrs by luciferase reporter gene assay in presence of hPXR relative to control2014Bioorganic & medicinal chemistry letters, Dec-01, Volume: 24, Issue:23
Cycloartane-type triterpenes from Euphorbia fischeriana stimulate human CYP3A4 promoter activity.
AID1066590Antiinflammatory activity in mouse BV2 cells assessed as inhibition of LPS-induced nitric oxide production after 24 hrs by Griess method2014Journal of natural products, Feb-28, Volume: 77, Issue:2
Lupane triterpenoids from the stems of Euonymus carnosus.
AID400949Selectivity index, ratio of IC50 for african green monkey Vero cells to MIC for Mycobacterium tuberculosis H37Rv2004Journal of natural products, Apr, Volume: 67, Issue:4
Mycobacterium tuberculosis growth inhibition by constituents of Sapium haematospermum.
AID1066595Cytotoxicity against human HCT8 cells after 96 hrs by MTT assay2014Journal of natural products, Feb-28, Volume: 77, Issue:2
Lupane triterpenoids from the stems of Euonymus carnosus.
AID400948Cytotoxicity against african green monkey Vero cells2004Journal of natural products, Apr, Volume: 67, Issue:4
Mycobacterium tuberculosis growth inhibition by constituents of Sapium haematospermum.
AID1066592Cytotoxicity against human A549 cells after 96 hrs by MTT assay2014Journal of natural products, Feb-28, Volume: 77, Issue:2
Lupane triterpenoids from the stems of Euonymus carnosus.
AID1066591Cytotoxicity against human A2780 cells after 96 hrs by MTT assay2014Journal of natural products, Feb-28, Volume: 77, Issue:2
Lupane triterpenoids from the stems of Euonymus carnosus.
AID1066593Cytotoxicity against human BGC823 cells after 96 hrs by MTT assay2014Journal of natural products, Feb-28, Volume: 77, Issue:2
Lupane triterpenoids from the stems of Euonymus carnosus.
AID400947Antitubercular activity against Mycobacterium tuberculosis H37Rv by microplate alamar blue assay2004Journal of natural products, Apr, Volume: 67, Issue:4
Mycobacterium tuberculosis growth inhibition by constituents of Sapium haematospermum.
AID1066594Cytotoxicity against human Bel7402 cells after 96 hrs by MTT assay2014Journal of natural products, Feb-28, Volume: 77, Issue:2
Lupane triterpenoids from the stems of Euonymus carnosus.
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.
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.
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.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (16.67)29.6817
2010's3 (50.00)24.3611
2020's2 (33.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 13.26

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 Index13.26 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index5.21 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (13.26)

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%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
paclitaxel
Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).		2.110taxane diterpenoid;
tetracyclic diterpenoid		antineoplastic agent;
human metabolite;
metabolite;
microtubule-stabilising agent
betulin
betulin: isolated from various white birch bark (BETULA). betulin : A pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-hydroxymethyl substituents.		2.110diol;
pentacyclic triterpenoid		analgesic;
anti-inflammatory agent;
antineoplastic agent;
antiviral agent;
metabolite
beta-amyrin
beta-amyrin: alpha-amyrin is also available; a 5 ring triterpene derived from oleanane that differs from alpha-amyrin in having the 29-carbon at the 20 position; RN given refers to (3 beta)-isomer. beta-amyrin : A pentacyclic triterpenoid that is oleanane substituted at the 3beta-position by a hydroxy group and containing a double bond between positions 12 and 13. It is one of the most commonly occurring triterpenoids in higher plants.		2.0210pentacyclic triterpenoid;
secondary alcohol		Aspergillus metabolite;
plant metabolite
lupeol
[no description available]		2.7530pentacyclic triterpenoid;
secondary alcohol		anti-inflammatory drug;
plant metabolite
quercetin 3-o-glucopyranoside
quercetin 3-O-glucopyranoside: structure in first source. quercetin 3-O-beta-D-glucopyranoside : A quercetin O-glucoside that is quercetin with a beta-D-glucosyl residue attached at position 3. Isolated from Lepisorus contortus, it exhibits antineoplastic activityand has been found to decrease the rate of polymerization and sickling of red blood cells		2.0210beta-D-glucoside;
monosaccharide derivative;
quercetin O-glucoside;
tetrahydroxyflavone		antineoplastic agent;
antioxidant;
antipruritic drug;
bone density conservation agent;
geroprotector;
histamine antagonist;
osteogenesis regulator;
plant metabolite
astragalin
kaempferol-3-O-glucoside: isolated from the pit of Mahkota dewa; structure in first source. kaempferol 3-O-beta-D-glucoside : A kaempferol O-glucoside in which a glucosyl residue is attached at position 3 of kaempferol via a beta-glycosidic linkage.		2.0210beta-D-glucoside;
kaempferol O-glucoside;
monosaccharide derivative;
trihydroxyflavone		plant metabolite;
trypanocidal drug
betulone
[no description available]		2.110triterpenoidmetabolite
rifampin
Rifampin: A semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1160)		2.4520cyclic ketal;
hydrazone;
N-iminopiperazine;
N-methylpiperazine;
rifamycins;
semisynthetic derivative;
zwitterion		angiogenesis inhibitor;
antiamoebic agent;
antineoplastic agent;
antitubercular agent;
DNA synthesis inhibitor;
EC 2.7.7.6 (RNA polymerase) inhibitor;
Escherichia coli metabolite;
geroprotector;
leprostatic drug;
neuroprotective agent;
pregnane X receptor agonist;
protein synthesis inhibitor
ConditionIndicatedRelationship StrengthStudiesTrials
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