Compounds > withangulatin a
Page last updated: 2024-12-08

withangulatin a

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

Description

withangulatin A: a withanolide from Physalis angulata; promotes type II DNA topoisomerase-mediated DNA damage [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
PhysalisgenusA plant genus of the family SOLANACEAE. Members contain physalin and withangulatin.[MeSH]SolanaceaeA plant family of the order SOLANALES, class MAGNOLIOPSIDA. Among the most noted are POTATOES; TOMATOES; CAPSICUM (green and red peppers); TOBACCO; and BELLADONNA.[MeSH]

Cross-References

ID SourceID
PubMed CID147647
CHEMBL ID4786754
CHEBI ID168477
MeSH IDM0164396

Synonyms (11)

Synonym
withangulatin a
120824-03-5
[(1s,2r,6s,7r,9r,11r,12r,13s,16r)-15-[(1s)-1-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-6,12-dihydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadeca-4,14-dien-13-yl] acetate
CHEBI:168477
ergosta-2,16,24-trien-26-oic acid, 15-(acetyloxy)-5,6-epoxy-4,14,22-trihydroxy-1-oxo-, delta-lactone, (4beta,5alpha,6beta,15alpha,22r)-
DTXSID60923569
4,14-dihydroxy-1,26-dioxo-5,6:22,26-diepoxyergosta-2,16,24-trien-15-yl acetate
CHEMBL4786754
CS-0373796
HY-N10303
PD170170

Research Excerpts

Overview

Withangulatin A is a newly identified in vitro topoisomerase II inhibitor isolated from the Chinese antitumor herb Physalis angulata.

ExcerptReferenceRelevance
"Withangulatin A is a newly identified in vitro topoisomerase II inhibitor isolated from the Chinese antitumor herb Physalis angulata. "( Induction of heat-shock response and alterations of protein phosphorylation by a novel topoisomerase II inhibitor, withangulatin A, in 9L rat brain tumor cells.
Chen, CM; Chen, ZT; Lai, YK; Lee, WC; Lin, KY; Liu, HJ, 1991)		1.93

Effects

ExcerptReferenceRelevance
"Withangulatin A (WA) has been reported to exhibit potent antitumor activity. "( Cellular target identification of Withangulatin A using fluorescent analogues and subsequent chemical proteomics.
Chen, C; Kong, L; Li, L; Luo, J; Wang, S; Zhang, Y; Zhu, D; Zhu, T, 2019)		2.24

Bioavailability

ExcerptReferenceRelevance
"The oral bioavailability of withangulatin A (WA) is low and may undergo first-pass metabolism because of the presence of two esters bonds."( Hydrolytic Metabolism of Withangulatin A Mediated by Serum Albumin Instead of Common Esterases in Plasma.
Li, N; Li, Z; Luo, J; Meng, H; Qiu, Z; Wang, Y; Zhuang, Y, 2023)		1.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
withanolideAny steroid lactone that is a C28 steroid with a modified side chain forming a lactone ring and its substituted derivatives.
[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 (18)

Assay IDTitleYearJournalArticle
AID1676061Antiproliferative activity against human MCF7 cells assessed as reduction in cell viability incubated for 24 hrs by MTT assay2020Journal of medicinal chemistry, 10-08, Volume: 63, Issue:19
Design and SAR of Withangulatin A Analogues that Act as Covalent TrxR Inhibitors through the Michael Addition Reaction Showing Potential in Cancer Treatment.
AID1676065Inhibition of TrxR (unknown origin) in presence of NADPH by Ellman's method2020Journal of medicinal chemistry, 10-08, Volume: 63, Issue:19
Design and SAR of Withangulatin A Analogues that Act as Covalent TrxR Inhibitors through the Michael Addition Reaction Showing Potential in Cancer Treatment.
AID1676072Covalent inhibition of TrxR (unknown origin) assessed as ratio of Kinact to ki incubated up to 30 mins in presence of NADPH by Ellman's method2020Journal of medicinal chemistry, 10-08, Volume: 63, Issue:19
Design and SAR of Withangulatin A Analogues that Act as Covalent TrxR Inhibitors through the Michael Addition Reaction Showing Potential in Cancer Treatment.
AID1676069Inhibition of TrxR in human HT-29 cells incubated for 90 mins in presence of insulin, NADPH and Trx by DTNB reagent based assay2020Journal of medicinal chemistry, 10-08, Volume: 63, Issue:19
Design and SAR of Withangulatin A Analogues that Act as Covalent TrxR Inhibitors through the Michael Addition Reaction Showing Potential in Cancer Treatment.
AID1676071Covalent inhibition of TrxR (unknown origin) assessed as inactivation rate constant incubated up to 30 mins in presence of NADPH by Ellman's method2020Journal of medicinal chemistry, 10-08, Volume: 63, Issue:19
Design and SAR of Withangulatin A Analogues that Act as Covalent TrxR Inhibitors through the Michael Addition Reaction Showing Potential in Cancer Treatment.
AID1676060Antiproliferative activity against human HepG2 cells assessed as reduction in cell viability incubated for 24 hrs by MTT assay2020Journal of medicinal chemistry, 10-08, Volume: 63, Issue:19
Design and SAR of Withangulatin A Analogues that Act as Covalent TrxR Inhibitors through the Michael Addition Reaction Showing Potential in Cancer Treatment.
AID1676066Inhibition of Escherichia coli Trx incubated for 1.5 hrs in presence of DTT and insulin2020Journal of medicinal chemistry, 10-08, Volume: 63, Issue:19
Design and SAR of Withangulatin A Analogues that Act as Covalent TrxR Inhibitors through the Michael Addition Reaction Showing Potential in Cancer Treatment.
AID1676091Inhibition of TrxR in human HT-29 cells incubated for 24 hrs in presence of insulin, NADPH and Trx by DTNB reagent based assay2020Journal of medicinal chemistry, 10-08, Volume: 63, Issue:19
Design and SAR of Withangulatin A Analogues that Act as Covalent TrxR Inhibitors through the Michael Addition Reaction Showing Potential in Cancer Treatment.
AID1676092Inhibition of Trx in human HT-29 cells incubated for 24 hrs in presence of insulin, NADPH and DTT2020Journal of medicinal chemistry, 10-08, Volume: 63, Issue:19
Design and SAR of Withangulatin A Analogues that Act as Covalent TrxR Inhibitors through the Michael Addition Reaction Showing Potential in Cancer Treatment.
AID1676070Covalent inhibition of TrxR (unknown origin) assessed as covalent bond formation incubated up to 30 mins in presence of NADPH by Ellman's method2020Journal of medicinal chemistry, 10-08, Volume: 63, Issue:19
Design and SAR of Withangulatin A Analogues that Act as Covalent TrxR Inhibitors through the Michael Addition Reaction Showing Potential in Cancer Treatment.
AID1676067Inhibition of TrxR in human HT-29 cells incubated for 30 mins in presence of insulin, NADPH and Trx by DTNB reagent based assay2020Journal of medicinal chemistry, 10-08, Volume: 63, Issue:19
Design and SAR of Withangulatin A Analogues that Act as Covalent TrxR Inhibitors through the Michael Addition Reaction Showing Potential in Cancer Treatment.
AID1676068Inhibition of TrxR in human HT-29 cells incubated for 60 mins in presence of insulin, NADPH and Trx by DTNB reagent based assay2020Journal of medicinal chemistry, 10-08, Volume: 63, Issue:19
Design and SAR of Withangulatin A Analogues that Act as Covalent TrxR Inhibitors through the Michael Addition Reaction Showing Potential in Cancer Treatment.
AID1676094Inhibition of GPx in human HT-29 cells incubated for 24 hrs in presence of GSH, NADPH and GR measured at 10 secs interval for 4 mins2020Journal of medicinal chemistry, 10-08, Volume: 63, Issue:19
Design and SAR of Withangulatin A Analogues that Act as Covalent TrxR Inhibitors through the Michael Addition Reaction Showing Potential in Cancer Treatment.
AID1676062Cytotoxicity against human L02 cells assessed as cell viability incubated for 24 hrs by MTT assay2020Journal of medicinal chemistry, 10-08, Volume: 63, Issue:19
Design and SAR of Withangulatin A Analogues that Act as Covalent TrxR Inhibitors through the Michael Addition Reaction Showing Potential in Cancer Treatment.
AID1676059Antiproliferative activity against human HCT-116 cells assessed as reduction in cell viability incubated for 24 hrs by MTT assay2020Journal of medicinal chemistry, 10-08, Volume: 63, Issue:19
Design and SAR of Withangulatin A Analogues that Act as Covalent TrxR Inhibitors through the Michael Addition Reaction Showing Potential in Cancer Treatment.
AID1676063Cytotoxicity against human HK2 cells assessed as cell viability incubated for 24 hrs by MTT assay2020Journal of medicinal chemistry, 10-08, Volume: 63, Issue:19
Design and SAR of Withangulatin A Analogues that Act as Covalent TrxR Inhibitors through the Michael Addition Reaction Showing Potential in Cancer Treatment.
AID1676093Inhibition of GR in human HT-29 cells incubated for 24 hrs in presence of GSSG and NADPH2020Journal of medicinal chemistry, 10-08, Volume: 63, Issue:19
Design and SAR of Withangulatin A Analogues that Act as Covalent TrxR Inhibitors through the Michael Addition Reaction Showing Potential in Cancer Treatment.
AID1676058Antiproliferative activity against human HT-29 cells assessed as reduction in cell viability incubated for 24 hrs by MTT assay2020Journal of medicinal chemistry, 10-08, Volume: 63, Issue:19
Design and SAR of Withangulatin A Analogues that Act as Covalent TrxR Inhibitors through the Michael Addition Reaction Showing Potential in Cancer Treatment.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (14)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (7.14)18.7374
1990's4 (28.57)18.2507
2000's0 (0.00)29.6817
2010's4 (28.57)24.3611
2020's5 (35.71)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.49

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 Index12.49 (24.57)
Research Supply Index2.71 (2.92)
Research Growth Index5.20 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.49)

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%
Other14 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
coumarin
2H-chromen-2-one: coumarin derivative		2.2110coumarinsfluorescent dye;
human metabolite;
plant metabolite
colchicine
(S)-colchicine : A colchicine that has (S)-configuration. It is a secondary metabolite, has anti-inflammatory properties and is used to treat gout, crystal-induced joint inflammation, familial Mediterranean fever, and many other conditions.		1.9810alkaloid;
colchicine		anti-inflammatory agent;
gout suppressant;
mutagen
cycloheximide
Cycloheximide: Antibiotic substance isolated from streptomycin-producing strains of Streptomyces griseus. It acts by inhibiting elongation during protein synthesis.. cycloheximide : A dicarboximide that is 4-(2-hydroxyethyl)piperidine-2,6-dione in which one of the hydrogens attached to the carbon bearing the hydroxy group is replaced by a 3,5-dimethyl-2-oxocyclohexyl group. It is an antibiotic produced by the bacterium Streptomyces griseus.		1.9710antibiotic fungicide;
cyclic ketone;
dicarboximide;
piperidine antibiotic;
piperidones;
secondary alcohol		anticoronaviral agent;
bacterial metabolite;
ferroptosis inhibitor;
neuroprotective agent;
protein synthesis inhibitor
dactinomycin
Dactinomycin: A compound composed of a two CYCLIC PEPTIDES attached to a phenoxazine that is derived from STREPTOMYCES parvullus. It binds to DNA and inhibits RNA synthesis (transcription), with chain elongation more sensitive than initiation, termination, or release. As a result of impaired mRNA production, protein synthesis also declines after dactinomycin therapy. (From AMA Drug Evaluations Annual, 1993, p2015)		1.9710actinomycinmutagen
myricetin
[no description available]		2.25107-hydroxyflavonol;
hexahydroxyflavone		antineoplastic agent;
antioxidant;
cyclooxygenase 1 inhibitor;
food component;
geroprotector;
hypoglycemic agent;
plant metabolite
arginine
Teniposide: A semisynthetic derivative of PODOPHYLLOTOXIN that exhibits antitumor activity. Teniposide inhibits DNA synthesis by forming a complex with topoisomerase II and DNA. This complex induces breaks in double stranded DNA and prevents repair by topoisomerase II binding. Accumulated breaks in DNA prevent cells from entering into the mitotic phase of the cell cycle, and lead to cell death. Teniposide acts primarily in the G2 and S phases of the cycle.. teniposide : A furonaphthodioxole that is a synthetic derivative of podophyllotoxin with anti-tumour activity; causes single- and double-stranded breaks in DNA and DNA-protein cross-links and prevents repair by topoisomerase II binding.		1.9710
warfarin
Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.		2.2110benzenes;
hydroxycoumarin;
methyl ketone
glutaminase
[no description available]		7.3110
cytochalasin d
Cytochalasin D: A fungal metabolite that blocks cytoplasmic cleavage by blocking formation of contractile microfilament structures resulting in multinucleated cell formation, reversible inhibition of cell movement, and the induction of cellular extrusion. Additional reported effects include the inhibition of actin polymerization, DNA synthesis, sperm motility, glucose transport, thyroid secretion, and growth hormone release.. cytochalasin D : An organic heterotricyclic compound that is a mycotoxin produced by Helminthosporium and other moulds which is cell permeable and a potent inhibitor of actin polymerisation and DNA synthesis.		1.9810
ConditionIndicatedRelationship StrengthStudiesTrials
Benign Neoplasms
[description not available]		02.2510
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		02.2510
Carcinoma, Non-Small Cell Lung
[description not available]		02.3110
Cancer of Lung
[description not available]		02.3110
Carcinoma, Non-Small-Cell Lung
A heterogeneous aggregate of at least three distinct histological types of lung cancer, including SQUAMOUS CELL CARCINOMA; ADENOCARCINOMA; and LARGE CELL CARCINOMA. They are dealt with collectively because of their shared treatment strategy.		02.3110
Lung Neoplasms
Tumors or cancer of the LUNG.		02.3110
ER-Negative PR-Negative HER2-Negative Breast Cancer
[description not available]		02.3110
Triple Negative Breast Neoplasms
Breast neoplasms that do not express ESTROGEN RECEPTORS; PROGESTERONE RECEPTORS; and do not overexpress the NEU RECEPTOR/HER-2 PROTO-ONCOGENE PROTEIN.		02.3110
Innate Inflammatory Response
[description not available]		02.0510
Inflammation
A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.		02.0510
Bright Disease
A historical classification which is no longer used. It described acute glomerulonephritis, acute nephritic syndrome, or acute nephritis. Named for Richard Bright.		02.0610
Libman-Sacks Disease
[description not available]		02.0610
Enlarged Spleen
[description not available]		02.0610
Glomerulonephritis
Inflammation of the renal glomeruli (KIDNEY GLOMERULUS) that can be classified by the type of glomerular injuries including antibody deposition, complement activation, cellular proliferation, and glomerulosclerosis. These structural and functional abnormalities usually lead to HEMATURIA; PROTEINURIA; HYPERTENSION; and RENAL INSUFFICIENCY.		02.0610
Lupus Erythematosus, Systemic
A chronic, relapsing, inflammatory, and often febrile multisystemic disorder of connective tissue, characterized principally by involvement of the skin, joints, kidneys, and serosal membranes. It is of unknown etiology, but is thought to represent a failure of the regulatory mechanisms of the autoimmune system. The disease is marked by a wide range of system dysfunctions, an elevated erythrocyte sedimentation rate, and the formation of LE cells in the blood or bone marrow.		02.0610
Proteinuria
The presence of proteins in the urine, an indicator of KIDNEY DISEASES.		02.0610
Benign Neoplasms, Brain
[description not available]		02.6730
Brain Neoplasms
Neoplasms of the intracranial components of the central nervous system, including the cerebral hemispheres, basal ganglia, hypothalamus, thalamus, brain stem, and cerebellum. Brain neoplasms are subdivided into primary (originating from brain tissue) and secondary (i.e., metastatic) forms. Primary neoplasms are subdivided into benign and malignant forms. In general, brain tumors may also be classified by age of onset, histologic type, or presenting location in the brain.		02.6730