Compounds > withanolide a
Page last updated: 2024-10-14

withanolide a

Cross-References

ID SourceID
PubMed CID11294368
CHEMBL ID445041
CHEBI ID175683
MeSH IDM0514597

Synonyms (25)

Synonym
32911-62-9
CHEBI:175683
withanolide a
(1s,2s,4s,5r,10r,11s,14s,15s,18s)-15-[(1r)-1-[(2r)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.02,4.05,10.014,18]octadec-7-en-9-one
CHEMBL445041
(5alpha,6alpha,7alpha,22r)-5,20-dihydroxy-6,7:22,26-diepoxyergosta-2,24-diene-1,26-dione
unii-v903234s8g
(5.alpha.,6.alpha.,7.alpha.,22r)-5,20-dihydroxy-6,7:22,26-diepoxyergosta-2,24-diene-1,26-dione
V903234S8G ,
withanolide a, (+)-
withanolide a [usp-rs]
15-[1-(4,5-dimethyl-6-oxo-3,6-dihydro-2h-pyran-2-yl)-1-hydroxyethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.0^{2,4}.0^{5,10}.0^{14,18}]octadec-7-en-9-one
withanolide a, analytical standard
DTXSID70461487
withanolide a, united states pharmacopeia (usp) reference standard
withanolide a, >=95% (hplc)
HY-N7028
withanolide a(p)
Q27291676
CS-0068468
MS-28704
XW164988
15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.02,4.05,10.014,18]octadec-7-en-9-one
E87198
AKOS040760756
[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 (32)

Assay IDTitleYearJournalArticle
AID334282Induction of quinone reductase activity in mouse Hepa-1c1c7 cells assessed as drug level required to induce 4-fold increase in enzyme activity after 48 hrs by NADPH-dependent MTT reduction assay2002Journal of natural products, May, Volume: 65, Issue:5
Induction of quinone reductase by withanolides.
AID492135Increase in gamma-secretase avtivity in Sprague-Dawley rat primary cortical neurons assessed as increase in sAPPalpha level by immunoblot analysis2010Journal of natural products, Jul-23, Volume: 73, Issue:7
Withanolide A and asiatic acid modulate multiple targets associated with amyloid-beta precursor protein processing and amyloid-beta protein clearance.
AID492125Reduction of BACE1 expression in Sprague-Dawley rat primary cortical neurons after 24 hrs by immunoblot analysis2010Journal of natural products, Jul-23, Volume: 73, Issue:7
Withanolide A and asiatic acid modulate multiple targets associated with amyloid-beta precursor protein processing and amyloid-beta protein clearance.
AID334283Growth inhibition of mouse Hepa-1c1c7 cells by crystal violet staining2002Journal of natural products, May, Volume: 65, Issue:5
Induction of quinone reductase by withanolides.
AID1638849Cytotoxicity against human SK-MEL-2 cells after 72 hrs by SRB assay2019Journal of natural products, 04-26, Volume: 82, Issue:4
Cytotoxic Withanolides from the Roots of Indian Ginseng ( Withania somnifera).
AID1638847Cytotoxicity against human A549 cells after 72 hrs by SRB assay2019Journal of natural products, 04-26, Volume: 82, Issue:4
Cytotoxic Withanolides from the Roots of Indian Ginseng ( Withania somnifera).
AID1544147Agonist activity at MR transfected in human HEK293 cells at 1 uM incubated for 24 hrs by luciferase reporter gene assay2019Bioorganic & medicinal chemistry, 06-15, Volume: 27, Issue:12
Profiling withanolide A for therapeutic targets in neurodegenerative diseases.
AID360408Inhibition of TNF-induced NF-kappaB-mediated IL6 promoter expression in mouse L929sA cells by luciferase reporter gene assay2007The Journal of biological chemistry, Feb-16, Volume: 282, Issue:7
Withaferin a strongly elicits IkappaB kinase beta hyperphosphorylation concomitant with potent inhibition of its kinase activity.
AID492130Induction of NEP levels in Sprague-Dawley rat primary cortical neurons after 24 hrs by immunoblot analysis2010Journal of natural products, Jul-23, Volume: 73, Issue:7
Withanolide A and asiatic acid modulate multiple targets associated with amyloid-beta precursor protein processing and amyloid-beta protein clearance.
AID360406Induction of IKK-beta-mediated IkappaBalpha degradation in IFN-stimulated mouse L929sA cells at 2.8 ug/ml by Western blot2007The Journal of biological chemistry, Feb-16, Volume: 282, Issue:7
Withaferin a strongly elicits IkappaB kinase beta hyperphosphorylation concomitant with potent inhibition of its kinase activity.
AID1544148Induction of neurite outgrowth in human SH-SY5Y cells assessed as increase in neurite length of more than 50 micrometer by measuring cell differentiation at 1 uM incubated for 6 days by Giemsa staining based phase contrast microscopic analysis relative to2019Bioorganic & medicinal chemistry, 06-15, Volume: 27, Issue:12
Profiling withanolide A for therapeutic targets in neurodegenerative diseases.
AID492128Induction of IDE levels in Sprague-Dawley rat primary cortical neurons after 24 hrs by immunoblot analysis2010Journal of natural products, Jul-23, Volume: 73, Issue:7
Withanolide A and asiatic acid modulate multiple targets associated with amyloid-beta precursor protein processing and amyloid-beta protein clearance.
AID1544145Antagonist activity at GR transfected in human HEK293 cells assessed as effect on cortisol-induced receptor activation at 1 uM incubated for 24 hrs by luciferase reporter gene assay2019Bioorganic & medicinal chemistry, 06-15, Volume: 27, Issue:12
Profiling withanolide A for therapeutic targets in neurodegenerative diseases.
AID1544149Induction of neurite outgrowth in human SH-SY5Y cells assessed as increase in neurite length of more than 50 micrometer by measuring cell differentiation at 1 uM in presence of dexamethasone incubated for 6 days by Giemsa staining based phase contrast mic2019Bioorganic & medicinal chemistry, 06-15, Volume: 27, Issue:12
Profiling withanolide A for therapeutic targets in neurodegenerative diseases.
AID492136Induction of IDE levels in Sprague-Dawley rat Alzheimer's disease model primary cortical neurons after 24 hrs by immunoblot analysis2010Journal of natural products, Jul-23, Volume: 73, Issue:7
Withanolide A and asiatic acid modulate multiple targets associated with amyloid-beta precursor protein processing and amyloid-beta protein clearance.
AID1544139Displacement of [3H] dexamethasone from human recombinant GR expressed in Sf9 insect cells at up to 10 uM incubated for 4 hrs by scintillation counting method2019Bioorganic & medicinal chemistry, 06-15, Volume: 27, Issue:12
Profiling withanolide A for therapeutic targets in neurodegenerative diseases.
AID1638850Cytotoxicity against human HCT15 cells after 72 hrs by SRB assay2019Journal of natural products, 04-26, Volume: 82, Issue:4
Cytotoxic Withanolides from the Roots of Indian Ginseng ( Withania somnifera).
AID1130018Induction of HSP90B' (unknown origin)-mediated heat shock response expressed in human 293T cells coexpressing GFP assessed as heat shock index after overnight incubation by luciferase reporter gene assay relative to control2014Journal of medicinal chemistry, Apr-10, Volume: 57, Issue:7
Structure-activity relationships for withanolides as inducers of the cellular heat-shock response.
AID1544144Agonist activity at MR transfected in human HEK293 cells at 10 uM incubated for 24 hrs by luciferase reporter gene assay2019Bioorganic & medicinal chemistry, 06-15, Volume: 27, Issue:12
Profiling withanolide A for therapeutic targets in neurodegenerative diseases.
AID334284Chemoprevention index, ratio of IC50 for mouse Hepa-1c1c7 cells to drug level required to double specific quinone reductase activity in mouse Hepa-1c1c7 cells2002Journal of natural products, May, Volume: 65, Issue:5
Induction of quinone reductase by withanolides.
AID334281Induction of quinone reductase activity in mouse Hepa-1c1c7 cells assessed as drug level required to double enzyme activity after 48 hrs by NADPH-dependent MTT reduction assay2002Journal of natural products, May, Volume: 65, Issue:5
Induction of quinone reductase by withanolides.
AID492126Induction of ADAM10 activation in Sprague-Dawley rat primary cortical neurons after 24 hrs by immunoblot analysis2010Journal of natural products, Jul-23, Volume: 73, Issue:7
Withanolide A and asiatic acid modulate multiple targets associated with amyloid-beta precursor protein processing and amyloid-beta protein clearance.
AID492121Cytotoxicity against Sprague-Dawley rat primary cortical neurons assessed as cell death at 100 uM after 24 hrs by MAP2 immunostaining2010Journal of natural products, Jul-23, Volume: 73, Issue:7
Withanolide A and asiatic acid modulate multiple targets associated with amyloid-beta precursor protein processing and amyloid-beta protein clearance.
AID1130019Cytotoxicity against human NCI-H929 cells after 3 days by Alamar blue assay2014Journal of medicinal chemistry, Apr-10, Volume: 57, Issue:7
Structure-activity relationships for withanolides as inducers of the cellular heat-shock response.
AID334285Chemoprevention index, ratio of IC50 for mouse Hepa-1c1c7 cells to drug level required to induce 4-fold increase in quinone reductase activity in mouse Hepa-1c1c7 cells2002Journal of natural products, May, Volume: 65, Issue:5
Induction of quinone reductase by withanolides.
AID360407Induction of IKK-beta-hyperphosphorylation in IFN-stimulated mouse L929sA cells at 2.8 ug/ml by Western blot2007The Journal of biological chemistry, Feb-16, Volume: 282, Issue:7
Withaferin a strongly elicits IkappaB kinase beta hyperphosphorylation concomitant with potent inhibition of its kinase activity.
AID1638848Cytotoxicity against human SKOV3 cells after 72 hrs by SRB assay2019Journal of natural products, 04-26, Volume: 82, Issue:4
Cytotoxic Withanolides from the Roots of Indian Ginseng ( Withania somnifera).
AID492123Cytotoxicity against Sprague-Dawley rat primary cortical neurons assessed as cell morphology at 100 uM after 24 hrs by MAP2 immunostaining2010Journal of natural products, Jul-23, Volume: 73, Issue:7
Withanolide A and asiatic acid modulate multiple targets associated with amyloid-beta precursor protein processing and amyloid-beta protein clearance.
AID1544150Induction of neurite outgrowth in human SH-SY5Y cells assessed as increase in neurite length of more than 50 micrometer by measuring cell differentiation at 1 uM in presence of mifepristone incubated for 6 days by Giemsa staining based phase contrast micr2019Bioorganic & medicinal chemistry, 06-15, Volume: 27, Issue:12
Profiling withanolide A for therapeutic targets in neurodegenerative diseases.
AID1544143Agonist activity at GR transfected in human HEK293 cells at 10 uM incubated for 24 hrs by luciferase reporter gene assay2019Bioorganic & medicinal chemistry, 06-15, Volume: 27, Issue:12
Profiling withanolide A for therapeutic targets in neurodegenerative diseases.
AID492134Increase in gamma-secretase activity in Sprague-Dawley rat primary cortical neurons assessed as increase in C38 level by immunoblot analysis2010Journal of natural products, Jul-23, Volume: 73, Issue:7
Withanolide A and asiatic acid modulate multiple targets associated with amyloid-beta precursor protein processing and amyloid-beta protein clearance.
AID492127Induction of matured ADAM10 level in Sprague-Dawley rat primary cortical neurons after 24 hrs by immunoblot analysis2010Journal of natural products, Jul-23, Volume: 73, Issue:7
Withanolide A and asiatic acid modulate multiple targets associated with amyloid-beta precursor protein processing and amyloid-beta protein clearance.
[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's2 (33.33)29.6817
2010's4 (66.67)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

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
sulforaphane
sulforaphane: from Cardaria draba L.. sulforaphane : An isothiocyanate having a 4-(methylsulfinyl)butyl group attached to the nitrogen.		2.0110isothiocyanate;
sulfoxide		antineoplastic agent;
antioxidant;
EC 3.5.1.98 (histone deacetylase) inhibitor;
plant metabolite
helenalin
helenalin: toxic principle of Helenium microcephalum (smallhead sneezeweed); structure. helenalin : A sesquiterpene lactone that is 3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione substituted by a hydroxy group at position 4, methyl groups at positions 4a and 8 and a methylidene group at position 3 (the 3aS,4S,4aR,7aR,8R,9aR stereoisomer).. NF-kappaB inhibitor : An inhibitor of NF-kappaB (nuclear factor kappa-light-chain-enhancer of activated B cells), a protein complex involved in the transcription of DNA.		2.0310cyclic ketone;
gamma-lactone;
organic heterotricyclic compound;
secondary alcohol;
sesquiterpene lactone		anti-inflammatory agent;
antineoplastic agent;
metabolite;
plant metabolite
etoposide
[no description available]		2.2110beta-D-glucoside;
furonaphthodioxole;
organic heterotetracyclic compound		antineoplastic agent;
DNA synthesis inhibitor
mifepristone
Mifepristone: A progestational and glucocorticoid hormone antagonist. Its inhibition of progesterone induces bleeding during the luteal phase and in early pregnancy by releasing endogenous prostaglandins from the endometrium or decidua. As a glucocorticoid receptor antagonist, the drug has been used to treat hypercortisolism in patients with nonpituitary CUSHING SYNDROME.		2.21103-oxo-Delta(4) steroid;
acetylenic compound;
tertiary amino compound		abortifacient;
contraceptive drug;
hormone antagonist;
synthetic oral contraceptive
asiatic acid
[no description available]		7.0510monocarboxylic acid;
pentacyclic triterpenoid;
triol		angiogenesis modulating agent;
metabolite
tretinoin
Tretinoin: An important regulator of GENE EXPRESSION during growth and development, and in NEOPLASMS. Tretinoin, also known as retinoic acid and derived from maternal VITAMIN A, is essential for normal GROWTH; and EMBRYONIC DEVELOPMENT. An excess of tretinoin can be teratogenic. It is used in the treatment of PSORIASIS; ACNE VULGARIS; and several other SKIN DISEASES. It has also been approved for use in promyelocytic leukemia (LEUKEMIA, PROMYELOCYTIC, ACUTE).. retinoic acid : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraenoic acid substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).. all-trans-retinoic acid : A retinoic acid in which all four exocyclic double bonds have E- (trans-) geometry.		2.2110retinoic acid;
vitamin A		anti-inflammatory agent;
antineoplastic agent;
antioxidant;
AP-1 antagonist;
human metabolite;
keratolytic drug;
retinoic acid receptor agonist;
retinoid X receptor agonist;
signalling molecule
benzyloxycarbonylleucyl-leucyl-leucine aldehyde
benzyloxycarbonylleucyl-leucyl-leucine aldehyde: proteasome inhibitor. N-benzyloxycarbonyl-L-leucyl-L-leucyl-L-leucinal : A tripeptide that is L-leucyl-L-leucyl-L-leucine in which the C-terminal carboxy group has been reduced to the corresponding aldehyde and the N-terminal amino group is protected as its benzyloxycarbonyl derivative.		2.110amino aldehyde;
carbamate ester;
tripeptide		proteasome inhibitor
2,3-dihydrowithaferin A
2,3-dihydrowithaferin A : A withanolide that is the 2,3-dihydro derivative of withaferin A. It has been isolated from the aerial parts of Physalis longifolia.		2.11027-hydroxy steroid;
4-hydroxy steroid;
delta-lactone;
epoxy steroid;
ergostanoid;
primary alcohol;
secondary alcohol;
withanolide		plant metabolite
salpichrolide g
salpichrolide G: withanolide from Salpichroa origanifolia; structure in first source		2.0110
2,3-dihydro-3beta-O-sulfate withaferin A
2,3-dihydro-3beta-O-sulfate withaferin A : A withanolide that is 2,3-dihydrowithaferin A substituted by a sulfoxy group at position 3. Isolated from Physalis longifolia, it exhibits antineoplastic activity.		2.11027-hydroxy steroid;
4-hydroxy steroid;
delta-lactone;
epoxy steroid;
ergostanoid;
primary alcohol;
steroid sulfate;
withanolide		antineoplastic agent;
metabolite;
plant metabolite
nimorazole
[no description available]		2.4620
ConditionIndicatedRelationship StrengthStudiesTrials
Hepatocellular Carcinoma
[description not available]		02.0110
Carcinoma, Hepatocellular
A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.		02.0110
Innate Inflammatory Response
[description not available]		02.0310
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.		02.0310
Acute Confusional Senile Dementia
[description not available]		02.0510
Alzheimer Disease
A degenerative disease of the BRAIN characterized by the insidious onset of DEMENTIA. Impairment of MEMORY, judgment, attention span, and problem solving skills are followed by severe APRAXIAS and a global loss of cognitive abilities. The condition primarily occurs after age 60, and is marked pathologically by severe cortical atrophy and the triad of SENILE PLAQUES; NEUROFIBRILLARY TANGLES; and NEUROPIL THREADS. (From Adams et al., Principles of Neurology, 6th ed, pp1049-57)		02.0510
Bone Cancer
[description not available]		02.110
Ewing Sarcoma
[description not available]		02.110
Bone Neoplasms
Tumors or cancer located in bone tissue or specific BONES.		02.110
Sarcoma, Ewing
A malignant tumor of the bone which always arises in the medullary tissue, occurring more often in cylindrical bones. The tumor occurs usually before the age of 20, about twice as frequently in males as in females.		02.110
Degenerative Diseases, Central Nervous System
[description not available]		02.2110
Neurodegenerative Diseases
Hereditary and sporadic conditions which are characterized by progressive nervous system dysfunction. These disorders are often associated with atrophy of the affected central or peripheral nervous system structures.		07.2110