Compounds > 2,3-dihydrowithaferin A
Page last updated: 2024-11-12

2,3-dihydrowithaferin A

Description

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. [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
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 CID15411208
CHEMBL ID1934585
CHEBI ID69124
SCHEMBL ID21164151

Synonyms (14)

Synonym
(22r)-4beta,27-dihydroxy-5beta,6beta:22,26-diepoxyergost-24-ene-1,26-dione
2,3-dihydrowithaferin a
CHEMBL1934585
chebi:69124 ,
2,3-dihydro-withaferin a
dihydrowithaferin a
Q27137464
SCHEMBL21164151
HY-N5120
CS-0032441
MS-28752
E88629
(1s,2r,6s,7r,9r,11s,12s,15r,16s)-6-hydroxy-15-[(1s)-1-[(2r)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecan-3-one
AKOS040760371
[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 (8)

ClassDescription
delta-lactoneA lactone having a six-membered lactone ring.
27-hydroxy steroid
4-hydroxy steroidAny steroid bearing a 4-hydroxy substituent.
ergostanoid
primary alcoholA primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen 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.
withanolideAny steroid lactone that is a C28 steroid with a modified side chain forming a lactone ring and its substituted derivatives.
epoxy steroidAny steroid whose structure includes an epoxy group.
[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 (30)

Assay IDTitleYearJournalArticle
AID1379654Cytotoxicity against human MCF7 cells assessed as reduction in cell viability using compound addition to cell culture cells in lag phase of growth and incubated for 48 hrs by MTT assay2017European journal of medicinal chemistry, Nov-10, Volume: 140Structure-based design, synthesis, and biological evaluation of withaferin A-analogues as potent apoptotic inducers.
AID1379651Cytotoxicity against human HeLa cells assessed as reduction in cell viability using compound addition to cell culture cells in log phase of growth and incubated for 48 hrs by MTT assay2017European journal of medicinal chemistry, Nov-10, Volume: 140Structure-based design, synthesis, and biological evaluation of withaferin A-analogues as potent apoptotic inducers.
AID1240133Inhibition of GST-GLI1 (unknown origin) interaction with DNA assessed as reduction of protein-DNA complex level at 100 uM after 20 mins by electrophoretic mobility shift assay2015Bioorganic & medicinal chemistry letters, Sep-01, Volume: 25, Issue:17
Hedgehog inhibitors from Withania somnifera.
AID639258Cytotoxicity against human SK-MEL-28 cells after 72 hrs by MTS assay2011Journal of natural products, Dec-27, Volume: 74, Issue:12
Cytotoxic withanolide constituents of Physalis longifolia.
AID1379657Cytotoxicity against African green monkey Vero cells assessed as reduction in cell viability using compound addition to cell culture cells in log phase of growth and incubated for 48 hrs by MTT assay2017European journal of medicinal chemistry, Nov-10, Volume: 140Structure-based design, synthesis, and biological evaluation of withaferin A-analogues as potent apoptotic inducers.
AID1240125Cytotoxicity against human MCF7 cells after 24 hrs by FMCA2015Bioorganic & medicinal chemistry letters, Sep-01, Volume: 25, Issue:17
Hedgehog inhibitors from Withania somnifera.
AID670605Cytotoxicity against human A549 cells assessed as cell viability after 72 hrs by MTT assay2012European journal of medicinal chemistry, Aug, Volume: 54Withaferin A-related steroids from Withania aristata exhibit potent antiproliferative activity by inducing apoptosis in human tumor cells.
AID1240123Cytotoxicity against human PANC1 cells after 24 hrs by FMCA2015Bioorganic & medicinal chemistry letters, Sep-01, Volume: 25, Issue:17
Hedgehog inhibitors from Withania somnifera.
AID670608Cytotoxicity against african green monkey Vero cells assessed as cell viability after 48 hrs by MTT assay2012European journal of medicinal chemistry, Aug, Volume: 54Withaferin A-related steroids from Withania aristata exhibit potent antiproliferative activity by inducing apoptosis in human tumor cells.
AID1240124Cytotoxicity against human DU145 cells after 24 hrs by FMCA2015Bioorganic & medicinal chemistry letters, Sep-01, Volume: 25, Issue:17
Hedgehog inhibitors from Withania somnifera.
AID670606Cytotoxicity against human MCF7 cells assessed as cell viability after 48 hrs by MTT assay2012European journal of medicinal chemistry, Aug, Volume: 54Withaferin A-related steroids from Withania aristata exhibit potent antiproliferative activity by inducing apoptosis in human tumor cells.
AID670609Cytotoxicity against african green monkey Vero cells assessed as cell viability after 72 hrs by MTT assay2012European journal of medicinal chemistry, Aug, Volume: 54Withaferin A-related steroids from Withania aristata exhibit potent antiproliferative activity by inducing apoptosis in human tumor cells.
AID639261Cytotoxicity against human MCR5 cells after 72 hrs by MTS assay2011Journal of natural products, Dec-27, Volume: 74, Issue:12
Cytotoxic withanolide constituents of Physalis longifolia.
AID670603Cytotoxicity against human A549 cells assessed as cell viability after 48 hrs by MTT assay2012European journal of medicinal chemistry, Aug, Volume: 54Withaferin A-related steroids from Withania aristata exhibit potent antiproliferative activity by inducing apoptosis in human tumor cells.
AID1379652Cytotoxicity against human A549 cells assessed as reduction in cell viability using compound addition to cell culture cells in lag phase of growth and incubated for 48 hrs by MTT assay2017European journal of medicinal chemistry, Nov-10, Volume: 140Structure-based design, synthesis, and biological evaluation of withaferin A-analogues as potent apoptotic inducers.
AID670604Cytotoxicity against human HeLa cells assessed as cell viability after 72 hrs by MTT assay2012European journal of medicinal chemistry, Aug, Volume: 54Withaferin A-related steroids from Withania aristata exhibit potent antiproliferative activity by inducing apoptosis in human tumor cells.
AID1379650Cytotoxicity against human HeLa cells assessed as reduction in cell viability using compound addition to cell culture cells in lag phase of growth and incubated for 48 hrs by MTT assay2017European journal of medicinal chemistry, Nov-10, Volume: 140Structure-based design, synthesis, and biological evaluation of withaferin A-analogues as potent apoptotic inducers.
AID670602Cytotoxicity against human HeLa cells assessed as cell viability after 48 hrs by MTT assay2012European journal of medicinal chemistry, Aug, Volume: 54Withaferin A-related steroids from Withania aristata exhibit potent antiproliferative activity by inducing apoptosis in human tumor cells.
AID1379655Cytotoxicity against human MCF7 cells assessed as reduction in cell viability using compound addition to cell culture cells in log phase of growth and incubated for 48 hrs by MTT assay2017European journal of medicinal chemistry, Nov-10, Volume: 140Structure-based design, synthesis, and biological evaluation of withaferin A-analogues as potent apoptotic inducers.
AID670610Selectivity index, ratio of IC50 for african green monkey Vero cells to IC50 for human MCF7 cells after 48 hrs2012European journal of medicinal chemistry, Aug, Volume: 54Withaferin A-related steroids from Withania aristata exhibit potent antiproliferative activity by inducing apoptosis in human tumor cells.
AID1240126Cytotoxicity against mouse C3H10T1/2 cells after 24 hrs by FMCA2015Bioorganic & medicinal chemistry letters, Sep-01, Volume: 25, Issue:17
Hedgehog inhibitors from Withania somnifera.
AID639257Cytotoxicity against mouse B16F10 cells after 72 hrs by MTS assay2011Journal of natural products, Dec-27, Volume: 74, Issue:12
Cytotoxic withanolide constituents of Physalis longifolia.
AID639259Cytotoxicity against human JMAR cells after 72 hrs by MTS assay2011Journal of natural products, Dec-27, Volume: 74, Issue:12
Cytotoxic withanolide constituents of Physalis longifolia.
AID1379656Cytotoxicity against African green monkey Vero cells assessed as reduction in cell viability using compound addition to cell culture cells in lag phase of growth and incubated for 48 hrs by MTT assay2017European journal of medicinal chemistry, Nov-10, Volume: 140Structure-based design, synthesis, and biological evaluation of withaferin A-analogues as potent apoptotic inducers.
AID1379653Cytotoxicity against human A549 cells assessed as reduction in cell viability using compound addition to cell culture cells in log phase of growth and incubated for 48 hrs by MTT assay2017European journal of medicinal chemistry, Nov-10, Volume: 140Structure-based design, synthesis, and biological evaluation of withaferin A-analogues as potent apoptotic inducers.
AID1240122Inhibition of hedgehog/GLI1-mediated transcriptional activity in human HaCaT cells after 12 hrs by luciferase assay2015Bioorganic & medicinal chemistry letters, Sep-01, Volume: 25, Issue:17
Hedgehog inhibitors from 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.
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.
AID639260Cytotoxicity against human MDA1986 cells after 72 hrs by MTS assay2011Journal of natural products, Dec-27, Volume: 74, Issue:12
Cytotoxic withanolide constituents of Physalis longifolia.
AID670607Cytotoxicity against human MCF7 cells assessed as cell viability after 72 hrs by MTT assay2012European journal of medicinal chemistry, Aug, Volume: 54Withaferin A-related steroids from Withania aristata exhibit potent antiproliferative activity by inducing apoptosis in human tumor cells.
[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's5 (100.00)24.3611
2020's0 (0.00)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
staurosporine
[no description available]		2.0710indolocarbazole alkaloid;
organic heterooctacyclic compound		apoptosis inducer;
bacterial metabolite;
EC 2.7.11.13 (protein kinase C) inhibitor;
geroprotector
withaferin a
withaferin A: an antiestrogen and phytogenic antineoplastic agent isolated from leaves of Withania somnifera Dun.; structure. withaferin A : A withanolide that is 5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione substituted by hydroxy groups at positions 4 and 27 (the 4beta,5beta,6beta,22R stereoisomer). Isolated from Physalis longifolia, it exhibits cytotoxic activity.		2.151027-hydroxy steroid;
4-hydroxy steroid;
delta-lactone;
enone;
epoxy steroid;
ergostanoid;
primary alcohol;
secondary alcohol;
withanolide		antineoplastic agent;
apoptosis inducer
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)		2.5120actinomycinmutagen
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
mercaptopurine
Mercaptopurine: An antimetabolite antineoplastic agent with immunosuppressant properties. It interferes with nucleic acid synthesis by inhibiting purine metabolism and is used, usually in combination with other drugs, in the treatment of or in remission maintenance programs for leukemia.. purine-6-thiol : A thiol that is the tautomer of mercaptopurine.. mercaptopurine : A member of the class of purines that is 6,7-dihydro-1H-purine carrying a thione group at position 6. An adenine analogue, it is used in the treatment of acute lymphocytic leukemia (ALL), chronic myeloid leukemia (CML), Crohn's disease, and ulcerative colitis.		2.5120aryl thiol;
purines;
thiocarbonyl compound		anticoronaviral agent;
antimetabolite;
antineoplastic agent
2,3-dihydro-3beta-methoxy withaferin A
2,3-dihydro-3beta-methoxy withaferin A : A withanolide that is 2,3-dihydrowithaferin A substituted by a beta-methoxy group at position 3. It has been isolated from the aerial parts of Physalis longifolia.		2.793027-hydroxy steroid;
4-hydroxy steroid;
delta-lactone;
epoxy steroid;
ergostanoid;
primary alcohol;
secondary alcohol;
withanolide		metabolite;
plant metabolite
withanolide a
[no description available]		2.110withanolide
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.		2.783027-hydroxy steroid;
4-hydroxy steroid;
delta-lactone;
epoxy steroid;
ergostanoid;
primary alcohol;
steroid sulfate;
withanolide		antineoplastic agent;
metabolite;
plant metabolite
nimorazole
[no description available]		340
ConditionIndicatedRelationship StrengthStudiesTrials
Carcinoma, Epidermoid
[description not available]		02.0610
Carcinoma, Squamous Cell
A carcinoma derived from stratified SQUAMOUS EPITHELIAL CELLS. It may also occur in sites where glandular or columnar epithelium is normally present. (From Stedman, 25th ed)		02.0610
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
Benign Neoplasms
[description not available]		02.1110
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.		02.1110
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