Withaferin A (Q6606395)

(1S,2R,6R,7R,9R,11S,12S,15S,16R)-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]octadec-4-en-3-one

inferred from SMILES

stereoisomer of

2 references

inferred from InChIKey

(1S,2R,6S,7R,9R,11S,12S,15R,16S)-6-hydroxy-15-[(1R)-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]octadec-4-en-3-one

1 reference

(1S,2R,6S,7R,9R,11S,12S,15R,16S)-6-hydroxy-15-[(1S)-1-[(2S)-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]octadec-4-en-3-one

1 reference

(1S,2R,6R,7R,9R,11S,12S,15R,16S)-6-hydroxy-15-[(1S)-1-[(2S)-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]octadec-4-en-3-one

1 reference

chemical formula

C₂₈H₃₈O₆

1 reference

PubChem

canonical SMILES

O=C1OC(CC(=C1CO)C)C(C)C2CCC3C4CC5OC65C(O)C=CC(=O)C6(C)C4CCC23C

0 references

isomeric SMILES

O=C/1O[C@H](CC(=C\1CO)\C)[C@@H](C)[C@H]6CC[C@@H]4[C@]6(C)CC[C@@H]3[C@]5(C(=O)\C=C/[C@H](O)[C@]52O[C@@H]2C[C@H]34)C

1 reference

Distribution of the chemotypes ofWithania somnifera in some areas of Israel: Feeding studies withSpodoptera littoralis larvae and chemical examination of withanolide content

34 references

Effects of glycowithanolides fromWithania somnifera on morphine-induced inhibition of intestinal motility and tolerance to analgesia in mice

Cholinesterase inhibiting withanolides from Withania somnifera

A New Withanolide from the Roots of Withania somnifera

Anti-stress activity of sitoindosides VII and VIII, new acylsterylglucosides fromWithania somnifera

Growth inhibition of human tumor cell lines by withanolides from Withania somnifera leaves

A standardized root extract of Withania somnifera and its major constituent withanolide-A elicit humoral and cell-mediated immune responses by up regulation of Th1-dominant polarization in BALB/c mice.

Cyclooxygenase-2 enzyme inhibitory withanolides from Withania somnifera leaves

Withanolide synthesis in cultures of Withania somnifera transformed with Agrobacterium tumefaciens

Quantitative HPLC analysis of withanolides in Withania somnifera

Structures of withanosides I, II, III, IV, V, VI, and VII, new withanolide glycosides, from the roots of Indian Withania somnifera DUNAL. and inhibitory activity for tachyphylaxis to clonidine in isolated guinea-pig ileum

In vitro propagation of Withania somnifera and isolation of withanolides with immunosuppressive activity

Production of withaferin A in shoot cultures of Withania somnifera.

Effect of Withania somnifera glycowithanolides on a rat model of tardive dyskinesia

Effect of Withaferin A on the development and decay of thermotolerance in B16F1 melanoma: a preliminary study

Cell Differentiation Inducing Steroids from Withania somnifera L. (DUN.).

Withanolide derivatives from the roots of Withania somnifera and their neurite outgrowth activities.

Modification of bone marrow radiosensensitivity by medicinal plant extracts

Cholinesterase Inhibiting Withanolides from Withania somnifera.

2,3-Dihydrowithaferin A-3beta-O-sulfate, a new potential prodrug of withaferin A from aeroponically grown Withania somnifera

Withaferin A, a steroidal lactone from Withania somnifera, induces mitotic catastrophe and growth arrest in prostate cancer cells

Chlorinated and diepoxy withanolides from Withania somnifera and their cytotoxic effects against human lung cancer cell line

Effect of the alcoholic extract of Ashwagandha leaves and its components on proliferation, migration, and differentiation of glioblastoma cells: combinational approach for enhanced differentiation.

Comprehensive metabolic fingerprinting of Withania somnifera leaf and root extracts

Chlorinated and diepoxy withanolides from Withania somnifera and their cytotoxic effects against human lung cancer cell line

Phytochemical and genetic analysis in selected chemotypes of Withania somnifera

In vitro propagation of Withania somnifera and isolation of withanolides with immunosuppressive activity

Cyclooxygenase-2 enzyme inhibitory withanolides from Withania somnifera leaves

Cell Differentiation Inducing Steroids from Withania somnifera L. (DUN.).

Unusually sulfated and oxygenated steroids from Withania somnifera.

Withanolides from Withania somnifera roots

Unusual withanolides from aeroponically grown Withania somnifera

Withanolide derivatives from the roots of Withania somnifera and their neurite outgrowth activities.

Par-4-dependent apoptosis by the dietary compound withaferin A in prostate cancer cells

Acnistus arborescens

1 reference

Finding the needle in the haystack. The dereplication of natural product extracts

Vassobia breviflora

6 references

Biosynthesis of withanolides in Acnistus breviflorus: biogenetic relationships among the main withanolides

2,3-dihydrojaborosalactone A, a withanolide from Acnistus breviflorus

Biosynthesis of withanolides in Acnistus breviflorus. Incorporation of labelled 24-methylenecholesterol

Withanolides of Acnistus breviflorus

2,3-dihydrojaborosalactone A, a withanolide from Acnistus breviflorus

Withaferin A, a cytotoxic steroid from Vassobia breviflora, induces apoptosis in human head and neck squamous cell carcinoma

Iochroma coccinea

1 reference

Lochromolide: A New Acetylated Withanolide from Iochroma coccineum

Withania coagulans

1 reference

Withacoagin, a New Withanolide fromWithania coagulansRoots

Physalis longifolia

3 references

Cytotoxic withanolide constituents of Physalis longifolia.

Cytotoxic withanolide constituents of Physalis longifolia.

Cytotoxic withanolide constituents of Physalis longifolia

Withania aristata

1 reference

Iochroma gesnerioides

1 reference

Lochromolide: A New Acetylated Withanolide from Iochroma coccineum

Identifiers

InChI

InChI=1S/C28H38O6/c1-14-11-21(33-25(32)17(14)13-29)15(2)18-5-6-19-16-12-24-28(34-24)23(31)8-7-22(30)27(28,4)20(16)9-10-26(18,19)3/h7-8,15-16,18-21,23-24,29,31H,5-6,9-13H2,1-4H3/t15-,16-,18+,19-,20-,21+,23-,24+,26+,27-,28+/m0/s1

1 reference

PubChem

2 references

PubChem

ChEBI release 2020-09-01

CAS Registry Number

5119-48-2

2 references

https://commonchemistry.cas.org/detail?cas_rn=5119-48-2

8 April 2021

ChemSpider ID

233064

1 reference

PubChem CID

265237

2 references

ChEBI ID

69120

mapping relation type

exact match

2 references

International Chemical Identifier

InChI

InChI=1S/C28H38O6/c1-14-11-21(33-25(32)17(14)13-29)15(2)18-5-6-19-16-12-24-28(34-24)23(31)8-7-22(30)27(28,4)20(16)9-10-26(18,19)3/h7-8,15-16,18-21,23-24,29,31H,5-6,9-13H2,1-4H3/t15-,16-,18+,19-,20-,21+,23-,24+,26+,27-,28+/m0/s1

ChEMBL ID

CHEMBL1221986

1 reference

2 references

inferred from InChIKey

splash10-001i-0891100000-85b25b9052ec41684fe5

1 reference

0 references

splash10-0006-0000900000-68fb259bb9a18733de80

0 references

DSSTox substance ID

DTXSID10965459

1 reference

DSSTOX compound identifier

0 references

0 references

0 references

0 references

1 reference

http://www.lipidmaps.org/rest/compound/lm_id/LM/all/download

0 references

0 references

1 reference

retrieved

15 January 2022