Basic information
- CAS
5119-48-2- Standard SMILES
CC1=C(CO)C(=O)O[C@@H]([C@@H](C)[C@H]2CC[C@H]3[C@@H]4C[C@H]5O[C@]56[C@@H](O)C=CC(=O)[C@]6(C)[C@H]4CC[C@]23C)C1- InChIKey
DBRXOUCRJQVYJQ-CKNDUULBSA-N- Molecular formula
- C28H38O6
- Average molar mass
- 470.6 g/mol
- Monoisotopic mass
- 470.26683893
Overview
Withaferin A is 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. It has a role as an antineoplastic agent and an apoptosis inducer. It is an epoxy steroid, a primary alcohol, a delta-lactone, a secondary alcohol, a 27-hydroxy steroid, an ergostanoid, an enone, a 4-hydroxy steroid and a withanolide.
Names & identifiers
- Preferred name
- Withaferin A
- IUPAC
- (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]octadec-4-en-3-one
- English name
- WITHAFERIN A
- Molecular formula
- C28H38O6
- Molecular weight
- 470.6
Names & synonyms
Withaferin A5119-48-2Withaferine ANSC-101088NSC 273757WITHAFERIN DERIV JPR, IOWA U. COMPOUNDL6DO3QW4K5NSC-273757CHEBI:69120DTXSID109654594beta,27-dihydroxy-1-oxo-5beta,6beta-epoxywitha-2,24-dienolide(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]octadec-4-en-3-one
Show more names
upeferinA.WithaferinewithaferineaWithaferin A-RMWithaferin A (WFA)Withaferin A Standard
5,6-epoxy-4,22,27-trihydroxy-1-oxoergosta-2,24-dienoic acid delta-lactone(4beta,5beta,6beta,22R)-4,27-dihydroxy-5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione(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)octadec-4-en-3-oneRefChem:934222DTXCID901393128(4 beta,5 beta,6 beta,22R)-5,6-epoxy-4,22,27-trihydroxy-1-oxoergosta-2,24-dien-26-oic acid, delta-lactoneMFCD10687098Withaferin A (Standard)
Properties
Computed structural properties
- XLogP
- 3.8
- Topological polar surface area
- 96.4 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 3
- Heavy atoms
- 34
- Formal charge
- 0
- Complexity
- 999
Experimental & physicochemical properties
LipidsLipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Withanolides and derivatives [ST0116]
Physicochemical properties
- Melting point
- 252 · 252-253℃
- alpha
- 28 · D28 +125° (c = 1.30 in CHCl3)
- Boiling point
- 680.7 · 680.7±55.0 °C(Predicted)
- Density
- 1.28 · 1.28
- Flash point
- 226 ℃ · 226℃
- storage temp.
- -20 °C · Desiccate at -20°C
- solubility
- Soluble in DMSO (up to 20 mg/ml)
- pka
- 13.49 · 13.49±0.70(Predicted)
- form
- White solid
- color
- White
- biological source
- plant (Withania somnifera)
- Stability
- 1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- rtecs
- KE7288500
- hs_code
- 29322090
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- T
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P271-P280
Chemistry & industry
Applications
DescriptionWithaferin A (5119-48-2) displays potent antiangiogenesis activity inhibiting endothelial cell sprouting in vitro(IC50= 12 nM) andin vivo.1Potently inhibits NF-κB activation by preventing TNFα-induced activation of IKKβ.2Covalently binds to the intermediate filament protein, vimentin3inducing its disassembly and serine 56 phosphorylation4. Inhibits reactive gliosis and blocks TNFα-mediated neuronal apoptosis inin vivomodels.5
UsesWithaferin A is a promising anticancer constituent of Ayurvedic medicinal plant Withania somnifera. Withaferin A showed potent cytotoxicity against human head and neck squamous cell carcinoma (JMAR and MDA-1986). Withaferin A has recently been found to be a leptin sensitizer that can reduce the weight in obese mice fed in a high-fat diet (see C249500).
Suppliers100 total
南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
宁波君龙新材料有限公司0574 88552218 18969899212 · [email protected]
銘瑞集團有限公司17318633522 · [email protected]
武汉敬康恩生物医药科技有限公司13720134139 086-15871494362 13720134139 · [email protected]
成都埃法生物科技有限公司028-028-85142057 19983342022 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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