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| SKU | Size | Availability |
Price | Qty |
|---|---|---|---|---|
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W133732-1mg
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1mg |
3
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$97.90
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W133732-5mg
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5mg |
3
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$369.90
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Naturally occurring withanolide/steroidal lactone with anticancer properties
| Synonyms | NSC273757 | NSC-273757 | WITHAFERIN A [MI] | NCGC00180796-02_C28H38O6_(4beta,5beta,6beta,22R)-4,27-Dihydroxy-5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione | A1-06845 | C08841 | DS-13282 | SMR004701668 | Ashwagandha | NSC-101088 | Withaferine A | 5.beta.- |
|---|---|
| Specifications & Purity | ≥98%(HPLC) |
| Biochemical and Physiological Mechanisms | Naturally occurring withanolide/steroidal lactone with anticancer properties. Demonstrates a number of cellular effects including the covalent binding to annexin II, inhibition of chymotrypsin-like activity, PKC and caspase 3. Causes translocation of cyct |
| Storage Temp | Store at 2-8°C |
| Shipped In |
Wet ice This product requires cold chain shipping. Ground and other economy services are not available. |
| Note | Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details. |
Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Lipids and lipid-like molecules |
| Class | Steroids and steroid derivatives |
| Subclass | Steroid lactones |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Withanolides and derivatives |
| Alternative Parents | 5,6-epoxysteroids Oxepanes Dihydropyranones Cyclohexenones Enoate esters Secondary alcohols Lactones Oxacyclic compounds Monocarboxylic acids and derivatives Epoxides Dialkyl ethers Primary alcohols Organic oxides Hydrocarbon derivatives |
| Molecular Framework | Aliphatic heteropolycyclic compounds |
| Substituents | Withanolide-skeleton - 5,6-epoxysteroid - Dihydropyranone - Oxepane - Cyclohexenone - Pyran - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Carboxylic acid ester - Ketone - Lactone - Secondary alcohol - Oxacycle - Carboxylic acid derivative - Organoheterocyclic compound - Dialkyl ether - Oxirane - Ether - Monocarboxylic acid or derivatives - Carbonyl group - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Alcohol - Organooxygen compound - Primary alcohol - Aliphatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring. |
| External Descriptors | Steroids |
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| IUPAC Name | (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 |
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| 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 |
| InChIKey | DBRXOUCRJQVYJQ-CKNDUULBSA-N |
| Smiles | CC1=C(C(=O)OC(C1)C(C)C2CCC3C2(CCC4C3CC5C6(C4(C(=O)C=CC6O)C)O5)C)CO |
| Isomeric SMILES | CC1=C(C(=O)O[C@H](C1)[C@@H](C)[C@H]2CC[C@@H]3[C@@]2(CC[C@H]4[C@H]3C[C@@H]5[C@]6([C@@]4(C(=O)C=C[C@@H]6O)C)O5)C)CO |
| PubChem CID | 265237 |
| Molecular Weight | 470.6 |
| Molecular Weight | 470.600 g/mol |
|---|---|
| XLogP3 | 3.800 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 3 |
| Exact Mass | 470.267 Da |
| Monoisotopic Mass | 470.267 Da |
| Topological Polar Surface Area | 96.400 Ų |
| Heavy Atom Count | 34 |
| Formal Charge | 0 |
| Complexity | 999.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 11 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |