(1S,2R,6S,7R,9R,11S,12S,15R,16S)-6-hydroxy-15-[(1S)-1-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]ethyl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-3-one

• ChemBase ID: 130192
• Molecular Formular: C28H38O6
• Molecular Mass: 470.59772
• Monoisotopic Mass: 470.26683894
• SMILES: O=C1O[C@H](CC(=C1CO)C)[C@@H](C)[C@H]1CC[C@@H]2[C@]1(C)CC[C@@H]1[C@]3(C(=O)C=C[C@H](O)[C@@]43O[C@@H]4C[C@@H]21)C
• Canonical SMILES: OCC1=C(C)C[C@@H](OC1=O)[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2C[C@@H]2[C@]3([C@]1(C)C(=O)C=C[C@@H]3O)O2)C
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,6S,7R,9R,11S,12S,15R,16S)-6-hydroxy-15-[(1S)-1-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]ethyl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0^2,^7.0^7,^9.0^1^2,^1^6]octadec-4-en-3-one
• IUPAC Traditional name: withaferin A
• Synonyms: (4β,5β,6β,22R)-5,6-Epoxy-4,22,27-trihydroxy-1-oxoergosta-2,24-dien-26-oic Acid δ-Lactone; (20S,22R)-5,6β-Epoxy-4β,22,27-trihydroxy-1-oxo-5β-ergosta-2,24-dien-26-oic Acid δ-Lactone; NSC 101088; NSC 273757; Withaferine; Withaferine A; Withaferin A; 5,6-Epoxy-4,27-dihydroxy-1-oxowitha-2,24-dienolide; Withaferin A; 4β,5β,6β,22R)-5,6-Epoxy-4,22,27-trihydroxy-1-oxo-ergosta-2,24-dien-26-oic acid δ-lactone

Database IDs

• CAS Number: 5119-48-2
• MDL Number: MFCD10687098
• PubChem SID: 162224476
• PubChem CID: 265237
• CHEMBL: 1221986
• Chemspider ID: 233064
• Wikipedia Title: Withaferin_A

CALCULATED PROPERTIES

• Acid pKa: 13.428069
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 3.581974
• LogD (pH = 7.4): 3.5819738
• Log P: 3.581974
• Molar Refractivity: 127.1947 cm^3
• Polarizability: 50.23607 Å^3
• Polar Surface Area: 96.36 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 228-230°C; 252-253 °C
• Flash Point: 226 °C; 438.8 °F

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: KE7288500
• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95% (HPLC); ≥95.0% (HPLC)
• Grade: analytical standard
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C28H38O6

DETAILS

Sigma Aldrich - W4394

Frequently Asked Questions
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Biochem/physiol Actions
Steroidal lactone that exhibits cytotoxicity towards tumor cells. Protective effects attributed to anti-lipid peroxidative, antioxidant and detoxifying functionality.

Toronto Research Chemicals - W499200

Withaferin 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).

REFERENCES

• Shohat, B., et al.: Cancer Chemother. Rep., 51, 271 (1967)
• Shohat, B., et al.: Int. J. Cancer., 8, 487 (1967)