Home > Compound List > Compound details
5119-48-2 molecular structure
click picture or here to close

(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 and InChIs

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

Cite this record

CBID:130192 http://www.chembase.cn/molecule-130192.html

Collapse All Expand All

NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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[9.7.0.02,7.07,9.012,16]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
CAS Number
5119-48-2
MDL Number
MFCD10687098
PubChem SID
162224476
PubChem CID
265237
CHEMBL
1221986
Chemspider ID
233064
Wikipedia Title
Withaferin_A

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 13.428069  H Acceptors
H Donor LogD (pH = 5.5) 3.581974 
LogD (pH = 7.4) 3.5819738  Log P 3.581974 
Molar Refractivity 127.1947 cm3 Polarizability 50.23607 Å3
Polar Surface Area 96.36 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
Methanol expand Show data source
Apperance
White Solid expand Show data source
Melting Point
228-230°C expand Show data source
252-253 °C expand Show data source
Flash Point
226 °C expand Show data source
438.8 °F expand Show data source
Storage Condition
-20°C Freezer expand Show data source
RTECS
KE7288500 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥95% (HPLC) expand Show data source
≥95.0% (HPLC) expand Show data source
Grade
analytical standard expand Show data source
Certificate of Analysis
Download expand Show data source
Shelf Life
(limited shelf life, expiry date on the label) expand Show data source
Empirical Formula (Hill Notation)
C28H38O6 expand Show data source

DETAILS

DETAILS

Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
Sigma Aldrich - W4394 external link
Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
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 external link
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Shohat, B., et al.: Cancer Chemother. Rep., 51, 271 (1967)
  • • Shohat, B., et al.: Int. J. Cancer., 8, 487 (1967)
  • Searching...Please wait...

PATENTS

PATENTS

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

INTERNET

INTERNET

Baidu iconBaidu google iconGoogle