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(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
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ChemBase ID:
130192
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Molecular Formular:
C28H38O6
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Molecular Mass:
470.59772
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Monoisotopic Mass:
470.26683894
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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
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Cite this record
CBID:130192 http://www.chembase.cn/molecule-130192.html
NAMES AND DATABASE IDS
NAMES AND DATABASE IDS
Names Database IDs
IUPAC name
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(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
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IUPAC Traditional name
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Synonyms
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(4β,5β,6β,22R)-5,6-Epoxy-4,22,27-trihydroxy-1-oxoergosta-2,24-dien-26-oic Acid δ-Lactone
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(20S,22R)-5,6β-Epoxy-4β,22,27-trihydroxy-1-oxo-5β-ergosta-2,24-dien-26-oic Acid δ-Lactone
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NSC 101088
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NSC 273757
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Withaferine
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Withaferine A
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Withaferin A
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5,6-Epoxy-4,27-dihydroxy-1-oxowitha-2,24-dienolide
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Withaferin A
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4β,5β,6β,22R)-5,6-Epoxy-4,22,27-trihydroxy-1-oxo-ergosta-2,24-dien-26-oic acid δ-lactone
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CAS Number
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MDL Number
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PubChem SID
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PubChem CID
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CHEMBL
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Chemspider ID
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Wikipedia Title
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DATA SOURCES
DATA SOURCES
All Sources Commercial Sources Non-commercial Sources
CALCULATED PROPERTIES
CALCULATED PROPERTIES
JChem
Acid pKa
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13.428069
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H Acceptors
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5
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H Donor
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2
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LogD (pH = 5.5)
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3.581974
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LogD (pH = 7.4)
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3.5819738
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Log P
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3.581974
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Molar Refractivity
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127.1947 cm3
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Polarizability
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50.23607 Å3
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Polar Surface Area
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96.36 Å2
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Rotatable Bonds
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3
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Lipinski's Rule of Five
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true
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DETAILS
DETAILS
Wikipedia
Sigma Aldrich
TRC
Sigma Aldrich -
W4394
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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
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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). |
PATENTS
PATENTS
PubChem Patent
Google Patent