(1S,2S,4S,5R,10R,11S,14S,15S,18S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-1-hydroxyethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.02,4.05,10.014,18]octadec-7-en-9-one

• ChemBase ID: 154848
• Molecular Formular: C28H38O6
• Molecular Mass: 470.59772
• Monoisotopic Mass: 470.26683894
• SMILES: CC1=C(C(=O)O[C@H](C1)C(C)([C@H]1CC[C@@H]2[C@@]1(CC[C@H]1[C@H]2[C@H]2[C@H](O2)[C@@]2([C@@]1(C(=O)C=CC2)C)O)C)O)C
• Canonical SMILES: CC1=C(C)C(=O)O[C@H](C1)C([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2[C@@H]2O[C@@H]2[C@@]2([C@]1(C)C(=O)C=CC2)O)(O)C
• InChI: InChI=1S/C28H38O6/c1-14-13-20(33-24(30)15(14)2)27(5,31)18-9-8-16-21-17(10-12-25(16,18)3)26(4)19(29)7-6-11-28(26,32)23-22(21)34-23/h6-7,16-18,20-23,31-32H,8-13H2,1-5H3/t16-,17-,18-,20+,21-,22-,23-,25-,26-,27+,28-/m0/s1
• InChIKey: DXWHOKCXBGLTMQ-SFQAJKIESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,4S,5R,10R,11S,14S,15S,18S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-1-hydroxyethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.0^2,^4.0^5,^1^0.0^1^4,^1^8]octadec-7-en-9-one
• IUPAC Traditional name: (1S,2S,4S,5R,10R,11S,14S,15S,18S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.0^2,^4.0^5,^1^0.0^1^4,^1^8]octadec-7-en-9-one
• Synonyms: (5α,6α,7α,22R)-6,7-Epoxy-5,20,22-trihydroxy-1-oxo-ergosta-2,24-dien-26-oic acid δ-lactone; Withanolide A

Database IDs

• CAS Number: 32911-62-9
• MDL Number: MFCD07779143
• PubChem SID: 162248986
• PubChem CID: 11294368

CALCULATED PROPERTIES

• Acid pKa: 13.016009
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 3.7034454
• LogD (pH = 7.4): 3.7034445
• Log P: 3.7034454
• Molar Refractivity: 126.9481 cm^3
• Polarizability: 50.23607 Å^3
• Polar Surface Area: 96.36 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: methanol: soluble1 mg/mL, clear, colorless
• Apperance: white powder

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°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 - W2145

Biochem/physiol Actions
C28-steroidal lactone that can induce nerve development and improve nervous system function. Potential therapeutic for neurologic disorders like Alzheimer’s and Parkinson’s disease.1 In primary rat cortical neurons, withanolide A significantly up-regulated IDE levels, a prominent enzyme involved in degrading amyloid β protein, which may help to clear excess amyloid β protein from an Alzheimer′s-inflicted brain.2

Sigma Aldrich - 74776

Biochem/physiol Actions
C28-steroidal lactone that can induce nerve development and improve nervous system function. Potential therapeutic for neurologic disorders like Alzheimer’s and Parkinson’s disease.1 In primary rat cortical neurons, withanolide A significantly up-regulated IDE levels, a prominent enzyme involved in degrading amyloid β protein, which may help to clear excess amyloid β protein from an Alzheimer′s-inflicted brain.2