(2R,4S,5R,7S,11S,15R,17R)-14-[(2R,3R)-2,3-dihydroxy-6-methylheptan-2-yl]-4,5,7,11,17-pentahydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-9-en-8-one

• ChemBase ID: 155568
• Molecular Formular: C27H44O8
• Molecular Mass: 496.63346
• Monoisotopic Mass: 496.30361837
• SMILES: CC(C)CC[C@H](C(C)(C1CC[C@@]2([C@@]1(C[C@H](C1C2=CC(=O)[C@]2([C@@]1(C[C@@H]([C@@H](C2)O)O)C)O)O)C)O)O)O
• Canonical SMILES: CC(CC[C@H](C(C1CC[C@@]2([C@]1(C)C[C@@H](O)C1C2=CC(=O)[C@]2([C@]1(C)C[C@H](O)[C@@H](C2)O)O)O)(O)C)O)C
• InChI: InChI=1S/C27H44O8/c1-14(2)6-7-20(31)25(5,33)19-8-9-26(34)15-10-21(32)27(35)13-17(29)16(28)11-24(27,4)22(15)18(30)12-23(19,26)3/h10,14,16-20,22,28-31,33-35H,6-9,11-13H2,1-5H3/t16-,17+,18+,19?,20+,22?,23+,24+,25+,26+,27+/m0/s1
• InChIKey: LRJUYAVTHIEHAI-WRENIRACSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4S,5R,7S,11S,15R,17R)-14-[(2R,3R)-2,3-dihydroxy-6-methylheptan-2-yl]-4,5,7,11,17-pentahydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-9-en-8-one
• IUPAC Traditional name: (2R,4S,5R,7S,11S,15R,17R)-14-[(2R,3R)-2,3-dihydroxy-6-methylheptan-2-yl]-4,5,7,11,17-pentahydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-9-en-8-one
• Synonyms: 2β,3β,5β,11α,14α,20R,22R-Hepta-hydroxy-cholest-7-en-6-one; MurA; Muristerone A

Database IDs

• MDL Number: MFCD00056450
• PubChem SID: 162249706; 24897194
• PubChem CID: 16219690

CALCULATED PROPERTIES

• Acid pKa: 12.479193
• H Acceptors: 8
• H Donor: 7
• LogD (pH = 5.5): -0.048007082
• LogD (pH = 7.4): -0.04801065
• Log P: -0.048007037
• Molar Refractivity: 129.9886 cm^3
• Polarizability: 51.783863 Å^3
• Polar Surface Area: 158.68 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥90%
• Linear Formula: C27H44O8

DETAILS

Sigma Aldrich - M7888

Biochem/physiol Actions
Muristerone A is a native phytosteroid known to have insecticidal properties. Induces apoptosis in cell transfected with wild-type Bax and ecdysone-inducible gene expression systems in mammalian cells and transgenic animals.