(2R,3R,4S,5S,6R)-2-{[(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.02,7.011,15]heptadec-7-en-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

• ChemBase ID: 154678
• Molecular Formular: C33H56O6
• Molecular Mass: 548.79414
• Monoisotopic Mass: 548.40768951
• SMILES: C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]1[C@H]2CC=C2[C@@]1(CC[C@@H](C2)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)C)C
• Canonical SMILES: OC[C@H]1O[C@@H](O[C@H]2CC[C@]3(C(=CC[C@@H]4[C@@H]3CC[C@]3([C@H]4CC[C@@H]3[C@@H](CCCC(C)C)C)C)C2)C)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C33H56O6/c1-19(2)7-6-8-20(3)24-11-12-25-23-10-9-21-17-22(13-15-32(21,4)26(23)14-16-33(24,25)5)38-31-30(37)29(36)28(35)27(18-34)39-31/h9,19-20,22-31,34-37H,6-8,10-18H2,1-5H3/t20-,22+,23+,24-,25+,26+,27-,28-,29+,30-,31-,32+,33-/m1/s1
• InChIKey: FSMCJUNYLQOAIM-UQBZCTSOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5S,6R)-2-{[(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: cholesteryl glucoside
• Synonyms: Cholesteryl β-D-glucopyranoside; Cholesterol β-D-glucoside

Database IDs

• CAS Number: 7073-61-2
• MDL Number: MFCD00273002
• PubChem SID: 162248816
• PubChem CID: 440145

CALCULATED PROPERTIES

• Acid pKa: 12.210562
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 5.3420534
• LogD (pH = 7.4): 5.3420467
• Log P: 5.3420534
• Molar Refractivity: 153.0298 cm^3
• Polarizability: 61.48665 Å^3
• Polar Surface Area: 99.38 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Optical Rotation: [α]/D -49.0±3.0°, c = 0.5 in pyridine

Safety Information

• German water hazard class: 3

Product Information

• Purity: ≥97% (TLC)
• Empirical Formula (Hill Notation): C33H56O6

DETAILS

Sigma Aldrich - 28609

Biochem/physiol Actions
A lipid mediator in heat stress responses in animals1,2, shows anti-ulcer effect3.