(3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-(acetyloxy)-4-(butanoyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-[(2-methylbut-2-enoyl)oxy]-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,8H,9bH-azuleno[4,5-b]furan-7-yl hexanoate

• ChemBase ID: 155585
• Molecular Formular: C32H46O12
• Molecular Mass: 622.70044
• Monoisotopic Mass: 622.29892691
• SMILES: CCCCCC(=O)O[C@H]1[C@H]2C(=C([C@@H]1OC(=O)/C(=C\C)/C)C)[C@H]1[C@]([C@H](C[C@]2(C)OC(=O)C)OC(=O)CCC)([C@](C(=O)O1)(C)O)O
• Canonical SMILES: CCCCCC(=O)O[C@@H]1[C@@H](OC(=O)/C(=C\C)/C)C(=C2[C@H]1[C@@](C)(OC(=O)C)C[C@@H]([C@]1([C@H]2OC(=O)[C@@]1(C)O)O)OC(=O)CCC)C
• InChI: InChI=1S/C32H46O12/c1-9-12-13-15-22(35)41-26-24-23(18(5)25(26)42-28(36)17(4)11-3)27-32(39,31(8,38)29(37)43-27)20(40-21(34)14-10-2)16-30(24,7)44-19(6)33/h11,20,24-27,38-39H,9-10,12-16H2,1-8H3/t20-,24+,25-,26-,27-,30-,31+,32+/m0/s1
• InChIKey: LXWLOFYIORKNSA-SMLFKXMWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-(acetyloxy)-4-(butanoyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-[(2-methylbut-2-enoyl)oxy]-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,8H,9bH-azuleno[4,5-b]furan-7-yl hexanoate
• IUPAC Traditional name: (3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-(acetyloxy)-4-(butanoyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-[(2-methylbut-2-enoyl)oxy]-2-oxo-4H,5H,6aH,7H,8H,9bH-azuleno[4,5-b]furan-7-yl hexanoate
• Synonyms: Thapsigargicin

Database IDs

• CAS Number: 67526-94-7
• MDL Number: MFCD00214081
• PubChem SID: 162249723
• PubChem CID: 10258363

CALCULATED PROPERTIES

• Acid pKa: 11.135566
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 3.495387
• LogD (pH = 7.4): 3.4953084
• Log P: 3.4953883
• Molar Refractivity: 154.6138 cm^3
• Polarizability: 62.235687 Å^3
• Polar Surface Area: 171.96 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥90%
• Empirical Formula (Hill Notation): C32H46O12

DETAILS

Sigma Aldrich - T4557

Biochem/physiol Actions
Mobilizes intracellular Ca2+.
Linkage
Less potent and less hydrophobic analog of thapsigargin.