18-(methoxymethyl)-1,5-dimethyl-6,11,16-trioxo-13,17-dioxapentacyclo[10.6.1.0^{2,10}.0^{5,9}.0^{15,19}]nonadeca-2(10),12(19),14-trien-3-yl acetate

• ChemBase ID: 105996
• Molecular Formular: C23H24O8
• Molecular Mass: 428.43186
• Monoisotopic Mass: 428.14711773
• SMILES: COCC1OC(=O)c2coc3c2C1(C)C1=C(C2CCC(=O)C2(C)CC1OC(=O)C)C3=O
• Canonical SMILES: COCC1OC(=O)c2c3C1(C)C1=C(C(=O)c3oc2)C2C(CC1OC(=O)C)(C)C(=O)CC2
• InChI: InChI=1S/C23H24O8/c1-10(24)30-13-7-22(2)12(5-6-14(22)25)16-18(13)23(3)15(9-28-4)31-21(27)11-8-29-20(17(11)23)19(16)26/h8,12-13,15H,5-7,9H2,1-4H3
• InChIKey: QDLHCMPXEPAAMD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 18-(methoxymethyl)-1,5-dimethyl-6,11,16-trioxo-13,17-dioxapentacyclo[10.6.1.0^{2,10}.0^{5,9}.0^{15,19}]nonadeca-2(10),12(19),14-trien-3-yl acetate
• IUPAC Traditional name: wortmannin
• Synonyms: WORTMANNIN

Database IDs

• CAS Number: 19545-26-7
• PubChem SID: 162087206
• PubChem CID: 5691

CALCULATED PROPERTIES

• Acid pKa: 19.667614
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 1.4426177
• LogD (pH = 7.4): 1.4426177
• Log P: 1.4426177
• Molar Refractivity: 106.8572 cm^3
• Polarizability: 41.506565 Å^3
• Polar Surface Area: 109.11 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C, Desiccate
• RTECS: CB9641000

DETAILS

MP Biomedicals - 02195690

A fungal metabolite which potently and selectively inhibits phosphatidylinositol 3-kinase. It also inhibits fMLP induced PIP₃ and superoxide anion production in guinea pig neutrophils. It blocks insulin metabolic effects in rat adipocytes without affecting the insulin receptor tyrosine kinase activity.