3,13,14-trihydroxy-5-methoxy-8,17-dioxatetracyclo[8.7.0.02,7.011,16]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-9-one

• ChemBase ID: 130184
• Molecular Formular: C16H10O7
• Molecular Mass: 314.2464
• Monoisotopic Mass: 314.04265266
• SMILES: O=c1oc2cc(OC)cc(O)c2c2oc3c(cc(O)c(O)c3)c12
• Canonical SMILES: COc1cc(O)c2c(c1)oc(=O)c1c2oc2c1cc(c(c2)O)O
• InChI: InChI=1S/C16H10O7/c1-21-6-2-10(19)14-12(3-6)23-16(20)13-7-4-8(17)9(18)5-11(7)22-15(13)14/h2-5,17-19H,1H3
• InChIKey: XQDCKJKKMFWXGB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,13,14-trihydroxy-5-methoxy-8,17-dioxatetracyclo[8.7.0.0^2,^7.0^1^1,^1^6]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-9-one
• IUPAC Traditional name: wedelolactone
• Synonyms: 1,8,9-Trihydroxy-3-methoxy-6H-benzofuro[3,2-c][1]benzopyran-6-one; 7-Methoxy-5,11,12-trihydroxycoumestan; Wedelolactone; 5,11,12-Trihydroxy-7-methoxycoumestan; Wedelolactone

Database IDs

• CAS Number: 524-12-9
• MDL Number: MFCD07778564
• PubChem SID: 24724667; 162224468
• PubChem CID: 5281813
• CHEMBL: 97453
• Chemspider ID: 4445124
• KEGG ID: C10541
• Wikipedia Title: Wedelolactone

CALCULATED PROPERTIES

• Acid pKa: 6.6253104
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.9049144
• LogD (pH = 7.4): 1.0707927
• Log P: 1.9360847
• Molar Refractivity: 78.0636 cm^3
• Polarizability: 31.853857 Å^3
• Polar Surface Area: 109.36 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble >10 mg/mL
• Apperance: pale yellow solid; Yellow powder

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-43
• Safety Statements: 36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H317
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC); 98.5
• Empirical Formula (Hill Notation): C16H10O7

DETAILS

Sigma Aldrich - W4016

Biochem/physiol Actions
Wedelolactone inhibits NF-κB-mediated gene transcription in cells by blocking the phosphorylation and degradation of IκBα. Irreversible inhibitor of IKKα and β kinase activity (IC50 < 10 μM). Wedelolactone has no effects on p38 MAP kinase or Akt.