(3S,8S,9S)-8,9,16-trihydroxy-14-methoxy-3-methyl-3,4,7,8,9,10-hexahydro-1H-2-benzoxacyclotetradecine-1,7-dione

• ChemBase ID: 154708
• Molecular Formular: C19H22O7
• Molecular Mass: 362.37378
• Monoisotopic Mass: 362.13655304
• SMILES: C[C@H]1C/C=C\C(=O)[C@H]([C@H](C/C=C/c2cc(cc(c2C(=O)O1)O)OC)O)O
• Canonical SMILES: COc1cc2/C=C/C[C@H](O)[C@H](O)C(=O)/C=C\C[C@@H](OC(=O)c2c(c1)O)C
• InChI: InChI=1S/C19H22O7/c1-11-5-3-7-14(20)18(23)15(21)8-4-6-12-9-13(25-2)10-16(22)17(12)19(24)26-11/h3-4,6-7,9-11,15,18,21-23H,5,8H2,1-2H3/t11-,15-,18+/m0/s1
• InChIKey: NEQZWEXWOFPKOT-GEWABHDNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,8S,9S)-8,9,16-trihydroxy-14-methoxy-3-methyl-3,4,7,8,9,10-hexahydro-1H-2-benzoxacyclotetradecine-1,7-dione
• IUPAC Traditional name: (3S,8S,9S)-8,9,16-trihydroxy-14-methoxy-3-methyl-4,8,9,10-tetrahydro-3H-2-benzoxacyclotetradecine-1,7-dione
• Synonyms: C 292; F 152; FR148083; L 783279; LL-Z1640-2; 5Z-7-Oxozeaenol

Database IDs

• CAS Number: 253863-19-3
• MDL Number: MFCD12912700
• PubChem SID: 162248846
• PubChem CID: 9863776

CALCULATED PROPERTIES

• Acid pKa: 9.592829
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 2.571879
• LogD (pH = 7.4): 2.5691597
• Log P: 2.5719137
• Molar Refractivity: 96.7688 cm^3
• Polarizability: 36.525272 Å^3
• Polar Surface Area: 113.29 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: white to off-white powder

Safety Information

• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C19H22O7

DETAILS

Sigma Aldrich - O9890

Biochem/physiol Actions
5Z-7-oxozeaenol is a potent ATP-competitive irreversible inhibitor of ERK2 (IC50= 80 nM), TAK1 (MKK7), and MEK1, which all contain a common cysteine residue in the ATP-binding site. It has no activity against other MAP kinases. 5Z-7-oxozeaenol is also anti-inflammatory.