(1R,2R,6S,7S,8R,10S,12R,16S,17R,18R)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.01,11.02,6.08,10.012,16]nonadec-3-en-17-yl 5-phenylpenta-2,4-dienoate

• ChemBase ID: 155150
• Molecular Formular: C38H38O10
• Molecular Mass: 654.70232
• Monoisotopic Mass: 654.24649742
• SMILES: C[C@@H]1[C@H]([C@]2([C@H]3C4[C@]1([C@@H]1C=C(C(=O)[C@]1([C@@H]([C@@]1([C@H]4O1)CO)O)O)C)OC(O3)(O2)c1ccccc1)C(=C)C)OC(=O)/C=C/C=C/c1ccccc1
• Canonical SMILES: OC[C@]12O[C@H]1C1[C@H]3OC4(O[C@]1([C@H]1[C@@]([C@@H]2O)(O)C(=O)C(=C1)C)[C@@H]([C@H]([C@@]3(O4)C(=C)C)OC(=O)/C=C/C=C/c1ccccc1)C)c1ccccc1
• InChI: InChI=1S/C38H38O10/c1-21(2)36-30(44-27(40)18-12-11-15-24-13-7-5-8-14-24)23(4)37-26-19-22(3)29(41)35(26,43)33(42)34(20-39)31(45-34)28(37)32(36)46-38(47-36,48-37)25-16-9-6-10-17-25/h5-19,23,26,28,30-33,39,42-43H,1,20H2,2-4H3/t23-,26-,28?,30-,31+,32-,33-,34+,35-,36+,37+,38?/m1/s1
• InChIKey: DLEDLHFNQDHEOJ-KXXIKYRHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R,6S,7S,8R,10S,12R,16S,17R,18R)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0^1,^1^1.0^2,^6.0^8,^1^0.0^1^2,^1^6]nonadec-3-en-17-yl 5-phenylpenta-2,4-dienoate
• IUPAC Traditional name: (1R,2R,6S,7S,8R,10S,12R,16S,17R,18R)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0^1,^1^1.0^2,^6.0^8,^1^0.0^1^2,^1^6]nonadec-3-en-17-yl 5-phenylpenta-2,4-dienoate
• Synonyms: 12β-[(E,E)-5-Phenyl-2,4-pentadienoyloxy]daphnetoxin; Mezerein

Database IDs

• CAS Number: 34807-41-5
• MDL Number: MFCD00135953
• Beilstein Number: 1675867
• PubChem SID: 24897019; 162249288
• PubChem CID: 9549167

CALCULATED PROPERTIES

• Acid pKa: 11.64635
• H Acceptors: 9
• H Donor: 3
• LogD (pH = 5.5): 4.8631706
• LogD (pH = 7.4): 4.8631463
• Log P: 4.8631706
• Molar Refractivity: 173.7069 cm^3
• Polarizability: 68.03486 Å^3
• Polar Surface Area: 144.28 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: HB5425500
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 38
• Safety Statements: 22-24/25
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H317
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥97% (HPLC)
• Biological Source: from Daphne mezereum
• Empirical Formula (Hill Notation): C38H38O10

DETAILS

Sigma Aldrich - M5518

Biochem/physiol Actions
Potent second stage tumor promotor and inflammatory agent; activates protein kinase C at nanomolar concentrations.
Other Notes
Phorbol ester analog from the plant Daphne mezereum.