(1S,4S,5S,6R,9R,10R,12R,14R)-5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dien-4-yl 2-methylbut-2-enoate

• ChemBase ID: 153207
• Molecular Formular: C25H34O6
• Molecular Mass: 430.53386
• Monoisotopic Mass: 430.23553881
• SMILES: C/C=C(\C)/C(=O)O[C@H]1C(=C[C@@]23[C@@]1([C@@H](C(=C[C@@H](C2=O)[C@H]1[C@H](C1(C)C)C[C@H]3C)CO)O)O)C
• Canonical SMILES: C/C=C(/C(=O)O[C@H]1C(=C[C@]23[C@]1(O)[C@H](O)C(=C[C@@H](C3=O)[C@H]1[C@@H](C[C@H]2C)C1(C)C)CO)C)\C
• InChI: InChI=1S/C25H34O6/c1-7-12(2)22(29)31-21-13(3)10-24-14(4)8-17-18(23(17,5)6)16(20(24)28)9-15(11-26)19(27)25(21,24)30/h7,9-10,14,16-19,21,26-27,30H,8,11H2,1-6H3/t14-,16-,17-,18+,19-,21+,24+,25+/m1/s1
• InChIKey: VDJHFHXMUKFKET-ZRGDBSFMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,4S,5S,6R,9R,10R,12R,14R)-5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0^1,^5.0^1^0,^1^2]pentadeca-2,7-dien-4-yl 2-methylbut-2-enoate
• IUPAC Traditional name: (1S,4S,5S,6R,9R,10R,12R,14R)-5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0^1,^5.0^1^0,^1^2]pentadeca-2,7-dien-4-yl 2-methylbut-2-enoate
• Synonyms: I3A; PEP005; Ingenol-3-angelate

Database IDs

• CAS Number: 75567-37-2
• MDL Number: MFCD07784504
• PubChem SID: 24724507; 162247346
• PubChem CID: 71311612

CALCULATED PROPERTIES

• Acid pKa: 12.091182
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 2.5056052
• LogD (pH = 7.4): 2.5055964
• Log P: 2.5056052
• Molar Refractivity: 117.8567 cm^3
• Polarizability: 45.852844 Å^3
• Polar Surface Area: 104.06 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >1 mg/mL
• Apperance: clear amorphous

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C25H34O6

DETAILS

Sigma Aldrich - I0659

Biochem/physiol Actions
Protein kinase C activator; anti-cancer drug; active ingredient in Euphorbia peplus