(1S,4S,5R,8R,11S,12R,14R,16R)-4-hydroxy-9-(hydroxymethyl)-3,13,13,16-tetramethyl-6,7-dioxapentacyclo[9.5.1.01,5.05,8.012,14]heptadeca-2,9-dien-17-one

• ChemBase ID: 133433
• Molecular Formular: C20H26O5
• Molecular Mass: 346.41744
• Monoisotopic Mass: 346.17802393
• SMILES: C[C@@H]1C[C@@H]2[C@@H](C2(C)C)[C@@H]2C=C([C@@H]3[C@]4([C@@]1(C2=O)C=C([C@@H]4O)C)OO3)CO
• Canonical SMILES: OCC1=C[C@H]2[C@H]3[C@H](C3(C)C)C[C@H]([C@]3([C@]4([C@@H]1OO4)[C@@H](O)C(=C3)C)C2=O)C
• InChI: InChI=1S/C20H26O5/c1-9-7-19-10(2)5-13-14(18(13,3)4)12(16(19)23)6-11(8-21)17-20(19,15(9)22)25-24-17/h6-7,10,12-15,17,21-22H,5,8H2,1-4H3/t10-,12+,13-,14+,15+,17-,19+,20-/m1/s1
• InChIKey: VDVYIMWLGLOPHL-CRAGLPIHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,4S,5R,8R,11S,12R,14R,16R)-4-hydroxy-9-(hydroxymethyl)-3,13,13,16-tetramethyl-6,7-dioxapentacyclo[9.5.1.0^1,^5.0^5,^8.0^1^2,^1^4]heptadeca-2,9-dien-17-one
• IUPAC Traditional name: (1S,4S,5R,8R,11S,12R,14R,16R)-4-hydroxy-9-(hydroxymethyl)-3,13,13,16-tetramethyl-6,7-dioxapentacyclo[9.5.1.0^1,^5.0^5,^8.0^1^2,^1^4]heptadeca-2,9-dien-17-one
• Synonyms: (1aR,2S,5R,5aR,6S,8aS,9R,10aR)-1a,2,5,5a,6,9,10,10a-Octahydro-5,5a,6-trihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-1H-2,8a-methanocyclopenta[a]cyclopropa[e]cyclodecen-11-one; Ingenol

Database IDs

• CAS Number: 30220-46-3
• PubChem SID: 24896033; 162227710
• PubChem CID: 71308671

CALCULATED PROPERTIES

• Acid pKa: 13.136096
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.6385412
• LogD (pH = 7.4): 1.6385404
• Log P: 1.6385412
• Molar Refractivity: 91.5981 cm^3
• Polarizability: 36.168175 Å^3
• Polar Surface Area: 75.99 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble; hexane: soluble
• Apperance: colorless film

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 38-41
• Safety Statements: 26-36
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H318
• GHS Precautionary statements: P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - I3381

Biochem/physiol Actions
Activates PKC (protein kinase C), especially δ and ε; diterpene related to phorbol.
包装
Product supplied in a sealed glass ampule.