Ingenol

Names

[ Name ]:
Ingenol

[Synonym ]:
(1S,4S,5R,6R,9S,10R,12R,14R)-4,5,6-Trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.0.0]pentadeca-2,7-dien-15-one
1aa,2a,5b,5ab,6b,8ab,9a,10,10aa-Octahydro-5,5a,6-trihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-1H-2,8a-methanocyclopenta[a]cyclopropa[e]cyclodecen-11-one
(1aR,2S,5R,5aR,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one
1H-2,8a-Methanocyclopenta[a]cyclopropa[e]cyclodecen-11-one, 1a,2,5,5a,6,9,10,10a-octahydro-5,5a,6-trihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-, (1aR,2S,5R,5aR,6S,8aS,9R,10aR)-
(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
MFCD00056380
1alpha,2,5,5alpha,6,9,10,10alpha-Octahydro-5,5alpha,6-trihydroxy-4-hydroxymethyl-1,1,7,9,-retramethyl-1H-2,8alpha-m
1A,2,5,5A,6,9,10,10A OCTAHYDRO-5,5A,6-TRIHYDROXY4(HYDROXYMETHYL)1,1,7,9-TETRAMETHYL1H-2,8 AMETHANOCYCLOPENTA[A]CYCLOPROPA[E]CYCLODECEN-11 ONE

Biological Activity

[Description]:

Ingenol is a PKC activator, with a Ki of 30 μM, with antitumor activity.

[Related Catalog]:

Natural Products >> Terpenoids and Glycosides

Research Areas >> Cancer

[Target]

PKC:30 μM (Ki)

[In Vitro]

Ingenol is a PKC activator, with a Ki of 30 μM. Ingenol induces ornithine decarboxylase activity (1, 3 mM), and causes morphological changes (1 mM) in primary mouse epidermal keratinocytes. Ingenol (125 μM, 250 μM, 500 μM, 1 mM) also inhibits cell-cell communication[1].

[References]

[1]. Hasler CM, et al. Specific binding to protein kinase C by ingenol and its induction of biological responses. Cancer Res. 1992 Jan 1;52(1):202-8.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
523.8±50.0 °C at 760 mmHg

[ Melting Point ]:
153 °C

[ Molecular Formula ]:
C₂₀H₂₈O₅

[ Molecular Weight ]:
348.433

[ Flash Point ]:
284.7±26.6 °C

[ Exact Mass ]:
348.193665

[ PSA ]:
97.99000

[ LogP ]:
2.95

[ Vapour Pressure ]:
0.0±3.1 mmHg at 25°C

[ Index of Refraction ]:
1.625

MSDS

Click to get detail MSDS

Safety Information

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R38;R41

[ Safety Phrases ]:
26-36