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Ingenol

CAT: 0931-T5S2017-03Size: 1 mL - 10 mM (in DMSO)Dry Ice: NoHazardous: No
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CAT#:0931-T5S2017-03Size:1 mL - 10 mM (in DMSO)
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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CAS Number
30220-46-3
Target
PKC
Related Pathways
Chromatin/Epigenetic, Cytoskeletal Signaling
Purity
0.9987
Bioactivity
1. Ingenol ((-) -Ingenol) mebutate is an effective treatment for actinic keratosis. 2. Formulating novel derivatives from Ingenol esters may be an innovative approach to develop new lead compounds to reactivate latent HIV. 3. Ingenol is a weak PKC activator and possesses important anticancer activity.
Smiles
C[C@@H]1C[C@@H]2[C@H]([C@@H]3C=C(CO)[C@@H](O)[C@]4(O)[C@@H](O)C(C)=C[C@@]14C3=O)C2(C)C
Molecular Formula
C20H28O5
Molecular Weight
348.43
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

Chemical Information

Ingenol

Ingenol is a tetracyclic diterpenoid that is 1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one substituted at positions 5, 5a and 6 by hydroxy groups, positions 1, 1, 7 and 9 by methyl groups, position 4 by a hydroxymethyl group and position 1 by an oxo group (the 1aR,2S,5R,5aR,6S,8aS,9R,10aR diastereomer). It is a cyclic terpene ketone and a tetracyclic diterpenoid.

CAS Number30220-46-3
PubChem CID442042
IUPAC Name(1S,4S,5R,6R,9S,10R,12R,14R)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dien-15-one
Molecular FormulaC20H28O5
Molecular Weight348.4
XLogP0.2
Topological Polar Surface Area98
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count5
Rotatable Bond Count1
Heavy Atom Count25
Formal Charge0
Complexity707
SMILES
C[C@@H]1C[C@@H]2[C@@H](C2(C)C)[C@@H]3C=C([C@H]([C@]4([C@@]1(C3=O)C=C([C@@H]4O)C)O)O)CO
InChI
InChI=1S/C20H28O5/c1-9-7-19-10(2)5-13-14(18(13,3)4)12(17(19)24)6-11(8-21)16(23)20(19,25)15(9)22/h6-7,10,12-16,21-23,25H,5,8H2,1-4H3/t10-,12+,13-,14+,15+,16-,19+,20-/m1/s1
InChIKey
VEBVPUXQAPLADL-POYOOMFHSA-N
Chemical Structure
2D Structure
2D structure of Ingenol
CAS: 30220-46-3
CID: 442042
Formula: C20H28O5
MW: 348.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight348.4
XLogP30.2
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count5
Rotatable Bond Count1
Exact Mass348.19367399
Monoisotopic Mass348.19367399
Topological Polar Surface Area98 Ų
Heavy Atom Count25
Formal Charge0
Complexity707
Isotope Atom Count0
Defined Atom Stereocenter Count8
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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Alternative Products

CatalogName
FI73952-01Ingenol
MBS3617531-01Ingenol mebutate

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