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Ingenol Mebutate

CAT: 0804-HY-B0719-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-B0719-01Size:1 mg
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Description
Ingenol Mebutate is an active ingredient in Euphorbia peplus, acts as a potent PKC modulator, with Kis of 0.3, 0.105, 0.162, 0.376, and 0.171 nM for PKC-α, PKC-β, PKC-γ, PKC-δ, and PKC-ε, respectively, and has antiinflammatory and antitumor activity.
CAS Number
75567-37-2
Product Name Alternative
Ingenol 3-angelate; PEP005
UNSPSC
12352211
Hazard Statement
H302, H315, H319, H335
Target
PKC
Type
Natural Products
Related Pathways
Epigenetics; TGF-beta/Smad
Applications
Cancer-Kinase/protease
Field of Research
Cancer; Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/Ingenol-Mebutate.html
Purity
99.65
Solubility
DMSO : ≥ 100 mg/mL
Smiles
C/C=C(C)\C(O[C@H]1C(C)=C[C@]23[C@]1(O)[C@H](O)C(CO)=C[C@@](C3=O)([H])[C@@]4([H])[C@@](C4(C)C)([H])C[C@H]2C)=O
Molecular Formula
C25H34O6
Molecular Weight
430.53
Precautions
H302, H315, H319, H335
References & Citations
[1]Kedei N, et al. Characterization of the interaction of ingenol 3-angelate with protein kinase C. Cancer Res. 2004 May 1;64 (9) :3243-55.|[2]Hampson P, et al. PEP005, a selective small-molecule activator of protein kinase C, has potent antileukemic activity mediated via the delta isoform of PKC. Blood. 2005 Aug 15;106 (4) :1362-8.|[3]Ghoul A, et al. Epithelial-to-mesenchymal transition and resistance to ingenol 3-angelate, a novel protein kinase C modulator, in colon cancer cells. Cancer Res. 2009 May 15;69 (10) :4260-9.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Natural Products
Clinical Information
Launched
Isoform
PKCα; PKCβ; PKCγ; PKCδ; PKCε

Chemical Information

Ingenol Mebutate

Ingenol mebutate is a tetracyclic diterpenoid ester obtained by formal condensation of the carboxy group of (2Z)-2-methylbut-2-enoic (angelic) acid with the 3-hydroxy group of ingenol. Used for the topical treatment of actinic keratosis. It has a role as an antineoplastic agent. It is a carboxylic ester, a cyclic terpene ketone and a tetracyclic diterpenoid. It is functionally related to an angelic acid and an ingenol.

CAS Number75567-37-2
PubChem CID6918670
IUPAC Name[(1S,4S,5S,6R,9S,10R,12R,14R)-5,6-dihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxo-4-tetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dienyl] (Z)-2-methylbut-2-enoate
Molecular FormulaC25H34O6
Molecular Weight430.5
XLogP2
Topological Polar Surface Area104
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count4
Heavy Atom Count31
Formal Charge0
Complexity926
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]4[C@H](C4(C)C)C[C@H]3C)CO)O)O)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/b12-7-/t14-,16+,17-,18+,19-,21+,24+,25+/m1/s1
InChIKey
VDJHFHXMUKFKET-WDUFCVPESA-N
Chemical Structure
2D Structure
2D structure of Ingenol Mebutate
CAS: 75567-37-2
CID: 6918670
Formula: C25H34O6
MW: 430.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight430.5
XLogP32
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count4
Exact Mass430.23553880
Monoisotopic Mass430.23553880
Topological Polar Surface Area104 Ų
Heavy Atom Count31
Formal Charge0
Complexity926
Isotope Atom Count0
Defined Atom Stereocenter Count8
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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Alternative Products

CatalogName
MBS3617531-01Ingenol mebutate
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MBS385904-01Ingenol Mebutate (PEP005)
A12963-5Ingenol Mebutate 5mg
A12963-2Ingenol Mebutate 2mg
A12963-10Ingenol Mebutate (PEP005) 10mg
A12963-25Ingenol Mebutate (PEP005) 25mg
A12963-10mM-DIngenol Mebutate (PEP005) 10mM * 1mL in DMSO

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