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Ingenol Mebutate

CAS No.:
75567-37-2
Catalog Number:
AG00G3OQ
Molecular Formula:
C25H34O6
Molecular Weight:
430.5339
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
99%
1 week
United States
$160
- +
5mg
99%
1 week
United States
$382
- +
10mg
99%
1 week
United States
$593
- +
Product Description
Catalog Number:
AG00G3OQ
Chemical Name:
Ingenol Mebutate
CAS Number:
75567-37-2
Molecular Formula:
C25H34O6
Molecular Weight:
430.5339
MDL Number:
MFCD07784504
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
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
InChI Key:
VDJHFHXMUKFKET-WDUFCVPESA-N
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
UNII:
7686S50JAH
Properties
Complexity:
926  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
8  
Defined Bond Stereocenter Count:
1  
Exact Mass:
430.236g/mol
Formal Charge:
0
Heavy Atom Count:
31  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0
Molecular Weight:
430.541g/mol
Monoisotopic Mass:
430.236g/mol
Rotatable Bond Count:
4  
Topological Polar Surface Area:
104A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2  
Literature
Title Journal
Topical therapies for periorbital cutaneous malignancies: indications and treatment regimens. Current opinion in ophthalmology 20120901
Ingenol mebutate gel for actinic keratosis. The New England journal of medicine 20120315
Ivacaftor, vismodegib, and ingenol mebutate. Journal of the American Pharmacists Association : JAPhA 20120101
What's new in the treatment of actinic keratoses? Cutis 20110201
Topical antineoplastic agents in the treatment of mucocutaneous diseases. Current problems in dermatology 20110101
Novel antileukemic compound ingenol 3-angelate inhibits T cell apoptosis by activating protein kinase Ctheta. The Journal of biological chemistry 20100730
The skin cancer chemotherapeutic agent ingenol-3-angelate (PEP005) is a substrate for the epidermal multidrug transporter (ABCB1) and targets tumor vasculature. Cancer research 20100601
Primary human acute myelogenous leukemia cells release matrix metalloproteases and their inhibitors: release profile and pharmacological modulation. European journal of haematology 20100301
Epithelial-to-mesenchymal transition and resistance to ingenol 3-angelate, a novel protein kinase C modulator, in colon cancer cells. Cancer research 20090515
PEP005 (ingenol mebutate) gel, a novel agent for the treatment of actinic keratosis: results of a randomized, double-blind, vehicle-controlled, multicentre, phase IIa study. The Australasian journal of dermatology 20090201
Antiproliferative activity of PEP005, a novel ingenol angelate that modulates PKC functions, alone and in combination with cytotoxic agents in human colon cancer cells. British journal of cancer 20081202
Neutrophils are a key component of the antitumor efficacy of topical chemotherapy with ingenol-3-angelate. Journal of immunology (Baltimore, Md. : 1950) 20061201
Induction of senescence in diterpene ester-treated melanoma cells via protein kinase C-dependent hyperactivation of the mitogen-activated protein kinase pathway. Cancer research 20061015
HIV type 1 inhibition by protein kinase C modulatory compounds. AIDS research and human retroviruses 20060901
PEP005, a selective small-molecule activator of protein kinase C, has potent antileukemic activity mediated via the delta isoform of PKC. Blood 20050815
Ingenol 3-angelate induces dual modes of cell death and differentially regulates tumor necrosis factor-related apoptosis-inducing ligand-induced apoptosis in melanoma cells. Molecular cancer therapeutics 20041201
Characterization of the interaction of ingenol 3-angelate with protein kinase C. Cancer research 20040501
Antitumor activity of 3-ingenyl angelate: plasma membrane and mitochondrial disruption and necrotic cell death. Cancer research 20040415
Properties