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Merck
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SML1318

Sigma-Aldrich

Ingenol-3-angelate

≥95% (HPLC)

别名:

(1aR,2S,5R,5aS,6S,8aS,9R,10aR)-5,5a-Dihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-11-oxo-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclpropa[e][10]annulen-6-yl (2Z)-2-methylbut-2-enoate, 3-Angeloylingenol, 3-Ingenyl angelate, I3A, Ingenol mebutate, PEP005

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About This Item

经验公式（希尔记法）:
C25H34O6
CAS号:
75567-37-2
分子量:
430.53
UNSPSC代码:
12352200
PubChem化学物质编号:
329825782
NACRES:
NA.77

生物来源

semisynthetic

质量水平

100

方案

≥95% (HPLC)

表单

powder

颜色

white to beige

溶解性

DMSO: 15 mg/mL, clear

储存温度

−20°C

SMILES字符串

O=C1[C@@]2(C=C(C)[C@@H]3OC(/C(C)=C\C)=O)[C@]3(O)[C@H](O)C(CO)=C[C@@]1([H])[C@@](C4(C)C)([H])[C@@]4([H])C[C@H]2C

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

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生化/生理作用

Ingenol 3-Angelate is a diterpenoid ester isolated from Euphorbia peplus that induces rapid cell death with keratinocytes and some cancer cell lines. Ingenol 3-Angelate is a protein kinase C activator that displays potent antileukemic activity. Ingenol 3-Angelate (ingenol mebutate) is used for treatment of actinic keratosis.
Ingenol 3-Angelate is a protein kinase C activator.
Ingenol-3-angelate, is a phorbol ester-like compound or a diacylglycerol analog that is used in the treatment of several disorders like skin cancer. It is also known as PEP005. Ingenol-3-angelate stimulates the initiation of the enzyme by providing PKCs (protein kinase C) to cellular membranes.

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
0000285824
0000264284
0000241566
0000238089
0000197997

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Ingenol-3-Angelate Suppresses Growth of Melanoma Cells and Skin Tumor Development by Downregulation of NF-kappaB-Cox2 Signaling
Wang D and Liu P
Medical Science Monitor : International Medical Journal of Experimental and Clinical Research, 24, 486-486 (2018)
Parama Paul et al.
PloS one, 14(5), e0216220-e0216220 (2019-05-07)
Autosomal dominant polycystic kidney disease (ADPKD) is caused mostly by mutations in polycystin-1 or polycystin-2. Fluid flow leads to polycystin-dependent calcium influx and nuclear export of histone deacetylase 5 (HDAC5), which facilitates the maintenance of renal epithelial architecture by de-repression
Mian Yu et al.
Journal of controlled release : official journal of the Controlled Release Society, 304, 242-258 (2019-05-10)
Cancer-Immunotherapy was the most exciting topic. However, either insensitivity due to singleness of therapeutic target or immune evasion leads to the failure of the treatment. Ingenol-3-mebutate (I3A) can inhibit cancer through synergy between immunotherapy and chemotherapy, however, the speculation and
Yunci Ma et al.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 113, 108753-108753 (2019-03-12)
The objective of this study was to investigate the effects of ferulic acid (FA) on nonalcoholic fatty liver disease (NAFLD) and gut microbiota, and its regulation mechanism in ApoE-/- mice fed on a high-fat diet (HFD). Liver morphology, blood lipids
Xiaohua Song et al.
PloS one, 8(8), e72331-e72331 (2013-08-31)
Ingenol-3-angelate (I3A) is a non-tumor promoting phorbol ester-like compound identified in the sap of Euphoria peplus. Similar to tumor promoting phorbol esters, I3A is a diacylglycerol (DAG) analogue that binds with high affinity to the C1 domains of PKCs, recruits
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