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SML1318

Ingenol-3-angelate

Name: Ingenol-3-angelate
Brand: SIGMA

From semisynthetic, ≥95% (HPLC), protein kinase C activator, powder

Synonym(s):

(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

Empirical Formula (Hill Notation):

C₂₅H₃₄O₆

CAS Number:

75567-37-2

Molecular Weight:

430.53

UNSPSC Code:

12352200

PubChem Substance ID:

329825782

NACRES:

NA.77

Assay:

≥95% (HPLC)

Form:

powder

Quality level:

100

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Product Name

Ingenol-3-angelate, ≥95% (HPLC)

biological source

semisynthetic

Quality Level

100

assay

≥95% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 15 mg/mL, clear

storage temp.

−20°C

SMILES string

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

Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

Biochem/physiol Actions

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.

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Ferulic acid ameliorates nonalcoholic fatty liver disease and modulates the gut microbiota composition in high-fat diet fed ApoE-/- mice.

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

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)

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

Dopamine receptor antagonists as potential therapeutic agents for ADPKD.

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

Oncolytic Reactivation of KSHV as a Therapeutic Approach for Primary Effusion Lymphoma

Zhou F, et al.

Molecular Cancer Therapeutics (2017)

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Global Trade Item Number

SKU	GTIN
SML1318-1MG	04061826132937

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