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Structure Database (LMSD)

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Common Name

phorbol 13-acetate 12-myristate

Systematic Name

Synonyms

12-O-Tetradecanoylphorbol 13-acetate
12-Tetradecanoylphorbol 13-acetate
PMA
Phorbol 12-myristate 13-acetate
phorbol 12-tetradecanoate 13-acetate
phorbol-12-myristate-13-acetate
tetradecanoylphorbol acetate

LM ID

LMPR0104330002

Formula

C₃₆H₅₆O₈

Exact Mass

Calculate m/z

616.39752

Status

Curated

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Classification

Biological Context

Phorbol 12-myristate 13-acetate (PMA), also known as 12-O-tetradecanoylphorbol 13-acetate (TPA), is a phorbol ester and PKC activator.^1,2,3,4,5 It activates the PKC isoforms PKCα, -β, -γ, -δ, -ε, -η, and -θ but not PKCζ or -ι/λ.² PMA (1-10 ng/ml) induces NF-κB-dependent gene expression in a reporter assay.³ It promotes the differentiation of THP-1 monocytes into pro-inflammatory macrophages, as well as induces the formation of neutrophil extracellular traps (NETs), in vitro.^4,5 PMA, in combination with 7,12-dimethylbenz[a]anthracene (DMBA), promotes papilloma formation in a rat two-stage model of skin carcinogenesis.⁶

This information has been provided by Cayman Chemical

References

1. Goel, G., Makkar, H.P.S., Francis, G., et al. Phorbol esters: Structure, biological activity, and toxicity in animals. Int. J. Toxicol. 26(4), 279-288 (2007).

2. Steinberg, S.F. Structural basis of protein kinase C isoform function. Physiol. Rev. 88(4), 1341-1378 (2008).

3. Hellweg, C.E., Arenz, A., Bogner, S., et al. Activation of nuclear factor κB by different agents: Influence of culture conditions in a cell-based assay. Ann. N. Y. Acad. Sci. 1091, 191-204 (2006).

4. Lund, M.E., To, J., O'Brien, B.A., et al. The choice of phorbol 12-myristate 13-acetate differentiation protocol influences the response of THP-1 macrophages to a pro-inflammatory stimulus. J. Immunol. Methods 430, 64-70 (2016).

5. Petretto, A., Bruschi, M., Pratesi, F., et al. Neutrophil extracellular traps (NET) induced by different stimuli: A comparative proteomic analysis. PLoS One 14(7), e0218946 (2019).

6. Vähätupa, M., Pemmari, T., Junttila, I., et al. Chemical-Induced Skin Carcinogenesis Model Using Dimethylbenz[a]Anthracene and 12-O-Tetradecanoyl Phorbol-13-Acetate (DMBA-TPA). J. Vis. Exp. 154 (2019).

String Representations

InChiKey (Click to copy)

PHEDXBVPIONUQT-RGYGYFBISA-N

InChi (Click to copy)

InChI=1S/C36H56O8/c1-7-8-9-10-11-12-13-14-15-16-17-18-29(39)43-32-24(3)35(42)27(30-33(5,6)36(30,32)44-25(4)38)20-26(22-37)21-34(41)28(35)19-23(2)31(34)40/h19-20,24,27-28,30,32,37,41-42H,7-18,21-22H2,1-6H3/t24-,27+,28-,30-,32-,34-,35-,36-/m1/s1

SMILES (Click to copy)

C1=C(CO)C[C@]2(O)C(C(C)=C[C@@]2([H])[C@@]2(O)[C@@H]([C@@H](OC(CCCCCCCCCCCCC)=O)[C@@]3(OC(C)=O)C(C)(C)[C@@]3([H])[C@@]21[H])C)=O