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Structure Database (LMSD)

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Common Name

Cytochalasin A

Systematic Name

Synonyms

LM ID

LMPK11000001

Formula

C₂₉H₃₅NO₅

Exact Mass

Calculate m/z

477.251524

Status

Curated

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Classification

Biological Context

Cytochalasin A is an oxidized analog of cytochalasin B that uniquely inhibits HIV-1 protease (IC50 = 3 μM).¹ Cytochalasins A and B differ from other cytochalasins in being able to rapidly and reversibly inhibit glucose transport by competitively binding glucose transporters (Ki = 4.0 and 0.6 μM, respectively).^2,3 Cytochalasin A also induces the phosphorylation of the tyrosine phosphatase PTP3 of Dictyostelium, activating STATc.⁴

This information has been provided by Cayman Chemical

References

1. Araki, T., and Williams, J.G. Perturbations of the actin cytoskeleton activate a Dictyostelium STAT signalling pathway. Eur. J. Cell Biol. 91(5), 420-425 (2012).

2. Griffin, J.F., Rampal, A.L., and Jung, C.Y. Inhibition of glucose transport in human erythrocytes by cytochalasins: A model based on diffraction studies. Proc. Natl. Acad. Sci. USA 79(12), 3759-3763 (1982).

3. Kletzien, R.F., Perdue, J.F., and Springer, A. Cytochalasin A and B. Inhibition of sugar uptake in cultured cells. The Journal of Biological Chemisty 247(9), 2964-2966 (1972).

4. Lingham, R.B., Hsu, A., Silverman, K.C., et al. L-696,474, a novel cytochalasin as an inhibitor of HIV-1 protease. III. Biological activity. J. Antibiot. (Tokyo) 45(5), 686-691 (1992).

References

Reference

The Journal of Cell Biology, Vol 92, 69-78, 1982

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Pyrenophora dematioidea (#139229)

Dothideomycetes (#147541)

The cytochalasins, a new class of biologically active mould metabolites,
Chem Commun, 1967

DOI: 10.1039/C19670000026

String Representations

InChiKey (Click to copy)

ZMAODHOXRBLOQO-TZVKRXPSSA-N

InChi (Click to copy)

InChI=1S/C29H35NO5/c1-18-9-7-13-22(31)15-16-25(32)35-29-23(14-8-10-18)27(33)20(3)19(2)26(29)24(30-28(29)34)17-21-11-5-4-6-12-21/h4-6,8,11-12,14-16,18-19,23-24,26-27,33H,3,7,9-10,13,17H2,1-2H3,(H,30,34)/b14-8+,16-15+/t18-,19-,23+,24+,26+,27-,29-/m1/s1

SMILES (Click to copy)

[C@@H]1(C)C(=C)[C@@H](O)[C@@H]2C=CC[C@H](C)CCCC(=O)C=CC(=O)O[C@@]32C(=O)N[C@@H](CC2C=CC=CC=2)[C@]13[H]