A β-tubulin inhibitor
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Phomopsin A

Item No. 19448

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2E)-(βS)-3-chloro-β,5-dihydroxy-N-methyl-L-tyrosyl-3,4-didehydro-L-valyl-3-hydroxy-L-isoleucyl-3,4-didehydro-L-prolyl-(2E)-2,3-didehydroisoleucyl-2,3-didehydro-aspartic acid, cyclic (15→3)-ether
CAS Number
64925-80-0
Synonyms
  • NSC 381839
Molecular Formula
C36H45ClN6O12
Formula Weight
789.2
Purity
≥85%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
OC(/C(NC(/C(NC([C@H]1N(C([C@@H]2NC([C@H](C(C)=C)NC([C@@H](NC)[C@H](C3=CC(O[C@@]2(CC)C)=C(O)C(Cl)=C3)O)=O)=O)=O)CC=C1)=O)=C(CC)/C)=O)=C\C(O)=O)=O
InChi Code
InChI=1S/C36H45ClN6O12/c1-8-17(5)25(32(50)39-20(35(53)54)15-23(44)45)41-30(48)21-11-10-12-43(21)34(52)29-36(6,9-2)55-22-14-18(13-19(37)28(22)47)27(46)26(38-7)33(51)40-24(16(3)4)31(49)42-29/h10-11,13-15,21,24,26-27,29,38,46-47H,3,8-9,12H2,1-2,4-7H3,(H
InChi Key
FAFRRYBYQKPKSY-MSBSFVTFSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    Phomopsin A is a cyclic hexapeptide mycotoxin that binds β-tubulin in a vinca domain, overlapping with the site targeted by vinblastine (Item No. 11762) and other tubulin inhibitors.1,2 It binds β-tubulin from higher organisms but not α-tubulin or fungal mycelial tubulin.3,4 Phomopsin A blocks microtubule growth, modulates the dynamics of microtubules, and interferes with mitosis.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hamel, E. Natural products which interact with tubulin in the vinca domain: maytansine, rhizoxin, phomopsin A, dolastatins 10 and 15 and halichondrin B. Pharmacol. Therapeut. 55(1), 31-51 (1992).

    2. Cormier, A., Marchand, M., Ravelli, R.B.G., et al. Structural insight into the inhibition of tubulin by vinca domain peptide ligands. EMBO reports 9(11), 1101-1106 (2008).

    3. Li, Y., Kobayashi, H., Hashimoto, Y., et al. Binding selectivity of rhizoxin, phomopsin A, vinblastine, and ansamitocin P-3 to fungal tubulins: differential interactions of these antimitotic agents with brain and fungal tubulins. Biochem. Bioph. Res. Co. 187(2), 722-729 (1992).

    4. Mitra, A., and Sept, D. Localization of the antimitotic peptide and depsipeptide binding site on β-tubulin. Biochemistry 43(44), 13955-13962 (2004).