Rhizoxin

Rhizoxin

Identifiers
CAS Number	90996-54-6 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:72590
ChEMBL	ChEMBL379989 N
ChemSpider	10405026
PubChem	11969567
InChI InChI=1S/C35H47NO9/c1-19(13-25-18-41-23(5)36-25)9-8-10-21(3)32(40-7)22(4)27-17-29(37)35(6)30(45-35)12-11-20(2)26-14-24(16-31(38)42-26)15-28-33(43-28)34(39)44-27/h8-13,18,20,22,24,26-30,32-33,37H,14-17H2,1-7H3/b9-8+,12-11+,19-13+,21-10+/t20-,22+,24+,26-,27+,28+,29+,30-,32+,33-,35-/m1/s1 Key: OWPCHSCAPHNHAV-QIPOKPRISA-N
SMILES O=C1C[C@@](C[C@H]3[C@H]2O3)([H])C[C@@]([C@H](C)/C=C/[C@@H](O4)[C@]4(C)[C@@H](O)C[C@]([C@H](C)[C@@H](OC)/C(C)=C/C=C/C(C)=C/C5=COC(C)=N5)([H])OC2=O)([H])O1
Properties
Chemical formula	C35H47NO9
Molar mass	625.749 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Rhizoxin is an antimitotic agent with anti-tumor activity. It is isolated from a pathogenic plant fungus (Rhizopus microsporus) which causes rice seedling blight.

Rhizoxin is biosynthesised by Burkholderia rhizoxinica, a bacterial endosymbiont of the fungus Rhizopus microsporus. It is one of a large group of rhizoxin-like compounds produced by the bacteria. The bacterial endosymbiont can be grown independently in culture. This may allow easy harvesting of rhizoxin and the related compounds avoiding total chemical synthesis, although total chemical synthesis is possible.

Rhizoxin binds beta tubulin in eukaryotic cells disrupting microtubule formation. This, in turn, prevents formation of the mitotic spindle inhibiting cell division. Additionally rhizoxin can depolymerise assembled microtubules. The function of rhizoxin is similar to Vinca alkaloids.

Rhizoxin has undergone clinical trials as an anti-cancer drug although it did not reach later stages of clinical trials due to low activity in vivo. Related compounds to rhizoxin may have improved biological activity.

Rhizoxin is a 16-membered lactone ring connected to an oxazole ring by a long unsaturated chain.