Huratoxin

Huratoxin
Names
	IUPAC name (1R,2R,6S,7S,8R,10S,11S,12R,14S,16R,18R)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-16-prop-1-en-2-yl-14-[(1E,3E)-trideca-1,3-dienyl]-9,13,15,19-tetraoxahexacyclo[12.4.1.01,11.02,6.08,10.012,16]nonadec-3-en-5-one
Identifiers
CAS Number	33465-16-6;
3D model (JSmol)	Interactive image;
PubChem CID	6440991;
UNII	GXV3CR7BC8;
CompTox Dashboard (EPA)	DTXSID601318664 ;
	InChI InChI=1S/C34H48O8/c1-6-7-8-9-10-11-12-13-14-15-16-17-32-40-27-25-28-31(20-35,39-28)29(37)33(38)24(18-22(4)26(33)36)34(25,42-32)23(5)19-30(27,41-32)21(2)3/h14-18,23-25,27-29,35,37-38H,2,6-13,19-20H2,1,3-5H3/b15-14+,17-16+/t23-,24-,25-,27-,28+,29-,30-,31+,32-,33-,34+/m1/s1 Key: VWGORPXMXKBHER-PAAMMUKASA-N;
	SMILES C=C(C)[C@]12C[C@@H](C)[C@@]34O[C@](/C=C/C=C/CCCCCCCCC)(O[C@@H]1[C@@H]3[C@@H]1O[C@]1(CO)[C@@H](O)[C@]1(O)C(=O)C(C)=C[C@H]14)O2;
Properties
Chemical formula	C34H48O8
Molar mass	584.750 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Huratoxin is a naturally occurring daphnane-type diterpene found in the sap of Hura crepitans.^[1] It is extremely toxic to both land and aquatic life. Ingestion causes symptoms resembling those of Pimelea.^[2]

Huratoxin strongly activates protein kinase C, a property that has led it to be studied in the context of cancer treatment.^[1]

References

1 2 Sakata, Kanzo; Kawazu, Kazuyoshi; Mitsui, Tetsuo (1971-07-01). "Studies on a Piscicidal Constituent of Hura crepitans: Part I. Isolation and Characterization of Huratoxin and its Piscicidal Activity". Agricultural and Biological Chemistry. 35 (7): 1084–1091. doi:10.1080/00021369.1971.10860026. ISSN 0002-1369.
↑ McClure, T. J.; Mulley, R. C. (1984). "Some cytotoxic effects of mixtures of simplexin and huratoxin obtained from the desert rice flower, Pimelea simplex". Toxicon: Official Journal of the International Society on Toxinology. 22 (5): 775–782. Bibcode:1984Txcn...22..775M. doi:10.1016/0041-0101(84)90160-0. ISSN 0041-0101. PMID 6523506.

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[:0-1] 1 2 Sakata, Kanzo; Kawazu, Kazuyoshi; Mitsui, Tetsuo (1971-07-01). "Studies on a Piscicidal Constituent of Hura crepitans: Part I. Isolation and Characterization of Huratoxin and its Piscicidal Activity". Agricultural and Biological Chemistry. 35 (7): 1084–1091. doi:10.1080/00021369.1971.10860026. ISSN 0002-1369.

[2] McClure, T. J.; Mulley, R. C. (1984). "Some cytotoxic effects of mixtures of simplexin and huratoxin obtained from the desert rice flower, Pimelea simplex". Toxicon: Official Journal of the International Society on Toxinology. 22 (5): 775–782. Bibcode:1984Txcn...22..775M. doi:10.1016/0041-0101(84)90160-0. ISSN 0041-0101. PMID 6523506.

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