Chemistry:Terpestacin

Terpestacin

Names
Preferred IUPAC name (3aR,5E,7S,10E,14E,16aS)-2,7-Dihydroxy-3-[(2S)-1-hydroxypropan-2-yl]-6,10,14,16a-tetramethyl-4,7,8,9,12,13,16,16a-octahydrocyclopenta[15]annulen-1(3aH)-one
Identifiers
CAS Number	146436-22-8 N
3D model (JSmol)	Interactive image
ChEBI	CHEBI:167861
ChEMBL	ChEMBL1669042
ChemSpider	4976965
PubChem CID	6475118
CompTox Dashboard (EPA)	DTXSID701017681
InChI InChI=1S/C25H38O4/c1-16-7-6-8-17(2)13-14-25(5)20(11-10-18(3)21(27)12-9-16)22(19(4)15-26)23(28)24(25)29/h7,10,13,19-21,26-28H,6,8-9,11-12,14-15H2,1-5H3/b16-7+,17-13+,18-10+/t19-,20-,21+,25+/m1/s1 Key: UTGBBPSEQPITLF-IXRUDUFRSA-N InChI=1/C25H38O4/c1-16-7-6-8-17(2)13-14-25(5)20(11-10-18(3)21(27)12-9-16)22(19(4)15-26)23(28)24(25)29/h7,10,13,19-21,26-28H,6,8-9,11-12,14-15H2,1-5H3/b16-7+,17-13+,18-10+/t19-,20-,21+,25+/m1/s1 Key: UTGBBPSEQPITLF-IXRUDUFRBX
SMILES C/C/1=C\CC/C(=C/C[C@]2([C@H](C/C=C(/[C@H](CC1)O)\C)C(=C(C2=O)O)[C@H](C)CO)C)/C
Properties
Chemical formula	C25H38O4
Molar mass	402.575 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

Terpestacin is a fungal metabolite with anticancer activity.

External links

• "Alteration of membrane polarization by (−)-terpestacin, a biologically active fungal metabolite". Die Pharmazie 57 (9): 653–4. September 2002. PMID 12369460. 
• "Terpestacin inhibits tumor angiogenesis by targeting UQCRB of mitochondrial complex III and suppressing hypoxia-induced reactive oxygen species production and cellular oxygen sensing". J Biol Chem 285 (15): 11584–95. April 2010. doi:10.1074/jbc.M109.087809. PMID 20145250. 
• "Effects of endostatin and a new drug terpestacin against human neuroblastoma xenograft and cell lines". Pediatric Surgery International 29 (12): 1327–40. December 2013. doi:10.1007/s00383-013-3398-1. PMID 24072200.