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Terpestacin

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Terpestacin

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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

Grigoriev PA, Schlegel B, Schmidtke M, Gräfe U (September 2002). "Alteration of membrane polarization by (−)-terpestacin, a biologically active fungal metabolite". Die Pharmazie. 57 (9): 653–4. PMID 12369460.
Jung HJ, Shim JS, Lee J, Song YM, Park KC, Choi SH, Kim ND, Yoon JH, Mungai PT, Schumacker PT, Kwon HJ (April 2010). "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. doi:10.1074/jbc.M109.087809. PMC 2857036. PMID 20145250.
Park KC, Choi SH (December 2013). "Effects of endostatin and a new drug terpestacin against human neuroblastoma xenograft and cell lines". Pediatric Surgery International. 29 (12): 1327–40. doi:10.1007/s00383-013-3398-1. PMID 24072200. S2CID 13088535.