Misplaced Pages

Stigmatellin

Article snapshot taken from[REDACTED] with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.

This is an old revision of this page, as edited by NotWith (talk | contribs) at 08:40, 30 December 2011 (Category:Chemical compounds found in bacteria). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Revision as of 08:40, 30 December 2011 by NotWith (talk | contribs) (Category:Chemical compounds found in bacteria)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff)
Stigmatellin
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.149.842 Edit this at Wikidata
MeSH Stigmatellin
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C30H42O7/c1-10-18(2)13-11-12-14-22(33-6)21(5)29(36-9)19(3)15-16-23-20(4)27(31)26-24(34-7)17-25(35-8)28(32)30(26)37-23/h10-14,17,19,21-22,29,32H,15-16H2,1-9H3/b13-11+,14-12+,18-10+/t19-,21+,22-,29-/m0/s1Key: UZHDGDDPOPDJGM-CVOZLMQJSA-N
  • InChI=1/C30H42O7/c1-10-18(2)13-11-12-14-22(33-6)21(5)29(36-9)19(3)15-16-23-20(4)27(31)26-24(34-7)17-25(35-8)28(32)30(26)37-23/h10-14,17,19,21-22,29,32H,15-16H2,1-9H3/b13-11+,14-12+,18-10+/t19-,21+,22-,29-/m0/s1Key: UZHDGDDPOPDJGM-CVOZLMQJBZ
SMILES
  • O=C\1c2c(O/C(=C/1C)CC(C)(OC)(C)(OC)\C=C\C=C\C(=C\C)C)c(O)c(OC)cc2OC
Properties
Chemical formula C30H42O7
Molar mass 514.65 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Stigmatellin is a potent inhibitor of the quinol oxidation (Qo) site of the cytochrome bc1 complex in mitochondria and the cytochrome b6f complex of thylakoid membranes.

Stigmatellin is isolated from the myxobacterium Stigmatella aurantica, and contains a 5,7-dimethoxy-8-hydroxychromone aromatic headgroup with a hydrophobic alkenyl chain in position 2 . Crystal structures for stigmatellin-inhibited bovine and yeast (Saccharomyces cerevisiae) bc1 complex are available. Stigmatellin binds at the cytochrome b Qo site in the '(heme) bl distal' position, and associates with the Rieske iron-sulfur protein via a hydrogen bond to histidine residue 181 (His-181), a ligand to the iron-sulfur cluster of this subunit. This association raises the midpoint potential of the iron-sulfur cluster from 290 to 540 mV and restricts movement of the cytoplasmic domain of the Rieske protein.

References

  • von Jagow, G., and Link, T.A. Methods in Enzymology 126: 253-271 (1986)
Stub icon

This chemistry-related article is a stub. You can help Misplaced Pages by expanding it.

Categories:
Stigmatellin Add topic