Stemodene

Stemodene
Names
IUPAC name
(14S)-9,15:14,20-Dicyclo-8α-labd-13(16)-ene
Systematic IUPAC name
(4aS,6aS,8S,11aR,11bS)-4,4,11b-Trimethyl-9-methylidenetetradecahydro-8,11a-methanocyclohepta[a]naphthalene
Identifiers
CAS Number
  • 929635-55-2 checkY UNII_Ref =  checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
 10812290
ChEBI
  • CHEBI:50068
ChemSpider
  • 24785627
KEGG
  • C18224
PubChem CID
  • 24798689
UNII
  • B473VDT3WP
CompTox Dashboard (EPA)
  • DTXSID801027728 Edit this at Wikidata
InChI
  • InChI=1S/C20H32/c1-14-8-11-20-13-15(14)12-16(20)6-7-17-18(2,3)9-5-10-19(17,20)4/h15-17H,1,5-13H2,2-4H3/t15-,16-,17-,19-,20+/m0/s1
    Key: GNNRCBBKCVNPSC-VDWQKOAOSA-N
  • [H][C@@]12CC[C@@]3([H])C(C)(C)CCC[C@]3(C)[C@]1(CCC4=C)C[C@@H]4C2
Properties
Chemical formula
 C20H32
Molar mass 272.476 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
Chemical compound

Stemodene is a labdane-related diterpene whose corresponding class I terpene synthase has been discovered in rice and subsequently cloned and functionally characterized. The gene responsible for stemodene production has not been found in the completed rice genome, thus suggesting that perhaps other genes are as yet undiscovered in the "completed" genome. Stemarene synthase demonstrates high sequence homology with stemodene synthase, thus accounting for the latter's discovery by Dana Morrone in 2005.[1] Additionally, the corresponding olefin produced by each cyclase shows structural similarities and is derived from the common precursor of syn-copalyl diphosphate.

References

  1. ^ Morrone, Dana; Yinghua Jin; Meimei Xu; Suh-Yeon Choi; Robert M. Coates; Reuben J. Peters (April 15, 2006). "An unexpected diterpene cyclase from rice: functional identification of a stemodene synthase" (PDF). Archives of Biochemistry and Biophysics. 448 (1–2): 133–140. doi:10.1016/j.abb.2005.09.001. PMID 16256063. Archived from the original (PDF) on 2007-09-28. Retrieved 2006-11-07.


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