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 UNII_Ref = ;
3D model (JSmol)	Interactive image;
Beilstein Reference	10812290
ChEBI	CHEBI:50068;
ChemSpider	24785627;
KEGG	C18224;
PubChem CID	24798689;
UNII	B473VDT3WP;
CompTox Dashboard (EPA)	DTXSID801027728 ;
	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;
	SMILES [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

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

^ 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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[Morrone_et_al_2005-1] 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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