Unreferenced stub auto yes date December 2009 Chembox verifiedrevid 443546056 ImageFile Cycloartenol.png ImageSize 200px IUPACName OtherNames 9beta,19 cyclo 24 lanosten 3beta ol, br 3beta 9,19 Cyclolanost 24 en 3 ol Section1 Chembox Identifiers InChI1 1 C30H50O c1 20 2 9 8 10 21 3 22 13 16 28 7 24 12 11 23 26 4,5 15 14 25 31 30 23 19 29 24,30 18 17 27 22,28 6 h14,20 24,31H,8 13,15 19H2,1 7H3 t21 ,22 ,23 ,24 ,27 ,28 ,29 ,30 m1 s1 InChIKey1 UYPYBUZTJLFCHS DGUMGERNBH SMILES1 CC C CCC C H C C H 5CC C 1 C C 5 C CC C 24C C 34C O C C C C C C H 3CC C H 12 CASNo 469 38 5 PubChem 92110 ChemSpiderID Ref chemspidercite correct chemspider ChemSpiderID 16788581 StdInChI Ref stdinchicite correct chemspider StdInChI 1S C30H50O c1 20 2 9 8 10 21 3 22 13 16 28 7 24 12 11 23 26 4,5 15 14 25 31 30 23 19 29 24,30 18 17 27 22,28 6 h14,20 24,31H,8 13,15 19H2,1 7H3 t21 ,22 ,23 ,24 ,27 ,28 ,29 ,30 m1 s1 StdInChIKey Ref stdinchicite correct chemspider StdInChIKey UYPYBUZTJLFCHS DGUMGERNSA N SMILES CC CCC C C C C1CCC2 C1 CCC34C2CCC5C3 C4 CCC C5 C C O C C Section2 Chembox Properties Formula C sub 30 sub H sub 50 sub O MolarMass 426.72 g mol Appearance Density MeltingPt BoilingPt Solubility Section3 Chembox Hazards MainHazards FlashPt Autoignition Cycloartenol is an important type of stanol found in plants. The biosynthesis of cycloartenol starts from the triterpenoid squalene . It is the first precursor in the biosynthesis of other stanols and sterol s, referred to as phytostanols and phytosterol s in photosynthesis photosynthetic organisms and plants. The identities and distribution of phytostanols and phytosterols is characteristic of a plant species. One notable product of cycloartenol biosynthesis is the triterpenoid lanosterol . Category Sterols Category Triterpenes Alcohol stub pl Cykloartenol ... more details
enzyme Name cycloartenol synthase EC number 5.4.99.8 CAS number 9075 25 6 IUBMB EC number 5 4 99 8 GO code 0016871 image width caption In enzymology , a cycloartenol synthase EC number 5.4.99.8 is an enzyme that catalysis catalyzes the chemical reaction S 2,3 epoxysqualene math rightleftharpoons math cycloartenol Hence, this enzyme has one substrate biochemistry substrate , S 2,3 epoxy squalene , and one product chemistry product , cycloartenol . This enzyme belongs to the family of isomerase s, specifically those intramolecular transferase s transferring other groups. The systematic name of this enzyme class is S 2,3 epoxysqualene mutase cyclizing, cycloartenol forming . Other names in common use include 2,3 epoxysqualene cycloartenol cyclase , squalene 2,3 epoxide cycloartenol cyclase , 2,3 epoxysqualene cycloartenol cyclase , 2,3 epoxysqualene cycloartenol cyclase , and 2,3 oxidosqualene cycloartenol cyclase . This enzyme participates in biosynthesis of steroids . References reflist 1 cite journal author Rees HH, Goad LJ, Goodwin TW date 1969 title 2,3 oxidosqualene cycloartenol cyclase from Ochromonas malhamensis journal Biochim. Biophys. Acta. volume 176 pages 892&ndash 4 pmid 5797101 issue 4 isomerase stub Category EC 5.4.99 Category Enzymes of unknown structure ... more details
enzyme Name cycloartenol 24 C methyltransferase EC number 2.1.1.142 CAS number IUBMB EC number 2 1 1 142 GO code 0030796 image width caption In enzymology , a cycloartenol 24 C methyltransferase EC number 2.1.1.142 is an enzyme that catalysis catalyzes the chemical reaction S adenosyl L methionine cycloartenol math rightleftharpoons math S adenosyl L homocysteine 24R 24 methylcycloart 25 en 3beta ol Thus, the two substrate biochemistry substrates of this enzyme are S Adenosyl methionine S adenosyl methionine and cycloartenol , whereas its two product chemistry products are S adenosylhomocysteine and 24R 24 methylcycloart 25 en 3beta ol . This enzyme belongs to the family of transferase s, specifically those transferring one carbon group methyltransferases. The systematic name of this enzyme class is S adenosyl L methionine cycloartenol 24 C methyltransferase . This enzyme is also called sterol C methyltransferase . References reflist 1 cite journal author Mangla AT, Nes WD date 2000 title Sterol C methyl transferase from Prototheca wickerhamii mechanism, sterol specificity and inhibition journal Bioorg. Med. Chem. volume 8 pages 925&ndash 36 pmid 10882005 doi 10.1016 S0968 0896 00 00040 7 issue 5 transferase stub Category EC 2.1.1 Category Enzymes of unknown structure it Cicloartenolo 24 C metiltransferasi ... more details
DISPLAYTITLE C sub 30 sub H sub 50 sub O The molecular formula C sub 30 sub H sub 50 sub O molar mass 426.71 g mol, exact mass 426.386166 may refer to Cycloartenol , a sterol precursor in photosynthetic organisms and plants Lanosterol , a tetracyclic triterpenoid Lupeol 2,3 Oxidosqualene molFormDisambig ... more details
chembox verifiedrevid 399199419 ImageFile 2,3 oxidosqualene.svg ImageSize 300px IUPACName 2,2 Dimethyl 3 3E,7E,11E,15E 3,7,12,16,20 pentamethylhenicosa 3,7,11,15,19 pentaenyl oxirane OtherNames Squalene oxide br 2,3 Squalene oxide Section1 Chembox Identifiers InChI 1 C30H50O c1 24 2 14 11 17 27 5 20 12 18 25 3 15 9 10 16 26 4 19 13 21 28 6 22 23 29 30 7,8 31 29 h14 16,20 21,29H,9 13,17 19,22 23H2,1 8H3 b25 15 ,26 16 ,27 20 ,28 21 InChIKey QYIMSPSDBYKPPY BANQPHDMBU SMILES1 CC CCC C C CC C C CC C C C CC C C C CCC1C O1 C C C C C StdInChI Ref stdinchicite correct chemspider StdInChI 1S C30H50O c1 24 2 14 11 17 27 5 20 12 18 25 3 15 9 10 16 26 4 19 13 21 28 6 22 23 29 30 7,8 31 29 h14 16,20 21,29H,9 13,17 19,22 23H2,1 8H3 b25 15 ,26 16 ,27 20 ,28 21 StdInChIKey Ref stdinchicite correct chemspider StdInChIKey QYIMSPSDBYKPPY BANQPHDMSA N CASNo 7200 26 2 PubChem 5366020 ChemSpiderID Ref chemspidercite correct chemspider ChemSpiderID 4517951 SMILES O1C C C C1CC C C CC C C CC C C C CC C C C CC C C C C C C MeSHName 2,3 oxidosqualene Section2 Chembox Properties Formula C sub 30 sub H sub 50 sub O MolarMass 426.717 g mol Appearance Density MeltingPt BoilingPt Solubility Section3 Chembox Hazards MainHazards FlashPt Autoignition 2,3 S Oxidosqualene S 2,3 epoxysqualene is an intermediate in the synthesis of the membrane sterol precursors lanosterol and cycloartenol , as well as saponin s. It is formed from squalene by squalene monooxygenase . 2,3 oxidosqualene is the Substrate biochemistry substrate of various oxidosqualene cyclase s, including lanosterol synthase , which produces lanosterol , a precursor to cholesterol. ref name Abe cite journal author Abe I. year 2007 title Enzymatic synthesis of cyclic triterpenes journal Natural Products Reports volume 24 pages 1311 31 pmid 18033581 doi 10.1039 b616857b issue 6 ref 2,3 R Oxidosqualene is an inhibitor of lanosterol synthase. References references Cholesterol metabolism intermediates DEFAULTSORT Oxidosqualene, 2,3 Category Epoxid ... more details
10.1016 0968 0004 94 90276 3 ref Cycloartenol synthase EC number 5.4.99.8 2,3 epoxysqualene cycloartenol cyclase is a plant enzyme that catalyzes the cyclization of S 2,3 epoxysqualene to cycloartenol ... more details
, but is generally found to come from cycloartenol. ref Dewick, P. M. Medicinal Natural Products .... ref The biosynthesis of cycloartenol begins as one molecule of isopentenyl diphosphate IPP and two ... with 2,3 oxidosqualene 6 as an intermediate forms cycloartenol. The biosynthesis of sitosterol from cycloartenol is summarized below. The double bond of cycloartenol is methylated by SAM to give a carbocation ... more details
chembox Verifiedfields changed Watchedfields changed verifiedrevid 393354387 ImageFile Lanosterol skeletal.svg ImageSize ImageFile2 Lanosterol 3D sticks.png IUPACName lanosta 8,24 dien 3 ol OtherNames Section1 Chembox Identifiers CASNo Ref cascite correct CAS CASNo 79 63 0 PubChem 4861 ChEMBL Ref ebicite changed EBI ChEMBL 225111 UNII Ref fdacite changed FDA UNII 1J05Z83K3M SMILES C C H CCC C C C C H 1CC br C 2 C C1CCC3 C2CC C H br 4C C C C H O CC C 34C MeSHName Lanosterol Section2 Chembox Properties Formula C sub 30 sub H sub 50 sub O MolarMass 426.71 g mol ExactMass 426.386166 Appearance Density MeltingPt 138 140 C BoilingPt Section3 Chembox Hazards Solubility MainHazards FlashPt Autoignition Lanosterol is a tetracyclic terpene triterpenoid , which is the compound from which all steroid s are derived. Role in creation of steroids Elaboration of lanosterol under enzyme catalysis leads to the core structure of steroids. 14 Demethylation of lanosterol by cytochrome P450 CYP51 eventually yields cholesterol . Image Sterol synthesis.svg thumb center 350px Simplified version of the lanosterol synthesis pathway with the intermediates isopentenyl pyrophosphate IPP , dimethylallyl pyrophosphate DMAPP , geranyl pyrophosphate GPP , and squalene shown. Some intermediates are omitted. Biosynthesis class wikitable Description Illustration Enzyme Two molecules of farnesyl pyrophosphate condense with reduction by NADPH to form squalene Image Cholesterol Synthesis Reaction10.png 400px squalene synthase Squalene is oxidized to 2,3 oxidosqualene squalene epoxide Image Cholesterol Synthesis Reaction11.png 400px squalene monooxygenase 2,3 Oxidosqualene is converted to a protosterol cation and finally to lanosterol Image Cholesterol Synthesis Reaction12.png 400px lanosterol synthase step 2 Image Cholesterol Synthesis Reaction13.png 400px step 2 See also Cycloartenol CYP51 References cite journal author E. J. Corey , W. E. Russey, P. R. Ortiz de Montellano title 2,3 Oxidosqualene, a ... more details
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