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CYCLOARTENOL

CAS No.:
469-38-5
Catalog Number:
AG00D8OH
Molecular Formula:
Molecular Weight:
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Product Description
Catalog Number:
AG00D8OH
Chemical Name:
CYCLOARTENOL
CAS Number:
469-38-5
MDL Number:
MFCD00200959
IUPAC Name:
(1S,3R,6S,8R,11S,12S,15R,16R)-7,7,12,16-tetramethyl-15-[(2R)-6-methylhept-5-en-2-yl]pentacyclo[9.7.0.01,3.03,8.012,16]octadecan-6-ol
InChI:
InChI=1S/C30H50O/c1-20(2)9-8-10-21(3)22-13-15-28(7)24-12-11-23-26(4,5)25(31)14-16-29(23)19-30(24,29)18-17-27(22,28)6/h9,21-25,31H,8,10-19H2,1-7H3/t21-,22-,23+,24+,25+,27-,28+,29-,30+/m1/s1
InChI Key:
ONQRKEUAIJMULO-YBXTVTTCSA-N
UNII:
YU32VE82N3
Properties
Complexity:
760  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
9  
Defined Bond Stereocenter Count:
0
Exact Mass:
426.386g/mol
Formal Charge:
0
Heavy Atom Count:
31  
Hydrogen Bond Acceptor Count:
1  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
426.729g/mol
Monoisotopic Mass:
426.386g/mol
Rotatable Bond Count:
4  
Topological Polar Surface Area:
20.2A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
9.8  
Literature
Title Journal
Three new cycloartenol glycosides from the roots of Cimicifuga simplex. Planta medica 20120401
Triterpene cyclases from Oryza sativa L.: cycloartenol, parkeol and achilleol B synthases. Organic letters 20110520
Cloning and characterization of oxidosqualene cyclases from Kalanchoe daigremontiana: enzymes catalyzing up to 10 rearrangement steps yielding friedelin and other triterpenoids. The Journal of biological chemistry 20100924
Characterization of a potential nutraceutical ingredient: pomegranate (Punica granatum L.) seed oil unsaponifiable fraction. Plant foods for human nutrition (Dordrecht, Netherlands) 20100901
Phytosterols accumulation in the seeds of Linum usitatissimum L. Plant physiology and biochemistry : PPB 20091001
Cyclobranol: a substrate for C25-methyl sterol side chains and potent mechanism-based inactivator of plant sterol methyltransferase. Bioorganic & medicinal chemistry letters 20080715
Sterol C24-methyltransferase: mechanistic studies of the C-methylation reaction with 24-fluorocycloartenol. Bioorganic & medicinal chemistry letters 20080101
Cancer chemopreventive effects of cycloartane-type and related triterpenoids in in vitro and in vivo models. Journal of natural products 20070601
Plant lanosterol synthase: divergence of the sterol and triterpene biosynthetic pathways in eukaryotes. Plant & cell physiology 20060501
Mechanism involved in the spasmolytic effect of a mixture of two triterpenes, cycloartenol and cycloeucalenol, isolated from Herissanthia tiubae in the guinea-pig ileum. Planta medica 20051101
[Study on chemical constituents in rhizome of Pinellia ternata]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20050501
New cycloartenol esters from Ixora coccinea. Natural product research 20040801
Mechanism-based active site modification of the soybean sterol methyltransferase by 26,27-dehydrocycloartenol. Bioorganic & medicinal chemistry letters 20040105
[Studies on chemical constituents of Ervatamia hainanensis]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20031101
Biosynthesis of phytosterols. Kinetic mechanism for the enzymatic C-methylation of sterols. The Journal of biological chemistry 20030905
Steroid biosynthesis in prokaryotes: identification of myxobacterial steroids and cloning of the first bacterial 2,3(S)-oxidosqualene cyclase from the myxobacterium Stigmatella aurantiaca. Molecular microbiology 20030101
Inhibition of benzoyl peroxide and ultraviolet-B radiation induced oxidative stress and tumor promotion markers by cycloartenol in murine skin. Redox report : communications in free radical research 20030101
A genomics approach to the early stages of triterpene saponin biosynthesis in Medicago truncatula. The Plant journal : for cell and molecular biology 20021201
Sterol C-24 methyltransferase type 1 controls the flux of carbon into sterol biosynthesis in tobacco seed. Plant physiology 20020901
Inhibition of squalene synthase and squalene epoxidase in tobacco cells triggers an up-regulation of 3-hydroxy-3-methylglutaryl coenzyme a reductase. Plant physiology 20020901
Inhibition of the sterol pathway in leek seedlings impairs phosphatidylserine and glucosylceramide synthesis but triggers an accumulation of triacylglycerols. Biochimica et biophysica acta 20020808
The Pneumocystis carinii drug target S-adenosyl-L-methionine:sterol C-24 methyl transferase has a unique substrate preference. Molecular microbiology 20020501
Brassinosteroids. Plant counterparts to animal steroid hormones? Vitamins and hormones 20020101
An immunosuppressive tryptophan-derived alkaloid from Lepidagathis cristata. Phytochemistry 20011201
[Studies on chemical constituents of Fragaria ananassa Duch]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20010901
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