Home Other Building Blocks (4aR,5aS,6aS,6bS,9R,9aR,11aS,11bR)-9a,11b-dimethyl-9-((R)-6-methylheptan-2-yl)hexadecahydrocyclopenta[1,2]phenanthro[8a,9-b]oxiren-3-ol

(4aR,5aS,6aS,6bS,9R,9aR,11aS,11bR)-9a,11b-dimethyl-9-((R)-6-methylheptan-2-yl)hexadecahydrocyclopenta[1,2]phenanthro[8a,9-b]oxiren-3-ol

CAS No.:
1250-95-9
Catalog Number:
AG000MZ2
Molecular Formula:
C27H46O2
Molecular Weight:
402.6529
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
25mg
≥95%
1 week
United States
$97
- +
50mg
≥95%
1 week
United States
$133
- +
100mg
≥95%
1 week
United States
$201
- +
250mg
≥95%
1 week
United States
$400
- +
Product Description
Catalog Number:
AG000MZ2
Chemical Name:
(4aR,5aS,6aS,6bS,9R,9aR,11aS,11bR)-9a,11b-dimethyl-9-((R)-6-methylheptan-2-yl)hexadecahydrocyclopenta[1,2]phenanthro[8a,9-b]oxiren-3-ol
CAS Number:
1250-95-9
Molecular Formula:
C27H46O2
Molecular Weight:
402.6529
MDL Number:
MFCD00046980
IUPAC Name:
(1S,2R,5S,7R,9S,11S,12S,15R,16R)-2,16-dimethyl-15-[(2R)-6-methylheptan-2-yl]-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecan-5-ol
InChI:
InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-20-15-24-27(29-24)16-19(28)11-14-26(27,5)23(20)12-13-25(21,22)4/h17-24,28H,6-16H2,1-5H3/t18-,19+,20+,21-,22+,23+,24+,25-,26-,27+/m1/s1
InChI Key:
PRYIJAGAEJZDBO-ZEQHCUNVSA-N
SMILES:
CC(CCC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2C[C@H]2[C@@]3([C@]1(C)CC[C@@H](C3)O)O2)C)C
EC Number:
215-007-6
UNII:
3UQ9PF5XBD
NSC Number:
18176
Properties
Complexity:
630  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
10  
Defined Bond Stereocenter Count:
0
Exact Mass:
402.35g/mol
Formal Charge:
0
Heavy Atom Count:
29  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
402.663g/mol
Monoisotopic Mass:
402.35g/mol
Rotatable Bond Count:
5  
Topological Polar Surface Area:
32.8A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
8  
Literature
Title Journal
Surprising unreactivity of cholesterol-5,6-epoxides towards nucleophiles. Journal of lipid research 20120401
7-Ketocholesterol and cholesterol-5alpha,6alpha-epoxide induce smooth muscle cell migration and proliferation through the epidermal growth factor receptor/phosphoinositide 3-kinase/Akt signaling pathways. Toxicology letters 20100816
Effects of cholesterol oxidation products on exocytosis. Neuroscience letters 20100526
Synthesis of new alkylaminooxysterols with potent cell differentiating activities: identification of leads for the treatment of cancer and neurodegenerative diseases. Journal of medicinal chemistry 20091210
Efficient chemoenzymatic synthesis, cytotoxic evaluation, and SAR of epoxysterols. Journal of medicinal chemistry 20090709
Involvement of Fas signalling in 7beta-hydroxycholesterol-and cholesterol-5beta,6beta-epoxide-induced apoptosis. International journal of toxicology 20080101
Cholesterol oxides as biomarkers of oxidative stress in type 1 and type 2 diabetes mellitus. Diabetes/metabolism research and reviews 20070101
Death-signaling pathways in human myeloid cells by oxLDL and its cytotoxic components 7beta-hydroxycholesterol and cholesterol-5beta,6beta-epoxide. Journal of biochemical and molecular toxicology 20070101
Involvement of calcium in 7beta -hydroxycholesterol and cholesterol-5beta,6beta -epoxide-induced apoptosis. International journal of toxicology 20060101
The role of the mitochondria in apoptosis induced by 7beta-hydroxycholesterol and cholesterol-5beta,6beta-epoxide. The British journal of nutrition 20051001
Structure of an atypical epoxide hydrolase from Mycobacterium tuberculosis gives insights into its function. Journal of molecular biology 20050902
Regulation of JH epoxide hydrolase versus JH esterase activity in the cabbage looper, Trichoplusia ni, by juvenile hormone and xenobiotics. Journal of insect physiology 20050501
Cholesterol-3-beta, 5-alpha, 6-beta-triol induced genotoxicity through reactive oxygen species formation. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20050401
Comparison of the apoptotic processes induced by the oxysterols 7beta-hydroxycholesterol and cholesterol-5beta,6beta-epoxide. Cell biology and toxicology 20040901
Formation of biologically active oxysterols during ozonolysis of cholesterol present in lung surfactant. The Journal of biological chemistry 20040618
Oxidized cholesterol in the diet is a source of oxidized lipoproteins in human serum. Journal of lipid research 20030401
Cholesterol is superior to 7-ketocholesterol or 7 alpha-hydroxycholesterol as an allosteric activator for acyl-coenzyme A:cholesterol acyltransferase 1. The Journal of biological chemistry 20030328
Toxicity of cholesterol oxidation products to Caco-2 and HepG2 cells: modulatory effects of alpha- and gamma-tocopherol. Journal of applied toxicology : JAT 20030101
Comparative study of the cytotoxicity and apoptosis-inducing potential of commonly occurring oxysterols. Cell biology and toxicology 20010101
Effects of environmentally encountered epoxides on mouse liver epoxide-metabolizing enzymes. Biochemical pharmacology 19910601
Properties