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21956-47-8 | Benzenepropanoic acid, α-hydroxy-, (3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester, (αR)-
CAS No: 21956-47-8 Catalog No: AG002LW1 MDL No:
Product Description
Catalog Number:
AG002LW1
Chemical Name:
Benzenepropanoic acid, α-hydroxy-, (3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester, (αR)-
CAS Number:
21956-47-8
IUPAC Name:
[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (2R)-2-hydroxy-3-phenylpropanoate
InChI:
InChI=1S/C17H23NO3/c1-18-13-7-8-14(18)11-15(10-13)21-17(20)16(19)9-12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13-,14+,15?,16-/m1/s1
InChI Key:
FNRXUEYLFZLOEZ-VFSICIBPSA-N
UNII:
19Q4V37F3R
Properties
Complexity:
353
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
3
Defined Bond Stereocenter Count:
0
Exact Mass:
289.168g/mol
Formal Charge:
0
Heavy Atom Count:
21
Hydrogen Bond Acceptor Count:
4
Hydrogen Bond Donor Count:
1
Isotope Atom Count:
0
Molecular Weight:
289.375g/mol
Monoisotopic Mass:
289.168g/mol
Rotatable Bond Count:
5
Topological Polar Surface Area:
49.8A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.7
Literature
| Title | Journal |
|---|---|
| Norlittorine and norhyoscyamine identified as products of littorine and hyoscyamine metabolism by (13)C-labeling in Datura innoxia hairy roots. | Phytochemistry 20120201 |
| Mechanistic insights into the cytochrome P450-mediated oxidation and rearrangement of littorine in tropane alkaloid biosynthesis. | Chembiochem : a European journal of chemical biology 20090921 |
| The carbon-skeleton rearrangement in tropane alkaloid biosynthesis. | Journal of the American Chemical Society 20080813 |
| Capillary electrophoresis of tropane alkaloids and glycoalkaloids occurring in Solanaceae plants. | Methods in molecular biology (Clifton, N.J.) 20080101 |
| Functional genomic analysis of alkaloid biosynthesis in Hyoscyamus niger reveals a cytochrome P450 involved in littorine rearrangement. | Chemistry & biology 20060501 |
| Structural and functional comparison of HemN to other radical SAM enzymes. | Biological chemistry 20051001 |
| Biosynthetic studies on the tropane alkaloid hyoscyamine in Datura stramonium; hyoscyamine is stable to in vivo oxidation and is not derived from littorine via a vicinal interchange process. | Phytochemistry 20021001 |
| Kinetic study of littorine rearrangement in Datura innoxia hairy roots by (13)C NMR spectroscopy. | Journal of natural products 20020801 |
| Tropane alkaloid biosynthesis. A century old problem unresolved. | Natural product reports 20011001 |
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