Structure Database (LMSD)
Common Name
Lumisterol 3
Systematic Name
Synonyms
3D model of Lumisterol 3
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
Lumisterol 3 (L3) is a photoisomer of previtamin D3 .1 It is formed by photoisomerization of previtamin D3 in the epidermis by prolonged UVB exposure and is metabolized by the cytochrome P450 (CYP) isoform CYP11A1 in a variety of tissues to several hydroxylated metabolites, including the active metabolites 20-hydroxy L3, 24-hydroxy L3, and 20,22-dihydroxy L3.2,3
This information has been provided by Cayman Chemical
References
1. Slominski, A.T., Kim, T.-K., Hobrath, J.V., et al. Characterization of a new pathway that activates lumisterol in vivo to biologically active hydroxylumisterols. Sci. Rep. 7(1), 11434 (2017).
2. Holick, M.F. Photosynthesis of vitamin D in the skin: Effect of environmental and life-style variables. Fed. Proc. 46(5), 1876-1882 (1987).
String Representations
InChiKey (Click to copy)
UCTLRSWJYQTBFZ-XMVWLVNMSA-N
InChi (Click to copy)
InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9-10,18-19,21,23-25,28H,6-8,11-17H2,1-5H3/t19-,21+,23-,24+,25-,26-,27-/m1/s1
SMILES (Click to copy)
C12=CC=C3C[C@@H](O)CC[C@@]3(C)[C@]1([H])CC[C@]1(C)[C@@]([H])([C@]([H])(C)CCCC(C)C)CC[C@@]21[H]
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
28
Rings
4
Aromatic Rings
0
Rotatable Bonds
5
Van der Waals Molecular Volume
429.73
Topological Polar Surface Area
20.23
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
1
logP
7.60
Molar Refractivity
119.54
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Updated at
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