Structure Database (LMSD)

Common Name
(5E,10Z)-19-fluoro-1alpha-hydroxyvitamin-D3
Systematic Name
(5E,7E,10Z)-(1S,3R)-19-fluoro-9,10-seco-5,7,10(19)-cholestatriene-1,3-diol
Synonyms
  • (5E,10Z)-19-fluoro-1alpha-hydroxycholecalciferol
LM ID
LMST03020205
Formula
C27H43O2F
Exact Mass
Calculate m/z
418.324708
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Secosteroids [ST03]
Vitamin D3 and derivatives [ST0302]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Regioselective synthesis of 19-fluorovitamin D via fluorination of vitamin D-sulfur dioxide adducts,
Tetrahedron Letts, 1996

String Representations

InChiKey (Click to copy)
SDBKJGWYBRQPAF-LUUWCOLKSA-N
InChi (Click to copy)
InChI=1S/C27H43FO2/c1-18(2)7-5-8-19(3)24-12-13-25-20(9-6-14-27(24,25)4)10-11-21-15-22(29)16-26(30)23(21)17-28/h10-11,17-19,22,24-26,29-30H,5-9,12-16H2,1-4H3/b20-10+,21-11+,23-17-/t19-,22+,24-,25+,26-,27-/m1/s1
SMILES (Click to copy)
[C@H]1(O)C/C(=C\C=C2\[C@]3([H])CC[C@@]([C@@](C)([H])CCCC(C)C)([H])[C@@]3(C)CCC\2)/C(=C/F)/[C@H](O)C1

Other Databases

LIPIDBANK ID
VVD0223
PubChem CID
9547416

Calculated Physicochemical Properties

Heavy Atoms 30
Rings 3
Aromatic Rings 0
Rotatable Bonds 6
Van der Waals Molecular Volume 454.31
Topological Polar Surface Area 40.46
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 2
logP 7.46
Molar Refractivity 123.65

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Created at
-
Updated at
15th Jan 2024