Structure Database (LMSD)

Common Name
6-fluorovitamin D3
Systematic Name
(5E,7E)-(3S)-6-fluoro-9,10-seco-5,7,10(19)-cholestatrien-3-ol
Synonyms
  • 6-fluorocholecalciferol
LM ID
LMST03020197
Formula
C27H43OF
Exact Mass
Calculate m/z
402.329793
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)
6-Fluoro-vitamin D3: a new antagonist of the biological actions of vitamin D3 and its metabolites which interacts with the intestinal receptor for 1 alpha,25(OH)2-vitamin D3.,
Arch Biochem Biophys, 1984
Pubmed ID: 6087739

String Representations

InChiKey (Click to copy)
SAIDIROKDGVXPR-IERAOWPBSA-N
InChi (Click to copy)
InChI=1S/C27H43FO/c1-18(2)8-6-9-20(4)24-13-14-25-21(10-7-15-27(24,25)5)16-26(28)23-17-22(29)12-11-19(23)3/h16,18,20,22,24-25,29H,3,6-15,17H2,1-2,4-5H3/b21-16+,26-23+/t20-,22+,24-,25+,27-/m1/s1
SMILES (Click to copy)
C1C(=C)/C(=C(/F)\C=C2\[C@]3([H])CC[C@@]([C@@](C)([H])CCCC(C)C)([H])[C@@]3(C)CCC\2)/C[C@@H](O)C1

Other Databases

CHEBI ID
173062
LIPIDBANK ID
VVD0215
PubChem CID
9547408

Calculated Physicochemical Properties

Heavy Atoms 29
Rings 3
Aromatic Rings 0
Rotatable Bonds 6
Van der Waals Molecular Volume 445.52
Topological Polar Surface Area 20.23
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 1
logP 8.20
Molar Refractivity 121.75

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Created at
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Updated at
15th Feb 2022