Structure Database (LMSD)

F HO H H H
Common Name
22-fluorovitamin D3
Systematic Name
(5Z,7E)-(3S)-22-fluoro-9,10-seco-5,7,10(19)-cholestatrien-3-ol
Synonyms
  • 22-fluorocholecalciferol
LM ID
LMST03020202
Formula
C27H43OF
Exact Mass
Calculate m/z
402.329793
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Main

Classification

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

String Representations

InChiKey (Click to copy)
BULPIFATHWIAFY-BEDQNQFSSA-N
InChi (Click to copy)
InChI=1S/C27H43FO/c1-18(2)8-15-26(28)20(4)24-13-14-25-21(7-6-16-27(24,25)5)10-11-22-17-23(29)12-9-19(22)3/h10-11,18,20,23-26,29H,3,6-9,12-17H2,1-2,4-5H3/b21-10+,22-11-/t20-,23-,24+,25-,26?,27+/m0/s1
SMILES (Click to copy)
C1C(=C)/C(=C\C=C2\[C@]3([H])CC[C@@]([C@@](C)([H])C(F)CCC(C)C)([H])[C@@]3(C)CCC\2)/C[C@@H](O)C1

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
The synthesis and biological activity of 22-fluorovitamin D3: a new vitamin D analog.,
Steroids, 1986
Pubmed ID: 2821660

Other Databases

CHEBI ID
173063
LIPIDBANK ID
VVD0220
PubChem CID
9547413

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 8.14
Molar Refractivity 122.49

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Created at
-
Updated at
15th Feb 2022