Structure Database (LMSD)

Common Name
(20S,24S)-20-fluoro-1alpha,24-dihydroxy-26,27-cyclovitamin D3
Systematic Name
(5Z,7E)-(1S,3R,20S,24S)-20-fluoro-26,27-cyclo-9,10-seco-5,7,10(19)-cholestatriene-1,3,24-triol
Synonyms
  • (20S,24S)-20-fluoro-1alpha,24-dihydroxy-26,27-cyclocholecalciferol
LM ID
LMST03020130
Formula
C27H41O3F
Exact Mass
Calculate m/z
432.303973
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)
Synthesis of 20-fluorovitamin D analogues,
Tetrahedron, 1995

String Representations

InChiKey (Click to copy)
HWJFYSSICSOIHQ-ZRLKEYMCSA-N
InChi (Click to copy)
InChI=1S/C27H41FO3/c1-17-20(15-21(29)16-24(17)31)9-6-18-5-4-13-26(2)22(18)10-11-25(26)27(3,28)14-12-23(30)19-7-8-19/h6,9,19,21-25,29-31H,1,4-5,7-8,10-16H2,2-3H3/b18-6+,20-9-/t21-,22+,23+,24+,25+,26+,27+/m1/s1
SMILES (Click to copy)
[C@@H]1(O)C(=C)/C(=C\C=C2\[C@]3([H])CC[C@@]([C@](F)(C)CC[C@H](O)C4CC4)([H])[C@@]3(C)CCC\2)/C[C@@H](O)C1

Other Databases

LIPIDBANK ID
VVD0148
PubChem CID
9547375

Calculated Physicochemical Properties

Heavy Atoms 31
Rings 4
Aromatic Rings 0
Rotatable Bonds 6
Van der Waals Molecular Volume 450.74
Topological Polar Surface Area 60.69
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 3
logP 6.55
Molar Refractivity 124.25

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Created at
-
Updated at
15th Feb 2022