Structure Database (LMSD)

Common Name
26,26,26,27,27,27-hexafluoro-1alpha,25-dihydroxyvitamin D3
Systematic Name
(5Z,7E)-(1S,3R)-26,26,26,27,27,27-hexafluoro-9,10-seco-5,7,10(19)-cholestatriene-1,3,25-triol
Synonyms
  • 26,26,26,27,27,27-hexafluoro-1alpha,25-dihydroxycholecalciferol
LM ID
LMST03020089
Formula
C27H38O3F6
Exact Mass
Calculate m/z
524.272513
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)
Biological activity of fluorinated vitamin D analogs at C-26 and C-27 on human promyelocytic leukemia cells, HL-60.,
Arch Biochem Biophys, 1987
Pubmed ID: 2823715

String Representations

InChiKey (Click to copy)
XPYGGHVSFMUHLH-UUSULHAXSA-N
InChi (Click to copy)
InChI=1S/C27H38F6O3/c1-16(6-4-13-25(36,26(28,29)30)27(31,32)33)21-10-11-22-18(7-5-12-24(21,22)3)8-9-19-14-20(34)15-23(35)17(19)2/h8-9,16,20-23,34-36H,2,4-7,10-15H2,1,3H3/b18-8+,19-9-/t16-,20-,21-,22+,23+,24-/m1/s1
SMILES (Click to copy)
[C@@H]1(O)C(=C)/C(=C\C=C2\[C@]3([H])CC[C@@]([C@@](C)([H])CCCC(O)(C(F)(F)F)C(F)(F)F)([H])[C@@]3(C)CCC\2)/C[C@@H](O)C1

Other Databases

LIPIDBANK ID
VVD0099
PubChem CID
5282190
GuidePharm ID
2781

Calculated Physicochemical Properties

Heavy Atoms 36
Rings 3
Aromatic Rings 0
Rotatable Bonds 8
Van der Waals Molecular Volume 493.45
Topological Polar Surface Area 60.69
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 3
logP 8.22
Molar Refractivity 127.36

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Created at
-
Updated at
15th Feb 2022