Structure Database (LMSD)

Common Name
26,26,26,27,27,27-hexafluoro-1alphaa-hydroxyvitamin D3
Systematic Name
(5Z,7E)-(1S,3R)-26,26,26,27,27,27-hexafluoro-9,10-seco-5,7,10(19)-cholestatriene-1,3-diol
Synonyms
  • 26,26,26,27,27,27-hexafluoro-1alphaa-hydroxycholecalciferol
LM ID
LMST03020085
Formula
C27H38O2F6
Exact Mass
Calculate m/z
508.277598
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
saltans group (#32360)
Insecta (#50557)
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)
FBGKZXKSAGRAEZ-LIWPMISOSA-N
InChi (Click to copy)
InChI=1S/C27H38F6O2/c1-16(6-4-8-24(26(28,29)30)27(31,32)33)21-11-12-22-18(7-5-13-25(21,22)3)9-10-19-14-20(34)15-23(35)17(19)2/h9-10,16,20-24,34-35H,2,4-8,11-15H2,1,3H3/b18-9+,19-10-/t16-,20-,21-,22+,23+,25-/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(C(F)(F)F)C(F)(F)F)([H])[C@@]3(C)CCC\2)/C[C@@H](O)C1

Other Databases

LIPIDBANK ID
VVD0095
PubChem CID
9547336

Calculated Physicochemical Properties

Heavy Atoms 35
Rings 3
Aromatic Rings 0
Rotatable Bonds 8
Van der Waals Molecular Volume 484.66
Topological Polar Surface Area 40.46
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 2
logP 8.82
Molar Refractivity 125.39

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Created at
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Updated at
15th Feb 2022