Structure Database (LMSD)

Common Name
26,26,26,27,27,27-hexafluoro-1alpha,25-dihydroxy-16,17,23,23,24,24-hexadehydrovitamin D3
Systematic Name
(5Z,7E)-(1S,3R)-26,26,26,27,27,27-hexafluoro-9,10-seco-5,7,10(19),16-cholestatetraen-23-yne-1,3,25-triol
Synonyms
  • 26,26,26,27,27,27-hexafluoro-1alpha,25-dihydroxy-16,17,23,23,24,24-hexadehydrocholecalciferol
LM ID
LMST03020078
Formula
C27H32O3F6
Exact Mass
Calculate m/z
518.225563
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)
Development of a novel 1,25(OH)2-vitamin D3 analog with potent ability to induce HL-60 cell differentiation without modulating calcium metabolism.,
Blood, 1991
Pubmed ID: 1648977

String Representations

InChiKey (Click to copy)
WVQFESJNOSYLJI-GGYAEFIASA-N
InChi (Click to copy)
InChI=1S/C27H32F6O3/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/h8-10,16,20,22-23,34-36H,2,5-7,11-12,14-15H2,1,3H3/b18-8+,19-9-/t16-,20-,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])CC#CC(O)(C(F)(F)F)C(F)(F)F)[C@@]3(C)CCC\2)/C[C@@H](O)C1

Other Databases

LIPIDBANK ID
VVD0084
PubChem CID
9547330

Calculated Physicochemical Properties

Heavy Atoms 36
Rings 3
Aromatic Rings 0
Rotatable Bonds 5
Van der Waals Molecular Volume 485.53
Topological Polar Surface Area 60.69
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 3
logP 7.36
Molar Refractivity 125.88

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Created at
-
Updated at
15th Feb 2022