Structure Database (LMSD)

Common Name
4,4-difluoro-1alpha-hydroxyvitamin D3
Systematic Name
(5E,7E)-(1S,3S)-4,4-difluoro-9,10-seco-5,7,10(19)-cholestatriene-1,3-diol
Synonyms
  • 4,4-difluoro-1alpha-hydroxycholecalciferol
LM ID
LMST03020138
Formula
C27H42O2F2
Exact Mass
Calculate m/z
436.315286
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)
Fluorinated vitamin D analogs to probe the conformation of vitamin D in its receptor complex: 19F-NMR studies and biological activity.,
Chem Pharm Bull (Tokyo), 2002
Pubmed ID: 11963993

String Representations

InChiKey (Click to copy)
QVGZNWYNOVNFGG-PZDMXMQUSA-N
InChi (Click to copy)
InChI=1S/C27H42F2O2/c1-17(2)8-6-9-18(3)21-13-14-23-20(10-7-15-26(21,23)5)11-12-22-19(4)24(30)16-25(31)27(22,28)29/h11-12,17-18,21,23-25,30-31H,4,6-10,13-16H2,1-3,5H3/b20-11+,22-12+/t18-,21-,23+,24+,25-,26-/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)C)([H])[C@@]3(C)CCC\2)/C(F)(F)[C@H](O)C1

Other Databases

CHEBI ID
137764
LIPIDBANK ID
VVD0156
PubChem CID
9547383

Calculated Physicochemical Properties

Heavy Atoms 31
Rings 3
Aromatic Rings 0
Rotatable Bonds 6
Van der Waals Molecular Volume 460.38
Topological Polar Surface Area 40.46
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 2
logP 7.69
Molar Refractivity 124.44

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Created at
-
Updated at
3rd Feb 2022