Structure Database (LMSD)

Common Name
24,24-difluoro-25-hydroxyvitamin D3
Systematic Name
(5Z,7E)-(3S)-24,24-difluoro-9,10-seco-5,7,10(19)-cholestatriene-3,25-diol
Synonyms
  • 24,24-difluoro-25-hydroxycholecalciferol
LM ID
LMST03020141
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)
Studies on organic fluorine compounds. Part 37. Studies on steroids. Part 78. Synthesis of 24,24-difluoro- and 24ξ-fluoro-25-hydroxyvitamin D3,
J. Chem. Soc., Perkin Trans. 1, 1982

String Representations

InChiKey (Click to copy)
LRNVEDCUBISUTC-CMOHYRQESA-N
InChi (Click to copy)
InChI=1S/C27H42F2O2/c1-18-8-11-22(30)17-21(18)10-9-20-7-6-15-26(5)23(12-13-24(20)26)19(2)14-16-27(28,29)25(3,4)31/h9-10,19,22-24,30-31H,1,6-8,11-17H2,2-5H3/b20-9+,21-10-/t19-,22+,23-,24+,26-/m1/s1
SMILES (Click to copy)
C1C(=C)/C(=C\C=C2\[C@]3([H])CC[C@@]([C@@](C)([H])CCC(F)(F)C(O)(C)C)([H])[C@@]3(C)CCC\2)/C[C@@H](O)C1

Other Databases

LIPIDBANK ID
VVD0159
PubChem CID
9547386
PDB ID
SRF

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 7.84
Molar Refractivity 124.51

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Created at
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Updated at
27th Mar 2024