Structure Database (LMSD)

Common Name
4,4-difluoro-1alpha,25-dihydroxyvitamin D3
Systematic Name
(5E,7E)-(1S,3S)-4,4-difluoro-9,10-seco-5,7,10(19)-cholestatriene-1,3,25-triol
Synonyms
  • 4,4-difluoro-1alpha,25-dihydroxycholecalciferol
LM ID
LMST03020142
Formula
C27H42O3F2
Exact Mass
Calculate m/z
452.310201
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)
GCODTJZESMVHBK-RHDZNSGOSA-N
InChi (Click to copy)
InChI=1S/C27H42F2O3/c1-17(8-6-14-25(3,4)32)20-12-13-22-19(9-7-15-26(20,22)5)10-11-21-18(2)23(30)16-24(31)27(21,28)29/h10-11,17,20,22-24,30-32H,2,6-9,12-16H2,1,3-5H3/b19-10+,21-11+/t17-,20-,22+,23+,24+,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(O)(C)C)([H])[C@@]3(C)CCC\2)/C(F)(F)[C@@H](O)C1

Other Databases

LIPIDBANK ID
VVD0160
PubChem CID
9547387

Calculated Physicochemical Properties

Heavy Atoms 32
Rings 3
Aromatic Rings 0
Rotatable Bonds 6
Van der Waals Molecular Volume 469.17
Topological Polar Surface Area 60.69
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 3
logP 7.10
Molar Refractivity 126.42

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Created at
-
Updated at
15th Feb 2022