Structure Database (LMSD)

Common Name
1alpha-fluoro-25-hydroxy-16,17,23,23,24,24-hexadehydrovitamin D3
Systematic Name
(5Z,7E)-(1S,3R)-1-fluoro-9,10-seco-5,7,10(19),16-cholestatetraen-23-yne-3,25-diol
Synonyms
  • 1alpha-fluoro-25-hydroxy-16,17,23,23,24,24-hexadehydrocholecalciferol
LM ID
LMST03020084
Formula
C27H37O2F
Exact Mass
Calculate m/z
412.277758
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)
Structure-function studies on analogues of 1 alpha,25-dihydroxyvitamin D3: differential effects on leukemic cell growth, differentiation, and intestinal calcium absorption.,
Cancer Res, 1990
Pubmed ID: 2208153

String Representations

InChiKey (Click to copy)
NKOYFZVBKCJNED-RQJQXFIZSA-N
InChi (Click to copy)
InChI=1S/C27H37FO2/c1-18(8-6-14-26(3,4)30)23-12-13-24-20(9-7-15-27(23,24)5)10-11-21-16-22(29)17-25(28)19(21)2/h10-12,18,22,24-25,29-30H,2,7-9,13,15-17H2,1,3-5H3/b20-10+,21-11-/t18-,22-,24+,25+,27-/m1/s1
SMILES (Click to copy)
[C@@H]1(F)C(=C)/C(=C\C=C2\[C@]3([H])CC=C([C@@](C)([H])CC#CC(O)(C)C)[C@@]3(C)CCC\2)/C[C@@H](O)C1

Other Databases

CHEBI ID
191264
LIPIDBANK ID
VVD0094
PubChem CID
9547335

Calculated Physicochemical Properties

Heavy Atoms 30
Rings 3
Aromatic Rings 0
Rotatable Bonds 3
Van der Waals Molecular Volume 446.39
Topological Polar Surface Area 40.46
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 2
logP 6.68
Molar Refractivity 122.98

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Created at
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Updated at
15th Feb 2022