Structure Database (LMSD)

Common Name
(5E,10Z)-19-fluorovitamin D3
Systematic Name
(5E,7E,10Z)-(3S)-19-fluoro-9,10-seco-5,7,10(19)-cholestatrien-3-ol
Synonyms
  • (5E,10Z)-19-fluorocholecalciferol
LM ID
LMST03020200
Formula
C27H43OF
Exact Mass
Calculate m/z
402.329793
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)
Regioselective synthesis of 19-fluorovitamin D via fluorination of vitamin D-sulfur dioxide adducts,
Tetrahedron Letts, 1996

String Representations

InChiKey (Click to copy)
GBYUWSOLZWQQPT-IJIBJWTQSA-N
InChi (Click to copy)
InChI=1S/C27H43FO/c1-19(2)7-5-8-20(3)25-14-15-26-21(9-6-16-27(25,26)4)10-11-22-17-24(29)13-12-23(22)18-28/h10-11,18-20,24-26,29H,5-9,12-17H2,1-4H3/b21-10+,22-11+,23-18-/t20-,24+,25-,26+,27-/m1/s1
SMILES (Click to copy)
[C@@H]1(O)C/C(=C\C=C2\[C@]3([H])CC[C@@]([C@@](C)([H])CCCC(C)C)([H])[C@@]3(C)CCC\2)/C(=C\F)/CC1

Other Databases

LIPIDBANK ID
VVD0218
PubChem CID
9547411

Calculated Physicochemical Properties

Heavy Atoms 29
Rings 3
Aromatic Rings 0
Rotatable Bonds 6
Van der Waals Molecular Volume 445.52
Topological Polar Surface Area 20.23
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 1
logP 8.20
Molar Refractivity 121.75

Admin

Created at
-
Updated at
8th Dec 2023