Structure Database (LMSD)

Common Name
(22E)-(25R)-26,26,26-trifluoro-1alpha,25-dihydroxy-22,23-didehydrovitamin D3
Systematic Name
(5Z,7E,22E)-(1S,3R,25R)-26,26,26-trifluoro-9,10-seco-5,7,10(19),22-cholestatetraene-1,3,25-triol
Synonyms
  • (22E)-(25R)-26,26,26-trifluoro-1alpha,25-dihydroxy-22,23-didehydrocholecalciferol
LM ID
LMST03020098
Formula
C27H39O3F3
Exact Mass
Calculate m/z
468.285129
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 relationships in the vitamin D endocrine system.,
Endocr Rev, 1995
Pubmed ID: 7781594

String Representations

InChiKey (Click to copy)
UOZVIQWXUMJXHC-HNZKQKRBSA-N
InChi (Click to copy)
InChI=1S/C27H39F3O3/c1-17(7-5-14-26(4,33)27(28,29)30)22-11-12-23-19(8-6-13-25(22,23)3)9-10-20-15-21(31)16-24(32)18(20)2/h5,7,9-10,17,21-24,31-33H,2,6,8,11-16H2,1,3-4H3/b7-5+,19-9+,20-10-/t17-,21-,22-,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])/C=C/C[C@](O)(C)C(F)(F)F)([H])[C@@]3(C)CCC\2)/C[C@@H](O)C1

Other Databases

LIPIDBANK ID
VVD0112
PubChem CID
9547347

Calculated Physicochemical Properties

Heavy Atoms 33
Rings 3
Aromatic Rings 0
Rotatable Bonds 6
Van der Waals Molecular Volume 472.60
Topological Polar Surface Area 60.69
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 3
logP 7.17
Molar Refractivity 126.37

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Created at
-
Updated at
3rd Feb 2022