Structure Database (LMSD)

Common Name
(22E)-1beta-hydroxy-22,23-didehydrovitamin D3
Systematic Name
(5Z,7E,22E)-(1R,3R)-9,10-seco-5,7,10(19),22-cholestatetraene-1,3-diol
Synonyms
  • (22E)-1beta-hydroxy-22,23-didehydrocholecalciferol
LM ID
LMST03020149
Status
Active
Exact Mass
Calculate m/z
398.31848
Formula
C27H42O2
Show lipids differing only in stereochemistry/bond geometry
Download as...
MDLMOL SDF CSV TSV
MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".

Main

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Secosteroids [ST03]
Vitamin D3 and derivatives [ST0302]

String Representations

InChiKey (Click to copy)
ZSUIJCISCOHNAH-LPXCXVJTSA-N
InChi (Click to copy)
InChI=1S/C27H42O2/c1-18(2)8-6-9-19(3)24-13-14-25-21(10-7-15-27(24,25)5)11-12-22-16-23(28)17-26(29)20(22)4/h6,9,11-12,18-19,23-26,28-29H,4,7-8,10,13-17H2,1-3,5H3/b9-6+,21-11+,22-12-/t19-,23-,24-,25+,26-,27-/m1/s1
SMILES (Click to copy)
[C@H]1(O)C(=C)/C(=C\C=C2\[C@]3([H])CC[C@@]([H])([C@@]3(C)CCC\2)[C@]([H])(C)/C=C/CC(C)C)/C[C@@H](O)C1

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Delta22-Unsaturated analogs of vitamin D3 and their C(1)-hydroxylated derivatives,
Bioorg Chem, 1987

Other Databases

LIPIDBANK ID
VVD0167
PubChem CID
5283677

Calculated Physicochemical Properties

Heavy Atoms 29
Rings 3
Aromatic Rings 0
Rotatable Bonds 5
Van der Waals Molecular Volume 445.60
Topological Polar Surface Area 40.46
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 2
logP 6.94
Molar Refractivity 123.51

Admin

Created at
-
Updated at
15th Feb 2022