Structure Database (LMSD)

Common Name
(22R)-1alpha,22,25-trihydroxy-20-epivitamin D3
Systematic Name
(5Z,7E)-(1S,3R,20R,22R)-9,10-seco-5,7,10(19)-cholestatriene-1,3,22,25-tetrol
Synonyms
  • (22R)-1alpha,22,25-trihydroxy-20-epicholecalciferol
LM ID
LMST03020291
Formula
C27H44O4
Exact Mass
Calculate m/z
432.32396
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)
Chemistry and Biology of Highly Active 22-Oxy Analogs of 20-Epi Calcitriol with very low Binding Affinity to the Vitaamin D Receptor

String Representations

InChiKey (Click to copy)
MIKXPDZBDRLVDI-WREGPAIFSA-N
InChi (Click to copy)
InChI=1S/C27H44O4/c1-17-20(15-21(28)16-25(17)30)9-8-19-7-6-13-27(5)22(10-11-23(19)27)18(2)24(29)12-14-26(3,4)31/h8-9,18,21-25,28-31H,1,6-7,10-16H2,2-5H3/b19-8+,20-9-/t18-,21-,22-,23+,24-,25+,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@H](O)CCC(O)(C)C)/C[C@@H](O)C1

Other Databases

LIPIDBANK ID
VVD0318
PubChem CID
5283755

Calculated Physicochemical Properties

Heavy Atoms 31
Rings 3
Aromatic Rings 0
Rotatable Bonds 6
Van der Waals Molecular Volume 465.82
Topological Polar Surface Area 80.92
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 4
logP 5.82
Molar Refractivity 127.48

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Created at
-
Updated at
14th Apr 2022