Structure Database (LMSD)

Common Name
1alpha,25-dihydroxy-9,11-didehydrovitamin D3
Systematic Name
(5Z,7E)-(1S,3R)-9,10-seco-5,7,9(11),10(19)-cholestatetraene-1,3,25-triol
Synonyms
  • 1alpha,25-dihydroxy-9,11-didehydrocholecalciferol
LM ID
LMST03020170
Formula
C27H42O3
Exact Mass
Calculate m/z
414.313396
Status
Curated
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)
Synthesis and Biological Activity of 9,11-Dehydrovitamin D3 Analogues : Stereoselective Preparation of 6b-Vitamin D Vinylallenes and a Concise Studies of vitamin D (calciferol) and its analogs. 35. Synthesis and biological activity of 9,11-dehydrovitamin D3 analogs: stereoselective preparation of 6.beta.-vitamin D vinylallenes and a concise enynol synthesis for preparing the A-ringSynthesis for Preparing the A-Ring,
J Org Chem, 1989

String Representations

InChiKey (Click to copy)
JGAZABUQVPTSTD-NKMMMXOESA-N
InChi (Click to copy)
InChI=1S/C27H42O3/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(28)17-25(29)19(21)2/h7,9-11,18,22-25,28-30H,2,6,8,12-17H2,1,3-5H3/b20-10+,21-11-/t18-,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)CC=C\2)[C@]([H])(C)CCCC(O)(C)C)/C[C@@H](O)C1

Other Databases

LIPIDBANK ID
VVD0188
PubChem CID
5283695

Calculated Physicochemical Properties

Heavy Atoms 30
Rings 3
Aromatic Rings 0
Rotatable Bonds 6
Van der Waals Molecular Volume 454.39
Topological Polar Surface Area 60.69
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 3
logP 6.34
Molar Refractivity 125.48

Admin

Created at
-
Updated at
30th Jan 2024