Structure Database (LMSD)

Common Name
(22E)-(24S)-1alpha,24-dihydroxy-22,23-didehydrovitamin D3
Systematic Name
(5Z,7E,22E)-(1S,3R,24S)-9,10-seco-5,7,10(19),22-cholestatetraene-1,3,24-triol
Synonyms
  • (22E)-(24S)-1alpha,24-dihydroxy-22,23-didehydrocholecalciferol
LM ID
LMST03020169
Formula
C27H42O3
Exact Mass
Calculate m/z
414.313395
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)
Synthesis and biological activity of (22E,24R)- and (22E,24S)-1 alpha,24-dihydroxy-22-dehydrovitamin D3.,
Chem Pharm Bull (Tokyo), 1984
Pubmed ID: 6529792

String Representations

InChiKey (Click to copy)
UBJWUTCRXGEEAN-OPPMWEQISA-N
InChi (Click to copy)
InChI=1S/C27H42O3/c1-17(2)25(29)13-8-18(3)23-11-12-24-20(7-6-14-27(23,24)5)9-10-21-15-22(28)16-26(30)19(21)4/h8-10,13,17-18,22-26,28-30H,4,6-7,11-12,14-16H2,1-3,5H3/b13-8+,20-9+,21-10-/t18-,22-,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/[C@@H](O)C(C)C)/C[C@@H](O)C1

Other Databases

LIPIDBANK ID
VVD0187
PubChem CID
5283694

Calculated Physicochemical Properties

Heavy Atoms 30
Rings 3
Aromatic Rings 0
Rotatable Bonds 5
Van der Waals Molecular Volume 454.39
Topological Polar Surface Area 60.69
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 3
logP 6.20
Molar Refractivity 125.41

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Created at
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Updated at
29th Jan 2024