Structure Database (LMSD)

Common Name
(22E)-1alpha,25-dihydroxy-26-methyl-22,23-didehydrovitamin D3
Systematic Name
(5Z,7E,22E)-(1S,3R)-26-methyl-9,10-seco-5,7,10(19),22-cholestatetraene-1,3,25-triol
Synonyms
  • (22E)-1alpha,25-dihydroxy-26-methyl-22,23-didehydrocholecalciferol
LM ID
LMST03020320
Formula
C28H44O3
Exact Mass
Calculate m/z
428.329045
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)
Unique rearrangement of ergocalciferol side chain in vitro: production of a biologically highly active homologue of 1,25-dihydroxyvitamin D3.,
Biochemistry, 1986
Pubmed ID: 3022793

String Representations

InChiKey (Click to copy)
RQYBOLUOBVMUJB-YURBVYATSA-N
InChi (Click to copy)
InChI=1S/C28H44O3/c1-6-27(4,31)15-7-9-19(2)24-13-14-25-21(10-8-16-28(24,25)5)11-12-22-17-23(29)18-26(30)20(22)3/h7,9,11-12,19,23-26,29-31H,3,6,8,10,13-18H2,1-2,4-5H3/b9-7+,21-11+,22-12-/t19-,23-,24-,25+,26+,27?,28-/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(O)(C)CC)/C[C@@H](O)C1

Other Databases

LIPIDBANK ID
VVD0373
PubChem CID
5283768

Calculated Physicochemical Properties

Heavy Atoms 31
Rings 3
Aromatic Rings 0
Rotatable Bonds 6
Van der Waals Molecular Volume 471.69
Topological Polar Surface Area 60.69
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 3
logP 6.73
Molar Refractivity 130.10

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Created at
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Updated at
4th Oct 2024