Structure Database (LMSD)

Common Name
25-hydroxy-14-epivitamin D3
Systematic Name
(5Z,7E)-(3S)-9,10-seco-5,7,10(19)-cholestatriene-3,25-diol
Synonyms
  • 25-hydroxy-14-epicholecalciferol
LM ID
LMST03020247
Formula
C27H44O2
Exact Mass
Calculate m/z
400.33413
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)
14-epi stereoisomers of 25-hydroxy- and 1 alpha,25-dihydroxyvitamin D3: synthesis, isomerization to previtamins, and biological studies.,
J Med Chem, 1994
Pubmed ID: 8057286

String Representations

InChiKey (Click to copy)
JWUBBDSIWDLEOM-LBFATEQNSA-N
InChi (Click to copy)
InChI=1S/C27H44O2/c1-19-10-13-23(28)18-22(19)12-11-21-9-7-17-27(5)24(14-15-25(21)27)20(2)8-6-16-26(3,4)29/h11-12,20,23-25,28-29H,1,6-10,13-18H2,2-5H3/b21-11+,22-12-/t20-,23+,24-,25-,27-/m1/s1
SMILES (Click to copy)
C1C(=C)/C(=C\C=C2\[C@@]3([H])CC[C@@]([H])([C@@]3(C)CCC\2)[C@]([H])(C)CCCC(O)(C)C)/C[C@@H](O)C1

Other Databases

LIPIDBANK ID
VVD0274
PubChem CID
5283732

Calculated Physicochemical Properties

Heavy Atoms 29
Rings 3
Aromatic Rings 0
Rotatable Bonds 6
Van der Waals Molecular Volume 448.24
Topological Polar Surface Area 40.46
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 2
logP 7.31
Molar Refractivity 123.67

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Created at
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Updated at
8th Dec 2023