Structure Database (LMSD)

Common Name
1alpha,25-dihydroxy-14-epiprevitamin D3
Systematic Name
(6Z)-(1S,3R,14R)-9,10-seco-5(10),6,8-cholestatriene-1,3,25-triol
Synonyms
  • 1alpha,25-dihydroxy-14-epiprecholecalciferol
LM ID
LMST03020261
Formula
C27H44O3
Exact Mass
Calculate m/z
416.329046
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)
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)
DOIZGAFWGREMOD-FTNBFKHKSA-N
InChi (Click to copy)
InChI=1S/C27H44O3/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/h9-11,18,22-25,28-30H,6-8,12-17H2,1-5H3/b11-10-/t18-,22-,23-,24-,25+,27-/m1/s1
SMILES (Click to copy)
C(/C1C[C@@H](O)C[C@H](O)C=1C)=C/C1[C@@]2([H])CC[C@@]([H])([C@@]2(C)CCC=1)[C@]([H])(C)CCCC(O)(C)C

Other Databases

LIPIDBANK ID
VVD0288
PubChem CID
5283738

Calculated Physicochemical Properties

Heavy Atoms 30
Rings 3
Aromatic Rings 0
Rotatable Bonds 7
Van der Waals Molecular Volume 457.03
Topological Polar Surface Area 60.69
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 3
logP 6.56
Molar Refractivity 125.57

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Created at
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Updated at
11th Oct 2024