Structure Database (LMSD)

Common Name
(22E)-(24S,25S)-25,26-epoxy-1alpha,24-dihydroxy-22,23-didehydrovitamin D3
Systematic Name
(5Z,7E,22E)-(1S,3R,24S,25S)-25,26-epoxy-9,10-seco-5,7,10(19),22-cholestatetraene-1,3,24-triol
Synonyms
  • (22E)-(24S,25S)-25,26-epoxy-1alpha,24-dihydroxy-22,23-didehydrocholecalciferol
LM ID
LMST03020120
Formula
C27H40O4
Exact Mass
Calculate m/z
428.29266
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 evaluation of some 25,26-epoxy-1α,24-dihydroxyvitamin D3 analogues,
Bioorg Med Chem Letts, 1993

String Representations

InChiKey (Click to copy)
BHERBPSRYGFACH-QJZZCUHDSA-N
InChi (Click to copy)
InChI=1S/C27H40O4/c1-17(7-12-25(30)27(4)16-31-27)22-10-11-23-19(6-5-13-26(22,23)3)8-9-20-14-21(28)15-24(29)18(20)2/h7-9,12,17,21-25,28-30H,2,5-6,10-11,13-16H2,1,3-4H3/b12-7+,19-8+,20-9-/t17-,21-,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@@]([C@@](C)([H])/C=C/[C@H](O)[C@]4(OC4)C)([H])[C@@]3(C)CCC\2)/C[C@@H](O)C1

Other Databases

LIPIDBANK ID
VVD0135
PubChem CID
9547366

Calculated Physicochemical Properties

Heavy Atoms 31
Rings 4
Aromatic Rings 0
Rotatable Bonds 5
Van der Waals Molecular Volume 450.82
Topological Polar Surface Area 73.22
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 4
logP 5.90
Molar Refractivity 125.93

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Created at
-
Updated at
17th Mar 2022