Structure Database (LMSD)

Common Name
(22E)-1alpha-hydroxy-24-oxo-26,27-cyclo-22,23-didehydrovitamin D3
Systematic Name
(5Z,7E,22E)-(1S,3R)-1,3-dihydroxy-26,27-cyclo-9,10-seco-5,7,10(19),22-cholestatetraen-24-one
Synonyms
  • (22E)-1alpha-hydroxy-24-oxo-26,27-cyclo-22,23-didehydrocholecalciferol
LM ID
LMST03020092
Formula
C27H38O3
Exact Mass
Calculate m/z
410.282095
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 of mc 903, a biologically active vitamin D metabolite analogue,
Tetrahedron, 1987

String Representations

InChiKey (Click to copy)
KKDBQSPKXAUHPH-NRCQPIEOSA-N
InChi (Click to copy)
InChI=1S/C27H38O3/c1-17(6-13-25(29)20-8-9-20)23-11-12-24-19(5-4-14-27(23,24)3)7-10-21-15-22(28)16-26(30)18(21)2/h6-7,10,13,17,20,22-24,26,28,30H,2,4-5,8-9,11-12,14-16H2,1,3H3/b13-6+,19-7+,21-10-/t17-,22-,23-,24+,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(=O)C4CC4)([H])[C@@]3(C)CCC\2)/C[C@@H](O)C1

Other Databases

LIPIDBANK ID
VVD0102
PubChem CID
9547342

Calculated Physicochemical Properties

Heavy Atoms 30
Rings 4
Aromatic Rings 0
Rotatable Bonds 5
Van der Waals Molecular Volume 439.39
Topological Polar Surface Area 57.53
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 5.87
Molar Refractivity 121.78

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Created at
-
Updated at
31st Mar 2022