Structure Database (LMSD)

Common Name
(20S)-1alpha,25-dihydroxy-20-methoxy-26,27-dimethylvitamin D3
Systematic Name
(5Z,7E)-(1S,3R,20S)-20-methoxy-26,27-dimethyl-9,10-seco-5,7,10(19)-cholestatriene-1,3,25-triol
Synonyms
  • (20S)-1alpha,25-dihydroxy-20-methoxy-26,27-dimethylcholecalciferol
LM ID
LMST03020472
Formula
C30H50O4
Exact Mass
Calculate m/z
474.37091
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)
Chemistry and Biology of Highly Active 22-Oxy Analogs of 20-Epi Calcitriol with very low Binding Affinity to the Vitaamin D Receptor
synthetic construct (#32630)
Synthesis and Biological Activity of 20-Hydroxylated Vitamin D Analogues,
Vitamin D, 1994

String Representations

InChiKey (Click to copy)
XHSIUSQDKAIUKK-VYGJDNQCSA-N
InChi (Click to copy)
InChI=1S/C30H50O4/c1-7-30(33,8-2)18-10-17-29(5,34-6)27-15-14-25-22(11-9-16-28(25,27)4)12-13-23-19-24(31)20-26(32)21(23)3/h12-13,24-27,31-33H,3,7-11,14-20H2,1-2,4-6H3/b22-12+,23-13-/t24-,25+,26+,27+,28+,29+/m1/s1
SMILES (Click to copy)
[C@@H]1(O)C(=C)/C(=C\C=C2\[C@]3([H])CC[C@@]([C@](OC)(C)CCCC(O)(CC)CC)([H])[C@@]3(C)CCC\2)/C[C@@H](O)C1

Other Databases

LIPIDBANK ID
VVD0562
PubChem CID
9547577

Calculated Physicochemical Properties

Heavy Atoms 34
Rings 3
Aromatic Rings 0
Rotatable Bonds 9
Van der Waals Molecular Volume 517.72
Topological Polar Surface Area 69.92
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 4
logP 7.40
Molar Refractivity 141.57

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Created at
-
Updated at
31st May 2022