Structure Database (LMSD)

Common Name
1alpha,25-dihydroxy-26,27-dimethyl-20,21-methano-23-oxavitamin D3
Systematic Name
(5Z,7E)-(1S,3R)-26,27-dimethyl-20,21-methano-23-oxa-9,10-seco-5,7,10(19)-cholestatriene-1,3,25-triol
Synonyms
  • 1alpha,25-dihydroxy-26,27-dimethyl-20,21-methano-23-oxacholecalciferol
LM ID
LMST03020413
Formula
C29H46O4
Exact Mass
Calculate m/z
458.33961
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 Activity of 23-oxa Vitamin D Analogues,
Vitamin D, 1994

String Representations

InChiKey (Click to copy)
LFYYNWIVRBNDME-WRRMDWLZSA-N
InChi (Click to copy)
InChI=1S/C29H46O4/c1-5-29(32,6-2)19-33-18-28(14-15-28)26-12-11-24-21(8-7-13-27(24,26)4)9-10-22-16-23(30)17-25(31)20(22)3/h9-10,23-26,30-32H,3,5-8,11-19H2,1-2,4H3/b21-9+,22-10-/t23-,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@@](C4(CC4)COCC(O)(CC)CC)([H])[C@@]3(C)CCC\2)/C[C@@H](O)C1

Other Databases

LIPIDBANK ID
VVD0501
PubChem CID
9547520

Calculated Physicochemical Properties

Heavy Atoms 33
Rings 4
Aromatic Rings 0
Rotatable Bonds 8
Van der Waals Molecular Volume 488.06
Topological Polar Surface Area 69.92
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 4
logP 6.90
Molar Refractivity 135.26

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Created at
-
Updated at
22nd Jan 2024