Structure Database (LMSD)

Common Name
1alpha,25-dihydroxy-11alpha-[(1S)-oxiranyl]vitamin D3
Systematic Name
(5Z,7E)-(1S,3R,11S)-11-[(1S)-oxiranyl]-9,10-seco-5,7,10(19)-cholestatriene-1,3,25-triol
Synonyms
  • 1alpha,25-dihydroxy-11alpha-[(1S)-oxiranyl]cholecalciferol
LM ID
LMST03020412
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)
Structure-function relationships in the vitamin D endocrine system.,
Endocr Rev, 1995
Pubmed ID: 7781594

String Representations

InChiKey (Click to copy)
RVRKNKJCAWZWEY-ZPDFZRCISA-N
InChi (Click to copy)
InChI=1S/C29H46O4/c1-18(7-6-12-28(3,4)32)24-10-11-25-21(13-22(27-17-33-27)16-29(24,25)5)9-8-20-14-23(30)15-26(31)19(20)2/h8-9,18,22-27,30-32H,2,6-7,10-17H2,1,3-5H3/b20-8-,21-9+/t18-,22+,23-,24-,25+,26+,27-,29-/m1/s1
SMILES (Click to copy)
[C@@H]1(O)C(=C)/C(=C\C=C2\[C@]3([H])CC[C@@]([C@@](C)([H])CCCC(O)(C)C)([H])[C@@]3(C)C[C@@H]([C@]3([H])OC3)C\2)/C[C@@H](O)C1

Other Databases

LIPIDBANK ID
VVD0500
PubChem CID
11973054

Calculated Physicochemical Properties

Heavy Atoms 33
Rings 4
Aromatic Rings 0
Rotatable Bonds 7
Van der Waals Molecular Volume 488.06
Topological Polar Surface Area 73.22
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 4
logP 6.76
Molar Refractivity 135.19

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Created at
-
Updated at
21st Apr 2022