Structure Database (LMSD)

Common Name
(22S)-22-hydroxyvitamin D3
Systematic Name
(5Z,7E)-(3S,22S)-9,10-seco-5,7,10(19)-cholestatriene-3,22-diol
Synonyms
  • (22S)-22-hydroxycholecalciferol
LM ID
LMST03020243
Formula
C27H44O2
Exact Mass
Calculate m/z
400.33413
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, biologic activity, and protein binding characteristics of a new vitamin D analog, 22-hydroxyvitamin D3.,
J Steroid Biochem, 1987
Pubmed ID: 3041108

String Representations

InChiKey (Click to copy)
OCHNORYGWPYCAK-NIRSYVJSSA-N
InChi (Click to copy)
InChI=1S/C27H44O2/c1-18(2)8-15-26(29)20(4)24-13-14-25-21(7-6-16-27(24,25)5)10-11-22-17-23(28)12-9-19(22)3/h10-11,18,20,23-26,28-29H,3,6-9,12-17H2,1-2,4-5H3/b21-10+,22-11-/t20-,23-,24+,25-,26-,27+/m0/s1
SMILES (Click to copy)
C1C(=C)/C(=C\C=C2\[C@]3([H])CC[C@@]([H])([C@@]3(C)CCC\2)[C@]([H])(C)[C@@H](O)CCC(C)C)/C[C@@H](O)C1

Other Databases

CHEBI ID
191262
LIPIDBANK ID
VVD0270
PubChem CID
5283728

Calculated Physicochemical Properties

Heavy Atoms 29
Rings 3
Aromatic Rings 0
Rotatable Bonds 6
Van der Waals Molecular Volume 448.24
Topological Polar Surface Area 40.46
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 2
logP 7.16
Molar Refractivity 123.60

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Created at
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Updated at
27th Mar 2024