Structure Database (LMSD)

Common Name
1alpha,25-dihydroxyvitamin D2
Systematic Name
(5Z,7E,22E)-(1S,3R)-9,10-seco-5,7,10(19),22-ergostatetraene-1,3,25-triol
Synonyms
  • 1alpha,25-dihydroxyergocalciferol
LM ID
LMST03010040
Formula
C28H44O3
Exact Mass
Calculate m/z
428.329045
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Secosteroids [ST03]
Vitamin D2 and derivatives [ST0301]

Biological Context

1,25-dihydroxy Vitamin D2 is the active circulating metabolite of vitamin D2 formed by 25-hydroxylase in the liver and 25-hydroxyvitamin D-hydroxylase in the kidney.1 By binding to the vitamin D receptor (VDR), 1,25-dihydroxy Vitamin D2 activates VDR to interact with the retinoid X receptor (RXR), forming the VDR/RXR/cofactor complex, which regulates gene transcription.2 Because 1,25-dihydroxy Vitamin D2 circulates at picomolar concentrations and is highly lipophilic, it is difficult to quantify.1

This information has been provided by Cayman Chemical

References

1. Sudsakorn, S., Phatarphekar, A., O'Shea, T., et al. Determination of 1,25-dihydroxyvitamin D2 in rat serum using liquid chromatography with tandem mass spectrometry. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 879(2), 139-145 (2011).
2. Kato, S., Kim, M.S., Yamaoka, K., et al. Mechanisms of transcriptional repression by 1,25(OH)2 vitamin D. Curr. Opin. Nephrol. Hypertens. 16(4), 297-304 (2007).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Gallus gallus (#9031)
Aves (#8782)
Isolation and identification of 1,25-dihydroxyvitamin D2.,
Biochemistry, 1975
Pubmed ID: 1078978

String Representations

InChiKey (Click to copy)
ZGLHBRQAEXKACO-XJRQOBMKSA-N
InChi (Click to copy)
InChI=1S/C28H44O3/c1-18(9-10-19(2)27(4,5)31)24-13-14-25-21(8-7-15-28(24,25)6)11-12-22-16-23(29)17-26(30)20(22)3/h9-12,18-19,23-26,29-31H,3,7-8,13-17H2,1-2,4-6H3/b10-9+,21-11+,22-12-/t18-,19+,23-,24-,25+,26+,28-/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@H](C)C(O)(C)C)([H])[C@@]3(C)CCC\2)/C[C@@H](O)C1

Other Databases

HMDB ID
HMDB0006225
CHEBI ID
86320
LIPIDBANK ID
VVD0382
PubChem CID
9547243
SwissLipids ID
SLM:000485673
Cayman ID
11174
PDB ID
7ZU

Calculated Physicochemical Properties

Heavy Atoms 31
Rings 3
Aromatic Rings 0
Rotatable Bonds 5
Van der Waals Molecular Volume 471.69
Topological Polar Surface Area 60.69
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 3
logP 6.59
Molar Refractivity 130.03

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Created at
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Updated at
15th Feb 2022