Structure Database (LMSD)

Common Name
Vitamin D3
Systematic Name
(5Z,7E)-(3S)-9,10-seco-5,7,10(19)-cholestatrien-3-ol
Synonyms
  • Vitamin D3
LM ID
LMST03020001
Formula
Exact Mass
Calculate m/z
384.339216
Status
Curated





Classification

Biological Context

Vitamin D3 is a biologically inactive precursor to calcitriol that is converted to active metabolites in vivo.1,2 Vitamin D3 is obtained from dietary sources, including fish, or formed in the epidermis via photolytic conversion of 7-dehydro cholesterol to previtamin D3 by UVB radiation, followed by isomerization to vitamin D3.3,4 Vitamin D3 can then be converted to 25-hydroxy vitamin D3 in the liver by the cytochrome P450 (CYP) isoform CYP2R1 before being converted to calcitriol by CYP27B1 in the kidney.2,3 Formulations containing vitamin D3 have been used in the treatment of osteoporosis.

This information has been provided by Cayman Chemical

References

Reactions

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Reactions graph legend

String Representations

InChiKey (Click to copy)
QYSXJUFSXHHAJI-YRZJJWOYSA-N
InChi (Click to copy)
InChI=1S/C27H44O/c1-19(2)8-6-9-21(4)25-15-16-26-22(10-7-17-27(25,26)5)12-13-23-18-24(28)14-11-20(23)3/h12-13,19,21,24-26,28H,3,6-11,14-18H2,1-2,4-5H3/b22-12+,23-13-/t21-,24+,25-,26+,27-/m1/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)CCCC(C)C)/C[C@@H](O)C1

Other Databases

Wikipedia
KEGG ID
HMDB ID
CHEBI ID
LIPIDBANK ID
VVD0237
PubChem CID
SwissLipids ID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 28
Rings 3
Aromatic Rings 0
Rotatable Bonds 6
Van der Waals Molecular Volume 439.45
Topological Polar Surface Area 20.23
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 1
logP 7.91
Molar Refractivity 121.70

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Created at
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Updated at
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