Structure Database (LMSD)

HO H H H
Common Name
previtamin D3
Systematic Name
(6Z)-(3S)-9,10-seco-5(10),6,8-cholestatrien-3-ol
Synonyms
  • precholecalciferol
  • (6Z)-tacalciol
LM ID
LMST03020222
Formula
C27H44O
Exact Mass
Calculate m/z
384.339215
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Main

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Secosteroids [ST03]
Vitamin D3 and derivatives [ST0302]

String Representations

InChiKey (Click to copy)
YUGCAAVRZWBXEQ-WHTXLNIXSA-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/h10,12-13,19,21,24-26,28H,6-9,11,14-18H2,1-5H3/b13-12-/t21-,24+,25-,26+,27-/m1/s1
SMILES (Click to copy)
C(/C1C[C@@H](O)CCC=1C)=C/C1[C@]2([H])CC[C@@]([H])([C@@]2(C)CCC=1)[C@]([H])(C)CCCC(C)C

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Rattus norvegicus (#10116)
Mammalia (#40674)
Photometabolism of 7-dehydrocholesterol to previtamin D3 in skin.,
Biochem Biophys Res Commun, 1977
Pubmed ID: 194588

Other Databases

Wikipedia
Previtamin_D3
KEGG ID
C07711
HMDB ID
HMDB06500
CHEBI ID
8403
LIPIDBANK ID
VVD0241
PubChem CID
5281058
Cayman ID
33409

Calculated Physicochemical Properties

Heavy Atoms 28
Rings 3
Aromatic Rings 0
Rotatable Bonds 7
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

Reactions

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ⓘ Reactions are shown if the E.C. number of the enzyme catalysing it is annotated in the UniProt database for a species belonging to the selected taxonomic class.
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Reactions graph legend

Admin

Created at
-
Updated at
1st Feb 2024