Structure Database (LMSD)

Common Name
(23S)-1alpha,25-dihydroxy-22,23,23,24-tetradehydrovitamin D3
Systematic Name
(5Z,7E)-(1S,3R,23S)-9,10-seco-5,7,10(19),22,23-cholestapentaene-1,3,25-triol
Synonyms
  • (23S)-1alpha,25-dihydroxy-22,23,23,24-tetradehydrocholecalciferol
LM ID
LMST03020112
Formula
C27H40O3
Exact Mass
Calculate m/z
412.297745
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)
KMEXQTNJLXZADX-ARNNFMRQSA-N
InChi (Click to copy)
InChI=1S/C27H40O3/c1-18(8-6-14-26(3,4)30)23-12-13-24-20(9-7-15-27(23,24)5)10-11-21-16-22(28)17-25(29)19(21)2/h8,10-11,14,18,22-25,28-30H,2,7,9,12-13,15-17H2,1,3-5H3/b20-10+,21-11-/t6-,18-,22-,23-,24+,25+,27-/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(O)(C)C)([H])[C@@]3(C)CCC\2)/C[C@@H](O)C1

Other Databases

LIPIDBANK ID
VVD0127
PubChem CID
9547358

Calculated Physicochemical Properties

Heavy Atoms 30
Rings 3
Aromatic Rings 0
Rotatable Bonds 4
Van der Waals Molecular Volume 451.75
Topological Polar Surface Area 60.69
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 3
logP 6.10
Molar Refractivity 124.38

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Created at
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Updated at
4th Oct 2024