Structure Database (LMSD)

Common Name
(23S,25R)-1alpha,23,25,26-tetrahydroxyvitamin D3
Systematic Name
(5Z,7E)-(1S,3R,23S,25R)-9,10-seco-5,7,10(19)-cholestatriene-1,3,23,25,26-pentol
Synonyms
  • (23S,25R)-1alpha,23,25,26-tetrahydroxycholecalciferol
LM ID
LMST03020306
Formula
C27H44O5
Exact Mass
Calculate m/z
448.318875
Status
Curated
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
Gallus gallus (#9031)
Aves (#8782)
Metabolic pathways from 1 alpha,25-dihydroxyvitamin D3 to 1 alpha,25-dihydroxyvitamin D3-26,23-lactone. Stereo-retained and stereo-selective lactonization.,
J Biol Chem, 1987
Pubmed ID: 3034884

String Representations

InChiKey (Click to copy)
QDZSTMXTBPCCGE-CJJVECAQSA-N
InChi (Click to copy)
InChI=1S/C27H44O5/c1-17(12-22(30)15-26(3,32)16-28)23-9-10-24-19(6-5-11-27(23,24)4)7-8-20-13-21(29)14-25(31)18(20)2/h7-8,17,21-25,28-32H,2,5-6,9-16H2,1,3-4H3/b19-7+,20-8-/t17-,21-,22+,23-,24+,25+,26-,27-/m1/s1
SMILES (Click to copy)
[C@@H]1(O)C(=C)/C(=C\C=C2\[C@]3([H])CC[C@@]([H])([C@@]3(C)CCC\2)[C@]([H])(C)C[C@H](O)C[C@](O)(C)CO)/C[C@@H](O)C1

Other Databases

LIPIDBANK ID
VVD0333
PubChem CID
5283763

Calculated Physicochemical Properties

Heavy Atoms 32
Rings 3
Aromatic Rings 0
Rotatable Bonds 7
Van der Waals Molecular Volume 474.61
Topological Polar Surface Area 101.15
Hydrogen Bond Donors 5
Hydrogen Bond Acceptors 5
logP 5.08
Molar Refractivity 129.38

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Created at
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Updated at
22nd Jan 2024