Structure Database (LMSD)

Common Name
(23S)-1alpha,23,25-trihydroxy-24-oxovitamin D3
Systematic Name
(5Z,7E)-(1S,3R,23S)-1,3,23,25-tetrahydroxy-9-10-seco-5,7,10(19)-cholestatrien-24-one
Synonyms
  • (23S)-1alpha,23,25-trihydroxy-24-oxocholecalciferol
LM ID
LMST03020195
Formula
C27H42O5
Exact Mass
Calculate m/z
446.303226
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
Homo sapiens (#9606)
Mammalia (#40674)
Synthesis, stereochemistry, and biological activity of 1alpha,23,25-trihydroxy-24-oxovitamin D3, a major natural metabolite of 1alpha,25-dihydroxyvitamin D3.,
Biochemistry, 1997
Pubmed ID: 9235987

String Representations

InChiKey (Click to copy)
ARRIBDAUGOLZSJ-LOLJMGAMSA-N
InChi (Click to copy)
InChI=1S/C27H42O5/c1-16(13-24(30)25(31)26(3,4)32)21-10-11-22-18(7-6-12-27(21,22)5)8-9-19-14-20(28)15-23(29)17(19)2/h8-9,16,20-24,28-30,32H,2,6-7,10-15H2,1,3-5H3/b18-8+,19-9-/t16-,20-,21-,22+,23+,24+,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@H](O)C(=O)C(O)(C)C)([H])[C@@]3(C)CCC\2)/C[C@@H](O)C1

Other Databases

LIPIDBANK ID
VVD0213
PubChem CID
9547406

Calculated Physicochemical Properties

Heavy Atoms 32
Rings 3
Aromatic Rings 0
Rotatable Bonds 6
Van der Waals Molecular Volume 471.97
Topological Polar Surface Area 97.99
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 5
logP 5.00
Molar Refractivity 127.87

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Created at
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Updated at
25th Oct 2023