Structure Database (LMSD)

Common Name
(23S,25R)-1alpha,25-dihydroxyvitamin D3 26,23-lactone
Systematic Name
(5Z,7E)-(1S,3R,23S,25R)-1,3,25-trihydroxy-9,10-seco-5,7,10(19)-cholestatrieno-26,23-lactone
Synonyms
  • (23S,25R)-1alpha,25-dihydroxycholecalciferol 26,23-lactone
LM ID
LMST03020123
Formula
C27H40O5
Exact Mass
Calculate m/z
444.287575
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
Canis lupus familiaris (#9615)
Mammalia (#40674)
The stereochemical configuration of the natural 1 alpha,25-dihydroxyvitamin D3-26,23-lactone.,
Arch Biochem Biophys, 1985
Pubmed ID: 2996437

String Representations

InChiKey (Click to copy)
WMYIVSWWSRCZFA-RWVJFQLJSA-N
InChi (Click to copy)
InChI=1S/C27H40O5/c1-16(12-21-15-27(4,31)25(30)32-21)22-9-10-23-18(6-5-11-26(22,23)3)7-8-19-13-20(28)14-24(29)17(19)2/h7-8,16,20-24,28-29,31H,2,5-6,9-15H2,1,3-4H3/b18-7+,19-8-/t16-,20-,21+,22-,23+,24+,26-,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]4OC(=O)[C@@](O)(C)C4)([H])[C@@]3(C)CCC\2)/C[C@@H](O)C1

Other Databases

HMDB ID
HMDB0000969
CHEBI ID
156153
LIPIDBANK ID
VVD0138
PubChem CID
6438368
GuidePharm ID
2786

Calculated Physicochemical Properties

Heavy Atoms 32
Rings 4
Aromatic Rings 0
Rotatable Bonds 4
Van der Waals Molecular Volume 459.61
Topological Polar Surface Area 89.06
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 5
logP 5.37
Molar Refractivity 125.68

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Created at
-
Updated at
18th Jan 2024