Structure Database (LMSD)

Common Name
(23S,25R)-1alpha,25-dihydroxyvitamin D3 26,23-lactol
Systematic Name
(5Z,7E)-(1S,3R,23S,25R)-1,3,25-trihydroxy-9,10-seco- 5,7,10,(19)-cholestatrieno-26,23-lactol
Synonyms
  • (23S,25R)-1alpha,25-dihydroxycholecalciferol 26,23-lactol
LM ID
LMST03020193
Formula
C27H42O5
Exact Mass
Calculate m/z
446.303225
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
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)
IYBKBIPCYPEBEW-VYZDORMZSA-N
InChi (Click to copy)
InChI=1S/C27H42O5/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/h7-8,16,20-25,28-31H,2,5-6,9-15H2,1,3-4H3/b18-7+,19-8-/t16-,20-,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@@]([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

LIPIDBANK ID
VVD0211
PubChem CID
9547404

Calculated Physicochemical Properties

Heavy Atoms 32
Rings 4
Aromatic Rings 0
Rotatable Bonds 4
Van der Waals Molecular Volume 462.25
Topological Polar Surface Area 92.22
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 5
logP 5.44
Molar Refractivity 127.19

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Created at
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Updated at
22nd Jan 2024