Structure Database (LMSD)

Common Name
(23S,25R)-25-hydroxyvitamin D3 26,23-lactone
Systematic Name
(5Z,7E)-(3S,23S,25R)-3,25-dihydroxy-9,10-seco-5,7,10(19)-cholestatrieno-26,23-lactone
Synonyms
  • (23S,25R)-25-hydroxycholecalciferol 26,23-lactone
LM ID
LMST03020116
Formula
C27H40O4
Exact Mass
Calculate m/z
428.29266
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
Rattus norvegicus (#10116)
Mammalia (#40674)
Synthesis and determination of configuration of natural 25-hydroxyvitamin D(3) 26,23-lactone.,
Proc Natl Acad Sci U S A, 1981
Pubmed ID: 16593112
Gallus gallus (#9031)
Aves (#8782)
25-Hydroxyvitamin D3 26,23-lactone: a new in vivo metabolite of vitamin D.,
Biochemistry, 1979
Pubmed ID: 228698

String Representations

InChiKey (Click to copy)
IJNDMZIDDKVXHR-PDGVZUSRSA-N
InChi (Click to copy)
InChI=1S/C27H40O4/c1-17-7-10-21(28)15-20(17)9-8-19-6-5-13-26(3)23(11-12-24(19)26)18(2)14-22-16-27(4,30)25(29)31-22/h8-9,18,21-24,28,30H,1,5-7,10-16H2,2-4H3/b19-8+,20-9-/t18-,21+,22+,23-,24+,26-,27-/m1/s1
SMILES (Click to copy)
C1C(=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
VVD0131
PubChem CID
9547362

Calculated Physicochemical Properties

Heavy Atoms 31
Rings 4
Aromatic Rings 0
Rotatable Bonds 4
Van der Waals Molecular Volume 450.82
Topological Polar Surface Area 68.83
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 4
logP 6.11
Molar Refractivity 123.77

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Created at
-
Updated at
3rd Oct 2021