Structure Database (LMSD)

Common Name
1alpha-hydroxy-24-oxo-26,27-cyclovitamin D3
Systematic Name
(5Z,7E)-(1S,3R)-1,3-dihydroxy-26,27-cyclo-9,10-seco-5,7,10(19)-cholestatrien-24-one
Synonyms
  • 1alpha-hydroxy-24-oxo-26,27-cyclocholecalciferol
  • MC1080
LM ID
LMST03020103
Formula
C27H40O3
Exact Mass
Calculate m/z
412.297745
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
Homo sapiens (#9606)
Mammalia (#40674)
In vitro metabolism of the anti-psoriatic vitamin D analog, calcipotriol, in two cultured human keratinocyte models.,
J Biol Chem, 1994
Pubmed ID: 8106449
synthetic construct (#32630)
In vitro metabolism of the anti-psoriatic vitamin D analog, calcipotriol, in two cultured human keratinocyte models.,
J Biol Chem, 1994
Pubmed ID: 8106449

String Representations

InChiKey (Click to copy)
HQKYZTGFOOKQAV-HQKKLWNISA-N
InChi (Click to copy)
InChI=1S/C27H40O3/c1-17(6-13-25(29)20-8-9-20)23-11-12-24-19(5-4-14-27(23,24)3)7-10-21-15-22(28)16-26(30)18(21)2/h7,10,17,20,22-24,26,28,30H,2,4-6,8-9,11-16H2,1,3H3/b19-7+,21-10-/t17-,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])CCC(=O)C4CC4)([H])[C@@]3(C)CCC\2)/C[C@@H](O)C1

Other Databases

LIPIDBANK ID
VVD0118
PubChem CID
9547352

Calculated Physicochemical Properties

Heavy Atoms 30
Rings 4
Aromatic Rings 0
Rotatable Bonds 6
Van der Waals Molecular Volume 442.03
Topological Polar Surface Area 57.53
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 6.10
Molar Refractivity 121.88

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Created at
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Updated at
23rd Jan 2024