Structure Database (LMSD)

HO H H H OH OH OH
Common Name
(22S)-1alpha,22,25-trihydroxy-23,24-tetradehydro-24a-homo-20-epivitamin D3
Systematic Name
(5Z,7E)-(1S,3R,20R,22S)-24a-homo-9,10-seco-5,7,10(19)-cholestatrien-23-yne-1,3,22,25-tetrol
Synonyms
  • (22S)-1alpha,22,25-trihydroxy-23,24-tetradehydro-24a-homo-20-epicholecalciferol
LM ID
LMST03020315
Formula
C28H42O4
Exact Mass
Calculate m/z
442.30831
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Main

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Secosteroids [ST03]
Vitamin D3 and derivatives [ST0302]

String Representations

InChiKey (Click to copy)
UKQNCFNXBITWKF-JUOPNIRESA-N
InChi (Click to copy)
InChI=1S/C28H42O4/c1-18-21(16-22(29)17-26(18)31)11-10-20-8-6-15-28(5)23(12-13-24(20)28)19(2)25(30)9-7-14-27(3,4)32/h10-11,19,22-26,29-32H,1,6,8,12-17H2,2-5H3/b20-10+,21-11-/t19-,22-,23-,24+,25-,26+,28-/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@H](O)C#CCC(O)(C)C)([H])[C@@]3(C)CCC\2)/C[C@@H](O)C1

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Chemistry and Biology of Highly Active 22-Oxy Analogs of 20-Epi Calcitriol with very low Binding Affinity to the Vitaamin D Receptor

Other Databases

LIPIDBANK ID
VVD0347
PubChem CID
9547462

Calculated Physicochemical Properties

Heavy Atoms 32
Rings 3
Aromatic Rings 0
Rotatable Bonds 4
Van der Waals Molecular Volume 477.84
Topological Polar Surface Area 80.92
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 4
logP 5.43
Molar Refractivity 130.64

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Created at
-
Updated at
14th Apr 2022