Structure Database (LMSD)

OH H H H HO O OH
Common Name
(22S)-1alpha,25-dihydroxy-22-methoxy-26,27-dimethyl-23,24-tetradehydro-24a-homo-20-epivitamin D3
Systematic Name
(5Z,7E)-(1S,3R,20R,22S)-26,27-dimethyl-22-methoxy-24a-homo-9,10-seco-5,7,10(19)-cholestatrien-23-yne-1,3,25-triol
Synonyms
  • (22S)-1alpha,25-dihydroxy-22-methoxy-26,27-dimethyl-23,24-tetradehydro-24a-homo-20-epicholecalciferol
LM ID
LMST03020486
Formula
C31H48O4
Exact Mass
Calculate m/z
484.35526
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)
LWMYATUXOQDOCP-HQZNHLNTSA-N
InChi (Click to copy)
InChI=1S/C31H48O4/c1-7-31(34,8-2)18-10-12-29(35-6)22(4)26-15-16-27-23(11-9-17-30(26,27)5)13-14-24-19-25(32)20-28(33)21(24)3/h13-14,22,25-29,32-34H,3,7-9,11,15-20H2,1-2,4-6H3/b23-13+,24-14-/t22-,25-,26-,27+,28+,29-,30-/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](OC)C#CCC(O)(CC)CC)([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
VVD0576
PubChem CID
9547590

Calculated Physicochemical Properties

Heavy Atoms 35
Rings 3
Aromatic Rings 0
Rotatable Bonds 7
Van der Waals Molecular Volume 529.74
Topological Polar Surface Area 69.92
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 4
logP 6.87
Molar Refractivity 144.66

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Created at
-
Updated at
14th Apr 2022