Structure Database (LMSD)

H H HO OH OH H
Common Name
1alpha,25-dihydroxy-11beta-phenylvitamin D3
Systematic Name
(5Z,7E)-(1S,3R,11R)-11-phenyl-9,10-seco-5,7,10(19)-cholestatriene-1,3,25-triol
Synonyms
  • 1alpha,25-dihydroxy-11beta-phenylcholecalciferol
LM ID
LMST03020529
Formula
C33H48O3
Exact Mass
Calculate m/z
492.360345
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)
QSGFVSHXPKNUJN-GNOGHSAPSA-N
InChi (Click to copy)
InChI=1S/C33H48O3/c1-22(10-9-17-32(3,4)36)29-15-16-30-26(14-13-25-19-28(34)20-31(35)23(25)2)18-27(21-33(29,30)5)24-11-7-6-8-12-24/h6-8,11-14,22,27-31,34-36H,2,9-10,15-21H2,1,3-5H3/b25-13-,26-14+/t22-,27-,28-,29-,30+,31+,33-/m1/s1
SMILES (Click to copy)
[C@@H]1(O)C(=C)/C(=C\C=C2\[C@]3([H])CC[C@@]([C@@](C)([H])CCCC(O)(C)C)([H])[C@@]3(C)C[C@H](C3C=CC=CC=3)C\2)/C[C@@H](O)C1

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Structure function analysis of vitamin D analogs with C-ring modifications.,
J Biol Chem, 1992
Pubmed ID: 1310680

Other Databases

LIPIDBANK ID
VVD0619
PubChem CID
9547633

Calculated Physicochemical Properties

Heavy Atoms 36
Rings 4
Aromatic Rings 1
Rotatable Bonds 7
Van der Waals Molecular Volume 529.65
Topological Polar Surface Area 60.69
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 3
logP 7.96
Molar Refractivity 150.14

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Created at
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Updated at
30th Mar 2022