Structure Database (LMSD)

Common Name
1alpha-hydroxy-22-(4-hydroxyphenyl)-23,24,25,26,27-pentanorvitamin D3
Systematic Name
(5Z,7E)-(1S,3R)-22-(4-hydroxyphenyl)-23,24-dinor-9,10-seco-5,7,10(19)-cholatriene-1,3-diol
Synonyms
  • 1alpha-hydroxy-22-(4-hydroxyphenyl)-23,24,25,26,27-pentanorcholecalciferol
LM ID
LMST03020311
Formula
C28H38O3
Exact Mass
Calculate m/z
422.282095
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
synthetic construct (#32630)
AROCALCIFEROLS: A NEW CLASS OF SIDE-CHAIN ANALOGS OF l,25(OH)2D3,
Vitamin D, 1991

String Representations

InChiKey (Click to copy)
RYGBSZRPQTUWLJ-IOFFJAQLSA-N
InChi (Click to copy)
InChI=1S/C28H38O3/c1-18(15-20-6-10-23(29)11-7-20)25-12-13-26-21(5-4-14-28(25,26)3)8-9-22-16-24(30)17-27(31)19(22)2/h6-11,18,24-27,29-31H,2,4-5,12-17H2,1,3H3/b21-8+,22-9-/t18-,24-,25-,26+,27+,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])CC4C=CC(O)=CC=4)([H])[C@@]3(C)CCC\2)/C[C@@H](O)C1

Other Databases

LIPIDBANK ID
VVD0342
PubChem CID
9547459

Calculated Physicochemical Properties

Heavy Atoms 31
Rings 4
Aromatic Rings 1
Rotatable Bonds 4
Van der Waals Molecular Volume 443.15
Topological Polar Surface Area 60.69
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 3
logP 6.28
Molar Refractivity 126.72

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Created at
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Updated at
30th Mar 2022