Structure Database (LMSD)

O H H OH S O H H OH HO
Common Name
(6S)-1alpha,25-dihydroxyvitamin D3 6,19-sulfur dioxide adduct
Systematic Name
(7E)-(1S,3R,6S)-6,19-epithio-9,10-seco-5(10),7-cholestadiene-1,3,25-triol S,S-dioxide
Synonyms
  • (6S)-1alpha,25-dihydroxycholecalciferol 6,19-sulfur dioxide adduct
LM ID
LMST03020304
Formula
C27H44O5S
Exact Mass
Calculate m/z
480.290947
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)
BFYSIYCQJUMTBY-NEJHMDFESA-N
InChi (Click to copy)
InChI=1S/C27H44O5S/c1-17(7-5-11-26(2,3)30)22-9-10-23-18(8-6-12-27(22,23)4)13-25-20-14-19(28)15-24(29)21(20)16-33(25,31)32/h13,17,19,22-25,28-30H,5-12,14-16H2,1-4H3/b18-13+/t17-,19-,22-,23+,24+,25+,27-/m1/s1
SMILES (Click to copy)
[C@@H]1(O)CC2[C@@]([H])(S(=O)(=O)CC=2[C@@H](O)C1)/C=C1/[C@]2([H])CC[C@@]([C@@](C)([H])CCCC(O)(C)C)([H])[C@@]2(C)CCC/1

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Stereoselective synthesis of (5E)- and (5Z)-vitamin D3 19-alkanoic acids via vitamin D3-sulfur dioxide adducts,
J Org Chem, 1983

Other Databases

LIPIDBANK ID
VVD0331
PubChem CID
9547454

Calculated Physicochemical Properties

Heavy Atoms 33
Rings 4
Aromatic Rings 0
Rotatable Bonds 6
Van der Waals Molecular Volume 483.40
Topological Polar Surface Area 94.83
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 5
logP 6.83
Molar Refractivity 134.00

Admin

Created at
-
Updated at
17th Feb 2022