Structure Database (LMSD)

Common Name
(6S)-25-hydroxyvitamin D3 6,19-sulfur dioxide adduct
Systematic Name
(7E)-(3S,6S)-6,19-epithio-9,10-seco-5(10),7-cholestadiene-3,25-diol S,S-dioxide
Synonyms
  • (6S)-25-hydroxycholecalciferol 6,19-sulfur dioxide adduct
LM ID
LMST03020280
Formula
C27H44O4S
Exact Mass
Calculate m/z
464.296032
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)
Stereoselective synthesis of (5E)- and (5Z)-vitamin D3 19-alkanoic acids via vitamin D3-sulfur dioxide adducts,
J Org Chem, 1983

String Representations

InChiKey (Click to copy)
MUPXZOBTFTXPRP-XTDVUYCWSA-N
InChi (Click to copy)
InChI=1S/C27H44O4S/c1-18(7-5-13-26(2,3)29)23-11-12-24-19(8-6-14-27(23,24)4)15-25-22-16-21(28)10-9-20(22)17-32(25,30)31/h15,18,21,23-25,28-29H,5-14,16-17H2,1-4H3/b19-15+/t18-,21+,23-,24+,25+,27-/m1/s1
SMILES (Click to copy)
[C@@H]1(O)CC2[C@@]([H])(S(=O)(=O)CC=2CC1)/C=C1/[C@]2([H])CC[C@@]([C@@](C)([H])CCCC(O)(C)C)([H])[C@@]2(C)CCC/1

Other Databases

LIPIDBANK ID
VVD0307
PubChem CID
9547443

Calculated Physicochemical Properties

Heavy Atoms 32
Rings 4
Aromatic Rings 0
Rotatable Bonds 6
Van der Waals Molecular Volume 474.61
Topological Polar Surface Area 74.60
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 4
logP 7.57
Molar Refractivity 132.10

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Created at
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Updated at
17th Feb 2022