Structure Database (LMSD)

Common Name
(6S)-vitamin D3 6,19-sulfur dioxide adduct
Systematic Name
(7E)-(3S,6S)-6,19-epithio-9,10-seco-5(10),7-cholestadien-3-ol S,S-dioxide
Synonyms
  • (6S)-cholecalciferol 6,19-sulfur dioxide adduct
LM ID
LMST03020251
Formula
C27H44O3S
Exact Mass
Calculate m/z
448.301117
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)
HPBJDQZFOWHNAQ-QXHKUGGASA-N
InChi (Click to copy)
InChI=1S/C27H44O3S/c1-18(2)7-5-8-19(3)24-12-13-25-20(9-6-14-27(24,25)4)15-26-23-16-22(28)11-10-21(23)17-31(26,29)30/h15,18-19,22,24-26,28H,5-14,16-17H2,1-4H3/b20-15+/t19-,22+,24-,25+,26+,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(C)C)([H])[C@@]2(C)CCC/1

Other Databases

LIPIDBANK ID
VVD0278
PubChem CID
9547433

Calculated Physicochemical Properties

Heavy Atoms 31
Rings 4
Aromatic Rings 0
Rotatable Bonds 6
Van der Waals Molecular Volume 465.82
Topological Polar Surface Area 54.37
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 3
logP 8.17
Molar Refractivity 130.12

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Created at
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Updated at
17th Feb 2022