Structure Database (LMSD)

Common Name
Cholesteryl-alpha-D-glucoside
Systematic Name
Cholest-5-en-3?-yl ?-D-glucopyranoside
Synonyms
  • (3beta)-cholest-5-en-3-yl D-glucopyranoside
  • Cholesterol glucoside
  • Cholesteryl glucoside
  • Cholesteryl-alpha-D-glucoside
  • cholesteryl-alpha-D-glucopyranside
LM ID
LMST05050029
Status
Active
Exact Mass
Calculate m/z
548.40769
Formula
C33H56O6
Abbrev
ST 27:1;O;Hex
Show lipids differing only in stereochemistry/bond geometry
Download as...
MDLMOL SDF CSV TSV
MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".

Main

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Steroid conjugates [ST05]
Other Steroid conjugates [ST0505]

String Representations

InChiKey (Click to copy)
FSMCJUNYLQOAIM-HUAQYVKVSA-N
InChi (Click to copy)
InChI=1S/C33H56O6/c1-19(2)7-6-8-20(3)24-11-12-25-23-10-9-21-17-22(13-15-32(21,4)26(23)14-16-33(24,25)5)38-31-30(37)29(36)28(35)27(18-34)39-31/h9,19-20,22-31,34-37H,6-8,10-18H2,1-5H3/t20-,22+,23+,24-,25+,26+,27-,28-,29+,30-,31+,32+,33-/m1/s1
SMILES (Click to copy)
O([C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1)[C@H]1CC[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@H]([C@@H](CCCC(C)C)C)CC[C@@]4([H])[C@]3([H])CC=C2C1

References

Reference
J Bacteriol. 1995 Sep;177(18):5327-33.
Unique cholesteryl glucosides in Helicobacter pylori: composition and structural analysis.
Hirai Y1, Haque M, Yoshida T, Yokota K, Yasuda T, Oguma K.
DOI: 10.1128/jb.177.18.5327-5333.1995

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Helicobacter pylori (#210)
Epsilonproteobacteria (#29547)
Unique cholesteryl glucosides in Helicobacter pylori: composition and structural analysis.,
J. Bact., 1995
Pubmed ID: 7665522

Other Databases

PubChem CID
101155817

Calculated Physicochemical Properties

Heavy Atoms 39
Rings 5
Aromatic Rings 0
Rotatable Bonds 8
Van der Waals Molecular Volume 567.76
Topological Polar Surface Area 101.45
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 6
logP 7.22
Molar Refractivity 155.25

Admin

Created at
-
Updated at
2nd Aug 2021