Structure Database (LMSD)

Common Name
Glucopyranosyl aspecioside
Systematic Name
3-O-(β-D-glucopyranosyl-(1-4)-6-deoxy-β-D-allopyranosyl)-7-β,8β-epoxy-3-β,12β,14β-trihydroxy-5-α-card-20(22)-enolide
Synonyms
LM ID
LMST01120060
Formula
C35H52O15
Exact Mass
Calculate m/z
712.330626
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Sterols [ST01]
Cardanolides and derivatives [ST0112]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Asclepias syriaca (#48545)
Magnoliopsida (#3398)
Structure of aspecioside from the monarch butterfly larvae foodplants Asclepias speciosa and A. syriaca,
J Chem Soc Perkins Trans, 1987

String Representations

InChiKey (Click to copy)
MECLZPKUEHSELU-SKEOSEEBSA-N
InChi (Click to copy)
InChI=1S/C35H52O15/c1-14-29(49-31-27(42)25(40)24(39)19(12-36)48-31)26(41)28(43)30(46-14)47-17-4-6-32(2)16(9-17)10-22-35(50-22)20(32)11-21(37)33(3)18(5-7-34(33,35)44)15-8-23(38)45-13-15/h8,14,16-22,24-31,36-37,39-44H,4-7,9-13H2,1-3H3/t14-,16-,17+,18-,19-,20-,21-,22+,24-,25+,26+,27-,28-,29-,30+,31+,32+,33+,34-,35-/m1/s1
SMILES (Click to copy)
C1[C@@]2(C)[C@@]([H])(C[C@@H]3O[C@@]43[C@]2([H])C[C@@H](O)[C@@]2(C)[C@]4(O)CC[C@]2([H])C2=CC(=O)OC2)C[C@@H](O[C@H]2[C@H](O)[C@H](O)[C@H](O[C@H]3[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O3)[C@@H](C)O2)C1

Calculated Physicochemical Properties

Heavy Atoms 50
Rings 8
Aromatic Rings
Rotatable Bonds 6
Van der Waals Molecular Volume 641.75
Topological Polar Surface Area 243.80
Hydrogen Bond Donors 8
Hydrogen Bond Acceptors 15
logP 3.25
Molar Refractivity 175.13

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Created at
2nd Jan 2025
Updated at
2nd Jan 2025