Structure Database (LMSD)

Common Name
Ouabain
Systematic Name
1β,3β,5β,11α,14β,19β-hexahydroxy-5β-card-20(22)-enolide 3-O-(α-L-rhamnopyranoside)
Synonyms
  • 3beta-(alpha-L-rhamnopyranosyloxy)-1beta,5beta,11alpha,14beta,19beta-pentahydroxy-5beta-card-20(22)-enolide
  • G-Strophanthin
  • Ouabagenin L-Rhamnoside
  • Ouabagenin-L-rhamnosid
  • Ouabain
  • Ouabain anhydrous
  • Ouabaine
  • Oubain
LM ID
LMST01120022
Formula
C29H44O12
Exact Mass
Calculate m/z
584.28328
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View MassBank spectra

Classification

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

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Strophanthus gratus (#141614)
Magnoliopsida (#3398)
Clinical Use of Digitalis: A State of the Art Review.,
Am J Cardiovasc Drugs, 2018
Pubmed ID: 30066080

String Representations

InChiKey (Click to copy)
LPMXVESGRSUGHW-HBYQJFLCSA-N
InChi (Click to copy)
InChI=1S/C29H44O12/c1-13-22(34)23(35)24(36)25(40-13)41-15-8-19(32)28(12-30)21-17(3-5-27(28,37)9-15)29(38)6-4-16(14-7-20(33)39-11-14)26(29,2)10-18(21)31/h7,13,15-19,21-25,30-32,34-38H,3-6,8-12H2,1-2H3/t13-,15-,16+,17+,18+,19+,21+,22-,23+,24+,25-,26+,27-,28+,29-/m0/s1
SMILES (Click to copy)
O([C@H]1[C@H](O)[C@H](O)[C@@H](O)[C@H](C)O1)[C@@H]1C[C@@]2(O)CC[C@]3([H])[C@]([H])([C@H](O)C[C@]4(C)[C@@H](C5=CC(=O)OC5)CC[C@]34O)[C@@]2(CO)[C@H](O)C1

Other Databases

Wikipedia
Ouabain
KEGG ID
C01443
CHEBI ID
472805
PubChem CID
52931492
PDB ID
OBN
GuidePharm ID
4826

Calculated Physicochemical Properties

Heavy Atoms 41
Rings 6
Aromatic Rings 0
Rotatable Bonds 4
Van der Waals Molecular Volume 536.30
Topological Polar Surface Area 210.74
Hydrogen Bond Donors 8
Hydrogen Bond Acceptors 12
logP 1.92
Molar Refractivity 144.70

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Created at
-
Updated at
31st Aug 2021