Showing Compound Glycosides (FDB005482)

Record Information

Version

1.0

Creation date

2010-04-08 22:06:42 UTC

Update date

2019-11-26 03:00:35 UTC

Primary ID

FDB005482

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Glycosides

Description

Glycosides, also known as kombetin or strophosid, belongs to the class of organic compounds known as cardenolide glycosides and derivatives. Cardenolide glycosides and derivatives are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety. Based on a literature review a significant number of articles have been published on Glycosides.

CAS Number

630-60-4

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
Glycoside	MeSH
Kombetin	MeSH
Strophosid	MeSH
K-Strophanthin-beta	MeSH
Acocantherin	HMDB
Acolongifloriside K	HMDB
Astrobain	HMDB
g-Strophanthin	HMDB
g-Strophicor	HMDB
Gratibain	HMDB
Gratus strophanthin	HMDB
Ouabagenin L-rhamnoside	HMDB
Ouabain	HMDB
Ouabaine	HMDB
Purostrophan	HMDB
Rectobaina	HMDB
Solufantina	HMDB
Strodival	HMDB
Strophalen	HMDB
Strophanthin g	HMDB
Strophoperm	HMDB
Strophosan	HMDB
Uabaina	HMDB
Glycosides	MeSH
Acolongifloroside K	MeSH
g Strophanthin	MeSH
Acolongifloriside k	biospider
G-strophanthin	biospider
G-strophicor	biospider
Ouabagenin l-rhamnoside	biospider

Predicted Properties

Property	Value	Source
Water Solubility	4.61 g/L	ALOGPS
logP	-1	ALOGPS
logP	-2.8	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	7.18	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	206.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	140.83 m³·mol⁻¹	ChemAxon
Polarizability	60.53 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C29H44O12

IUPAC name

4-[(1S,2R,3S,5S,7R,10R,11R,14S,15R,17R)-3,7,11,17-tetrahydroxy-2-(hydroxymethyl)-15-methyl-5-{[(2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-2,5-dihydrofuran-2-one

InChI Identifier

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-/m1/s1

InChI Key

LPMXVESGRSUGHW-NZMIQZKWSA-N

Isomeric SMILES

C[C@H]1O[C@@H](O[C@H]2C[C@H](O)[C@]3(CO)[C@H]4[C@H](O)C[C@]5(C)[C@@H](CC[C@@]5(O)[C@@H]4CC[C@@]3(O)C2)C2=CC(=O)OC2)[C@H](O)[C@H](O)[C@@H]1O

Average Molecular Weight

584.6525

Monoisotopic Molecular Weight

584.283276872

Classification

Description

Belongs to the class of organic compounds known as cardenolide glycosides and derivatives. Cardenolide glycosides and derivatives are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Cardenolide glycosides and derivatives

Alternative Parents

Substituents

Cardanolide-glycoside
Steroidal glycoside
19-hydroxysteroid
1-hydroxysteroid
14-hydroxysteroid
5-hydroxysteroid
Hydroxysteroid
11-hydroxysteroid
11-alpha-hydroxysteroid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
2-furanone
Monosaccharide
Oxane
Tertiary alcohol
Cyclic alcohol
Dihydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
Lactone
Polyol
Acetal
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Alcohol
Primary alcohol
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Cell and elements:

Extracellular

Tissue and substructures:

Hepatic tissue

Biofluid and excreta:

Urine

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Biological role:

Molecular messenger:

Signaling molecule

Industrial application:

Pharmaceutical industry:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	200 oC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	-2.00	SANGSTER (1994)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Glycosides, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0aou-0209050000-ff5d29b9a71cc0dd04e9	Spectrum
Predicted GC-MS	Glycosides, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004u-2506409000-f6e6b4b9ec8f6ae25647	Spectrum
Predicted GC-MS	Glycosides, "Glycosides,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glycosides, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glycosides, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glycosides, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glycosides, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glycosides, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glycosides, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glycosides, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glycosides, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glycosides, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glycosides, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glycosides, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glycosides, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glycosides, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glycosides, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glycosides, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glycosides, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glycosides, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glycosides, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glycosides, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glycosides, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glycosides, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glycosides, TMS_2_15, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00r2-0000490000-ba806aa277f179583eec	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0101930000-7f40284ce7a78f730699	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-1112910000-f68efe23826a53a2145e	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-015i-0000590000-b6bd31b640d6b6350b74	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014r-1101940000-a2d91864bf2df81659a2	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4u-2005900000-252c65c11aeae5b683b8	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0000090000-968482c8635e1619bf2d	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00yi-5001790000-064fb537e519f8cf8882	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ar9-9400830000-73dd15954b9792c10eff	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0000590000-2a960a4409b7608be7c5	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00ri-0015950000-de41dfd1a10d9666d965	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00du-9403810000-bf99265a71ab714ec04c	2021-09-25	View Spectrum