ChemFOnt: Showing chemical card for Chasaponin (CFc000333513)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:13:40 UTC

Chemfont ID

CFc000333513

Molecule Identification

Common Name

Chasaponin

Definition

Theasaponin is a member of the class of compounds known as triterpene saponins. Triterpene saponins are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton. Theasaponin is slightly soluble (in water) and a weakly acidic compound (based on its pKa). Theasaponin can be found in tea, which makes theasaponin a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value

Source

(2S,3S,4S,5R,6R)-6-{[(3S,4R,4ar,6ar,6BS,8R,8ar,9R,10R,12as,14ar,14BR)-9-(acetyloxy)-8-hydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-{[(2Z)-2-methylbut-2-enoyl]oxy}-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-5-{[(2S,3R,4S,5S)-4,5-dihydroxy-3-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylate

Generator

Theasaponine

MeSH

Chemical Formula

C₅₉H₉₂O₂₇

Average Molecular Weight

1233.358

Monoisotopic Molecular Weight

1232.582597702

IUPAC Name

(2S,3S,4S,5R,6R)-6-{[(3S,4R,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-9-(acetyloxy)-8-hydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-{[(2Z)-2-methylbut-2-enoyl]oxy}-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-5-{[(2S,3R,4S,5S)-4,5-dihydroxy-3-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid

Traditional Name

theasaponin

CAS Registry Number

11055-93-9

SMILES

[H][C@@]12CC(C)(C)[C@@H](OC(=O)C(\C)=C/C)[C@H](OC(C)=O)[C@]1(CO)[C@H](O)C[C@]1(C)C2=CC[C@]2([H])[C@@]3(C)CC[C@H](O[C@@H]4O[C@@H]([C@@H](O)[C@H](O[C@@H]5O[C@H](CO)[C@H](O)[C@H](O)[C@H]5O)[C@H]4O[C@@H]4OC[C@H](O)[C@H](O)[C@H]4O[C@@H]4OC[C@@H](O)[C@H](O)[C@H]4O)C(O)=O)[C@@](C)(CO)[C@]3([H])CC[C@@]12C

InChI Identifier

InChI=1S/C59H92O27/c1-10-24(2)49(76)86-46-47(79-25(3)63)59(23-62)27(17-54(46,4)5)26-11-12-32-55(6)15-14-34(56(7,22-61)31(55)13-16-57(32,8)58(26,9)18-33(59)66)81-53-45(85-52-44(36(68)29(65)21-78-52)84-50-39(71)35(67)28(64)20-77-50)42(41(73)43(83-53)48(74)75)82-51-40(72)38(70)37(69)30(19-60)80-51/h10-11,27-47,50-53,60-62,64-73H,12-23H2,1-9H3,(H,74,75)/b24-10-/t27-,28+,29-,30+,31+,32+,33+,34-,35-,36-,37-,38-,39+,40+,41-,42-,43-,44+,45+,46-,47-,50-,51-,52-,53+,55-,56-,57+,58+,59-/m0/s1

InChI Key

BWPGKXYWPBQBPV-MWQJAWBESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Triterpene saponins

Alternative Parents

Substituents

Triterpene saponin
Triterpenoid
Oligosaccharide
Hydroxysteroid
16-oxosteroid
Oxosteroid
7-alpha-hydroxysteroid
7-hydroxysteroid
Steroid
Fatty acyl glycoside
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
O-glycosyl compound
Glycosyl compound
Tricarboxylic acid or derivatives
Beta-hydroxy acid
Fatty acid ester
Hydroxy acid
Fatty acyl
Pyran
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Cyclic alcohol
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Carboxylic acid derivative
Polyol
Carboxylic acid
Oxacycle
Acetal
Primary alcohol
Carbonyl group
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxide
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

triterpenoid saponin (CHEBI:9517 )
Triterpenoids (C30) (C08986 )

Functional Ontology

Not Available

Exogenous (FooDB: )

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.49 g/L	ALOGPS
logP	0.77	ALOGPS
logP	-1.4	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	3.3	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	25	ChemAxon
Hydrogen Donor Count	14	ChemAxon
Polar Surface Area	426.73 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	290.27 m³·mol⁻¹	ChemAxon
Polarizability	127.82 Å³	ChemAxon
Number of Rings	9	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0301860

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11953922

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Chasaponin (CFc000333513)

MOL for CFc000333513 (Chasaponin)

3D MOL for CFc000333513 (Chasaponin)

3D SDF for CFc000333513 (Chasaponin)

3D-SDF for CFc000333513 (Chasaponin)

PDB for CFc000333513 (Chasaponin)

3D PDB for CFc000333513 (Chasaponin)

SMILES for CFc000333513 (Chasaponin)

INCHI for CFc000333513 (Chasaponin)

Structure for CFc000333513 (Chasaponin)

3D Structure for CFc000333513 (Chasaponin)