ChemFOnt: Showing chemical card for Quillaic acid 3-[galactosyl-(1->2)-[rhamnosyl-(1->3)]-glucuronoside] 28-[xylosyl-(1->3)-xylosyl-(1->4)-rhamnosyl-(1->2)-[rhamnosyl-(1->3)]-4-acetyl-fucosyl] ester (CFc000017265)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:07:10 UTC

Chemfont ID

CFc000017265

Molecule Identification

Common Name

Quillaic acid 3-[galactosyl-(1->2)-[rhamnosyl-(1->3)]-glucuronoside] 28-[xylosyl-(1->3)-xylosyl-(1->4)-rhamnosyl-(1->2)-[rhamnosyl-(1->3)]-4-acetyl-fucosyl] ester

Definition

Quillaic acid 3-[galactosyl-(1->2)-[rhamnosyl-(1->3)]-glucuronoside] 28-[xylosyl-(1->3)-xylosyl-(1->4)-rhamnosyl-(1->2)-[rhamnosyl-(1->3)]-4-acetyl-fucosyl] ester is a constituent of Quillaja saponaria (soap-bark tree)

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value

Source

Quillaate 3-[galactosyl-(1->2)-[rhamnosyl-(1->3)]-glucuronoside] 28-[xylosyl-(1->3)-xylosyl-(1->4)-rhamnosyl-(1->2)-[rhamnosyl-(1->3)]-4-acetyl-fucosyl] ester

Generator

6-{[8a-({[5-(acetyloxy)-3-{[5-({3,5-dihydroxy-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-3,4-dihydroxy-6-methyloxan-2-yl]oxy}-6-methyl-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}carbonyl)-4-formyl-8-hydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-3-hydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxane-2-carboxylate

HMDB

Chemical Formula

C₇₈H₁₂₂O₄₁

Average Molecular Weight

1715.7787

Monoisotopic Molecular Weight

1714.746153406

IUPAC Name

Traditional Name

6-{[8a-({[5-(acetyloxy)-3-{[5-({3,5-dihydroxy-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-3,4-dihydroxy-6-methyloxan-2-yl]oxy}-6-methyl-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}carbonyl)-4-formyl-8-hydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-3-hydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxane-2-carboxylic acid

CAS Registry Number

287386-86-1

SMILES

CC1OC(OC2C(O)C(OC(OC3CCC4(C)C(CCC5(C)C4CC=C4C6CC(C)(C)CCC6(C(O)CC54C)C(=O)OC4OC(C)C(OC(C)=O)C(OC5OC(C)C(O)C(O)C5O)C4OC4OC(C)C(OC5OCC(O)C(OC6OCC(O)C(O)C6O)C5O)C(O)C4O)C3(C)C=O)C2OC2OC(CO)C(O)C(O)C2O)C(O)=O)C(O)C(O)C1O

InChI Identifier

InChI=1S/C78H122O41/c1-26-40(85)44(89)49(94)66(105-26)114-58-53(98)59(63(100)101)115-71(61(58)117-69-51(96)46(91)43(88)35(22-79)110-69)111-39-15-16-74(8)36(75(39,9)25-80)14-17-76(10)37(74)13-12-31-32-20-73(6,7)18-19-78(32,38(84)21-77(31,76)11)72(102)119-70-62(60(56(29(4)108-70)109-30(5)81)116-67-50(95)45(90)41(86)27(2)106-67)118-68-52(97)47(92)55(28(3)107-68)112-65-54(99)57(34(83)24-104-65)113-64-48(93)42(87)33(82)23-103-64/h12,25-29,32-62,64-71,79,82-99H,13-24H2,1-11H3,(H,100,101)

InChI Key

NIGZBYKDLOLGFB-UHFFFAOYSA-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
Steroid
Fatty acyl glycoside
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Glycosyl compound
O-glycosyl compound
Tricarboxylic acid or derivatives
Beta-hydroxy acid
Pyran
Oxane
Fatty acyl
Hydroxy acid
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Primary alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aldehyde
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036278)

Source

Endogenous

Endogenous (HMDB: HMDB0036278)

Animal

Animal (HMDB: HMDB0036278)

Exogenous

Food

Food (HMDB: HMDB0036278)

Exogenous (HMDB: HMDB0036278)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036278)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036278)

Lipid metabolism pathway (HMDB: HMDB0036278)

Cellular process

Cell signaling (HMDB: HMDB0036278)

Biochemical process

Lipid transport (HMDB: HMDB0036278)

Role

Biological role

Energy source (HMDB: HMDB0036278)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036278)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	4.32 g/L	ALOGPS
logP	0.29	ALOGPS
logP	-4.1	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	3.32	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	39	ChemAxon
Hydrogen Donor Count	20	ChemAxon
Polar Surface Area	629.79 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	386.18 m³·mol⁻¹	ChemAxon
Polarizability	172.17 Å³	ChemAxon
Number of Rings	13	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

HMDB0036278

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB015143

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751937

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Quillaic acid 3-[galactosyl-(1->2)-[rhamnosyl-(1->3)]-glucuronoside] 28-[xylosyl-(1->3)-xylosyl-(1->4)-rhamnosyl-(1->2)-[rhamnosyl-(1->3)]-4-acetyl-fucosyl] ester (CFc000017265)

MOL for CFc000017265 (Quillaic acid 3-[galactosyl-(1->2)-[rhamnosyl-(1->3)]-glucuronoside] 28-[xylosyl-(1->3)-xylosyl-(1->4)-rhamnosyl-(1->2)-[rhamnosyl-(1->3)]-4-acetyl-fucosyl] ester)

3D MOL for CFc000017265 (Quillaic acid 3-[galactosyl-(1->2)-[rhamnosyl-(1->3)]-glucuronoside] 28-[xylosyl-(1->3)-xylosyl-(1->4)-rhamnosyl-(1->2)-[rhamnosyl-(1->3)]-4-acetyl-fucosyl] ester)

3D SDF for CFc000017265 (Quillaic acid 3-[galactosyl-(1->2)-[rhamnosyl-(1->3)]-glucuronoside] 28-[xylosyl-(1->3)-xylosyl-(1->4)-rhamnosyl-(1->2)-[rhamnosyl-(1->3)]-4-acetyl-fucosyl] ester)

3D-SDF for CFc000017265 (Quillaic acid 3-[galactosyl-(1->2)-[rhamnosyl-(1->3)]-glucuronoside] 28-[xylosyl-(1->3)-xylosyl-(1->4)-rhamnosyl-(1->2)-[rhamnosyl-(1->3)]-4-acetyl-fucosyl] ester)

PDB for CFc000017265 (Quillaic acid 3-[galactosyl-(1->2)-[rhamnosyl-(1->3)]-glucuronoside] 28-[xylosyl-(1->3)-xylosyl-(1->4)-rhamnosyl-(1->2)-[rhamnosyl-(1->3)]-4-acetyl-fucosyl] ester)

3D PDB for CFc000017265 (Quillaic acid 3-[galactosyl-(1->2)-[rhamnosyl-(1->3)]-glucuronoside] 28-[xylosyl-(1->3)-xylosyl-(1->4)-rhamnosyl-(1->2)-[rhamnosyl-(1->3)]-4-acetyl-fucosyl] ester)

SMILES for CFc000017265 (Quillaic acid 3-[galactosyl-(1->2)-[rhamnosyl-(1->3)]-glucuronoside] 28-[xylosyl-(1->3)-xylosyl-(1->4)-rhamnosyl-(1->2)-[rhamnosyl-(1->3)]-4-acetyl-fucosyl] ester)

INCHI for CFc000017265 (Quillaic acid 3-[galactosyl-(1->2)-[rhamnosyl-(1->3)]-glucuronoside] 28-[xylosyl-(1->3)-xylosyl-(1->4)-rhamnosyl-(1->2)-[rhamnosyl-(1->3)]-4-acetyl-fucosyl] ester)

Structure for CFc000017265 (Quillaic acid 3-[galactosyl-(1->2)-[rhamnosyl-(1->3)]-glucuronoside] 28-[xylosyl-(1->3)-xylosyl-(1->4)-rhamnosyl-(1->2)-[rhamnosyl-(1->3)]-4-acetyl-fucosyl] ester)

3D Structure for CFc000017265 (Quillaic acid 3-[galactosyl-(1->2)-[rhamnosyl-(1->3)]-glucuronoside] 28-[xylosyl-(1->3)-xylosyl-(1->4)-rhamnosyl-(1->2)-[rhamnosyl-(1->3)]-4-acetyl-fucosyl] ester)