ContaminantDB: Quillaic acid 3-[rhamnosyl-(1->3)-[galactosyl-(1->2)]-glucuronide] 28-[glucosyl-(1->3)-[xylosyl-(1->4)]-rhamnosyl-(1->2)-4-[5-[[5-(arabinosyloxy)-3-hydroxy-6-methyl-1-oxooctyl]oxy]-3-hydroxy-6-methyl-1-oxooctyl]-fucosyl] ester

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 18:46:21 UTC

Update Date

2016-11-09 01:17:33 UTC

Accession Number

CHEM022672

Identification

Common Name

Quillaic acid 3-[rhamnosyl-(1->3)-[galactosyl-(1->2)]-glucuronide] 28-[glucosyl-(1->3)-[xylosyl-(1->4)]-rhamnosyl-(1->2)-4-[5-[[5-(arabinosyloxy)-3-hydroxy-6-methyl-1-oxooctyl]oxy]-3-hydroxy-6-methyl-1-oxooctyl]-fucosyl] ester

Class

Small Molecule

Description

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value

Source

Quillaate 3-[rhamnosyl-(1->3)-[galactosyl-(1->2)]-glucuronide] 28-[glucosyl-(1->3)-[xylosyl-(1->4)]-rhamnosyl-(1->2)-4-[5-[[5-(arabinosyloxy)-3-hydroxy-6-methyl-1-oxooctyl]oxy]-3-hydroxy-6-methyl-1-oxooctyl]-fucosyl] ester

Generator

6-{[8a-({[5-({5-[(5-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3-hydroxy-6-methyloctanoyl)oxy]-3-hydroxy-6-methyloctanoyl}oxy)-4-hydroxy-3-[(3-hydroxy-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl)oxy]-6-methyloxan-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

C₉₄H₁₅₂O₄₇

Average Molecular Mass

2034.185 g/mol

Monoisotopic Mass

2032.950 g/mol

CAS Registry Number

263259-76-3

IUPAC Name

Traditional Name

6-{[8a-({[5-({5-[(5-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3-hydroxy-6-methyloctanoyl)oxy]-3-hydroxy-6-methyloctanoyl}oxy)-4-hydroxy-3-[(3-hydroxy-6-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl)oxy]-6-methyloxan-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

SMILES

CCC(C)C(CC(O)CC(=O)OC(CC(O)CC(=O)OC1C(C)OC(OC(=O)C23CCC(C)(C)CC2C2=CCC4C5(C)CCC(OC6OC(C(O)C(OC7OC(C)C(O)C(O)C7O)C6OC6OC(CO)C(O)C(O)C6O)C(O)=O)C(C)(C=O)C5CCC4(C)C2(C)CC3O)C(OC2OC(C)C(OC3OCC(O)C(O)C3O)C(OC3OC(CO)C(O)C(O)C3O)C2O)C1O)C(C)CC)OC1OC(CO)C(O)C1O

InChI Identifier

InChI=1S/C94H152O47/c1-14-35(3)45(128-54(103)26-41(100)25-46(36(4)15-2)129-82-65(114)60(109)49(32-97)130-82)24-40(99)27-55(104)134-72-38(6)127-86(77(69(72)118)139-85-71(120)75(137-83-67(116)62(111)58(107)47(30-95)131-83)73(39(7)126-85)135-80-64(113)57(106)44(101)33-124-80)141-88(123)94-23-22-89(8,9)28-43(94)42-16-17-51-90(10)20-19-53(91(11,34-98)50(90)18-21-92(51,12)93(42,13)29-52(94)102)133-87-78(140-84-68(117)63(112)59(108)48(31-96)132-84)74(70(119)76(138-87)79(121)122)136-81-66(115)61(110)56(105)37(5)125-81/h16,34-41,43-53,56-78,80-87,95-97,99-102,105-120H,14-15,17-33H2,1-13H3,(H,121,122)

InChI Key

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

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	2.47 g/L	ALOGPS
logP	0.79	ALOGPS
logP	-3.5	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	3.32	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	44	ChemAxon
Hydrogen Donor Count	24	ChemAxon
Polar Surface Area	737.01 Å²	ChemAxon
Rotatable Bond Count	38	ChemAxon
Refractivity	467.36 m³·mol⁻¹	ChemAxon
Polarizability	208.59 Å³	ChemAxon
Number of Rings	13	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0gc0-5000140292-02ca8a78f08c7b26988a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0gc0-3100450981-3757f0338177bcc51ade	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gbi-2210520970-fc7b579edb281fb45e2d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0imi-7200240594-031fa07ec2d12506be50	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03fr-6701345290-946f33666fb8f23ffb4f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-2901420011-10f41b3dea48e1d739e0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-3521000192-cb2615770626421643aa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0089-7921000250-d73e93d7c3a6737bbeb7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03n9-7200000936-1d30fd68d97dfe26b1fd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-8400000494-dcd8ad240b610a2751dc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-5900000611-68e1672279d547fda1fc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zpi-7900002547-bfb6cf360e082e062794	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0036267

FooDB ID

FDB015132

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

131751926

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.

2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.

3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.

4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.

5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

6. The lipid handbook with CD-ROM

Quillaic acid 3-[rhamnosyl-(1->3)-[galactosyl-(1->2)]-glucuronide] 28-[glucosyl-(1->3)-[xylosyl-(1->4)]-rhamnosyl-(1->2)-4-[5-[[5-(arabinosyloxy)-3-hydroxy-6-methyl-1-oxooctyl]oxy]-3-hydroxy-6-methyl-1-oxooctyl]-fucosyl] ester (CHEM022672)

Structure for CHEM022672: Quillaic acid 3-[rhamnosyl-(1->3)-[galactosyl-(1->2)]-glucuronide] 28-[glucosyl-(1->3)-[xylosyl-(1->4)]-rhamnosyl-(1->2)-4-[5-[[5-(arabinosyloxy)-3-hydroxy-6-methyl-1-oxooctyl]oxy]-3-hydroxy-6-methyl-1-oxooctyl]-fucosyl] ester