Showing Compound (3b,16a)-Dihydroxy-12-oleanen-28-oic acid 3-glucoside 28-[glucosyl-(1->3)-[xylosyl-(1->3)-xylosyl-(1->4)-rhamnosyl-(1->2)]-arabinosyl] ester (FDB011430)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:38 UTC

Update date

2018-05-28 22:27:34 UTC

Primary ID

FDB011430

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(3b,16a)-Dihydroxy-12-oleanen-28-oic acid 3-glucoside 28-[glucosyl-(1->3)-[xylosyl-(1->3)-xylosyl-(1->4)-rhamnosyl-(1->2)]-arabinosyl] ester

Description

(3b,16a)-Dihydroxy-12-oleanen-28-oic acid 3-glucoside 28-[glucosyl-(1->3)-[xylosyl-(1->3)-xylosyl-(1->4)-rhamnosyl-(1->2)]-arabinosyl] ester 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. Based on a literature review a small amount of articles have been published on (3b,16a)-Dihydroxy-12-oleanen-28-oic acid 3-glucoside 28-[glucosyl-(1->3)-[xylosyl-(1->3)-xylosyl-(1->4)-rhamnosyl-(1->2)]-arabinosyl] ester.

CAS Number

168324-01-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(3b,16a)-Dihydroxy-12-oleanen-28-Oate 3-glucoside 28-[glucosyl-(1->3)-[xylosyl-(1->3)-xylosyl-(1->4)-rhamnosyl-(1->2)]-arabinosyl] ester	Generator
(3b,16a)-Dihydroxy-12-oleanen-28-oic acid 3-glucoside 28-[glucosyl-(1->3)-[xylosyl-(1->3)-xylosyl-(1->4)-rhamnosyl-(1->2)]-arabinosyl] ester	manual
(3b,16a)-Dihydroxy-12-oleanen-28-oic acid 3-O-b-D-glucopyranoside 28-O-[b-D-glucopyranosyl-(1->3)-[b-D-xylopyranosyl-(1->3)-b-D-xylopyranosyl-(1->4)-a-L-rhamnopyranosyl-(1->2)]-a-L-arabinopyranosyl] ester	manual
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}-5-hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl 5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid	Generator

Showing 1 to 4 of 4 entries

Predicted Properties

Property	Value	Source
Water Solubility	3.89 g/L	ALOGPS
logP	0.27	ALOGPS
logP	-2.8	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	11.61	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	29	ChemAxon
Hydrogen Donor Count	17	ChemAxon
Polar Surface Area	471.74 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	310.21 m³·mol⁻¹	ChemAxon
Polarizability	138.58 Å³	ChemAxon
Number of Rings	11	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C63H102O30

IUPAC name

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}-5-hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl 5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate

InChI Identifier

InChI=1S/C63H102O30/c1-24-47(89-52-46(80)48(28(67)22-83-52)90-51-42(76)36(70)27(66)21-82-51)41(75)45(79)53(85-24)92-50-49(91-55-44(78)40(74)38(72)31(20-65)87-55)29(68)23-84-56(50)93-57(81)63-16-15-58(2,3)17-26(63)25-9-10-33-60(6)13-12-35(88-54-43(77)39(73)37(71)30(19-64)86-54)59(4,5)32(60)11-14-61(33,7)62(25,8)18-34(63)69/h9,24,26-56,64-80H,10-23H2,1-8H3

InChI Key

VXYPUHHQOBARSV-UHFFFAOYSA-N

Isomeric SMILES

CC1OC(OC2C(OC(=O)C34CCC(C)(C)CC3C3=CCC5C6(C)CCC(OC7OC(CO)C(O)C(O)C7O)C(C)(C)C6CCC5(C)C3(C)CC4O)OCC(O)C2OC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1OC1OCC(O)C(OC2OCC(O)C(O)C2O)C1O

Average Molecular Weight

1339.466

Monoisotopic Molecular Weight

1338.645591924

Classification

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
Fatty acyl glycoside
Glycosyl compound
O-glycosyl compound
Beta-hydroxy acid
Fatty acyl
Hydroxy acid
Oxane
Cyclic alcohol
Carboxylic acid ester
Secondary alcohol
Acetal
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Polyol
Primary alcohol
Alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
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

Subcellular:

Source:

Biological:

Animal

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 56.49%; H 7.68%; O 35.83%	DFC
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0abi-4904114204-ebf62672ea7282fdbff9	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0cdi-9801303508-a3e0347b264031a37f91	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-044l-9812302617-556bbe1280945815221f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-066r-4829215012-24a846f336907837f031	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-066r-4926303103-985f0d0b5072ba7721d5	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01tc-8950200304-33bade49df1b653b1ec3	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0080-5759224100-90cde69b750f6c4ffa47	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05d0-6963000000-acf804863e50110b65e0	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-007a-4411090723-83405f867a65634bc394	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0550-1905000002-79d528bab64a9896b2c7	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0570-9823001012-1a983e3a29fb4d2823c1	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00ks-5923000000-d165df83cf8a10c2e3bd	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB33396

CRC / DFC (Dictionary of Food Compounds) ID

HNS80-T:GOS70-M

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

No data available in table

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Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound (3b,16a)-Dihydroxy-12-oleanen-28-oic acid 3-glucoside 28-[glucosyl-(1->3)-[xylosyl-(1->3)-xylosyl-(1->4)-rhamnosyl-(1->2)]-arabinosyl] ester (FDB011430)

Structure for FDB011430 ((3b,16a)-Dihydroxy-12-oleanen-28-oic acid 3-glucoside 28-[glucosyl-(1->3)-[xylosyl-(1->3)-xylosyl-(1->4)-rhamnosyl-(1->2)]-arabinosyl] ester)