ChemFOnt: Showing chemical card for (3beta,4alpha,22beta)-22-[[2-O-(6-Deoxy-alpha-L-mannopyranosyl)-alpha-L-arabinopyranosyl]oxy]-23-hydroxyolean-12-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1->2)-O-beta-D-galactopyranosyl-(1->2)-beta-D-glucopyranosiduronic acid (CFc000281532)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:33:00 UTC

Chemfont ID

CFc000281532

Molecule Identification

Common Name

(3beta,4alpha,22beta)-22-[[2-O-(6-Deoxy-alpha-L-mannopyranosyl)-alpha-L-arabinopyranosyl]oxy]-23-hydroxyolean-12-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1->2)-O-beta-D-galactopyranosyl-(1->2)-beta-D-glucopyranosiduronic acid

Definition

(3beta,4alpha,22beta)-22-[[2-o-(6-deoxy-alpha-l-mannopyranosyl)-alpha-l-arabinopyranosyl]oxy]-23-hydroxyolean-12-en-3-yl o-6-deoxy-alpha-l-mannopyranosyl-(1->2)-o-beta-d-galactopyranosyl-(1->2)-beta-d-glucopyranosiduronic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). (3beta,4alpha,22beta)-22-[[2-o-(6-deoxy-alpha-l-mannopyranosyl)-alpha-l-arabinopyranosyl]oxy]-23-hydroxyolean-12-en-3-yl o-6-deoxy-alpha-l-mannopyranosyl-(1->2)-o-beta-d-galactopyranosyl-(1->2)-beta-d-glucopyranosiduronic acid can be found in soy bean, which makes (3beta,4alpha,22beta)-22-[[2-o-(6-deoxy-alpha-l-mannopyranosyl)-alpha-l-arabinopyranosyl]oxy]-23-hydroxyolean-12-en-3-yl o-6-deoxy-alpha-l-mannopyranosyl-(1->2)-o-beta-d-galactopyranosyl-(1->2)-beta-d-glucopyranosiduronic acid 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,6ar,6BS,8ar,9R,14BR)-9-{[(2S,3R,4S,5S)-4,5-dihydroxy-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-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,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-3,4-dihydroxyoxane-2-carboxylate	Generator
(3b,4a,22b)-22-[[2-O-(6-Deoxy-a-L-mannopyranosyl)-a-L-arabinopyranosyl]oxy]-23-hydroxyolean-12-en-3-yl O-6-deoxy-a-L-mannopyranosyl-(1->2)-O-b-D-galactopyranosyl-(1->2)-b-D-glucopyranosiduronate	Generator
(3b,4a,22b)-22-[[2-O-(6-Deoxy-a-L-mannopyranosyl)-a-L-arabinopyranosyl]oxy]-23-hydroxyolean-12-en-3-yl O-6-deoxy-a-L-mannopyranosyl-(1->2)-O-b-D-galactopyranosyl-(1->2)-b-D-glucopyranosiduronic acid	Generator
(3beta,4alpha,22beta)-22-[[2-O-(6-Deoxy-alpha-L-mannopyranosyl)-alpha-L-arabinopyranosyl]oxy]-23-hydroxyolean-12-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1->2)-O-beta-D-galactopyranosyl-(1->2)-beta-D-glucopyranosiduronate	Generator
(3Β,4α,22β)-22-[[2-O-(6-deoxy-α-L-mannopyranosyl)-α-L-arabinopyranosyl]oxy]-23-hydroxyolean-12-en-3-yl O-6-deoxy-α-L-mannopyranosyl-(1->2)-O-β-D-galactopyranosyl-(1->2)-β-D-glucopyranosiduronate	Generator
(3Β,4α,22β)-22-[[2-O-(6-deoxy-α-L-mannopyranosyl)-α-L-arabinopyranosyl]oxy]-23-hydroxyolean-12-en-3-yl O-6-deoxy-α-L-mannopyranosyl-(1->2)-O-β-D-galactopyranosyl-(1->2)-β-D-glucopyranosiduronic acid	Generator

Chemical Formula

C₅₉H₉₆O₂₆

Average Molecular Weight

1221.3779

Monoisotopic Molecular Weight

1220.618983244

IUPAC Name

(2S,3S,4S,5R,6R)-6-{[(3S,4R,6aR,6bS,8aR,9R,14bR)-9-{[(2S,3R,4S,5S)-4,5-dihydroxy-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-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,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-3,4-dihydroxyoxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6R)-6-{[(3S,4R,6aR,6bS,8aR,9R,14bR)-9-{[(2S,3R,4S,5S)-4,5-dihydroxy-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-5-{[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-3,4-dihydroxyoxane-2-carboxylic acid

CAS Registry Number

441045-23-4

SMILES

C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@@H](O)CO[C@H]2O[C@@H]2CC(C)(C)CC3C4=CCC5[C@@]6(C)CC[C@H](O[C@@H]7O[C@@H]([C@@H](O)[C@H](O)[C@H]7O[C@@H]7O[C@H](CO)[C@H](O)[C@H](O)[C@H]7O[C@@H]7O[C@@H](C)[C@H](O)[C@@H](O)[C@H]7O)C(O)=O)[C@@](C)(CO)C6CC[C@@]5(C)[C@]4(C)CC[C@@]23C)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C59H96O26/c1-23-33(63)37(67)42(72)49(77-23)83-45-35(65)27(62)21-76-51(45)81-32-19-54(3,4)18-26-25-10-11-30-56(6)14-13-31(57(7,22-61)29(56)12-15-59(30,9)58(25,8)17-16-55(26,32)5)80-53-47(41(71)40(70)44(82-53)48(74)75)85-52-46(39(69)36(66)28(20-60)79-52)84-50-43(73)38(68)34(64)24(2)78-50/h10,23-24,26-47,49-53,60-73H,11-22H2,1-9H3,(H,74,75)/t23-,24-,26?,27-,28+,29?,30?,31-,32+,33-,34-,35-,36-,37+,38+,39-,40-,41-,42+,43+,44-,45+,46+,47+,49-,50-,51-,52-,53+,55+,56-,57-,58+,59+/m0/s1

InChI Key

SOUGUYQVKJLLLQ-OPHZAVDESA-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
Beta-hydroxy acid
Fatty acyl
Pyran
Hydroxy acid
Oxane
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Acetal
Monocarboxylic acid or derivatives
Polyol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Primary alcohol
Alcohol
Organooxygen compound
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302016)

Food

Soy

Soy bean (FooDB: FOOD00085)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.87 g/L	ALOGPS
logP	0.95	ALOGPS
logP	-0.92	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	3.32	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	26	ChemAxon
Hydrogen Donor Count	15	ChemAxon
Polar Surface Area	412.82 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	288.08 m³·mol⁻¹	ChemAxon
Polarizability	127.78 Å³	ChemAxon
Number of Rings	10	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

HMDB0302016

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001749

KNApSAcK ID

Not Available

Chemspider ID

8411140

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10235652

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for (3beta,4alpha,22beta)-22-[[2-O-(6-Deoxy-alpha-L-mannopyranosyl)-alpha-L-arabinopyranosyl]oxy]-23-hydroxyolean-12-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1->2)-O-beta-D-galactopyranosyl-(1->2)-beta-D-glucopyranosiduronic acid (CFc000281532)

MOL for CFc000281532 ((3beta,4alpha,22beta)-22-[[2-O-(6-Deoxy-alpha-L-mannopyranosyl)-alpha-L-arabinopyranosyl]oxy]-23-hydroxyolean-12-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1->2)-O-beta-D-galactopyranosyl-(1->2)-beta-D-glucopyranosiduronic acid)

3D MOL for CFc000281532 ((3beta,4alpha,22beta)-22-[[2-O-(6-Deoxy-alpha-L-mannopyranosyl)-alpha-L-arabinopyranosyl]oxy]-23-hydroxyolean-12-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1->2)-O-beta-D-galactopyranosyl-(1->2)-beta-D-glucopyranosiduronic acid)

3D SDF for CFc000281532 ((3beta,4alpha,22beta)-22-[[2-O-(6-Deoxy-alpha-L-mannopyranosyl)-alpha-L-arabinopyranosyl]oxy]-23-hydroxyolean-12-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1->2)-O-beta-D-galactopyranosyl-(1->2)-beta-D-glucopyranosiduronic acid)

3D-SDF for CFc000281532 ((3beta,4alpha,22beta)-22-[[2-O-(6-Deoxy-alpha-L-mannopyranosyl)-alpha-L-arabinopyranosyl]oxy]-23-hydroxyolean-12-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1->2)-O-beta-D-galactopyranosyl-(1->2)-beta-D-glucopyranosiduronic acid)

PDB for CFc000281532 ((3beta,4alpha,22beta)-22-[[2-O-(6-Deoxy-alpha-L-mannopyranosyl)-alpha-L-arabinopyranosyl]oxy]-23-hydroxyolean-12-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1->2)-O-beta-D-galactopyranosyl-(1->2)-beta-D-glucopyranosiduronic acid)

3D PDB for CFc000281532 ((3beta,4alpha,22beta)-22-[[2-O-(6-Deoxy-alpha-L-mannopyranosyl)-alpha-L-arabinopyranosyl]oxy]-23-hydroxyolean-12-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1->2)-O-beta-D-galactopyranosyl-(1->2)-beta-D-glucopyranosiduronic acid)

SMILES for CFc000281532 ((3beta,4alpha,22beta)-22-[[2-O-(6-Deoxy-alpha-L-mannopyranosyl)-alpha-L-arabinopyranosyl]oxy]-23-hydroxyolean-12-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1->2)-O-beta-D-galactopyranosyl-(1->2)-beta-D-glucopyranosiduronic acid)

INCHI for CFc000281532 ((3beta,4alpha,22beta)-22-[[2-O-(6-Deoxy-alpha-L-mannopyranosyl)-alpha-L-arabinopyranosyl]oxy]-23-hydroxyolean-12-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1->2)-O-beta-D-galactopyranosyl-(1->2)-beta-D-glucopyranosiduronic acid)

Structure for CFc000281532 ((3beta,4alpha,22beta)-22-[[2-O-(6-Deoxy-alpha-L-mannopyranosyl)-alpha-L-arabinopyranosyl]oxy]-23-hydroxyolean-12-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1->2)-O-beta-D-galactopyranosyl-(1->2)-beta-D-glucopyranosiduronic acid)

3D Structure for CFc000281532 ((3beta,4alpha,22beta)-22-[[2-O-(6-Deoxy-alpha-L-mannopyranosyl)-alpha-L-arabinopyranosyl]oxy]-23-hydroxyolean-12-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1->2)-O-beta-D-galactopyranosyl-(1->2)-beta-D-glucopyranosiduronic acid)