ChemFOnt: Showing chemical card for 3-O-{beta-D-Glucopyranosyl(1_2)-[alpha-L-arabinopyranosyl(1_6)]-beta-D-glucopyranosyl}-oleanolic acid (CFc000284119)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:38:00 UTC

Chemfont ID

CFc000284119

Molecule Identification

Common Name

3-O-{beta-D-Glucopyranosyl(1_2)-[alpha-L-arabinopyranosyl(1_6)]-beta-D-glucopyranosyl}-oleanolic acid

Definition

3-O-{beta-D-Glucopyranosyl(1_2)-[alpha-L-arabinopyranosyl(1_6)]-beta-D-glucopyranosyl}-oleanolic acid, also known as 3b-[2-O-(b-D-glucopyranosyl)-6-O-(a-L-arabinopyranosyl)-b-D-glucopyranosyloxy]oleana-12-ene-28-Oate or (3β)-3-[(O-α-L-arabinopyranosyl-(1→6)-O-[β-D-glucopyranosyl-(1→2)]-β-D-glucopyranosyl)oxy]olean-12-en-28-Oic acid, 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 3-O-{beta-D-Glucopyranosyl(1_2)-[alpha-L-arabinopyranosyl(1_6)]-beta-D-glucopyranosyl}-oleanolic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-O-{beta-D-glucopyranosyl(1_2)-[a-L-arabinopyranosyl(1_6)]-b-D-glucopyranosyl}-oleanolate	Generator
3-O-{beta-D-glucopyranosyl(1_2)-[a-L-arabinopyranosyl(1_6)]-b-D-glucopyranosyl}-oleanolic acid	Generator
3-O-{beta-D-glucopyranosyl(1_2)-[alpha-L-arabinopyranosyl(1_6)]-beta-D-glucopyranosyl}-oleanolate	Generator
3-O-{beta-D-glucopyranosyl(1_2)-[α-L-arabinopyranosyl(1_6)]-β-D-glucopyranosyl}-oleanolate	Generator
3-O-{beta-D-glucopyranosyl(1_2)-[α-L-arabinopyranosyl(1_6)]-β-D-glucopyranosyl}-oleanolic acid	Generator
3b-[2-O-(b-D-Glucopyranosyl)-6-O-(a-L-arabinopyranosyl)-b-D-glucopyranosyloxy]oleana-12-ene-28-Oate	HMDB
3b-[2-O-(b-D-Glucopyranosyl)-6-O-(a-L-arabinopyranosyl)-b-D-glucopyranosyloxy]oleana-12-ene-28-Oic acid	HMDB
3beta-[2-O-(beta-D-Glucopyranosyl)-6-O-(alpha-L-arabinopyranosyl)-beta-D-glucopyranosyloxy]oleana-12-ene-28-Oate	HMDB
3Β-[2-O-(β-D-glucopyranosyl)-6-O-(α-L-arabinopyranosyl)-β-D-glucopyranosyloxy]oleana-12-ene-28-Oate	HMDB
3Β-[2-O-(β-D-glucopyranosyl)-6-O-(α-L-arabinopyranosyl)-β-D-glucopyranosyloxy]oleana-12-ene-28-Oic acid	HMDB
(4AS,6as,6BR,8ar,10S,12ar,12BR,14BS)-10-{[(2R,3R,4S,5S,6R)-4,5-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-({[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate	HMDB
(3beta)-3-[(O-alpha-L-Arabinopyranosyl-(1->6)-O-[beta-D-glucopyranosyl-(1->2)]-beta-D-glucopyranosyl)oxy]olean-12-en-28-Oic acid	HMDB
(3Β)-3-[(O-α-L-arabinopyranosyl-(1→6)-O-[β-D-glucopyranosyl-(1→2)]-β-D-glucopyranosyl)oxy]olean-12-en-28-Oic acid	HMDB
3-O-{beta-D-glucopyranosyl(1->2)-[alpha-L-arabinopyranosyl(1->6)]-beta-D-glucopyranosyl}-oleanolic acid	HMDB
3-O-{β-D-glucopyranosyl(1→2)-[α-L-arabinopyranosyl(1→6)]-β-D-glucopyranosyl}-oleanolic acid	HMDB

Chemical Formula

C₄₇H₇₆O₁₇

Average Molecular Weight

913.108

Monoisotopic Molecular Weight

912.508250987

IUPAC Name

(4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-{[(2R,3R,4S,5S,6R)-4,5-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-({[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

Traditional Name

(4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-{[(2R,3R,4S,5S,6R)-4,5-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-({[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

CAS Registry Number

None

SMILES

[H][C@@]1(O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO[C@@H]3OC[C@H](O)[C@H](O)[C@H]3O)O[C@@]2([H])O[C@H]2CC[C@@]3(C)[C@@]([H])(CC[C@]4(C)[C@]3([H])CC=C3[C@]5([H])CC(C)(C)CC[C@@]5(CC[C@@]43C)C(O)=O)C2(C)C)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C47H76O17/c1-42(2)14-16-47(41(57)58)17-15-45(6)22(23(47)18-42)8-9-28-44(5)12-11-29(43(3,4)27(44)10-13-46(28,45)7)63-40-37(64-39-36(56)33(53)31(51)25(19-48)61-39)34(54)32(52)26(62-40)21-60-38-35(55)30(50)24(49)20-59-38/h8,23-40,48-56H,9-21H2,1-7H3,(H,57,58)/t23-,24-,25+,26+,27-,28+,29-,30-,31+,32+,33-,34-,35+,36+,37+,38-,39-,40-,44-,45+,46+,47-/m0/s1

InChI Key

NTJJBQYFTZCIAP-BZBJXUGXSA-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
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Disaccharide
Glycosyl compound
O-glycosyl compound
Fatty acyl
Oxane
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Acetal
Monocarboxylic acid or derivatives
Polyol
Organic oxygen compound
Organic oxide
Alcohol
Carbonyl group
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0304603)

Food

Vegetable

Albizia gummifera (FooDB: FOOD00896)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	2.25	ALOGPS
logP	1.91	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	4.74	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	274.75 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	224.9 m³·mol⁻¹	ChemAxon
Polarizability	99.41 Å³	ChemAxon
Number of Rings	8	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

HMDB0304603

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB093553

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

102237586

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 3-O-{beta-D-Glucopyranosyl(1_2)-[alpha-L-arabinopyranosyl(1_6)]-beta-D-glucopyranosyl}-oleanolic acid (CFc000284119)

MOL for CFc000284119 (3-O-{beta-D-Glucopyranosyl(1_2)-[alpha-L-arabinopyranosyl(1_6)]-beta-D-glucopyranosyl}-oleanolic acid)

3D MOL for CFc000284119 (3-O-{beta-D-Glucopyranosyl(1_2)-[alpha-L-arabinopyranosyl(1_6)]-beta-D-glucopyranosyl}-oleanolic acid)

3D SDF for CFc000284119 (3-O-{beta-D-Glucopyranosyl(1_2)-[alpha-L-arabinopyranosyl(1_6)]-beta-D-glucopyranosyl}-oleanolic acid)

3D-SDF for CFc000284119 (3-O-{beta-D-Glucopyranosyl(1_2)-[alpha-L-arabinopyranosyl(1_6)]-beta-D-glucopyranosyl}-oleanolic acid)

PDB for CFc000284119 (3-O-{beta-D-Glucopyranosyl(1_2)-[alpha-L-arabinopyranosyl(1_6)]-beta-D-glucopyranosyl}-oleanolic acid)

3D PDB for CFc000284119 (3-O-{beta-D-Glucopyranosyl(1_2)-[alpha-L-arabinopyranosyl(1_6)]-beta-D-glucopyranosyl}-oleanolic acid)

SMILES for CFc000284119 (3-O-{beta-D-Glucopyranosyl(1_2)-[alpha-L-arabinopyranosyl(1_6)]-beta-D-glucopyranosyl}-oleanolic acid)

INCHI for CFc000284119 (3-O-{beta-D-Glucopyranosyl(1_2)-[alpha-L-arabinopyranosyl(1_6)]-beta-D-glucopyranosyl}-oleanolic acid)

Structure for CFc000284119 (3-O-{beta-D-Glucopyranosyl(1_2)-[alpha-L-arabinopyranosyl(1_6)]-beta-D-glucopyranosyl}-oleanolic acid)

3D Structure for CFc000284119 (3-O-{beta-D-Glucopyranosyl(1_2)-[alpha-L-arabinopyranosyl(1_6)]-beta-D-glucopyranosyl}-oleanolic acid)