ChemFOnt: Showing chemical card for 3beta-O-beta-D-Glucopyranosiduronic acid (1_2)-beta-D-glucopyranosyloxy]-machaerinic acid

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

CFc000284122

Molecule Identification

Common Name

3beta-O-beta-D-Glucopyranosiduronic acid (1_2)-beta-D-glucopyranosyloxy]-machaerinic acid _-lactone

Definition

(2S,3S,4S,5R,6R)-6-{[(2R,3R,4S,5S,6R)-2-{[(1R,4S,5R,8R,10S,13R,14R,18R,21S)-4,5,9,9,13,20,20-heptamethyl-23-oxo-22-oxahexacyclo[19.2.1.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-16-en-10-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic 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 very few articles have been published on (2S,3S,4S,5R,6R)-6-{[(2R,3R,4S,5S,6R)-2-{[(1R,4S,5R,8R,10S,13R,14R,18R,21S)-4,5,9,9,13,20,20-heptamethyl-23-oxo-22-oxahexacyclo[19.2.1.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-16-en-10-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S,3S,4S,5R,6R)-6-{[(2R,3R,4S,5S,6R)-2-{[(1R,4S,5R,8R,10S,13R,14R,18R,21S)-4,5,9,9,13,20,20-heptamethyl-23-oxo-22-oxahexacyclo[19.2.1.0,.0,.0,.0,]tetracos-16-en-10-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate	Generator
(2S,3S,4S,5R,6R)-6-{[(2R,3R,4S,5S,6R)-2-{[(1R,4S,5R,8R,10S,13R,14R,18R,21S)-4,5,9,9,13,20,20-heptamethyl-23-oxo-22-oxahexacyclo[19.2.1.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-16-en-10-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate	Generator
3beta-O-beta-D-glucopyranosiduronic acid (1->2)-beta-D-glucopyranosyloxy]-machaerinic acid gamma-lactone	PhytoBank
3β-O-β-D-glucopyranosiduronic acid (1→2)-β-D-glucopyranosyloxy]-machaerinic acid γ-lactone	PhytoBank

Chemical Formula

C₄₂H₆₄O₁₄

Average Molecular Weight

792.96

Monoisotopic Molecular Weight

792.429606741

IUPAC Name

(2S,3S,4S,5R,6R)-6-{[(2R,3R,4S,5S,6R)-2-{[(1R,4S,5R,8R,10S,13R,14R,18R,21S)-4,5,9,9,13,20,20-heptamethyl-23-oxo-22-oxahexacyclo[19.2.1.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tetracos-16-en-10-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

CAS Registry Number

None

SMILES

[H][C@]12C[C@@]3(CC[C@]4(C)C(=CC[C@]5([H])[C@@]6(C)CC[C@H](O[C@]7([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O[C@]7([H])O[C@@H]([C@@H](O)[C@H](O)[C@H]7O)C(O)=O)C(C)(C)[C@]6([H])CC[C@@]45C)[C@@]3([H])CC1(C)C)C(=O)O2

InChI Identifier

InChI=1S/C42H64O14/c1-37(2)16-20-19-8-9-23-39(5)12-11-24(38(3,4)22(39)10-13-41(23,7)40(19,6)14-15-42(20)17-25(37)54-36(42)51)53-35-32(28(46)26(44)21(18-43)52-35)56-34-30(48)27(45)29(47)31(55-34)33(49)50/h8,20-32,34-35,43-48H,9-18H2,1-7H3,(H,49,50)/t20-,21-,22+,23-,24+,25+,26-,27+,28+,29+,30-,31+,32-,34+,35+,39+,40-,41-,42-/m1/s1

InChI Key

LIBFICRLZUXATQ-HUTCXTCQSA-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
O-glucuronide
1-o-glucuronide
Glucuronic acid or derivatives
O-glycosyl compound
Glycosyl compound
Disaccharide
Caprolactone
Oxepane
Beta-hydroxy acid
Pyran
Oxane
Hydroxy acid
Gamma butyrolactone
Dicarboxylic acid or derivatives
Tetrahydrofuran
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0304606)

Food

Vegetable

Albizia gummifera (FooDB: FOOD00896)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.063 g/L	ALOGPS
logP	3.38	ALOGPS
logP	2.81	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	3.13	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	221.9 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	196.34 m³·mol⁻¹	ChemAxon
Polarizability	86.27 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

HMDB0304606

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB093556

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 3beta-O-beta-D-Glucopyranosiduronic acid (1_2)-beta-D-glucopyranosyloxy]-machaerinic acid _-lactone (CFc000284122)

MOL for CFc000284122 (3beta-O-beta-D-Glucopyranosiduronic acid (1_2)-beta-D-glucopyranosyloxy]-machaerinic acid _-lactone)

3D MOL for CFc000284122 (3beta-O-beta-D-Glucopyranosiduronic acid (1_2)-beta-D-glucopyranosyloxy]-machaerinic acid _-lactone)

3D SDF for CFc000284122 (3beta-O-beta-D-Glucopyranosiduronic acid (1_2)-beta-D-glucopyranosyloxy]-machaerinic acid _-lactone)

3D-SDF for CFc000284122 (3beta-O-beta-D-Glucopyranosiduronic acid (1_2)-beta-D-glucopyranosyloxy]-machaerinic acid _-lactone)

PDB for CFc000284122 (3beta-O-beta-D-Glucopyranosiduronic acid (1_2)-beta-D-glucopyranosyloxy]-machaerinic acid _-lactone)

3D PDB for CFc000284122 (3beta-O-beta-D-Glucopyranosiduronic acid (1_2)-beta-D-glucopyranosyloxy]-machaerinic acid _-lactone)

SMILES for CFc000284122 (3beta-O-beta-D-Glucopyranosiduronic acid (1_2)-beta-D-glucopyranosyloxy]-machaerinic acid _-lactone)

INCHI for CFc000284122 (3beta-O-beta-D-Glucopyranosiduronic acid (1_2)-beta-D-glucopyranosyloxy]-machaerinic acid _-lactone)

Structure for CFc000284122 (3beta-O-beta-D-Glucopyranosiduronic acid (1_2)-beta-D-glucopyranosyloxy]-machaerinic acid _-lactone)

3D Structure for CFc000284122 (3beta-O-beta-D-Glucopyranosiduronic acid (1_2)-beta-D-glucopyranosyloxy]-machaerinic acid _-lactone)