ChemFOnt: Showing chemical card for Medicagenic acid 28-O-[b-D-xylosyl-(1->4)-a-L-rhamnosyl-(1->2)-a-L-arabinosyl] ester (CFc000020189)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:11:28 UTC

Chemfont ID

CFc000020189

Molecule Identification

Common Name

Medicagenic acid 28-O-[b-D-xylosyl-(1->4)-a-L-rhamnosyl-(1->2)-a-L-arabinosyl] ester

Definition

Medicagenic acid 28-O-[b-D-xylosyl-(1->4)-a-L-rhamnosyl-(1->2)-a-L-arabinosyl] ester is found in cereals and cereal products. Medicagenic acid 28-O-[b-D-xylosyl-(1->4)-a-L-rhamnosyl-(1->2)-a-L-arabinosyl] ester is isolated from the roots of Medicago sativa (alfalfa).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Medicagenate 28-O-[b-D-xylosyl-(1->4)-a-L-rhamnosyl-(1->2)-a-L-arabinosyl] ester	Generator
8a-({[3-({3,4-dihydroxy-6-methyl-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-4,5-dihydroxyoxan-2-yl]oxy}carbonyl)-2,3-dihydroxy-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-icosahydropicene-4-carboxylate	Generator

Chemical Formula

C₄₆H₇₂O₁₈

Average Molecular Weight

913.0531

Monoisotopic Molecular Weight

912.4718655

IUPAC Name

8a-({[3-({3,4-dihydroxy-6-methyl-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-4,5-dihydroxyoxan-2-yl]oxy}carbonyl)-2,3-dihydroxy-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-icosahydropicene-4-carboxylic acid

Traditional Name

8a-({[3-({3,4-dihydroxy-6-methyl-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-4,5-dihydroxyoxan-2-yl]oxy}carbonyl)-2,3-dihydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4-carboxylic acid

CAS Registry Number

129570-95-2

SMILES

CC1OC(OC2C(O)C(O)COC2OC(=O)C23CCC(C)(C)CC2C2=CCC4C5(C)CC(O)C(O)C(C)(C5CCC4(C)C2(C)CC3)C(O)=O)C(O)C(O)C1OC1OCC(O)C(O)C1O

InChI Identifier

InChI=1S/C46H72O18/c1-20-33(62-36-31(53)28(50)24(48)18-59-36)30(52)32(54)37(61-20)63-34-29(51)25(49)19-60-38(34)64-40(58)46-14-12-41(2,3)16-22(46)21-8-9-26-42(4)17-23(47)35(55)45(7,39(56)57)27(42)10-11-44(26,6)43(21,5)13-15-46/h8,20,22-38,47-55H,9-19H2,1-7H3,(H,56,57)

InChI Key

NVYDZIYMAONXJL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Oligosaccharide
12-hydroxysteroid
15-hydroxysteroid
Hydroxysteroid
Steroid
O-glycosyl compound
Glycosyl compound
Beta-hydroxy acid
Oxane
Dicarboxylic acid or derivatives
Hydroxy acid
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Acetal
Carboxylic acid derivative
Polyol
Carboxylic acid
Oxacycle
Alcohol
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039295)

Source

Endogenous

Endogenous (HMDB: HMDB0039295)

Plant

Poaceae (HMDB: HMDB0039295)

Animal

Animal (HMDB: HMDB0039295)

Exogenous

Food

Food (HMDB: HMDB0039295)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Exogenous (HMDB: HMDB0039295)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0039295)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0039295)

Lipid metabolism pathway (HMDB: HMDB0039295)

Cellular process

Cell signaling (HMDB: HMDB0039295)

Biochemical process

Lipid transport (HMDB: HMDB0039295)

Role

Biological role

Energy source (HMDB: HMDB0039295)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0039295)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.38 g/L	ALOGPS
logP	1.45	ALOGPS
logP	1.21	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	4.47	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	291.82 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	220.49 m³·mol⁻¹	ChemAxon
Polarizability	95.25 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

HMDB0039295

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB018841

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

131752601

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Medicagenic acid 28-O-[b-D-xylosyl-(1->4)-a-L-rhamnosyl-(1->2)-a-L-arabinosyl] ester (CFc000020189)

MOL for CFc000020189 (Medicagenic acid 28-O-[b-D-xylosyl-(1->4)-a-L-rhamnosyl-(1->2)-a-L-arabinosyl] ester)

3D MOL for CFc000020189 (Medicagenic acid 28-O-[b-D-xylosyl-(1->4)-a-L-rhamnosyl-(1->2)-a-L-arabinosyl] ester)

3D SDF for CFc000020189 (Medicagenic acid 28-O-[b-D-xylosyl-(1->4)-a-L-rhamnosyl-(1->2)-a-L-arabinosyl] ester)

3D-SDF for CFc000020189 (Medicagenic acid 28-O-[b-D-xylosyl-(1->4)-a-L-rhamnosyl-(1->2)-a-L-arabinosyl] ester)

PDB for CFc000020189 (Medicagenic acid 28-O-[b-D-xylosyl-(1->4)-a-L-rhamnosyl-(1->2)-a-L-arabinosyl] ester)

3D PDB for CFc000020189 (Medicagenic acid 28-O-[b-D-xylosyl-(1->4)-a-L-rhamnosyl-(1->2)-a-L-arabinosyl] ester)

SMILES for CFc000020189 (Medicagenic acid 28-O-[b-D-xylosyl-(1->4)-a-L-rhamnosyl-(1->2)-a-L-arabinosyl] ester)

INCHI for CFc000020189 (Medicagenic acid 28-O-[b-D-xylosyl-(1->4)-a-L-rhamnosyl-(1->2)-a-L-arabinosyl] ester)

Structure for CFc000020189 (Medicagenic acid 28-O-[b-D-xylosyl-(1->4)-a-L-rhamnosyl-(1->2)-a-L-arabinosyl] ester)

3D Structure for CFc000020189 (Medicagenic acid 28-O-[b-D-xylosyl-(1->4)-a-L-rhamnosyl-(1->2)-a-L-arabinosyl] ester)