ChemFOnt: Showing chemical card for 1alpha,3beta,22R-Trihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-b-D-glucosyl ester (CFc000021278)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:13:01 UTC

Chemfont ID

CFc000021278

Molecule Identification

Common Name

1alpha,3beta,22R-Trihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-b-D-glucosyl ester

Definition

1alpha,3beta,22R-Trihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-b-D-glucosyl ester is found in fruits. 1alpha,3beta,22R-Trihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-b-D-glucosyl ester is a constituent of Physalis peruviana (Cape gooseberry).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1a,3b,22R-Trihydroxyergosta-5,24E-dien-26-Oate 3-O-b-D-glucoside 26-O-b-D-glucosyl ester	Generator
1a,3b,22R-Trihydroxyergosta-5,24E-dien-26-Oic acid 3-O-b-D-glucoside 26-O-b-D-glucosyl ester	Generator
1alpha,3beta,22R-Trihydroxyergosta-5,24E-dien-26-Oate 3-O-b-D-glucoside 26-O-b-D-glucosyl ester	Generator
1Α,3β,22R-trihydroxyergosta-5,24E-dien-26-Oate 3-O-b-D-glucoside 26-O-b-D-glucosyl ester	Generator
1Α,3β,22R-trihydroxyergosta-5,24E-dien-26-Oic acid 3-O-b-D-glucoside 26-O-b-D-glucosyl ester	Generator
3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl (2Z)-5-hydroxy-6-(3-hydroxy-2,15-dimethyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl)-2,3-dimethylhept-2-enoic acid	Generator

Chemical Formula

C₄₀H₆₄O₁₅

Average Molecular Weight

784.9272

Monoisotopic Molecular Weight

784.424521378

IUPAC Name

3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2Z)-5-hydroxy-6-(3-hydroxy-2,15-dimethyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl)-2,3-dimethylhept-2-enoate

Traditional Name

CAS Registry Number

155510-72-8

SMILES

CC(C(O)C\C(C)=C(\C)C(=O)OC1OC(CO)C(O)C(O)C1O)C1CCC2C3CC=C4CC(CC(O)C4(C)C3CCC12C)OC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C40H64O15/c1-17(18(2)36(51)55-38-35(50)33(48)31(46)28(16-42)54-38)12-26(43)19(3)23-8-9-24-22-7-6-20-13-21(52-37-34(49)32(47)30(45)27(15-41)53-37)14-29(44)40(20,5)25(22)10-11-39(23,24)4/h6,19,21-35,37-38,41-50H,7-16H2,1-5H3/b18-17-

InChI Key

JPXWUHUTNQDPDE-ZCXUNETKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Steroidal glycosides

Alternative Parents

Substituents

Diterpene glycoside
Ergostane-skeleton
Steroidal glycoside
Dihydroxy bile acid, alcohol, or derivatives
Hydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
22-hydroxysteroid
Diterpenoid
1-hydroxysteroid
Hydroxysteroid
Delta-5-steroid
Terpene glycoside
O-glycosyl compound
Glycosyl compound
Oxane
Monosaccharide
Cyclic alcohol
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Polyol
Acetal
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organooxygen compound
Primary alcohol
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0040398)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0040398)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040398)

Source

Endogenous

Endogenous (HMDB: HMDB0040398)

Plant

Plant (HMDB: HMDB0040398)

Animal

Animal (HMDB: HMDB0040398)

Exogenous

Food

Food (HMDB: HMDB0040398)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0040398)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0040398)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0040398)

Lipid metabolism pathway (HMDB: HMDB0040398)

Cellular process

Cell signaling (HMDB: HMDB0040398)

Biochemical process

Lipid transport (HMDB: HMDB0040398)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0040398)

Molecular messenger

Signaling molecule (HMDB: HMDB0040398)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0040398)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.33 g/L	ALOGPS
logP	-0.26	ALOGPS
logP	-0.28	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	11.9	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	256.29 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	195.37 m³·mol⁻¹	ChemAxon
Polarizability	85.63 Å³	ChemAxon
Number of Rings	6	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

HMDB0040398

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB020130

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

131752809

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 1alpha,3beta,22R-Trihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-b-D-glucosyl ester (CFc000021278)

MOL for CFc000021278 (1alpha,3beta,22R-Trihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-b-D-glucosyl ester)

3D MOL for CFc000021278 (1alpha,3beta,22R-Trihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-b-D-glucosyl ester)

3D SDF for CFc000021278 (1alpha,3beta,22R-Trihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-b-D-glucosyl ester)

3D-SDF for CFc000021278 (1alpha,3beta,22R-Trihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-b-D-glucosyl ester)

PDB for CFc000021278 (1alpha,3beta,22R-Trihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-b-D-glucosyl ester)

3D PDB for CFc000021278 (1alpha,3beta,22R-Trihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-b-D-glucosyl ester)

SMILES for CFc000021278 (1alpha,3beta,22R-Trihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-b-D-glucosyl ester)

INCHI for CFc000021278 (1alpha,3beta,22R-Trihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-b-D-glucosyl ester)

Structure for CFc000021278 (1alpha,3beta,22R-Trihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-b-D-glucosyl ester)

3D Structure for CFc000021278 (1alpha,3beta,22R-Trihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-b-D-glucosyl ester)