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-(1->2)-6-acetyl-b-D-glucosyl] ester (CFc000021280)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:13:02 UTC

Chemfont ID

CFc000021280

Molecule Identification

Common Name

1alpha,3beta,22R-Trihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->2)-6-acetyl-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-(1->2)-6-acetyl-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-(1->2)-6-acetyl-b-D-glucosyl] ester is a constituent of Physalis peruviana (Cape gooseberry).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-Bornyl acetic acid	Generator
(1S,2R,4S)-(-)-Bornyl acetate	HMDB
endo-(1S)-1,7,7-Trimethylbicyclo[2.2.1]hept-2-yl acetate	HMDB
FEMA 2159	HMDB
L-alpha-Bornyl acetate	HMDB
L-Born-2-yl acetate	HMDB
L-Bornyl acetate	HMDB
Levo-bornyl acetate	HMDB
6-[(Acetyloxy)methyl]-4,5-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}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
1a,3b,22R-Trihydroxyergosta-5,24E-dien-26-Oate 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->2)-6-acetyl-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-(1->2)-6-acetyl-b-D-glucosyl] ester	Generator
1alpha,3beta,22R-Trihydroxyergosta-5,24E-dien-26-Oate 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] ester	Generator
1Α,3β,22R-trihydroxyergosta-5,24E-dien-26-Oate 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->2)-6-acetyl-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-(1->2)-6-acetyl-b-D-glucosyl] ester	Generator

Chemical Formula

C₄₈H₇₆O₂₁

Average Molecular Weight

989.1044

Monoisotopic Molecular Weight

988.487909494

IUPAC Name

6-[(acetyloxy)methyl]-4,5-dihydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}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

155510-74-0

SMILES

CC(C(O)C\C(C)=C(\C)C(=O)OC1OC(COC(C)=O)C(O)C(O)C1OC1OC(CO)C(O)C(O)C1O)C1CCC2C3CC=C4CC(CC(O)C4(C)C3CCC12C)OC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C48H76O21/c1-19(20(2)43(62)69-46-42(39(59)36(56)32(67-46)18-63-22(4)51)68-45-41(61)38(58)35(55)31(17-50)66-45)13-29(52)21(3)26-9-10-27-25-8-7-23-14-24(64-44-40(60)37(57)34(54)30(16-49)65-44)15-33(53)48(23,6)28(25)11-12-47(26,27)5/h7,21,24-42,44-46,49-50,52-61H,8-18H2,1-6H3/b20-19-

InChI Key

CBKQGELSNULPLY-VXPUYCOJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Bicyclic monoterpenoid
Bornane monoterpenoid
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0040400)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0040400)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040400)

Source

Endogenous

Endogenous (HMDB: HMDB0040400)

Plant

Plant (HMDB: HMDB0040400)

Animal

Animal (HMDB: HMDB0040400)

Exogenous

Food

Food (HMDB: HMDB0040400)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0040400)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0040400)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0040400)

Lipid metabolism pathway (HMDB: HMDB0040400)

Cellular process

Cell signaling (HMDB: HMDB0040400)

Biochemical process

Lipid transport (HMDB: HMDB0040400)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0040400)

Molecular messenger

Signaling molecule (HMDB: HMDB0040400)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0040400)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.6 g/L	ALOGPS
logP	-0.98	ALOGPS
logP	-1.6	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	11.85	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	341.51 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	236.94 m³·mol⁻¹	ChemAxon
Polarizability	104.34 Å³	ChemAxon
Number of Rings	7	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

HMDB0040397

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB020129

KNApSAcK ID

Not Available

Chemspider ID

6207

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6448

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-(1->2)-6-acetyl-b-D-glucosyl] ester (CFc000021280)

MOL for CFc000021280 (1alpha,3beta,22R-Trihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] ester)

3D MOL for CFc000021280 (1alpha,3beta,22R-Trihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] ester)

3D SDF for CFc000021280 (1alpha,3beta,22R-Trihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] ester)

3D-SDF for CFc000021280 (1alpha,3beta,22R-Trihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] ester)

PDB for CFc000021280 (1alpha,3beta,22R-Trihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] ester)

3D PDB for CFc000021280 (1alpha,3beta,22R-Trihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] ester)

SMILES for CFc000021280 (1alpha,3beta,22R-Trihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] ester)

INCHI for CFc000021280 (1alpha,3beta,22R-Trihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] ester)

Structure for CFc000021280 (1alpha,3beta,22R-Trihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] ester)

3D Structure for CFc000021280 (1alpha,3beta,22R-Trihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] ester)