ChemFOnt: Showing chemical card for 1-Acetyl-3,27-dihydroxywitha-5,24-dienolide 3-glucoside (CFc000014813)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:03:41 UTC

Chemfont ID

CFc000014813

Molecule Identification

Common Name

1-Acetyl-3,27-dihydroxywitha-5,24-dienolide 3-glucoside

Definition

1-Acetyl-3,27-dihydroxywitha-5,24-dienolide 3-glucoside is found in fruits. 1-Acetyl-3,27-dihydroxywitha-5,24-dienolide 3-glucoside is a constituent of Physalis peruviana (Cape gooseberry).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
14-{1-[5-(hydroxymethyl)-4-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]ethyl}-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-3-yl acetic acid	Generator

Chemical Formula

C₃₆H₅₄O₁₁

Average Molecular Weight

662.8074

Monoisotopic Molecular Weight

662.36661257

IUPAC Name

14-{1-[5-(hydroxymethyl)-4-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]ethyl}-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-3-yl acetate

Traditional Name

14-{1-[5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl}-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-3-yl acetate

CAS Registry Number

227179-08-0

SMILES

CC(C1CCC2C3CC=C4CC(CC(OC(C)=O)C4(C)C3CCC12C)OC1OC(CO)C(O)C(O)C1O)C1CC(C)=C(CO)C(=O)O1

InChI Identifier

InChI=1S/C36H54O11/c1-17-12-27(46-33(43)23(17)15-37)18(2)24-8-9-25-22-7-6-20-13-21(45-34-32(42)31(41)30(40)28(16-38)47-34)14-29(44-19(3)39)36(20,5)26(22)10-11-35(24,25)4/h6,18,21-22,24-32,34,37-38,40-42H,7-16H2,1-5H3

InChI Key

SKADEWVNQSRPEJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as withanolide glycosides and derivatives. These are withanolides in which at least one hydroxyl group is glycosylated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Withanolide glycosides and derivatives

Alternative Parents

Substituents

Withanolide-glycoside
Diterpene glycoside
26-hydroxysteroid
Steroidal glycoside
Steroid ester
Diterpene lactone
Diterpenoid
Delta-5-steroid
Terpene glycoside
Glycosyl compound
O-glycosyl compound
Dihydropyranone
Pyran
Dicarboxylic acid or derivatives
Oxane
Monosaccharide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid derivative
Polyol
Hydrocarbon derivative
Organic oxide
Primary alcohol
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen compound
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: HMDB0033729)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0033729)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033729)

Source

Endogenous

Endogenous (HMDB: HMDB0033729)

Plant

Plant (HMDB: HMDB0033729)

Animal

Animal (HMDB: HMDB0033729)

Exogenous

Food

Food (HMDB: HMDB0033729)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0033729)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0033729)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0033729)

Lipid metabolism pathway (HMDB: HMDB0033729)

Cellular process

Cell signaling (HMDB: HMDB0033729)

Biochemical process

Lipid transport (HMDB: HMDB0033729)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0033729)

Molecular messenger

Signaling molecule (HMDB: HMDB0033729)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0033729)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.029 g/L	ALOGPS
logP	2.11	ALOGPS
logP	1.82	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	172.21 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	170.38 m³·mol⁻¹	ChemAxon
Polarizability	74.14 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0033729

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB011852

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

85228887

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 1-Acetyl-3,27-dihydroxywitha-5,24-dienolide 3-glucoside (CFc000014813)

MOL for CFc000014813 (1-Acetyl-3,27-dihydroxywitha-5,24-dienolide 3-glucoside)

3D MOL for CFc000014813 (1-Acetyl-3,27-dihydroxywitha-5,24-dienolide 3-glucoside)

3D SDF for CFc000014813 (1-Acetyl-3,27-dihydroxywitha-5,24-dienolide 3-glucoside)

3D-SDF for CFc000014813 (1-Acetyl-3,27-dihydroxywitha-5,24-dienolide 3-glucoside)

PDB for CFc000014813 (1-Acetyl-3,27-dihydroxywitha-5,24-dienolide 3-glucoside)

3D PDB for CFc000014813 (1-Acetyl-3,27-dihydroxywitha-5,24-dienolide 3-glucoside)

SMILES for CFc000014813 (1-Acetyl-3,27-dihydroxywitha-5,24-dienolide 3-glucoside)

INCHI for CFc000014813 (1-Acetyl-3,27-dihydroxywitha-5,24-dienolide 3-glucoside)

Structure for CFc000014813 (1-Acetyl-3,27-dihydroxywitha-5,24-dienolide 3-glucoside)

3D Structure for CFc000014813 (1-Acetyl-3,27-dihydroxywitha-5,24-dienolide 3-glucoside)