ChemFOnt: Showing chemical card for 1-Acetyl-3,14,20-trihydroxywitha-5,24-dienolide 3-glucoside (CFc000014656)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:03:28 UTC

Chemfont ID

CFc000014656

Molecule Identification

Common Name

1-Acetyl-3,14,20-trihydroxywitha-5,24-dienolide 3-glucoside

Definition

1-Acetyl-3,14,20-trihydroxywitha-5,24-dienolide 3-glucoside is found in fruits. 1-Acetyl-3,14,20-trihydroxywitha-5,24-dienolide 3-glucoside is a constituent of Physalis peruviana (Cape gooseberry).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5-Hydroxy-7-(4'-hydroxy-3'-methoxyphenyl)-1-phenyl-3-heptanone	HMDB
HPH CPD	HMDB
14-[1-(4,5-Dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-hydroxyethyl]-11-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-3-yl acetic acid	Generator

Chemical Formula

C₃₆H₅₄O₁₂

Average Molecular Weight

678.8068

Monoisotopic Molecular Weight

678.361527192

IUPAC Name

14-[1-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-hydroxyethyl]-11-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-3-yl acetate

Traditional Name

14-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-11-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-3-yl acetate

CAS Registry Number

227179-07-9

SMILES

CC(=O)OC1CC(CC2=CCC3C(CCC4(C)C(CCC34O)C(C)(O)C3CC(C)=C(C)C(=O)O3)C12C)OC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C36H54O12/c1-17-13-27(48-31(42)18(17)2)35(6,43)25-10-12-36(44)23-8-7-20-14-21(46-32-30(41)29(40)28(39)24(16-37)47-32)15-26(45-19(3)38)34(20,5)22(23)9-11-33(25,36)4/h7,21-30,32,37,39-41,43-44H,8-16H2,1-6H3

InChI Key

ACXRDVCAKSUCPM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Diarylheptanoids

Sub Class

Linear diarylheptanoids

Direct Parent

Linear diarylheptanoids

Alternative Parents

Substituents

Linear 1,7-diphenylheptane skeleton
Methoxyphenol
Fatty alcohol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Beta-hydroxy ketone
Ketone
Secondary alcohol
Ether
Alcohol
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0033572)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0033572)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033572)

Source

Endogenous

Endogenous (HMDB: HMDB0033572)

Plant

Plant (HMDB: HMDB0033572)

Animal

Animal (HMDB: HMDB0033572)

Exogenous

Food

Food (HMDB: HMDB0033572)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0033572)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0033572)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0033572)

Lipid metabolism pathway (HMDB: HMDB0033572)

Cellular process

Cell signaling (HMDB: HMDB0033572)

Biochemical process

Lipid transport (HMDB: HMDB0033572)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0033572)

Molecular messenger

Signaling molecule (HMDB: HMDB0033572)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0033572)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.2 g/L	ALOGPS
logP	1.1	ALOGPS
logP	0.94	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	12.19	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	192.44 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	171.5 m³·mol⁻¹	ChemAxon
Polarizability	74.43 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

HMDB0029524

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000664

KNApSAcK ID

Not Available

Chemspider ID

4476840

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5318228

PDB ID

Not Available

ChEBI ID

1030794

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 1-Acetyl-3,14,20-trihydroxywitha-5,24-dienolide 3-glucoside (CFc000014656)

MOL for CFc000014656 (1-Acetyl-3,14,20-trihydroxywitha-5,24-dienolide 3-glucoside)

3D MOL for CFc000014656 (1-Acetyl-3,14,20-trihydroxywitha-5,24-dienolide 3-glucoside)

3D SDF for CFc000014656 (1-Acetyl-3,14,20-trihydroxywitha-5,24-dienolide 3-glucoside)

3D-SDF for CFc000014656 (1-Acetyl-3,14,20-trihydroxywitha-5,24-dienolide 3-glucoside)

PDB for CFc000014656 (1-Acetyl-3,14,20-trihydroxywitha-5,24-dienolide 3-glucoside)

3D PDB for CFc000014656 (1-Acetyl-3,14,20-trihydroxywitha-5,24-dienolide 3-glucoside)

SMILES for CFc000014656 (1-Acetyl-3,14,20-trihydroxywitha-5,24-dienolide 3-glucoside)

INCHI for CFc000014656 (1-Acetyl-3,14,20-trihydroxywitha-5,24-dienolide 3-glucoside)

Structure for CFc000014656 (1-Acetyl-3,14,20-trihydroxywitha-5,24-dienolide 3-glucoside)

3D Structure for CFc000014656 (1-Acetyl-3,14,20-trihydroxywitha-5,24-dienolide 3-glucoside)