ChemFOnt: Showing chemical card for 11,13-Dihydrotaraxinic acid glucosyl ester (CFc000016862)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:06:36 UTC

Chemfont ID

CFc000016862

Molecule Identification

Common Name

11,13-Dihydrotaraxinic acid glucosyl ester

Definition

11,13-Dihydrotaraxinic acid glucosyl ester is found in alcoholic beverages. 11,13-Dihydrotaraxinic acid glucosyl ester is a constituent of Taraxacum officinale (dandelion)

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
11,13-Dihydrotaraxinate glucosyl ester	Generator
(2R,3R,4S,5R,6R)-2,3,5-Trihydroxy-6-(hydroxymethyl)oxan-4-yl (3as,11as)-3,10-dimethyl-2-oxo-2H,3H,3ah,4H,5H,8H,9H,11ah-cyclodeca[b]furan-6-carboxylic acid	HMDB

Chemical Formula

C₂₁H₃₀O₉

Average Molecular Weight

426.4575

Monoisotopic Molecular Weight

426.188982558

IUPAC Name

(2R,3R,4S,5R,6R)-2,3,5-trihydroxy-6-(hydroxymethyl)oxan-4-yl (3aS,11aS)-3,10-dimethyl-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate

Traditional Name

(2R,3R,4S,5R,6R)-2,3,5-trihydroxy-6-(hydroxymethyl)oxan-4-yl (3aS,11aS)-3,10-dimethyl-2-oxo-3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate

CAS Registry Number

75911-16-9

SMILES

CC1[C@@H]2CCC(=CCC\C(C)=C\[C@H]2OC1=O)C(=O)O[C@@H]1[C@@H](O)[C@H](O)O[C@H](CO)[C@H]1O

InChI Identifier

InChI=1S/C21H30O9/c1-10-4-3-5-12(6-7-13-11(2)19(25)28-14(13)8-10)20(26)30-18-16(23)15(9-22)29-21(27)17(18)24/h5,8,11,13-18,21-24,27H,3-4,6-7,9H2,1-2H3/b10-8+,12-5+/t11?,13-,14+,15+,16+,17+,18-,21+/m0/s1

InChI Key

GHCVBVCIPFPICQ-RYCRGVOFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Saccharolipids

Sub Class

Not Available

Direct Parent

Saccharolipids

Alternative Parents

Substituents

Saccharolipid
Germacranolide
Terpene lactone
Germacrane sesquiterpenoid
Sesquiterpenoid
Hexose monosaccharide
Dicarboxylic acid or derivatives
Gamma butyrolactone
Monosaccharide
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Secondary alcohol
Carboxylic acid ester
Hemiacetal
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Polyol
Hydrocarbon derivative
Primary alcohol
Organic oxide
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

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035867)

Source

Endogenous

Endogenous (HMDB: HMDB0035867)

Plant

Plant (HMDB: HMDB0035867)
Coffea (HMDB: HMDB0035867)

Exogenous

Food

Food (HMDB: HMDB0035867)

Herb and spice

Herb

Dandelion (FooDB: FOOD00181)

Tea

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Beverages (FooDB: FOOD00870)

Exogenous (HMDB: HMDB0035867)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0035867)

Role

Biological role

Energy source (HMDB: HMDB0035867)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035867)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.56 g/L	ALOGPS
logP	0.26	ALOGPS
logP	0.83	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	11.3	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	142.75 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	104.29 m³·mol⁻¹	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0035867

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB014647

KNApSAcK ID

Not Available

Chemspider ID

30777145

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751877

PDB ID

Not Available

ChEBI ID

168344

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 11,13-Dihydrotaraxinic acid glucosyl ester (CFc000016862)

MOL for CFc000016862 (11,13-Dihydrotaraxinic acid glucosyl ester)

3D MOL for CFc000016862 (11,13-Dihydrotaraxinic acid glucosyl ester)

3D SDF for CFc000016862 (11,13-Dihydrotaraxinic acid glucosyl ester)

3D-SDF for CFc000016862 (11,13-Dihydrotaraxinic acid glucosyl ester)

PDB for CFc000016862 (11,13-Dihydrotaraxinic acid glucosyl ester)

3D PDB for CFc000016862 (11,13-Dihydrotaraxinic acid glucosyl ester)

SMILES for CFc000016862 (11,13-Dihydrotaraxinic acid glucosyl ester)

INCHI for CFc000016862 (11,13-Dihydrotaraxinic acid glucosyl ester)

Structure for CFc000016862 (11,13-Dihydrotaraxinic acid glucosyl ester)

3D Structure for CFc000016862 (11,13-Dihydrotaraxinic acid glucosyl ester)