ChemFOnt: Showing chemical card for Glucocapangulin (CFc000281953)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:33:50 UTC

Chemfont ID

CFc000281953

Molecule Identification

Common Name

Glucocapangulin

Definition

Glucocapangulin, also known as anthraglycoside b, is a member of the class of compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group. Thus, glucocapangulin is considered to be an aromatic polyketide lipid molecule. Glucocapangulin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Glucocapangulin can be found in capers, which makes glucocapangulin a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-beta-D-Glucopyranosyloxy-3-methyl-6-hydroxy-8-hydroxy-9,10-anthraquinone	Kegg
1-b-D-Glucopyranosyloxy-3-methyl-6-hydroxy-8-hydroxy-9,10-anthraquinone	Generator
1-Β-D-glucopyranosyloxy-3-methyl-6-hydroxy-8-hydroxy-9,10-anthraquinone	Generator
Anthraglycoside b	MeSH

Chemical Formula

C₂₁H₂₀O₁₀

Average Molecular Weight

432.381

Monoisotopic Molecular Weight

432.105646844

IUPAC Name

1,6-dihydroxy-3-methyl-8-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dihydroanthracene-9,10-dione

Traditional Name

emodin 8-glucoside

CAS Registry Number

38840-23-2

SMILES

[H][C@]1(CO)O[C@@]([H])(OC2=CC(O)=CC3=C2C(=O)C2=C(C=C(C)C=C2O)C3=O)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])O

InChI Identifier

InChI=1S/C21H20O10/c1-7-2-9-14(11(24)3-7)18(27)15-10(16(9)25)4-8(23)5-12(15)30-21-20(29)19(28)17(26)13(6-22)31-21/h2-5,13,17,19-24,26,28-29H,6H2,1H3/t13-,17-,19+,20-,21-/m1/s1

InChI Key

HSWIRQIYASIOBE-JNHRPPPUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Hydroxyanthraquinones

Alternative Parents

Substituents

Hydroxyanthraquinone
Phenolic glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monosaccharide
Oxane
Vinylogous acid
Ketone
Secondary alcohol
Acetal
Polyol
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Organic oxide
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxyanthraquinones (CHEBI:4783 )
Anthracenes and phenanthrenes (C10345 )
Anthraquinone type (C10345 )
Anthracenes and phenanthrenes (LMPK13040009 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302437)

Food

Herb and spice

Spice

Capers (FooDB: FOOD00039)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.23 g/L	ALOGPS
logP	0.71	ALOGPS
logP	0.9	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	7.24	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	173.98 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	104.28 m³·mol⁻¹	ChemAxon
Polarizability	41.98 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0302437

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

99649

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Glucocapangulin (CFc000281953)

MOL for CFc000281953 (Glucocapangulin)

3D MOL for CFc000281953 (Glucocapangulin)

3D SDF for CFc000281953 (Glucocapangulin)

3D-SDF for CFc000281953 (Glucocapangulin)

PDB for CFc000281953 (Glucocapangulin)

3D PDB for CFc000281953 (Glucocapangulin)

SMILES for CFc000281953 (Glucocapangulin)

INCHI for CFc000281953 (Glucocapangulin)

Structure for CFc000281953 (Glucocapangulin)

3D Structure for CFc000281953 (Glucocapangulin)