ChemFOnt: Showing chemical card for Caffeoylcalleryanin (CFc000283312)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:36:28 UTC

Chemfont ID

CFc000283312

Molecule Identification

Common Name

Caffeoylcalleryanin

Definition

Caffeoylcalleryanin is a member of the class of compounds known as phenolic glycosides. Phenolic glycosides are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Caffeoylcalleryanin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Caffeoylcalleryanin can be found in pear, which makes caffeoylcalleryanin a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(3-Hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₂₂H₂₄O₁₁

Average Molecular Weight

464.4194

Monoisotopic Molecular Weight

464.13186161

IUPAC Name

(3-hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

(3-hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

CAS Registry Number

20300-49-6

SMILES

OCC1OC(OC2=CC=C(COC(=O)\C=C\C3=CC(O)=C(O)C=C3)C=C2O)C(O)C(O)C1O

InChI Identifier

InChI=1S/C22H24O11/c23-9-17-19(28)20(29)21(30)22(33-17)32-16-5-2-12(8-15(16)26)10-31-18(27)6-3-11-1-4-13(24)14(25)7-11/h1-8,17,19-26,28-30H,9-10H2/b6-3+

InChI Key

VTHLSAOVZTYBRV-ZZXKWVIFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthocyanidin-7-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Anthocyanidin-7-O-Glycosides

Alternative Parents

Substituents

Anthocyanidin-3-o-glycoside
Anthocyanidin-7-o-glycoside
Flavonoid-7-o-glycoside
Flavonoid-3-o-glycoside
Hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Anthocyanidin
Phenolic glycoside
O-glycosyl compound
Glycosyl compound
Disaccharide
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Phenol
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Oxane
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Polyol
Acetal
Primary alcohol
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organooxygen compound
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0303796)

Food

Fruit

Pome

Pear (FooDB: FOOD00152)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.47 g/L	ALOGPS
logP	0.52	ALOGPS
logP	0.76	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9.07	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	186.37 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	112.51 m³·mol⁻¹	ChemAxon
Polarizability	45.63 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0303796

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021704

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Caffeoylcalleryanin (CFc000283312)

MOL for CFc000283312 (Caffeoylcalleryanin)

3D MOL for CFc000283312 (Caffeoylcalleryanin)

3D SDF for CFc000283312 (Caffeoylcalleryanin)

3D-SDF for CFc000283312 (Caffeoylcalleryanin)

PDB for CFc000283312 (Caffeoylcalleryanin)

3D PDB for CFc000283312 (Caffeoylcalleryanin)

SMILES for CFc000283312 (Caffeoylcalleryanin)

INCHI for CFc000283312 (Caffeoylcalleryanin)

Structure for CFc000283312 (Caffeoylcalleryanin)

3D Structure for CFc000283312 (Caffeoylcalleryanin)