ChemFOnt: Showing chemical card for trans-Caffeic acid [apiosyl-(1->6)-glucosyl] ester (CFc000014778)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:03:38 UTC

Chemfont ID

CFc000014778

Molecule Identification

Common Name

trans-Caffeic acid [apiosyl-(1->6)-glucosyl] ester

Definition

trans-Caffeic acid [apiosyl-(1->6)-glucosyl] ester is found in herbs and spices. trans-Caffeic acid [apiosyl-(1->6)-glucosyl] ester is a constituent of Salvia officinalis (sage).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
trans-Caffeate [apiosyl-(1->6)-glucosyl] ester	Generator
6-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₂₀H₂₆O₁₃

Average Molecular Weight

474.4126

Monoisotopic Molecular Weight

474.137340918

IUPAC Name

6-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

6-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

CAS Registry Number

501-16-6

SMILES

OCC1(O)COC(OCC2OC(OC(=O)\C=C\C3=CC(O)=C(O)C=C3)C(O)C(O)C2O)C1O

InChI Identifier

InChI=1S/C20H26O13/c21-7-20(29)8-31-19(17(20)28)30-6-12-14(25)15(26)16(27)18(32-12)33-13(24)4-2-9-1-3-10(22)11(23)5-9/h1-5,12,14-19,21-23,25-29H,6-8H2/b4-2+

InChI Key

LULOGYYPGZOKQW-DUXPYHPUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxycinnamic acid glycosides. These are glycosylated hydoxycinnamic acids derivatives.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acid glycosides

Alternative Parents

Substituents

Hydroxycinnamic acid glycoside
O-cinnamoyl glycoside
Cinnamic acid ester
Coumaric acid or derivatives
Disaccharide
Glycosyl compound
O-glycosyl compound
Styrene
Catechol
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
Phenol
1-hydroxy-4-unsubstituted benzenoid
Fatty acyl
Benzenoid
Oxane
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Polyol
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Primary alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033694)
Cytoplasm (HMDB: HMDB0033694)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033694)

Source

Exogenous

Exogenous (HMDB: HMDB0033694)

Food

Food (HMDB: HMDB0033694)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0033694)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033694)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	6.29 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-1.8	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	215.83 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	106.12 m³·mol⁻¹	ChemAxon
Polarizability	45.78 Å³	ChemAxon
Number of Rings	3	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

HMDB0033694

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB011803

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

131751480

PDB ID

Not Available

ChEBI ID

169593

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for trans-Caffeic acid [apiosyl-(1->6)-glucosyl] ester (CFc000014778)

MOL for CFc000014778 (trans-Caffeic acid [apiosyl-(1->6)-glucosyl] ester)

3D MOL for CFc000014778 (trans-Caffeic acid [apiosyl-(1->6)-glucosyl] ester)

3D SDF for CFc000014778 (trans-Caffeic acid [apiosyl-(1->6)-glucosyl] ester)

3D-SDF for CFc000014778 (trans-Caffeic acid [apiosyl-(1->6)-glucosyl] ester)

PDB for CFc000014778 (trans-Caffeic acid [apiosyl-(1->6)-glucosyl] ester)

3D PDB for CFc000014778 (trans-Caffeic acid [apiosyl-(1->6)-glucosyl] ester)

SMILES for CFc000014778 (trans-Caffeic acid [apiosyl-(1->6)-glucosyl] ester)

INCHI for CFc000014778 (trans-Caffeic acid [apiosyl-(1->6)-glucosyl] ester)

Structure for CFc000014778 (trans-Caffeic acid [apiosyl-(1->6)-glucosyl] ester)

3D Structure for CFc000014778 (trans-Caffeic acid [apiosyl-(1->6)-glucosyl] ester)