ChemFOnt: Showing chemical card for 1,2,2'-Triferuloylgentiobiose (CFc000281238)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:32:25 UTC

Chemfont ID

CFc000281238

Molecule Identification

Common Name

1,2,2'-Triferuloylgentiobiose

Definition

1,2,2'-triferuloylgentiobiose is a member of the class of compounds known as hydroxycinnamic acid glycosides. Hydroxycinnamic acid glycosides are glycosylated hydoxycinnamic acids derivatives. 1,2,2'-triferuloylgentiobiose is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 1,2,2'-triferuloylgentiobiose can be found in broccoli, which makes 1,2,2'-triferuloylgentiobiose a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2R,3R,4S,5S,6R)-2-{[(2R,3S,4S,5R,6S)-3,4-dihydroxy-5,6-bis({[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy})oxan-2-yl]methoxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₄₂H₄₆O₂₀

Average Molecular Weight

870.8026

Monoisotopic Molecular Weight

870.258243912

IUPAC Name

(2S,3R,4S,5S,6R)-6-({[(2R,3R,4S,5S,6R)-4,5-dihydroxy-3-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-4,5-dihydroxy-3-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}oxan-2-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Traditional Name

CAS Registry Number

None

SMILES

COC1=CC(\C=C\C(=O)O[C@@H]2O[C@H](CO[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3OC(=O)\C=C\C3=CC=C(O)C(OC)=C3)[C@@H](O)[C@H](O)[C@H]2OC(=O)\C=C\C2=CC=C(O)C(OC)=C2)=CC=C1O

InChI Identifier

InChI=1S/C42H46O20/c1-54-27-16-21(4-10-24(27)44)7-13-32(47)60-39-37(52)35(50)30(19-43)58-41(39)57-20-31-36(51)38(53)40(61-33(48)14-8-22-5-11-25(45)28(17-22)55-2)42(59-31)62-34(49)15-9-23-6-12-26(46)29(18-23)56-3/h4-18,30-31,35-46,50-53H,19-20H2,1-3H3/b13-7+,14-8+,15-9+/t30-,31-,35-,36-,37+,38+,39-,40-,41-,42+/m1/s1

InChI Key

KHUQBGCNTVZZRF-BQCRRWLHSA-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
Coumaric acid or derivatives
Cinnamic acid ester
Disaccharide
Glycosyl compound
O-glycosyl compound
Methoxyphenol
Tricarboxylic acid or derivatives
Anisole
Phenoxy compound
Phenol ether
Styrene
Methoxybenzene
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Alkyl aryl ether
Phenol
Benzenoid
Fatty acyl
Monocyclic benzene moiety
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Acetal
Ether
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Alcohol
Primary alcohol
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301722)

Food

Vegetable

Cabbage

Broccoli (FooDB: FOOD00034)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.045 g/L	ALOGPS
logP	2.76	ALOGPS
logP	3.01	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	9.39	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	296.12 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	212.37 m³·mol⁻¹	ChemAxon
Polarizability	85.68 Å³	ChemAxon
Number of Rings	5	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

HMDB0301722

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000270

KNApSAcK ID

Not Available

Chemspider ID

59696168

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101758855

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 1,2,2'-Triferuloylgentiobiose (CFc000281238)

MOL for CFc000281238 (1,2,2'-Triferuloylgentiobiose)

3D MOL for CFc000281238 (1,2,2'-Triferuloylgentiobiose)

3D SDF for CFc000281238 (1,2,2'-Triferuloylgentiobiose)

3D-SDF for CFc000281238 (1,2,2'-Triferuloylgentiobiose)

PDB for CFc000281238 (1,2,2'-Triferuloylgentiobiose)

3D PDB for CFc000281238 (1,2,2'-Triferuloylgentiobiose)

SMILES for CFc000281238 (1,2,2'-Triferuloylgentiobiose)

INCHI for CFc000281238 (1,2,2'-Triferuloylgentiobiose)

Structure for CFc000281238 (1,2,2'-Triferuloylgentiobiose)

3D Structure for CFc000281238 (1,2,2'-Triferuloylgentiobiose)