ChemFOnt: Showing chemical card for 1-Sinapoyl-2,2'-diferuloylgentiobiose (CFc000281237)

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

CFc000281237

Molecule Identification

Common Name

1-Sinapoyl-2,2'-diferuloylgentiobiose

Definition

1-sinapoyl-2,2'-diferuloylgentiobiose is a member of the class of compounds known as hydroxycinnamic acid glycosides. Hydroxycinnamic acid glycosides are glycosylated hydoxycinnamic acids derivatives. 1-sinapoyl-2,2'-diferuloylgentiobiose is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 1-sinapoyl-2,2'-diferuloylgentiobiose can be found in broccoli, which makes 1-sinapoyl-2,2'-diferuloylgentiobiose 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-6-{[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy}-5-{[(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

C₄₃H₄₈O₂₁

Average Molecular Weight

900.8286

Monoisotopic Molecular Weight

900.268808598

IUPAC Name

(2R,3R,4S,5S,6R)-2-{[(2R,3S,4S,5R,6S)-3,4-dihydroxy-6-{[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy}-5-{[(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-enoate

Traditional Name

CAS Registry Number

None

SMILES

COC1=CC(\C=C\C(=O)O[C@H]2[C@H](OC[C@H]3O[C@@H](OC(=O)\C=C\C4=CC(OC)=C(O)C(OC)=C4)[C@H](OC(=O)\C=C\C4=CC=C(O)C(OC)=C4)[C@@H](O)[C@@H]3O)O[C@H](CO)[C@@H](O)[C@@H]2O)=CC=C1O

InChI Identifier

InChI=1S/C43H48O21/c1-55-26-15-21(5-10-24(26)45)7-12-32(47)62-40-38(53)36(51)30(19-44)60-42(40)59-20-31-37(52)39(54)41(63-33(48)13-8-22-6-11-25(46)27(16-22)56-2)43(61-31)64-34(49)14-9-23-17-28(57-3)35(50)29(18-23)58-4/h5-18,30-31,36-46,50-54H,19-20H2,1-4H3/b12-7+,13-8+,14-9+/t30-,31-,36-,37-,38+,39+,40-,41-,42-,43+/m1/s1

InChI Key

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

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301721)

Food

Vegetable

Cabbage

Broccoli (FooDB: FOOD00034)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.049 g/L	ALOGPS
logP	2.81	ALOGPS
logP	2.86	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	9.1	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	305.35 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	218.84 m³·mol⁻¹	ChemAxon
Polarizability	88.81 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

HMDB0301721

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000269

KNApSAcK ID

Not Available

Chemspider ID

59696167

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101758854

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 1-Sinapoyl-2,2'-diferuloylgentiobiose (CFc000281237)

MOL for CFc000281237 (1-Sinapoyl-2,2'-diferuloylgentiobiose)

3D MOL for CFc000281237 (1-Sinapoyl-2,2'-diferuloylgentiobiose)

3D SDF for CFc000281237 (1-Sinapoyl-2,2'-diferuloylgentiobiose)

3D-SDF for CFc000281237 (1-Sinapoyl-2,2'-diferuloylgentiobiose)

PDB for CFc000281237 (1-Sinapoyl-2,2'-diferuloylgentiobiose)

3D PDB for CFc000281237 (1-Sinapoyl-2,2'-diferuloylgentiobiose)

SMILES for CFc000281237 (1-Sinapoyl-2,2'-diferuloylgentiobiose)

INCHI for CFc000281237 (1-Sinapoyl-2,2'-diferuloylgentiobiose)

Structure for CFc000281237 (1-Sinapoyl-2,2'-diferuloylgentiobiose)

3D Structure for CFc000281237 (1-Sinapoyl-2,2'-diferuloylgentiobiose)