ChemFOnt: Showing chemical card for Dimalonylawobanin (CFc000281416)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:32:47 UTC

Chemfont ID

CFc000281416

Molecule Identification

Common Name

Dimalonylawobanin

Definition

Dimalonylawobanin is a member of the class of compounds known as flavonoid 3-o-p-coumaroyl glycosides. Flavonoid 3-o-p-coumaroyl glycosides are flavonoid 3-O-glycosides where the carbohydrate moiety is esterified with a p-coumaric acid. P-coumaric acid is an organic derivative of cinnamic acid, that carries a hydroxyl group at the 4-position of the benzene ring. Dimalonylawobanin is practically insoluble (in water) and a moderately acidic compound (based on its pKa). Dimalonylawobanin can be found in hyssop, which makes dimalonylawobanin a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₄₂H₄₁O₂₅

Average Molecular Weight

945.7599

Monoisotopic Molecular Weight

945.193691862

IUPAC Name

5-{[(2S,3R,4R,5S,6R)-5-[(2-carboxyacetyl)oxy]-6-{[(2-carboxyacetyl)oxy]methyl}-3,4-dihydroxyoxan-2-yl]oxy}-7-hydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium

Traditional Name

CAS Registry Number

128508-49-6

SMILES

O[C@@H]1[C@@H](COC(=O)\C=C\C2=CC=C(O)C=C2)O[C@@H](OC2=CC3=C(C=C(O)C=C3O[C@@H]3O[C@H](COC(=O)CC(O)=O)[C@@H](OC(=O)CC(O)=O)[C@H](O)[C@H]3O)[O+]=C2C2=CC(O)=C(O)C(O)=C2)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C42H40O25/c43-18-4-1-16(2-5-18)3-6-30(51)60-14-26-34(55)35(56)37(58)41(65-26)64-25-11-20-23(62-39(25)17-7-21(45)33(54)22(46)8-17)9-19(44)10-24(20)63-42-38(59)36(57)40(67-32(53)13-29(49)50)27(66-42)15-61-31(52)12-28(47)48/h1-11,26-27,34-38,40-42,55-59H,12-15H2,(H6-,43,44,45,46,47,48,49,50,51,54)/p+1/t26-,27-,34-,35+,36-,37-,38-,40-,41-,42-/m1/s1

InChI Key

LVWQQRKFDAHVIR-KJEREKKNSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid 3-o-p-coumaroyl glycosides. These are flavonoid 3-O-glycosides where the carbohydrate moiety is esterified with a p-coumaric acid. P-coumaric acid is an organic derivative of cinnamic acid, that carries a hydroxyl group at the 4-position of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid 3-O-p-coumaroyl glycosides

Alternative Parents

Substituents

Flavonoid 3-o-6-p-coumaroyl-glycoside
Anthocyanidin-3-o-glycoside
Anthocyanin
Anthocyanidin-5-o-glycoside
Flavonoid-3-o-glycoside
Hydroxyflavonoid
3'-hydroxyflavonoid
4'-hydroxyflavonoid
7-hydroxyflavonoid
Anthocyanidin
Pentacarboxylic acid or derivatives
Phenolic glycoside
Coumaric acid ester
Coumaric acid or derivatives
Cinnamic acid ester
Hydroxycinnamic acid or derivatives
Cinnamic acid or derivatives
O-glycosyl compound
Glycosyl compound
Benzopyran
1-benzopyran
Pyrogallol derivative
Benzenetriol
Styrene
Fatty acid ester
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Fatty acyl
Benzenoid
1,3-dicarbonyl compound
Oxane
Monosaccharide
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Heteroaromatic compound
Carboxylic acid ester
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Acetal
Oxacycle
Polyol
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Carbonyl group
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301900)

Food

Herb and spice

Herb

Hyssop (FooDB: FOOD00089)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.21 g/L	ALOGPS
logP	2.49	ALOGPS
logP	1.43	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	2.94	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	21	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	405.86 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	222.92 m³·mol⁻¹	ChemAxon
Polarizability	87.88 Å³	ChemAxon
Number of Rings	6	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

HMDB0301900

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001590

KNApSAcK ID

Not Available

Chemspider ID

30780073

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101633885

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Dimalonylawobanin (CFc000281416)

MOL for CFc000281416 (Dimalonylawobanin)

3D MOL for CFc000281416 (Dimalonylawobanin)

3D SDF for CFc000281416 (Dimalonylawobanin)

3D-SDF for CFc000281416 (Dimalonylawobanin)

PDB for CFc000281416 (Dimalonylawobanin)

3D PDB for CFc000281416 (Dimalonylawobanin)

SMILES for CFc000281416 (Dimalonylawobanin)

INCHI for CFc000281416 (Dimalonylawobanin)

Structure for CFc000281416 (Dimalonylawobanin)

3D Structure for CFc000281416 (Dimalonylawobanin)