ChemFOnt: Showing chemical card for 3-{3-[3,4-dihydroxy-6-(hydroxymethyl)-5-(sulfooxy)oxan-2-yl]-2,3-dihydroxy-5-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-dioxocyclohex-1-en-1-yl}-3-(4-hydroxyphenyl)propanoic acid (CFc000128717)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 21:57:18 UTC

Chemfont ID

CFc000128717

Molecule Identification

Common Name

3-{3-[3,4-dihydroxy-6-(hydroxymethyl)-5-(sulfooxy)oxan-2-yl]-2,3-dihydroxy-5-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-dioxocyclohex-1-en-1-yl}-3-(4-hydroxyphenyl)propanoic acid

Definition

3-{3-[3,4-dihydroxy-6-(hydroxymethyl)-5-(sulfooxy)oxan-2-yl]-2,3-dihydroxy-5-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-dioxocyclohex-1-en-1-yl}-3-(4-hydroxyphenyl)propanoic acid belongs to the class of organic compounds known as curcuminoids. These are aromatic compounds containing a curcumin moiety, which is composed of two aryl buten-2-one (feruloyl) chromophores joined by a methylene group. Based on a literature review very few articles have been published on 3-{3-[3,4-dihydroxy-6-(hydroxymethyl)-5-(sulfooxy)oxan-2-yl]-2,3-dihydroxy-5-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-dioxocyclohex-1-en-1-yl}-3-(4-hydroxyphenyl)propanoic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-{3-[3,4-dihydroxy-6-(hydroxymethyl)-5-(sulfooxy)oxan-2-yl]-2,3-dihydroxy-5-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-dioxocyclohex-1-en-1-yl}-3-(4-hydroxyphenyl)propanoate	Generator
3-{3-[3,4-dihydroxy-6-(hydroxymethyl)-5-(sulphooxy)oxan-2-yl]-2,3-dihydroxy-5-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-dioxocyclohex-1-en-1-yl}-3-(4-hydroxyphenyl)propanoate	Generator
3-{3-[3,4-dihydroxy-6-(hydroxymethyl)-5-(sulphooxy)oxan-2-yl]-2,3-dihydroxy-5-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-dioxocyclohex-1-en-1-yl}-3-(4-hydroxyphenyl)propanoic acid	Generator

Chemical Formula

C₃₀H₃₀O₁₇S

Average Molecular Weight

694.61

Monoisotopic Molecular Weight

694.12037068

IUPAC Name

3-{3-[3,4-dihydroxy-6-(hydroxymethyl)-5-(sulfooxy)oxan-2-yl]-2,3-dihydroxy-5-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-dioxocyclohex-1-en-1-yl}-3-(4-hydroxyphenyl)propanoic acid

Traditional Name

3-{3-[3,4-dihydroxy-6-(hydroxymethyl)-5-(sulfooxy)oxan-2-yl]-2,3-dihydroxy-5-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-dioxocyclohex-1-en-1-yl}-3-(4-hydroxyphenyl)propanoic acid

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\[H])C1=CC=C(O)C=C1)C(=O)C1C(=O)C(C(CC(O)=O)C2=CC=C(O)C=C2)=C(O)C(O)(C2OC(CO)C(OS(O)(=O)=O)C(O)C2O)C1=O

InChI Identifier

InChI=1S/C30H30O17S/c31-12-19-26(47-48(43,44)45)24(38)25(39)29(46-19)30(42)27(40)21(17(11-20(35)36)14-4-8-16(33)9-5-14)23(37)22(28(30)41)18(34)10-3-13-1-6-15(32)7-2-13/h1-10,17,19,22,24-26,29,31-33,38-40,42H,11-12H2,(H,35,36)(H,43,44,45)/b10-3+

InChI Key

KNXVWXMZQPMPEY-XCVCLJGOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as curcuminoids. These are aromatic compounds containing a curcumin moiety, which is composed of two aryl buten-2-one (feruloyl) chromophores joined by a methylene group.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Diarylheptanoids

Sub Class

Linear diarylheptanoids

Direct Parent

Curcuminoids

Alternative Parents

Substituents

Bis-desmethoxycurcumin
Terpene glycoside
Hydroxycinnamic acid or derivatives
Hexose monosaccharide
Glycosyl compound
3-phenylpropanoic-acid
C-glycosyl compound
Aromatic monoterpenoid
Monocyclic monoterpenoid
Monoterpenoid
Styrene
M-benzoquinone
Quinone
1,3-diketone
1-hydroxy-2-unsubstituted benzenoid
Phenol
Cyclohexenone
Acyloin
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Oxane
Sulfuric acid ester
Alkyl sulfate
1,3-dicarbonyl compound
Sulfuric acid monoester
Sulfate-ester
Organic sulfuric acid or derivatives
Tertiary alcohol
Acryloyl-group
Alpha,beta-unsaturated ketone
Vinylogous acid
Enone
Cyclic ketone
Secondary alcohol
Ketone
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Dialkyl ether
Enol
Organoheterocyclic compound
Ether
Oxacycle
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Alcohol
Carbonyl group
Primary alcohol
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0148308)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.82 g/L	ALOGPS
logP	0.62	ALOGPS
logP	-1.7	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	-1.9	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	302.95 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	159.9 m³·mol⁻¹	ChemAxon
Polarizability	64.13 Å³	ChemAxon
Number of Rings	4	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

HMDB0148308

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

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 3-{3-[3,4-dihydroxy-6-(hydroxymethyl)-5-(sulfooxy)oxan-2-yl]-2,3-dihydroxy-5-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-dioxocyclohex-1-en-1-yl}-3-(4-hydroxyphenyl)propanoic acid (CFc000128717)

MOL for CFc000128717 (3-{3-[3,4-dihydroxy-6-(hydroxymethyl)-5-(sulfooxy)oxan-2-yl]-2,3-dihydroxy-5-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-dioxocyclohex-1-en-1-yl}-3-(4-hydroxyphenyl)propanoic acid)

3D MOL for CFc000128717 (3-{3-[3,4-dihydroxy-6-(hydroxymethyl)-5-(sulfooxy)oxan-2-yl]-2,3-dihydroxy-5-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-dioxocyclohex-1-en-1-yl}-3-(4-hydroxyphenyl)propanoic acid)

3D SDF for CFc000128717 (3-{3-[3,4-dihydroxy-6-(hydroxymethyl)-5-(sulfooxy)oxan-2-yl]-2,3-dihydroxy-5-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-dioxocyclohex-1-en-1-yl}-3-(4-hydroxyphenyl)propanoic acid)

3D-SDF for CFc000128717 (3-{3-[3,4-dihydroxy-6-(hydroxymethyl)-5-(sulfooxy)oxan-2-yl]-2,3-dihydroxy-5-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-dioxocyclohex-1-en-1-yl}-3-(4-hydroxyphenyl)propanoic acid)

PDB for CFc000128717 (3-{3-[3,4-dihydroxy-6-(hydroxymethyl)-5-(sulfooxy)oxan-2-yl]-2,3-dihydroxy-5-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-dioxocyclohex-1-en-1-yl}-3-(4-hydroxyphenyl)propanoic acid)

3D PDB for CFc000128717 (3-{3-[3,4-dihydroxy-6-(hydroxymethyl)-5-(sulfooxy)oxan-2-yl]-2,3-dihydroxy-5-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-dioxocyclohex-1-en-1-yl}-3-(4-hydroxyphenyl)propanoic acid)

SMILES for CFc000128717 (3-{3-[3,4-dihydroxy-6-(hydroxymethyl)-5-(sulfooxy)oxan-2-yl]-2,3-dihydroxy-5-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-dioxocyclohex-1-en-1-yl}-3-(4-hydroxyphenyl)propanoic acid)

INCHI for CFc000128717 (3-{3-[3,4-dihydroxy-6-(hydroxymethyl)-5-(sulfooxy)oxan-2-yl]-2,3-dihydroxy-5-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-dioxocyclohex-1-en-1-yl}-3-(4-hydroxyphenyl)propanoic acid)

Structure for CFc000128717 (3-{3-[3,4-dihydroxy-6-(hydroxymethyl)-5-(sulfooxy)oxan-2-yl]-2,3-dihydroxy-5-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-dioxocyclohex-1-en-1-yl}-3-(4-hydroxyphenyl)propanoic acid)

3D Structure for CFc000128717 (3-{3-[3,4-dihydroxy-6-(hydroxymethyl)-5-(sulfooxy)oxan-2-yl]-2,3-dihydroxy-5-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-4,6-dioxocyclohex-1-en-1-yl}-3-(4-hydroxyphenyl)propanoic acid)