Showing chemical card for N-(3',4'-Dihydroxycinnamoyl)-5-hydroxyanthranilic acid (CFc000234530)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 02:05:28 UTC

Chemfont ID

CFc000234530

Molecule Identification

Common Name

N-(3',4'-Dihydroxycinnamoyl)-5-hydroxyanthranilic acid

Definition

2-{[3-(3,4-dihydroxyphenyl)-1-hydroxyprop-2-en-1-ylidene]amino}-5-hydroxybenzoic acid belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 2-{[3-(3,4-dihydroxyphenyl)-1-hydroxyprop-2-en-1-ylidene]amino}-5-hydroxybenzoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI

MOL for CFc000234530 (N-(3',4'-Dihydroxycinnamoyl)-5-hydroxyanthranilic acid)

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3D MOL for CFc000234530 (N-(3',4'-Dihydroxycinnamoyl)-5-hydroxyanthranilic acid)

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3D SDF for CFc000234530 (N-(3',4'-Dihydroxycinnamoyl)-5-hydroxyanthranilic acid)

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3D-SDF for CFc000234530 (N-(3',4'-Dihydroxycinnamoyl)-5-hydroxyanthranilic acid)

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PDB for CFc000234530 (N-(3',4'-Dihydroxycinnamoyl)-5-hydroxyanthranilic acid)

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3D PDB for CFc000234530 (N-(3',4'-Dihydroxycinnamoyl)-5-hydroxyanthranilic acid)

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SMILES for CFc000234530 (N-(3',4'-Dihydroxycinnamoyl)-5-hydroxyanthranilic acid)

OC(=O)C1=CC(O)=CC=C1NC(=O)C=CC1=CC=C(O)C(O)=C1

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INCHI for CFc000234530 (N-(3',4'-Dihydroxycinnamoyl)-5-hydroxyanthranilic acid)

InChI=1S/C16H13NO6/c18-10-3-4-12(11(8-10)16(22)23)17-15(21)6-2-9-1-5-13(19)14(20)7-9/h1-8,18-20H,(H,17,21)(H,22,23)

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Structure for CFc000234530 (N-(3',4'-Dihydroxycinnamoyl)-5-hydroxyanthranilic acid)

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3D Structure for CFc000234530 (N-(3',4'-Dihydroxycinnamoyl)-5-hydroxyanthranilic acid)

Synonyms

Value	Source
2-{[3-(3,4-dihydroxyphenyl)-1-hydroxyprop-2-en-1-ylidene]amino}-5-hydroxybenzoate	Generator
N-(3',4'-Dihydroxycinnamoyl)-5-hydroxyanthranilate	Generator
Avenanthramide	MeSH
Avenanthramide 2C	MeSH
Avenanthramide-c	MeSH
Avenanthramide-2C	MeSH

Chemical Formula

C₁₆H₁₃NO₆

Average Molecular Weight

315.281

Monoisotopic Molecular Weight

315.074287143

IUPAC Name

2-[3-(3,4-dihydroxyphenyl)prop-2-enamido]-5-hydroxybenzoic acid

Traditional Name

2-[3-(3,4-dihydroxyphenyl)prop-2-enamido]-5-hydroxybenzoic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1=CC(O)=CC=C1NC(=O)C=CC1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C16H13NO6/c18-10-3-4-12(11(8-10)16(22)23)17-15(21)6-2-9-1-5-13(19)14(20)7-9/h1-8,18-20H,(H,17,21)(H,22,23)

InChI Key

IDUUXROOZBOOPH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Hydroxybenzoic acid derivatives

Alternative Parents

Benzoic acids
Styrenes
Catechols
Benzoyl derivatives
1-hydroxy-4-unsubstituted benzenoids
1-hydroxy-2-unsubstituted benzenoids
Propargyl-type 1,3-dipolar organic compounds
Carboxylic acids
Carboximidic acids
Organooxygen compounds
Organonitrogen compounds
Organic oxides
Hydrocarbon derivatives

Substituents

Hydroxybenzoic acid
Benzoic acid
Benzoyl
Styrene
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Carboximidic acid
Carboximidic acid derivative
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboxylic acid derivative
Carboxylic acid
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.086 g/L	ALOGPS
logP	2.55	ALOGPS
logP	2.97	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	3.31	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	127.09 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	84.54 m³·mol⁻¹	ChemAxon
Polarizability	31.1 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

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

68952594

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available