ChemFOnt: Showing chemical card for 3,5-Dihydroxyphenylpropionic acid (CFc000105942)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 21:23:07 UTC

Chemfont ID

CFc000105942

Molecule Identification

Common Name

3,5-Dihydroxyphenylpropionic acid

Definition

3,5-Dihydroxyphenylpropionic acid (3,5-DHPPA) is an alkylresorcinol metabolite. It is a potential urinary biomarker of whole grain intake (PMID: 15282102 ). BioTransformer predicts that 3,5-DHPPA is a product of 3,5-dihydroxycinnamic acid metabolism via a reduction-of-alpha-beta-unsaturated-compounds-pattern1 reaction occurring in human gut microbiota and catalyzed by the abkar1 enzyme (PMID: 30612223 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3,5-Dihydroxyphenylpropionate	Generator
3-(3,5-Dihydroxyphenyl)propanoate	Generator
3,5-DHPPA	HMDB
3,5-Dihydroxybenzenepropionic acid	HMDB
3,5-Dihydroxyphenylpropanoic acid	HMDB
3,5-Dihydroxyphenylpropionic acid	HMDB
3-(3,5-Dihydroxyphenyl)-1-propanoic acid	HMDB
3-(3,5-Dihydroxyphenyl)-1-propionic acid	HMDB
3-(3',5'-Dihydroxyphenyl)propanoic acid	HMDB
3-(3,5-Dihydroxyphenyl)propanoic acid	HMDB
3-(3,5-Dihydroxyphenyl)propanoic acid;	HMDB

Chemical Formula

C₉H₁₀O₄

Average Molecular Weight

182.175

Monoisotopic Molecular Weight

182.057908802

IUPAC Name

3-(3,5-dihydroxyphenyl)propanoic acid

Traditional Name

3-(3,5-dihydroxyphenyl)propanoic acid

CAS Registry Number

26539-01-5

SMILES

OC(=O)CCC1=CC(O)=CC(O)=C1

InChI Identifier

InChI=1S/C9H10O4/c10-7-3-6(1-2-9(12)13)4-8(11)5-7/h3-5,10-11H,1-2H2,(H,12,13)

InChI Key

ITPFIKQWNDGDLG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Phenylpropanoic acids

Sub Class

Not Available

Direct Parent

Phenylpropanoic acids

Alternative Parents

Substituents

3-phenylpropanoic-acid
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Carbonyl group
Organic oxygen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
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: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Source

Endogenous

Endogenous (HMDB: HMDB0125533)

Plant

Plant (HMDB: HMDB0125533)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Cocoa and cocoa product

Cocoa and cocoa products (HMDB: HMDB0125533)

Coffee and coffee product

Coffee product

Coffee products (HMDB: HMDB0125533)

Tea

Tea products (HMDB: HMDB0125533)

Fat and oil

Olive oil (HMDB: HMDB0125533)

Fruit

Fruits (HMDB: HMDB0125533)

Vegetable

Vegetables (HMDB: HMDB0125533)

Legumes (HMDB: HMDB0125533)

Cereal and cereal product

Cereal product

Whole grain cereal products (HMDB: HMDB0125533)

Nut

Nuts (HMDB: HMDB0125533)

Beverage

Alcoholic beverage

Red wine (HMDB: HMDB0125533)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.08 g/L	ALOGPS
logP	0.99	ALOGPS
logP	1.45	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	3.82	ChemAxon
pKa (Strongest Basic)	-5.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	45.93 m³·mol⁻¹	ChemAxon
Polarizability	17.89 Å³	ChemAxon
Number of Rings	1	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

HMDB0125533

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB084412

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

161525

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 3,5-Dihydroxyphenylpropionic acid (CFc000105942)

MOL for CFc000105942 (3,5-Dihydroxyphenylpropionic acid)

3D MOL for CFc000105942 (3,5-Dihydroxyphenylpropionic acid)

3D SDF for CFc000105942 (3,5-Dihydroxyphenylpropionic acid)

3D-SDF for CFc000105942 (3,5-Dihydroxyphenylpropionic acid)

PDB for CFc000105942 (3,5-Dihydroxyphenylpropionic acid)

3D PDB for CFc000105942 (3,5-Dihydroxyphenylpropionic acid)

SMILES for CFc000105942 (3,5-Dihydroxyphenylpropionic acid)

INCHI for CFc000105942 (3,5-Dihydroxyphenylpropionic acid)

Structure for CFc000105942 (3,5-Dihydroxyphenylpropionic acid)

3D Structure for CFc000105942 (3,5-Dihydroxyphenylpropionic acid)