ChemFOnt: Showing chemical card for 3-hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulphate (CFc000040435)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:41:55 UTC

Chemfont ID

CFc000040435

Molecule Identification

Common Name

3-hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulphate

Definition

3-hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulphate is the conjugate of 3-hydroxy-3-(3-hydroxyphenyl)propanoic acid and sulphate. (3-Hydroxyphenyl)hydracrylate (HPHPA) is an organic acid detected in human urine. It is thought that the presence of this acid is from nutritional sources (i.e. dietary phenylalanine). However, there has been a considerable degree of ambiguity in the origin and/or significance of this compound (PMID:11978597 ). Recently it has been reported that HPHPA is actually an abnormal phenylalanine metabolite arising from bacterial metabolism in the gastrointestinal tract. Specifically HPHPA appears to arise from the action of the anaerobic bacteria Clostrida sp. (PMID:20423563 ). Elevated levels of HPHPA have been reported in the urine of children with autism as well as in adult patients with schizophrenia. It has been proposed that HPHPA may be a bacterial metabolite of m-tyrosine, a tyrosine analog that causes symptoms of autism in experimental animals.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Hydroxy-3-(3-hydroxyphenyl)propanoate-O-sulfate	Generator
3-Hydroxy-3-(3-hydroxyphenyl)propanoate-O-sulphate	Generator
3-Hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulfuric acid	Generator
3-Hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulphuric acid	Generator
SulfO 3-hydroxy-3-(3-hydroxyphenyl)propanoic acid	Generator
SulphO 3-hydroxy-3-(3-hydroxyphenyl)propanoate	Generator
SulphO 3-hydroxy-3-(3-hydroxyphenyl)propanoic acid	Generator

Chemical Formula

C₉H₁₀O₇S

Average Molecular Weight

262.237

Monoisotopic Molecular Weight

262.014723364

IUPAC Name

sulfo 3-hydroxy-3-(3-hydroxyphenyl)propanoate

Traditional Name

sulfo 3-hydroxy-3-(3-hydroxyphenyl)propanoate

CAS Registry Number

None

SMILES

OC(CC(=O)OS(O)(=O)=O)C1=CC(O)=CC=C1

InChI Identifier

InChI=1S/C9H10O7S/c10-7-3-1-2-6(4-7)8(11)5-9(12)16-17(13,14)15/h1-4,8,10-11H,5H2,(H,13,14,15)

InChI Key

MDWXOTLIYUYWJP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Beta hydroxy acids and derivatives

Direct Parent

Beta hydroxy acids and derivatives

Alternative Parents

Substituents

1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Beta-hydroxy acid
Phenol
Monocyclic benzene moiety
Benzenoid
Sulfuric acid ester
Sulfuric acid monoester
Organic sulfuric acid or derivatives
Carboxylic acid salt
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic salt
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Urine (PMID: 22827565)

Source

Endogenous

Endogenous (HMDB: HMDB0059967)

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)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.31 g/L	ALOGPS
logP	-0.95	ALOGPS
logP	-1.7	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	-2.1	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	121.13 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	55.59 m³·mol⁻¹	ChemAxon
Polarizability	22.24 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0059967

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

124202083

PDB ID

Not Available

ChEBI ID

88716

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 3-hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulphate (CFc000040435)

MOL for CFc000040435 (3-hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulphate)

3D MOL for CFc000040435 (3-hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulphate)

3D SDF for CFc000040435 (3-hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulphate)

3D-SDF for CFc000040435 (3-hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulphate)

PDB for CFc000040435 (3-hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulphate)

3D PDB for CFc000040435 (3-hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulphate)

SMILES for CFc000040435 (3-hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulphate)

INCHI for CFc000040435 (3-hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulphate)

Structure for CFc000040435 (3-hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulphate)

3D Structure for CFc000040435 (3-hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulphate)