Livestock Metabolome Database: Showing metabocard for 3-(3-Hydroxyphenyl)propanoic acid (LMDB00148)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:43:24 UTC

Update Date

2016-07-20 20:56:57 UTC

Lmdb

LMDB00148

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3-(3-Hydroxyphenyl)propanoic acid

Description

3-(3-Hydroxyphenyl)propanoic (hMPP) acid is one of the major metabolites of ingested caffeic acid (PMID 15479001 ) and of the phenolic degradation products of proanthocyanidins (the most abundant polyphenol present in chocolate) by the microflora in the colon (PMID 12663291 ). mHPP is suspected to have antioxidants properties and is actively absorbed by the monocarboxylic acid transporter (MCT) in intestinal Caco-2 cell monolayers (PMID 15479001 , 12663291 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-(3-Hydroxy-phenyl)-propanoic acid	ChEBI
3-(m-Hydroxyphenyl)propionic acid	ChEBI
beta-(m-Hydroxyphenyl)propionic acid	ChEBI
Dihydro-3-coumaric acid	ChEBI
3-Hydroxyphenylpropanoate	Kegg
3-(3-Hydroxyphenyl)propanoate	Kegg
3-(3-Hydroxy-phenyl)-propanoate	Generator
3-(3-Hydroxyphenyl)propionate	Generator
3-(m-Hydroxyphenyl)propionate	Generator
b-(m-Hydroxyphenyl)propionate	Generator
b-(m-Hydroxyphenyl)propionic acid	Generator
beta-(m-Hydroxyphenyl)propionate	Generator
Β-(m-hydroxyphenyl)propionate	Generator
Β-(m-hydroxyphenyl)propionic acid	Generator
Dihydro-3-coumarate	Generator
3-Hydroxyphenylpropanoic acid	Generator
3-(3-Hydroxy-phenyl)-propionic acid	HMDB
3-Hydroxybenzenepropanoate	HMDB
3-Hydroxybenzenepropanoic acid	HMDB
3-Hydroxydihydrocinnamate	HMDB
3-Hydroxydihydrocinnamic acid	HMDB
3-Hydroxyhydrocinnamic acid	HMDB
3-Hydroxyphenylpropionate	HMDB
3-Hydroxyphenylpropionic acid	HMDB
b-(3-Hydroxyphenyl)propionate	HMDB
b-(3-Hydroxyphenyl)propionic acid	HMDB
beta-(3-Hydroxyphenyl)propionate	HMDB
beta-(3-Hydroxyphenyl)propionic acid	HMDB
dihydro-m-Coumarate	HMDB
dihydro-m-Coumaric acid	HMDB, MeSH
m-Hydrocoumaric acid	HMDB
m-Hydroxy-hydrocinnamate	HMDB
m-Hydroxy-hydrocinnamic acid	HMDB
m-Hydroxyphenylpropionate	HMDB
m-Hydroxyphenylpropionic acid	HMDB, MeSH
dihydro-3-Coumaric acid, monosodium salt	MeSH, HMDB
3-(3'-Hydroxyphenyl)propanoic acid	HMDB
3-(3-Hydroxyphenyl)propanoic acid	HMDB

Chemical Formula

C₉H₁₀O₃

Average Molecular Weight

166.1739

Monoisotopic Molecular Weight

166.062994186

IUPAC Name

3-(3-hydroxyphenyl)propanoic acid

Traditional Name

3-hydroxyphenylpropionic acid

CAS Registry Number

621-54-5

SMILES

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

InChI Identifier

InChI=1S/C9H10O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-3,6,10H,4-5H2,(H,11,12)

InChI Key

QVWAEZJXDYOKEH-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
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:1427 )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.14	ALOGPS
logP	1.75	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	4.21	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	43.95 m³·mol⁻¹	ChemAxon
Polarizability	16.92 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-01b9-1900000000-77779ae60312f591e17e	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4l-0930000000-cb674deffe8e93afca7e	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-01b9-1900000000-77779ae60312f591e17e	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4l-0930000000-cb674deffe8e93afca7e	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fr-3900000000-df46f44d343adb6bf4be	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00g0-9660000000-4030a1092b3837900ee3	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-0ef65243a7fdde063c52	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0avi-0900000000-f9b9f6b52e9e50218f53	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0avi-0900000000-de2d8585bc952e840460	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0aor-3900000000-a0c560a0e53e97f29b2b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-4a45085593200cc6c7d3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006t-1900000000-ac287061b5cdcc1f846b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f96-9400000000-1e275b3ba45b8048aa13	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-ec17e3f1692cb9469beb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ba-0900000000-4407c82bb7a72d9feb58	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00r5-4900000000-2b7cd80f8f959113fe79	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-0d7421595c1a4fe8a25e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-2900000000-efb21a9dd58f39dfcf57	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9300000000-258065f574b3915c0ac3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00xs-0900000000-3e37174dd2fc252c5cd1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0900000000-d6e289e9f660ec643659	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-3900000000-8e0c82231fc0135fc3cc	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Serum	Detected but not Quantified	Not Applicable	Not Available	Caprine	24214495	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0000375

FooDB ID

FDB021993

Phenol Explorer ID

Not Available

KNApSAcK ID

C00052683

BiGG ID

Not Available

BioCyc ID

3-HYDROXYPHENYL-PROPIONATE

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

ChEBI ID

1427

PubChem Compound ID

Kegg Compound ID

C11457

YMDB ID

Not Available

ECMDB ID

ECMDB00375

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Konishi Y, Kobayashi S: Microbial metabolites of ingested caffeic acid are absorbed by the monocarboxylic acid transporter (MCT) in intestinal Caco-2 cell monolayers. J Agric Food Chem. 2004 Oct 20;52(21):6418-24. [15479001 ]
Rios LY, Gonthier MP, Remesy C, Mila I, Lapierre C, Lazarus SA, Williamson G, Scalbert A: Chocolate intake increases urinary excretion of polyphenol-derived phenolic acids in healthy human subjects. Am J Clin Nutr. 2003 Apr;77(4):912-8. [12663291 ]

Showing metabocard for 3-(3-Hydroxyphenyl)propanoic acid (LMDB00148)

Structure for LMDB00148 (3-(3-Hydroxyphenyl)propanoic acid)