MiMeDB: Showing metabocard for 3-(3-Hydroxyphenyl)propanoic acid (MMDBc0000514)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:39:30 UTC

Update Date

2022-08-31 06:07:54 UTC

Metabolite ID

MMDBc0000514

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 ). hMPP has been found to be a metabolite of Clostridium, Escherichia, and Eubacterium (PMID: 28393285 , 19520845 ). 3-(3-Hydroxyphenyl)propanoic acid is a flavonoid metabolite. 3-(3-Hydroxyphenyl)propanoic acid is a phenolic acid metabolite formed by the gut microflora detected after the consumption of whole grain.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Molecular Formula

C₉H₁₀O₃

Average Mass

166.1739

Monoisotopic Mass

166.062994186

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

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

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192140	UDP-glucuronosyltransferase 1-1	Enzyme	P22309	Homo_sapiens
MMDBp0197061	Sulfotransferase 1A3	Enzyme	P0DMM9	Homo_sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Eosinophilic esophagitis		Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Irritable bowel syndrome	increased	Association	Human feces	PubMed	21330412

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Verrucomicrobia	1	Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Archaea	Euryarchaeota	1		Indirect association between microbiota composition and metabolites measured in host biospecimen
Archaea	Euryarchaeota	1	Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Firmicutes	4		Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Age	Sex	Health Condition	Data Source	Reference
Human	Detected but not Quantified					NULL	NULL	Consuming polyphenols described by Phenol-Explorer entry 961	HMDB	12663291
Human	Detected and Quantified	1.5	0.46			Adult (>18 years old)	Both	Normal	HMDB	12663291
Human	Detected but not Quantified					NULL	NULL	Consuming polyphenols described by Phenol-Explorer entry 961	HMDB	12663291
Human	Detected and Quantified	0.32		0.2	0.5	Adult (>18 years old)	Not Specified	Normal	HMDB	15315398
Human	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	18052033
Human	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	18085514
Human	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	19573517
Human	Detected but not Quantified					NULL	NULL	Consuming polyphenols described by Phenol-Explorer entry 961	HMDB	19671472
Human	Detected but not Quantified					NULL	NULL	Consuming polyphenols described by Phenol-Explorer entry 961	HMDB	19671472
Human	Detected and Quantified	0.039	0.012			Adult (>18 years old)	Male	Normal	HMDB	19812218
Human	Detected and Quantified	0.775	0.747			Adult (>18 years old)	Male	Normal	HMDB	19812218
Human	Detected and Quantified	0.084	0.022			Adult (>18 years old)	Male	Normal	HMDB	19812218
Human	Detected and Quantified	0.035	0.008			Adult (>18 years old)	Male	Normal	HMDB	19812218
Human	Detected and Quantified	0.04	0.008			Adult (>18 years old)	Male	Normal	HMDB	19812218
Human	Detected and Quantified	0.034	0.01			Adult (>18 years old)	Male	Normal	HMDB	19812218
Human	Detected and Quantified	0.086	0.021			Adult (>18 years old)	Male	Normal	HMDB	19812218
Human	Detected and Quantified	0.056	0.015			Adult (>18 years old)	Male	Normal	HMDB	19812218
Human	Detected and Quantified	0.043	0.006			Adult (>18 years old)	Male	Normal	HMDB	19812218
Human	Detected but not Quantified					Adult (>18 years old)	Both	Hypertension (mild)	HMDB	20013882
Human	Detected but not Quantified					Adult (>18 years old)	Both	Hypertension (mild)	HMDB	20013882
Human	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	20669995
Human	Detected but not Quantified					Adult (>18 years old)	Both	Irritable bowel syndrome	HMDB	21330412
Human	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	21330412
Human	Detected and Quantified	74.0188	139.011			Adult (>18 years old)	Both	Normal	HMDB	24010549
Human	Detected and Quantified	105.913	182.941			Adult (>18 years old)	Both	Normal	HMDB	24010549
Human	Detected and Quantified	288.854	717.321			Adult (>18 years old)	Both	Normal	HMDB	24010549
Human	Detected and Quantified	290.659	834.066			Adult (>18 years old)	Both	Normal	HMDB	24010549
Human	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	25496753
Human	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	25762808
Human	Detected but not Quantified					Adult (>18 years old)	Both	Colorectal Cancer	HMDB	27275383
Human	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	27543620
Human	Detected but not Quantified					Adult (>18 years old)	Not Specified	asymptomatic diverticulosis	HMDB	27622378
Human	Detected but not Quantified					Adult (>18 years old)	Not Specified	symptomatic uncomplicated diverticular disease	HMDB	27622378
Human	Detected but not Quantified					Adult (>18 years old)	Not Specified	Normal	HMDB	27622378
Human	Detected and Quantified	9.0508		0.0722	110.366	Adult (>18 years old)	Both	Normal	HMDB	28029051
Human	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	29808030
Human	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	32966057
Human	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	32966057
Human	Detected and Quantified	1.325				Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human	Detected and Quantified	2.292				Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human	Detected and Quantified	0.034	0.01			Adult (>18 years old)	Male	Normal	HMDB	19812218
Human	Detected and Quantified	0.035	0.008			Adult (>18 years old)	Male	Normal	HMDB	19812218
Human	Detected and Quantified	0.039	0.012			Adult (>18 years old)	Male	Normal	HMDB	19812218
Human	Detected and Quantified	0.04	0.008			Adult (>18 years old)	Male	Normal	HMDB	19812218
Human	Detected and Quantified	0.043	0.006			Adult (>18 years old)	Male	Normal	HMDB	19812218
Human	Detected and Quantified	0.056	0.015			Adult (>18 years old)	Male	Normal	HMDB	19812218
Human	Detected and Quantified	0.084	0.022			Adult (>18 years old)	Male	Normal	HMDB	19812218
Human	Detected and Quantified	0.086	0.021			Adult (>18 years old)	Male	Normal	HMDB	19812218
Human	Detected and Quantified	0.32		0.2	0.5	Adult (>18 years old)	Not Specified	Normal	HMDB	15315398
Human	Detected and Quantified	0.775	0.747			Adult (>18 years old)	Male	Normal	HMDB	19812218
Human	Detected and Quantified	1.5	0.46			Adult (>18 years old)	Both	Normal	HMDB	12663291
Human	Detected and Quantified	105.913	182.941			Adult (>18 years old)	Both	Normal	HMDB	24010549
Human	Detected and Quantified	288.854	717.321			Adult (>18 years old)	Both	Normal	HMDB	24010549
Human	Detected and Quantified	290.659	834.0660			Adult (>18 years old)	Both	Normal	HMDB	24010549
Human	Detected and Quantified	74.0188	139.0110			Adult (>18 years old)	Both	Normal	HMDB	24010549
Human	Detected and Quantified	9.0508		0.0722	110.366	Adult (>18 years old)	Both	Normal	HMDB	28029051
Human	Detected and Quantified	2.292				Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	18052033
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	18085514
Human Feces	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	19573517
Human Feces	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	20669995
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	21330412
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	25496753
Human Feces	Detected but not Quantified					Adult (>18 years old)	Not Specified	Normal	HMDB	27622378
Human Blood	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	25762808
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

Not Available

General References

Duran M, Wanders RJ, de Jager JP, Dorland L, Bruinvis L, Ketting D, Ijlst L, van Sprang FJ: 3-Hydroxydicarboxylic aciduria due to long-chain 3-hydroxyacyl-coenzyme A dehydrogenase deficiency associated with sudden neonatal death: protective effect of medium-chain triglyceride treatment. Eur J Pediatr. 1991 Jan;150(3):190-5. doi: 10.1007/BF01963564. [PubMed:2044590 ]
Nakazawa T, Ohsawa K: Metabolites of orally administered Perilla frutescens extract in rats and humans. Biol Pharm Bull. 2000 Jan;23(1):122-7. doi: 10.1248/bpb.23.122. [PubMed:10706426 ]
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. doi: 10.1093/ajcn/77.4.912. [PubMed:12663291 ]
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. doi: 10.1021/jf049560y. [PubMed:15479001 ]
Manso I, Torres B, Andreu JM, Menendez M, Rivas G, Alfonso C, Diaz E, Garcia JL, Galan B: 3-Hydroxyphenylpropionate and phenylpropionate are synergistic activators of the MhpR transcriptional regulator from Escherichia coli. J Biol Chem. 2009 Aug 7;284(32):21218-28. doi: 10.1074/jbc.M109.008243. Epub 2009 Jun 11. [PubMed:19520845 ]
Upadhyaya S, Banerjee G: Type 2 diabetes and gut microbiome: at the intersection of known and unknown. Gut Microbes. 2015;6(2):85-92. doi: 10.1080/19490976.2015.1024918. [PubMed:25901889 ]
Rowland I, Gibson G, Heinken A, Scott K, Swann J, Thiele I, Tuohy K: Gut microbiota functions: metabolism of nutrients and other food components. Eur J Nutr. 2018 Feb;57(1):1-24. doi: 10.1007/s00394-017-1445-8. Epub 2017 Apr 9. [PubMed:28393285 ]
Koistinen VM (2019). Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510. University of Eastern Finland.

Showing metabocard for 3-(3-Hydroxyphenyl)propanoic acid (MMDBc0000514)

MOL for #<Metabolite:0x00007f1240ec2bc0>

3D MOL for #<Metabolite:0x00007f1240ec2bc0>

3D SDF for #<Metabolite:0x00007f1240ec2bc0>

3D-SDF for #<Metabolite:0x00007f1240ec2bc0>

PDB for #<Metabolite:0x00007f1240ec2bc0>

3D PDB for #<Metabolite:0x00007f1240ec2bc0>

SMILES for #<Metabolite:0x00007f1240ec2bc0>

INCHI for #<Metabolite:0x00007f1240ec2bc0>

Structure for #<Metabolite:0x00007f1240ec2bc0>

3D Structure for #<Metabolite:0x00007f1240ec2bc0>