Human Metabolome Database: Showing metabocard for Hydrocinnamic acid (HMDB0000764)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

enzymes (1) Show 1 protein

Record Information

Version

4.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2020-11-09 23:14:33 UTC

HMDB ID

HMDB0000764

Secondary Accession Numbers

HMDB00764

Metabolite Identification

Common Name

Hydrocinnamic acid

Description

Hydrocinnamic acid, also known as phenylpropanoate or dihydrocinnamate, 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. Hydrocinnamic acid is a drug. Hydrocinnamic acid is a weakly acidic compound (based on its pKa). Hydrocinnamic acid exists in all living organisms, ranging from bacteria to humans. Phenylpropanoic acid can be prepared from cinnamic acid by hydrogenation. Hydrocinnamic acid is a sweet, balsamic, and cinnamon tasting compound. Outside of the human body, hydrocinnamic acid has been detected, but not quantified in, several different foods, such as macadamia nuts, watercress, bamboo shoots, lupines, and ohelo berries. This could make hydrocinnamic acid a potential biomarker for the consumption of these foods. This compound is used frequently in cosmetic products such as perfumes, bath gels, detergent powders, liquid detergents, fabric softeners, and soaps as it gives off a floral scent. A characteristic reaction of phenylpropanoic acid is its cyclization to indanones. Phenylpropanoic acid is used in the food industry to preserve and maintain the original aroma quality of frozen foods. Phenylpropanoic acid is also added to food for technological purposes in a wide variety including manufacturing, processing, preparation, treatment, packaging, transportation or storage, and food additives. This compound is used as a sweetener as well to sweeten food and can be found in table top sweeteners. It is a white, crystalline solid with a sweet, floral scent at room temperature.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Phenyl-propionic acid	ChEBI
3-Phenylpropanoic acid	ChEBI
3-Phenylpropionsaeure	ChEBI
3PP	ChEBI
Benzenepropanoic acid	ChEBI
Benzenepropionic acid	ChEBI
Benzylacetic acid	ChEBI
beta-Phenylpropionic acid	ChEBI
Dihydrocinnamic acid	ChEBI
Hydrozimtsaeure	ChEBI
Phenylpropanoate	ChEBI
3-Phenylpropionic acid	Kegg
3-Phenyl-propionate	Generator
3-Phenylpropanoate	Generator
Benzenepropanoate	Generator
Benzenepropionate	Generator
Benzylacetate	Generator
b-Phenylpropionate	Generator
b-Phenylpropionic acid	Generator
beta-Phenylpropionate	Generator
Β-phenylpropionate	Generator
Β-phenylpropionic acid	Generator
Dihydrocinnamate	Generator
Phenylpropanoic acid	Generator
3-Phenylpropionate	Generator
Hydrocinnamate	Generator
3-Phenyl-N-propionate	HMDB
3-Phenyl-N-propionic acid	HMDB
Omega-phenylpropanoate	HMDB
Omega-phenylpropanoic acid	HMDB
W-Phenylpropanoate	HMDB
W-Phenylpropanoic acid	HMDB
3-Phenylpropionic acid, sodium salt	HMDB
3-Phenyl propionic acid	HMDB
HYDROCINNAMIC ACID	ChEBI
Phenylpropionic acid	HMDB
beta-Phenylpropanoic acid	HMDB
β-Phenylpropanoic acid	HMDB
ω-Phenylpropanoic acid	HMDB

Chemical Formula

C₉H₁₀O₂

Average Molecular Weight

150.1745

Monoisotopic Molecular Weight

150.068079564

IUPAC Name

3-phenylpropanoic acid

Traditional Name

3-phenylpropionic acid

CAS Registry Number

501-52-0

SMILES

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

InChI Identifier

InChI=1S/C9H10O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,10,11)

InChI Key

XMIIGOLPHOKFCH-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
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:28631 )
benzenes (CHEBI:28631 )

Ontology

Ingestion

Source:

Biological location:

Organ and components:

Subcellular:

Biofluid and excreta:

Process

Naturally occurring process:

Biological process:

Biochemical pathway:

Prostate cancer

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Biological role:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	45 - 48 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	5.9 mg/mL	Not Available
LogP	1.84	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
Water Solubility	1.7 g/L	ALOGPS
logP	1.84	ALOGPS
logP	2.06	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	4.73	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	41.97 m³·mol⁻¹	ChemAxon
Polarizability	15.94 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0udi-1920000000-829ee511cbcb511eaa0d	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-0udi-6910000000-1df0ef2a35aedd93b1f0	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0udl-9600000000-685b73e7f17a8be64f76	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9400000000-6b08d11fe7d8828ea0b4	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0udi-0900000000-271b64525610b577f87c	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0udl-9300000000-faf8506e70502be88599	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0f6x-9800000000-6d3e3634b1663556c431	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0udi-1940000000-4bdbde45f0dac2b3ec59	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udi-1920000000-829ee511cbcb511eaa0d	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0udi-6910000000-1df0ef2a35aedd93b1f0	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udi-2910000000-b14f8ca2c631d87eb834	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f6x-8900000000-bbfe334bf7c6f8fab3ed	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0596-9510000000-32f6cb9988fbfb2c022e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0udi-0900000000-60af9a7ac23f78383156	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0006-9100000000-9009f92e094d3f88cea0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000f-9000000000-1009c57a9a26d3fd03a1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-0udl-9600000000-f55343cc6dbf913455ec	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-D-300) , Positive	splash10-0006-9400000000-6b08d11fe7d8828ea0b4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - CI-B (JEOL JMS-D-300) , Positive	splash10-0udi-0900000000-271b64525610b577f87c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-0udl-9300000000-0b08772b626dd7c66feb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0002-0900000000-56bd4f79b41d2e676de8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0002-0900000000-7cb5eea800e6e65e5ea1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-052b-2900000000-b4b013241fad936a6040	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9100000000-21973848f978136e5896	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-00dj-0229210000-3bd038d0275527aaf06e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-00dj-0229210000-3bd038d0275527aaf06e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-270ffc8363f873d177bd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-053r-1900000000-add76f4d7844f97853a1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pdi-9700000000-96205e3f347617fff0ef	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-270ffc8363f873d177bd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-053r-1900000000-add76f4d7844f97853a1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pdi-9700000000-96205e3f347617fff0ef	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-5b044bdcdf02a8a2de01	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0532-0900000000-c1c19922a709d7d6d7ce	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-053r-3900000000-c83fd537546837259692	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-5b044bdcdf02a8a2de01	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0532-0900000000-c1c19922a709d7d6d7ce	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-053r-3900000000-c83fd537546837259692	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.553 +/- 0.109 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	0.938 +/- 0.429 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	1.057 +/- 0.424 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	44.348 +/- 43.85 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	0.58 +/- 0.121 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	0.504 +/- 0.062 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	0.54 +/- 0.108 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	2.111 +/- 1.705 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	27355821	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 975	19812218	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21761941	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected and Quantified	199.768 +/- 141.169 nmol/g wet feces	Adult (>18 years old)	Both	Normal	24010549	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	20809621	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected and Quantified	200.433 +/- 195.772 nmol/g wet feces	Adult (>18 years old)	Both	Normal	24010549	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	20809621	details
Feces	Detected and Quantified	415.517 +/- 423.507 nmol/g wet feces	Adult (>18 years old)	Both	Normal	24010549	details
Feces	Detected and Quantified	543.368 +/- 417.514 nmol/g wet feces	Adult (>18 years old)	Both	Normal	24010549	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	19573517	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24029555	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	25985090	details
Feces	Detected and Quantified	514.735 +/- 219.611 nmol/g wet feces	Not Specified	Not Specified	Normal	19573517	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Available	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	18085514	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21330412	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected and Quantified	76.977 (44.868-308.974) nmol/g wet feces	Adult (>18 years old)	Both	Normal	28029051	details
Feces	Detected and Quantified	284.336 +/- 246.380 nmol/g wet feces	Not Specified	Not Specified	Normal	20669995	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	28842642	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	20669995	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27065191	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25670064	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected and Quantified	2.34 +/- 2.49 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	2.40 +/- 3.87 uM	Adult (>18 years old)	Not Specified	Normal	Sugimoto et al. (...	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Saliva	Detected and Quantified	44.28 +/- 23.39 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Saliva	Detected and Quantified	3.54 +/- 2.71 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	4.07 +/- 3.99 uM	Adult (>18 years old)	Not Specified	Normal	Sugimoto et al. (...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 975	19812218	details
Urine	Detected and Quantified	0.142 +/- 0.06 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	19812218	details
Urine	Detected and Quantified	0.181 +/- 0.038 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	19812218	details
Urine	Detected and Quantified	0.176 +/- 0.075 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	19812218	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.5 (0.0-1.0) uM	Adult (>18 years old)	Both	Prostate Cancer	19212411	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Irritable bowel syndrome	21761941	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative colitis	21761941	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Crohn disease	28842642	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Irritable bowel syndrome	21330412	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative colitis	28842642	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Attachment loss	31026179	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Missing teeth	31026179	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Periodontal Probing Depth	31026179	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Prosthesis/Missing teeth	31026179	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Supragingival Plaque	31026179	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Tooth Decay	31026179	details

Associated Disorders and Diseases

Disease References

Prostate cancer
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Irritable bowel syndrome
Ponnusamy K, Choi JN, Kim J, Lee SY, Lee CH: Microbial community and metabolomic comparison of irritable bowel syndrome faeces. J Med Microbiol. 2011 Jun;60(Pt 6):817-27. doi: 10.1099/jmm.0.028126-0. Epub 2011 Feb 17. [PubMed:21330412 ] Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
Ulcerative colitis
Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ] Azario I, Pievani A, Del Priore F, Antolini L, Santi L, Corsi A, Cardinale L, Sawamoto K, Kubaski F, Gentner B, Bernardo ME, Valsecchi MG, Riminucci M, Tomatsu S, Aiuti A, Biondi A, Serafini M: Neonatal umbilical cord blood transplantation halts skeletal disease progression in the murine model of MPS-I. Sci Rep. 2017 Aug 25;7(1):9473. doi: 10.1038/s41598-017-09958-9. [PubMed:28842642 ]
Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Crohn's disease
Azario I, Pievani A, Del Priore F, Antolini L, Santi L, Corsi A, Cardinale L, Sawamoto K, Kubaski F, Gentner B, Bernardo ME, Valsecchi MG, Riminucci M, Tomatsu S, Aiuti A, Biondi A, Serafini M: Neonatal umbilical cord blood transplantation halts skeletal disease progression in the murine model of MPS-I. Sci Rep. 2017 Aug 25;7(1):9473. doi: 10.1038/s41598-017-09958-9. [PubMed:28842642 ]
Attachment loss
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Missing teeth
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Periodontal Probing Depth
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Prosthesis/Missing teeth
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Supragingival Plaque
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Tooth Decay
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]

Associated OMIM IDs

176807 (Prostate cancer)
114500 (Colorectal cancer)
266600 (Crohn's disease)

External Links

DrugBank ID

DB02024

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008271

KNApSAcK ID

Not Available

Chemspider ID

10181339

KEGG Compound ID

C05629

BioCyc ID

3-PHENYLPROPIONATE

BiGG ID

Not Available

Wikipedia Link

Phenylpropanoic_acid

METLIN ID

4153

PubChem Compound

107

PDB ID

Not Available

ChEBI ID

28631

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000247

References

Synthesis Reference

Muller, August John; Bowers, Joseph Stanton, Jr.; Eubanks, John Robert Ira; Geiger, Carey Cecil; Santobianco, John Gabriel. Process for preparing hydrocinnamic acid from cinnamaldehyde. PCT Int. Appl. (1999), 18 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Allen MC, Stafford CG, Nocerini MR: Quantitation of 4-cyclohexyl-2-hydroxy-3-(3-methylsulfanyl-2- [2-[(morpholine-4-carbonyl)amino]-3-phenylpropionylamino]propi onylamino ) butyric acid isopropyl ester (CP-80,794), a renin inhibitor, and its hydrolytic cleavage metabolite 2-[(morpholine-4-carbonyl)amino]-3-phenylpropionic acid (CP-84,364) in dog and human plasma by high-performance liquid chromatography. J Chromatogr B Biomed Sci Appl. 1997 Aug 29;696(2):243-51. [PubMed:9323544 ]
Iyer RA, Malhotra B, Khan S, Mitroka J, Bonacorsi S Jr, Waller SC, Rinehart JK, Kripalani K: Comparative biotransformation of radiolabeled [(14)C]omapatrilat and stable-labeled [(13)C(2)]omapatrilat after oral administration to rats, dogs, and humans. Drug Metab Dispos. 2003 Jan;31(1):67-75. [PubMed:12485955 ]
Iyer RA, Mitroka J, Malhotra B, Bonacorsi S Jr, Waller SC, Rinehart JK, Roongta VA, Kripalani K: Metabolism of [(14)C]omapatrilat, a sulfhydryl-containing vasopeptidase inhibitor in humans. Drug Metab Dispos. 2001 Jan;29(1):60-9. [PubMed:11124231 ]
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 ]
Jellet JJ, Forrest TP, Macdonald IA, Marrie TJ, Holdeman LV: Production of indole-3-propanoic acid and 3-(p-hydroxyphenyl)propanoic acid by Clostridium sporogenes: a convenient thin-layer chromatography detection system. Can J Microbiol. 1980 Apr;26(4):448-53. [PubMed:7378938 ]
Koistinen VM (2019). Effects of Food Processing and Gut Microbial Metabolism on Whole Grain Phytochemicals: A Metabolomics Approach. In Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510 (pp. 26-58). University of Eastern Finland. [ISBN:978-952-61-3088-0 ]

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Hydrocinnamic acid → 3,4,5-trihydroxy-6-[(3-phenylpropanoyl)oxy]oxane-2-carboxylic acid	details

Showing metabocard for Hydrocinnamic acid (HMDB0000764)

Structure for HMDB0000764 (Hydrocinnamic acid)

Enzymes

Reactions