MiMeDB: Showing metabocard for Melilotate (MMDBc0049972)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-29 22:47:22 UTC

Update Date

2022-12-15 22:52:19 UTC

Metabolite ID

MMDBc0049972

Metabolite Identification

Common Name

Melilotate

Description

3-(2-Hydroxyphenyl)propanoic acid, also known as melilotic acid or melilotate, 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. 3-(2-Hydroxyphenyl)propanoic acid exists in all living organisms, ranging from bacteria to humans. 3-(2-Hydroxyphenyl)propanoic acid has been detected, but not quantified in, several different foods, such as bilberries (Vaccinium myrtillus), chinese cinnamons (Cinnamomum aromaticum), herbs and spices, pulses, and red beetroots (Beta vulgaris var. rubra). This could make 3-(2-hydroxyphenyl)propanoic acid a potential biomarker for the consumption of these foods. 3-(2-Hydroxyphenyl)propanoic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on 3-(2-Hydroxyphenyl)propanoic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    7                                                       
CONECT    4    2    8                                                       
CONECT    5    6    7                                                       
CONECT    6    5    9                                                       
CONECT    7    3    5    8                                                  
CONECT    8    4    7   10                                                  
CONECT    9    6   11   12                                                  
CONECT   10    8                                                            
CONECT   11    9                                                            
CONECT   12    9                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

Synonyms

Value	Source
2-Hydroxybenzenepropanoic acid	ChEBI
3-(2-Hydroxyphenyl)propionic acid	ChEBI
3-(O-Hydroxyphenyl) propionic acid	ChEBI
Melilotic acid	ChEBI
O-Hydroxyphenylpropionic acid	ChEBI
2-Hydroxyphenylpropanoate	Kegg
Melilotate	Kegg
3-(2-Hydroxyphenyl)propionate	Kegg
2-Hydroxybenzenepropanoate	Generator
3-(O-Hydroxyphenyl) propionate	Generator
O-Hydroxyphenylpropionate	Generator
2-Hydroxyphenylpropanoic acid	Generator
3-(2-Hydroxyphenyl)propanoate	Generator
2-Hydroxy-benzenepropanoic acid	HMDB
2-Hydroxybenzenepropanoic acid, 9ci	HMDB
3-(2-Hydroxyphenyl) propanoic acid	HMDB
3-(2-Hydroxyphenyl) propionate	HMDB
3-(O-Hydroxyphenyl)propionic acid, 8ci	HMDB
beta -(O-Hydroxyphenyl)propionic acid	HMDB
beta-(O-Hydroxyphenyl)propionic acid	HMDB
Hydrocoumaric acid	HMDB
O-Hydroxyhydrocinnamic acid	HMDB
OHPA	MeSH
Ortho-hydroxyphenylpropionic acid	MeSH

Molecular Formula

C₉H₁₀O₃

Average Mass

166.1739

Monoisotopic Mass

166.062994186

IUPAC Name

3-(2-hydroxyphenyl)propanoic acid

Traditional Name

melilotic acid

CAS Registry Number

Not Available

SMILES

OC(=O)CCC1=CC=CC=C1O

InChI Identifier

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

InChI Key

CJBDUOMQLFKVQC-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:16104 )
phenols (CHEBI:16104 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	2.76 g/L	ALOGPS
logP	1.12	ALOGPS
logP	1.75	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	4.22	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	16.77 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-01r6-1920000000-ecd488078d5985eafbfb	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-01r6-1920000000-ecd488078d5985eafbfb	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0910000000-b8cabfe5c488ee1ed604	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ab9-3900000000-58936d8a48b093519ddf	2017-07-27	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00g0-9660000000-6b8bf956c80314489670	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-9be30b68ac3a0ad3df6e	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-0900000000-0dbababdf59aa8829b0c	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-05fr-0900000000-168a901fccbb4f1968d0	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-1900000000-d8ea269e67bd24e633aa	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-5900000000-337a9131168ae129bf9e	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-00di-0900000000-43f2a467bcbee742fee2	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-0900000000-9adde0cc4bea462de661	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-de3ff31763098e280e32	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-05fr-0900000000-5777067548061cda18bf	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-00di-0900000000-d7b812ec743763dc8ed2	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-05fr-0900000000-ee2762870ca42fef2943	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-0900000000-5cf8803d756201d8053a	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05fs-2900000000-6784db2a14b98ff73d39	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056r-9300000000-20e163ee7cf68d1903d5	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-03d3c3e2a1e37e56c664	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01b9-1900000000-1aab1942696c4a143efb	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9400000000-e8222e98d8f7bc4e7bde	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-1900000000-b7a29c579ef060cdc630	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ab9-3900000000-b1e43f2b95b115732091	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9200000000-217c3ef57768e4d5c9a5	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-fdb6c955b5072a411a8f	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fk9-1900000000-940a0dff66b02484072d	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9400000000-209c76387b87ff609feb	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Feces

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

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0008171	Hydrogen Ion	3-(2,3-Dihydroxyphenyl)propanoate	Not Available	Melilotate 3-monooxygenase	VMH	30371894
MMDBr0012891	3,4-dihydrocoumarin	Melilotate	Bifunctional esterase/perhydrolase DCH	Ester hydrolysis	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	21	Human feces; Human sputum; Human ; Human subgingival plaque	Metabolic reconstruction
Bacteria	Actinobacteria	9	Human feces; Human	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0033752

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

873

PDB ID

Not Available

ChEBI ID

16104

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]
Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. Boca Raton: Chapman & Hall/CRC..

Showing metabocard for Melilotate (MMDBc0049972)

MOL for #<Metabolite:0x000055c79c2a8b68>

3D MOL for #<Metabolite:0x000055c79c2a8b68>

3D SDF for #<Metabolite:0x000055c79c2a8b68>

3D-SDF for #<Metabolite:0x000055c79c2a8b68>

PDB for #<Metabolite:0x000055c79c2a8b68>

3D PDB for #<Metabolite:0x000055c79c2a8b68>

SMILES for #<Metabolite:0x000055c79c2a8b68>

INCHI for #<Metabolite:0x000055c79c2a8b68>

Structure for #<Metabolite:0x000055c79c2a8b68>

3D Structure for #<Metabolite:0x000055c79c2a8b68>