MiMeDB: Showing metabocard for 3-(2,3-Dihydroxyphenyl)propanoate (MMDBc0029994)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:49:53 UTC

Update Date

2024-04-30 19:43:56 UTC

Metabolite ID

MMDBc0029994

Metabolite Identification

Common Name

3-(2,3-Dihydroxyphenyl)propanoate

Description

3-(2,3-dihydroxyphenyl)propanoate is a member of the chemical class known as Catechols. These are compounds containing a 1,2-benzenediol moeity. 3-(2,3-dihydroxyphenyl)propanoate is invovled in Phenylpropionic acid degradation. The compound 3-(2,3-dihydroxyphenyl)propionate (DHPP) is a common intermediate of both pathways which must be cleaved by the MhpB dioxygenase before entering into the primary cell metabolism. (PMID 19520845 )

Structure

MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 22-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-AUG-19         0                                  
HETATM    1  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    6                                                       
CONECT    3    1    7                                                       
CONECT    4    5    6                                                       
CONECT    5    4    8                                                       
CONECT    6    2    4    9                                                  
CONECT    7    3    9   10                                                  
CONECT    8    5   11   12                                                  
CONECT    9    6    7   13                                                  
CONECT   10    7                                                            
CONECT   11    8                                                            
CONECT   12    8                                                            
CONECT   13    9                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

COMPND    https://cactus.nci.nih.gov/chemical/structure/OC(=O)CCC1=C(O)C(O)=CC=C1/file?... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  O   UNL     1       4.186  -0.260  -1.111  1.00  0.00           O  
HETATM    2  C   UNL     1       3.265  -0.048  -0.158  1.00  0.00           C  
HETATM    3  O   UNL     1       3.598   0.004   1.002  1.00  0.00           O  
HETATM    4  C   UNL     1       1.817   0.125  -0.535  1.00  0.00           C  
HETATM    5  C   UNL     1       0.984   0.351   0.729  1.00  0.00           C  
HETATM    6  C   UNL     1      -0.465   0.524   0.352  1.00  0.00           C  
HETATM    7  C   UNL     1      -1.273  -0.588   0.179  1.00  0.00           C  
HETATM    8  O   UNL     1      -0.760  -1.836   0.349  1.00  0.00           O  
HETATM    9  C   UNL     1      -2.611  -0.425  -0.170  1.00  0.00           C  
HETATM   10  O   UNL     1      -3.408  -1.513  -0.341  1.00  0.00           O  
HETATM   11  C   UNL     1      -3.128   0.849  -0.341  1.00  0.00           C  
HETATM   12  C   UNL     1      -2.316   1.954  -0.166  1.00  0.00           C  
HETATM   13  C   UNL     1      -0.989   1.792   0.185  1.00  0.00           C  
HETATM   14  H   UNL     1       5.103  -0.365  -0.821  1.00  0.00           H  
HETATM   15  H   UNL     1       1.713   0.985  -1.196  1.00  0.00           H  
HETATM   16  H   UNL     1       1.465  -0.771  -1.046  1.00  0.00           H  
HETATM   17  H   UNL     1       1.087  -0.509   1.391  1.00  0.00           H  
HETATM   18  H   UNL     1       1.336   1.247   1.241  1.00  0.00           H  
HETATM   19  H   UNL     1      -0.832  -2.171   1.253  1.00  0.00           H  
HETATM   20  H   UNL     1      -3.858  -1.801   0.466  1.00  0.00           H  
HETATM   21  H   UNL     1      -4.165   0.978  -0.612  1.00  0.00           H  
HETATM   22  H   UNL     1      -2.720   2.947  -0.300  1.00  0.00           H  
HETATM   23  H   UNL     1      -0.358   2.658   0.320  1.00  0.00           H  
CONECT    1    2   14                                                 
CONECT    2    1    3    3    4                                       
CONECT    3    2    2                                                 
CONECT    4    2    5   15   16                                       
CONECT    5    4    6   17   18                                       
CONECT    6    5    7    7   13                                       
CONECT    7    6    6    8    9                                       
CONECT    8    7   19                                                 
CONECT    9    7   10   11   11                                       
CONECT   10    9   20                                                 
CONECT   11    9    9   12   21                                       
CONECT   12   11   13   13   22                                       
CONECT   13   12   12    6   23                                       
CONECT   14    1                                                      
CONECT   15    4                                                      
CONECT   16    4                                                      
CONECT   17    5                                                      
CONECT   18    5                                                      
CONECT   19    8                                                      
CONECT   20   10                                                      
CONECT   21   11                                                      
CONECT   22   12                                                      
CONECT   23   13                                                      
MASTER        0    0    0    0    0    0    0    0   23    0   23    0
END

Synonyms

Value	Source
2,3-DHP	ChEBI
2,3-Dhppa	ChEBI
2,3-Dihydroxy-beta-phenylpropionic acid	ChEBI
2,3-Dihydroxyphenylpropionic acid	ChEBI
2,3-Dihyrroxybenzenepropanoic acid	ChEBI
3,4-Dihydroxyhydrocinnamic acid	ChEBI
3-(2,3-Dihydroxyphenyl)propionic acid	ChEBI
Hydrocaffeic acid	ChEBI
2,3-Dihydroxyphenylpropanoate	Kegg
2,3-Dihydroxy-b-phenylpropionate	Generator
2,3-Dihydroxy-b-phenylpropionic acid	Generator
2,3-Dihydroxy-beta-phenylpropionate	Generator
2,3-Dihydroxy-β-phenylpropionate	Generator
2,3-Dihydroxy-β-phenylpropionic acid	Generator
2,3-Dihydroxyphenylpropionate	Generator
2,3-Dihyrroxybenzenepropanoate	Generator
3,4-Dihydroxyhydrocinnamate	Generator
3-(2,3-Dihydroxyphenyl)propionate	Generator
Hydrocaffeate	Generator
2,3-Dihydroxyphenylpropanoic acid	Generator
3-(2,3-Dihydroxyphenyl)propanoic acid	Generator
3-(2,3-Dihydroxyphenyl)propanoate	Generator

Molecular Formula

C₉H₁₀O₄

Average Mass

182.1733

Monoisotopic Mass

182.057908808

IUPAC Name

3-(2,3-dihydroxyphenyl)propanoic acid

Traditional Name

2,3-dhppa

CAS Registry Number

3714-73-6

SMILES

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

InChI Identifier

InChI=1S/C9H10O4/c10-7-3-1-2-6(9(7)13)4-5-8(11)12/h1-3,10,13H,4-5H2,(H,11,12)

InChI Key

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:18136 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	3.02 g/L	ALOGPS
logP	1.04	ALOGPS
logP	1.45	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	3.84	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	45.93 m³·mol⁻¹	ChemAxon
Polarizability	17.68 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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-00ai-8169000000-57d099213b80f74754f0	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dr-0900000000-42307d872084e0a43967	2017-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-843dd549d47692169f19	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00ri-1900000000-4c55ee3c98ded47a7c93	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9400000000-715c4800f53e00770bea	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-b898849ef0adfdcc8ba6	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01qi-1900000000-d3f406f1106a548a81a4	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9700000000-06658447e99ab7e422b5	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-d450fceaa753730689bc	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bu9-0900000000-dd7ac8bdd1c9a01f90a2	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05no-6900000000-2004de093c4ed2588082	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-85d7a58f912ce2360f62	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0abj-5900000000-afd351c121906895b1a4	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fsa-9200000000-3e44754ea683742401ac	2021-09-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0008143	3-(3-Hydroxyphenyl)propionate	3-(2,3-Dihydroxyphenyl)propanoate	Not Available	VMH	30371894
MMDBr0008149	Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol	3-(2,3-Dihydroxyphenyl)propanoate	Not Available	VMH	30371894
MMDBr0008171	Melilotate	3-(2,3-Dihydroxyphenyl)propanoate	Not Available	VMH	30371894

Multistep Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0012752	L-Phenylalanine	trans-Cinnamic acid	Not Available			Manually annotated by MiMeDB team
MMDBr0012819	3-(3-Hydroxyphenyl)propanoic acid	3-(2,3-Dihydroxyphenyl)propanoate	Not Available	3-(3-hydroxy-phenyl)propionate hydroxylase	KEGG	6345502

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	62	Human feces; Human sputum; Human ; Human supragingival plaque; Human feces; pleural fluid plaque; bal; Human stool	Unknown; Metabolic reconstruction
Bacteria	Actinobacteria	22	Human feces; Human ; Cattle	Metabolic reconstruction

Exposure Sources

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

HMDB0134042

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB091062

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C04044

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

PDB ID

Not Available

ChEBI ID

18136

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Burlingame R, Chapman PJ: Catabolism of phenylpropionic acid and its 3-hydroxy derivative by Escherichia coli. J Bacteriol. 1983 Jul;155(1):113-21. doi: 10.1128/jb.155.1.113-121.1983. [PubMed:6345502 ]
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 ]
Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]
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 ]
Djoumbou Feunang, Yannick (2017). Cheminformatics Tools for Enabling Metabolomics, 2017 (PhD thesis). University of Alberta.

Showing metabocard for 3-(2,3-Dihydroxyphenyl)propanoate (MMDBc0029994)

MOL for #<Metabolite:0x00007fdb44180228>

3D MOL for #<Metabolite:0x00007fdb44180228>

3D SDF for #<Metabolite:0x00007fdb44180228>

3D-SDF for #<Metabolite:0x00007fdb44180228>

PDB for #<Metabolite:0x00007fdb44180228>

3D PDB for #<Metabolite:0x00007fdb44180228>

SMILES for #<Metabolite:0x00007fdb44180228>

INCHI for #<Metabolite:0x00007fdb44180228>

Structure for #<Metabolite:0x00007fdb44180228>

3D Structure for #<Metabolite:0x00007fdb44180228>