MiMeDB: Showing metabocard for 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid (MMDBc0032832)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 02:33:02 UTC

Update Date

2022-08-31 18:51:53 UTC

Metabolite ID

MMDBc0032832

Metabolite Identification

Common Name

2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid

Description

NULL

Structure

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

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       0.713   1.961   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.705   3.492   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.614   1.185   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.046   1.192   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       2.039   4.261   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -0.628   4.254   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.614  -0.346   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.940  -1.115   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.734  -1.115   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.940  -2.667   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.734  -2.667   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.614  -3.450   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.628  -4.995   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1                                                            
CONECT    5    2                                                            
CONECT    6    2                                                            
CONECT    7    3    8    9                                                  
CONECT    8    7   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   12                                                       
CONECT   12   10   13   11                                                  
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

Synonyms

Value	Source
4,alpha-Dihydroxycinnamic acid	ChEBI
4-Hydroxy-enol-phenylpyruvate	Kegg
4,a-Dihydroxycinnamate	Generator
4,a-Dihydroxycinnamic acid	Generator
4,alpha-Dihydroxycinnamate	Generator
4,Α-dihydroxycinnamate	Generator
4,Α-dihydroxycinnamic acid	Generator
4-Hydroxy-enol-phenylpyruvic acid	Generator
2-Hydroxy-3-(4-hydroxyphenyl)propenoate	Generator

Molecular Formula

C₉H₈O₄

Average Mass

180.1574

Monoisotopic Mass

180.042258744

IUPAC Name

(2Z)-2-hydroxy-3-(4-hydroxyphenyl)prop-2-enoic acid

Traditional Name

4,α-dihydroxycinnamic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-5,10-11H,(H,12,13)/b8-5-

InChI Key

GQYBCIHRWMPOOF-YVMONPNESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylpyruvic acid derivatives

Direct Parent

Phenylpyruvic acid derivatives

Alternative Parents

Substituents

Cinnamic acid
Cinnamic acid or derivatives
Coumaric acid
Coumaric acid or derivatives
Hydroxycinnamic acid
Hydroxycinnamic acid or derivatives
Enol-phenylpyruvate
Phenol
1-hydroxy-2-unsubstituted benzenoid
Monocarboxylic acid or derivatives
Enol
Carboxylic acid
Carboxylic acid derivative
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:27683 )
2-hydroxy monocarboxylic acid (CHEBI:27683 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.81 g/L	ALOGPS
logP	1.28	ALOGPS
logP	1.31	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	3.16	ChemAxon
pKa (Strongest Basic)	-6	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	2	ChemAxon
Refractivity	47.01 m³·mol⁻¹	ChemAxon
Polarizability	17.25 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 (Non-derivatized) - 70eV, Positive	splash10-053r-1900000000-10c51d0329cb2a35dbb8	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-00gi-6259000000-cdf2744454615081e02f	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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0bu0-0900000000-a08730e02c84f43e7926	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0900000000-2eb4f2eaa5d547249a3e	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-7900000000-63f2942443ac7bfdce48	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-8576bdecf0b58e989df6	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-46e515a63da5ddf92de9	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-0900000000-3c0a27f480b5bb59093c	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-02f0fa9241cf4b1591c7	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9800000000-0e7b12140d77aa62a512	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0api-4900000000-6f21f2ecdec85109e7d5	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01qi-0900000000-28cf4812bb35ce056a15	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-1900000000-bd40f97e341181046c0f	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9200000000-c7f40face58730829b4a	2021-09-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	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
MMDBp0191773	Macrophage migration inhibitory factor	Enzyme	P14174	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0010412	4-Hydroxyphenylpyruvic acid	2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid	macrophage migration inhibitory factor (glycosylation-inhibiting factor)		VMH; KEGG	30371894

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	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

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

HMDB0006915

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB024152

KNApSAcK ID

Not Available

Chemspider ID

552441

KEGG Compound ID

C05350

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

636708

PDB ID

Not Available

ChEBI ID

27683

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 ]
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 ]

Showing metabocard for 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid (MMDBc0032832)

MOL for #<Metabolite:0x00007fed159230d8>

3D MOL for #<Metabolite:0x00007fed159230d8>

3D SDF for #<Metabolite:0x00007fed159230d8>

3D-SDF for #<Metabolite:0x00007fed159230d8>

PDB for #<Metabolite:0x00007fed159230d8>

3D PDB for #<Metabolite:0x00007fed159230d8>

SMILES for #<Metabolite:0x00007fed159230d8>

INCHI for #<Metabolite:0x00007fed159230d8>

Structure for #<Metabolite:0x00007fed159230d8>

3D Structure for #<Metabolite:0x00007fed159230d8>