MiMeDB: Showing metabocard for (3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoic acid (MMDBc0054887)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:37:10 UTC

Update Date

2022-08-12 20:09:07 UTC

Metabolite ID

MMDBc0054887

Metabolite Identification

Common Name

(3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoic acid

Description

(3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoate belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety. Based on a literature review very few articles have been published on (3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221372D          

 16 16  0  0  0  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  2  0  0  0  0
  7  3  2  0  0  0  0
  7  5  1  0  0  0  0
  8  4  2  0  0  0  0
  8  7  1  0  0  0  0
  9  6  1  0  0  0  0
 10  9  1  0  0  0  0
 11  8  1  0  0  0  0
 12  9  2  0  0  0  0
 13 10  1  0  0  0  0
 14 10  2  0  0  0  0
 15  5  1  0  0  0  0
 16  6  1  0  0  0  0
M  CHG  1  11  -1
M  END
> <DATABASE_ID>
MMDBc0054887

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(=C(\[H])C1=CC=CC=C1[O-])C(=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H8O4/c11-8-4-2-1-3-7(8)5-6-9(12)10(13)14/h1-6,11H,(H,13,14)/p-1/b6-5+

> <INCHI_KEY>
HMXOGGUFCBUALL-AATRIKPKSA-M

> <FORMULA>
C10H7O4

> <MOLECULAR_WEIGHT>
191.163

> <EXACT_MASS>
191.034982285

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
17.95078625822613

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1E)-3-carboxy-3-oxoprop-1-en-1-yl]benzen-1-olate

> <JCHEM_LOGP>
2.1217406059999995

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.866258802333414

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9273048818763874

> <JCHEM_PKA_STRONGEST_BASIC>
-6.441272584161891

> <JCHEM_POLAR_SURFACE_AREA>
77.43

> <JCHEM_REFRACTIVITY>
60.93710000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-[(1E)-3-carboxy-3-oxoprop-1-en-1-yl]benzenolate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         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      -1.334   3.850   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      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O-1
HETATM   12  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -4.001   6.930   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM   15  H   UNK     0      -2.667   1.540   0.000  0.00  0.00           H+0
HETATM   16  H   UNK     0       0.000   4.620   0.000  0.00  0.00           H+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    7                                                       
CONECT    4    2    8                                                       
CONECT    5    6    7   15                                                  
CONECT    6    5    9   16                                                  
CONECT    7    3    5    8                                                  
CONECT    8    4    7   11                                                  
CONECT    9    6   10   12                                                  
CONECT   10    9   13   14                                                  
CONECT   11    8                                                            
CONECT   12    9                                                            
CONECT   13   10                                                            
CONECT   14   10                                                            
CONECT   15    5                                                            
CONECT   16    6                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

Synonyms

Value	Source
(3E)-4-(2-Hydroxyphenyl)-2-oxobut-3-enoic acid	Generator

Molecular Formula

C₁₀H₇O₄

Average Mass

191.163

Monoisotopic Mass

191.034982285

IUPAC Name

2-[(1E)-3-carboxy-3-oxoprop-1-en-1-yl]benzen-1-olate

Traditional Name

2-[(1E)-3-carboxy-3-oxoprop-1-en-1-yl]benzenolate

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\[H])C1=CC=CC=C1[O-])C(=O)C(O)=O

InChI Identifier

InChI=1S/C10H8O4/c11-8-4-2-1-3-7(8)5-6-9(12)10(13)14/h1-6,11H,(H,13,14)/p-1/b6-5+

InChI Key

HMXOGGUFCBUALL-AATRIKPKSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Styrenes

Direct Parent

Styrenes

Alternative Parents

Substituents

Styrene
Phenoxide
Alpha-keto acid
Keto acid
Acryloyl-group
Alpha-hydroxy ketone
Alpha,beta-unsaturated ketone
Enone
Ketone
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic anion
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

2-oxo monocarboxylic acid anion (CHEBI:59353 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	2.12	ChemAxon
pKa (Strongest Acidic)	2.93	ChemAxon
pKa (Strongest Basic)	-6.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	77.43 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	60.94 m³·mol⁻¹	ChemAxon
Polarizability	17.95 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

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

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

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0014675	(3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoic acid	Pyruvic acid	Trans-O-hydroxybenzylidenepyruvate hydratase-aldolase	Aldol addition (or reverse)	RHEA	34755880
MMDBr0014677	2-hydroxychromene-2-carboxylic acid	(3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoic acid	2-hydroxychromene-2-carboxylate isomerase	Isomerization	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	2	Human ; Human sputum; Human subgingival plaque; Human feces
Bacteria/NULL	Proteobacteria	2	Human ; Human sputum; Human subgingival plaque; Human feces

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

7822158

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9543185

PDB ID

Not Available

ChEBI ID

59353

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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 ]

Showing metabocard for (3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoic acid (MMDBc0054887)

MOL for #<Metabolite:0x00007fa4e6f536a0>

3D MOL for #<Metabolite:0x00007fa4e6f536a0>

3D SDF for #<Metabolite:0x00007fa4e6f536a0>

3D-SDF for #<Metabolite:0x00007fa4e6f536a0>

PDB for #<Metabolite:0x00007fa4e6f536a0>

3D PDB for #<Metabolite:0x00007fa4e6f536a0>

SMILES for #<Metabolite:0x00007fa4e6f536a0>

INCHI for #<Metabolite:0x00007fa4e6f536a0>

Structure for #<Metabolite:0x00007fa4e6f536a0>

3D Structure for #<Metabolite:0x00007fa4e6f536a0>