MiMeDB: Showing metabocard for 2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid (MMDBc0032861)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 22:03:15 UTC

Update Date

2024-10-13 11:39:50 UTC

Metabolite ID

MMDBc0032861

Metabolite Identification

Common Name

2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid

Description

Penta-2,4-dienoic acid in which the hydrogen at position 2 is substituted by hydroxy and one of the hydrogens at position 5 is substituted by a benzoyl group. It is a metabolic product of biphenyl from Pseudomonas putida.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652311182123032D          

 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
    0.0000    3.3000    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    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
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    0.0000 O   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
  5  2  1  0  0  0  0
  6  3  2  0  0  0  0
  7  4  2  0  0  0  0
  8  4  1  4  0  0  0
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
  7 10  1  4  0  0  0
 10  9  1  0  0  0  0
 11  8  2  0  0  0  0
 12 11  1  0  0  0  0
 13 10  2  0  0  0  0
 14 11  1  0  0  0  0
 15 12  2  0  0  0  0
 16 12  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0032861

> <DATABASE_NAME>
MIME

> <SMILES>
OC(=O)C(O)=CC=CC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H10O4/c13-10(9-5-2-1-3-6-9)7-4-8-11(14)12(15)16/h1-8,14H,(H,15,16)

> <INCHI_KEY>
RDRDHXDYMGUCKE-UHFFFAOYSA-N

> <FORMULA>
C12H10O4

> <MOLECULAR_WEIGHT>
218.208

> <EXACT_MASS>
218.057908802

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
21.853266050194073

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid

> <ALOGPS_LOGP>
1.63

> <JCHEM_LOGP>
1.7218827096666667

> <ALOGPS_LOGS>
-2.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.639119892898057

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4799635726538467

> <JCHEM_PKA_STRONGEST_BASIC>
-6.117600815419245

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
60.710100000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.59e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
HDPA

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-NOV-21         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       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.000   9.240   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -4.001   8.470   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -2.667  10.780   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    7    8                                                       
CONECT    5    2    9                                                       
CONECT    6    3    9                                                       
CONECT    7    4   10                                                       
CONECT    8    4   11                                                       
CONECT    9    5    6   10                                                  
CONECT   10    7    9   13                                                  
CONECT   11    8   12   14                                                  
CONECT   12   11   15   16                                                  
CONECT   13   10                                                            
CONECT   14   11                                                            
CONECT   15   12                                                            
CONECT   16   12                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

Synonyms

Value	Source
2,6-Dioxo-6-phenylhexa-3-enoate	ChEBI
2-Hydroxy-6-oxo-6-phenyl-2,4-hexadienoic acid	ChEBI
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoate	ChEBI
HDPA	ChEBI
HOPDA	ChEBI
2,6-Dioxo-6-phenylhexa-3-enoic acid	Generator
2-Hydroxy-6-oxo-6-phenyl-2,4-hexadienoate	Generator

Molecular Formula

C₁₂H₁₀O₄

Average Mass

218.208

Monoisotopic Mass

218.057908802

IUPAC Name

2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid

Traditional Name

HDPA

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C12H10O4/c13-10(9-5-2-1-3-6-9)7-4-8-11(14)12(15)16/h1-8,14H,(H,15,16)

InChI Key

RDRDHXDYMGUCKE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Medium-chain keto acids and derivatives

Direct Parent

Medium-chain keto acids and derivatives

Alternative Parents

Substituents

Medium-chain keto acid
Benzoyl
Aryl ketone
Hydroxy fatty acid
Fatty acyl
Monocyclic benzene moiety
Benzenoid
Unsaturated fatty acid
Alpha,beta-unsaturated ketone
Acryloyl-group
Enone
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Enol
Carboxylic acid
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

enone (CHEBI:17820 )
alpha,beta-unsaturated monocarboxylic acid (CHEBI:17820 )
aromatic ketone (CHEBI:17820 )
enol (CHEBI:17820 )
6-oxo monocarboxylic acid (CHEBI:17820 )
2-hydroxy monocarboxylic acid (CHEBI:17820 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.36 g/L	ALOGPS
logP	1.63	ALOGPS
logP	1.72	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.48	ChemAxon
pKa (Strongest Basic)	-6.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	60.71 m³·mol⁻¹	ChemAxon
Polarizability	21.85 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 (TMS_1_2) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	View Spectrum

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

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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	5	Human ; Human sputum; Human subgingival plaque; Human feces	Unknown
Bacteria	Firmicutes	1
Bacteria	Actinobacteria	1

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

21607346

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

17820

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 2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid (MMDBc0032861)

MOL for #<Metabolite:0x00007fab522d4d08>

3D MOL for #<Metabolite:0x00007fab522d4d08>

3D SDF for #<Metabolite:0x00007fab522d4d08>

3D-SDF for #<Metabolite:0x00007fab522d4d08>

PDB for #<Metabolite:0x00007fab522d4d08>

3D PDB for #<Metabolite:0x00007fab522d4d08>

SMILES for #<Metabolite:0x00007fab522d4d08>

INCHI for #<Metabolite:0x00007fab522d4d08>

Structure for #<Metabolite:0x00007fab522d4d08>

3D Structure for #<Metabolite:0x00007fab522d4d08>