MiMeDB: Showing metabocard for 2-hydroxy-5-carboxymethylmuconic acid semialdehyde (MMDBc0055236)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:46:59 UTC

Update Date

2022-08-12 20:09:17 UTC

Metabolite ID

MMDBc0055236

Metabolite Identification

Common Name

2-hydroxy-5-carboxymethylmuconic acid semialdehyde

Description

5-formyl-2-hydroxyhepta-2,4-dienedioate, also known as 2-hydroxy-5-carboxymethylmuconate semialdehyde, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Based on a literature review very few articles have been published on 5-formyl-2-hydroxyhepta-2,4-dienedioate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221462D          

 16 15  0  0  0  0            999 V2000
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    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
    3.3000    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    0.7145    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  5  1  2  0  0  0  0
  5  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  2  2  0  0  0  0
  7  3  1  0  0  0  0
  8  6  1  0  0  0  0
  9  4  2  0  0  0  0
 10  6  1  0  0  0  0
 11  7  2  0  0  0  0
 12  7  1  0  0  0  0
 13  8  2  0  0  0  0
 14  8  1  0  0  0  0
 15  1  1  0  0  0  0
 16  2  1  0  0  0  0
M  CHG  2  10  -1  12  -1
M  END
> <DATABASE_ID>
MMDBc0055236

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O6/c9-4-5(3-7(11)12)1-2-6(10)8(13)14/h1-2,4,10H,3H2,(H,11,12)(H,13,14)/p-2/b5-1-,6-2-

> <INCHI_KEY>
NLXIEJRQAIHYPN-IOBHVTPZSA-L

> <FORMULA>
C8H6O6

> <MOLECULAR_WEIGHT>
198.131

> <EXACT_MASS>
198.017535073

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
16.62577956459168

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3Z,5Z)-6-carboxy-3-formyl-6-oxidohexa-3,5-dienoate

> <JCHEM_LOGP>
-0.6710952023333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.027284694795906

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1952610648560262

> <JCHEM_PKA_STRONGEST_BASIC>
-5.764754952448357

> <JCHEM_POLAR_SURFACE_AREA>
117.55999999999999

> <JCHEM_REFRACTIVITY>
67.9785

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3Z,5Z)-6-carboxy-3-formyl-6-oxidohexa-3,5-dienoate

> <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       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.620   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.160   2.667   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.160   0.000   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -0.770   1.334   0.000  0.00  0.00           O-1
HETATM   11  O   UNK     0       6.930   4.001   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       6.930   1.334   0.000  0.00  0.00           O-1
HETATM   13  O   UNK     0       0.000  -2.667   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -2.310  -1.334   0.000  0.00  0.00           O+0
HETATM   15  H   UNK     0       1.540   2.667   0.000  0.00  0.00           H+0
HETATM   16  H   UNK     0       2.310  -1.334   0.000  0.00  0.00           H+0
CONECT    1    2    5   15                                                  
CONECT    2    1    6   16                                                  
CONECT    3    5    7                                                       
CONECT    4    5    9                                                       
CONECT    5    1    3    4                                                  
CONECT    6    2    8   10                                                  
CONECT    7    3   11   12                                                  
CONECT    8    6   13   14                                                  
CONECT    9    4                                                            
CONECT   10    6                                                            
CONECT   11    7                                                            
CONECT   12    7                                                            
CONECT   13    8                                                            
CONECT   14    8                                                            
CONECT   15    1                                                            
CONECT   16    2                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

Synonyms

Value	Source
2-Hydroxy-5-carboxymethylmuconate semialdehyde	ChEBI
5-Formyl-2-hydroxyhepta-2,4-dienedioate dianion	ChEBI
5-Formyl-2-hydroxyhepta-2,4-dienedioate(2-)	ChEBI
2-Hydroxy-5-carboxymethylmuconic acid semialdehyde	Generator
5-Formyl-2-hydroxyhepta-2,4-dienedioic acid dianion	Generator
5-Formyl-2-hydroxyhepta-2,4-dienedioic acid(2-)	Generator
5-Formyl-2-hydroxyhepta-2,4-dienedioic acid	Generator

Molecular Formula

C₈H₆O₆

Average Mass

198.131

Monoisotopic Mass

198.017535073

IUPAC Name

(3Z,5Z)-6-carboxy-3-formyl-6-oxidohexa-3,5-dienoate

Traditional Name

(3Z,5Z)-6-carboxy-3-formyl-6-oxidohexa-3,5-dienoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C8H8O6/c9-4-5(3-7(11)12)1-2-6(10)8(13)14/h1-2,4,10H,3H2,(H,11,12)(H,13,14)/p-2/b5-1-,6-2-

InChI Key

NLXIEJRQAIHYPN-IOBHVTPZSA-L

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-chain fatty acids

Alternative Parents

Substituents

Medium-chain fatty acid
Branched fatty acid
Dicarboxylic acid or derivatives
Unsaturated fatty acid
Alpha,beta-unsaturated aldehyde
Enal
Enolate
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Organic oxide
Carbonyl group
Organic oxygen compound
Aldehyde
Hydrocarbon derivative
Organic anion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dicarboxylic acid dianion (CHEBI:58030 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	-0.67	ChemAxon
pKa (Strongest Acidic)	3.2	ChemAxon
pKa (Strongest Basic)	-5.8	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	117.56 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	67.98 m³·mol⁻¹	ChemAxon
Polarizability	16.63 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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
MMDBr0013448	3,4-Dihydroxybenzeneacetic acid	2-hydroxy-5-carboxymethylmuconic acid semialdehyde	3,4-dihydroxyphenylacetate 2,3-dioxygenase	Oxygenation	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	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool

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

26331014

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

58030

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-5-carboxymethylmuconic acid semialdehyde (MMDBc0055236)

MOL for #<Metabolite:0x00007fa4dbf0b298>

3D MOL for #<Metabolite:0x00007fa4dbf0b298>

3D SDF for #<Metabolite:0x00007fa4dbf0b298>

3D-SDF for #<Metabolite:0x00007fa4dbf0b298>

PDB for #<Metabolite:0x00007fa4dbf0b298>

3D PDB for #<Metabolite:0x00007fa4dbf0b298>

SMILES for #<Metabolite:0x00007fa4dbf0b298>

INCHI for #<Metabolite:0x00007fa4dbf0b298>

Structure for #<Metabolite:0x00007fa4dbf0b298>

3D Structure for #<Metabolite:0x00007fa4dbf0b298>