MiMeDB: Showing metabocard for 2-Aminomuconic acid (MMDBc0048172)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-29 21:52:23 UTC

Update Date

2022-12-15 22:52:18 UTC

Metabolite ID

MMDBc0048172

Metabolite Identification

Common Name

2-Aminomuconic acid

Description

(2Z,4E)-2-ammoniomuconate(1-), also known as (2Z,4E)-2-aminomuconic acid, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon) (2Z,4E)-2-ammoniomuconate(1-) is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on (2Z,4E)-2-ammoniomuconate(1-).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304292223522D          

 17 16  0  0  0  0            999 V2000
    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 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
    2.4750    0.0000    0.0000 H   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
    3.3000    1.4289    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.0625    2.1434    0.0000 O   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
    1.2375   -0.7145    0.0000 H   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
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  5  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
   -0.4125    0.7145    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 H   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
   -1.1270    0.3020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
M  CHG  3   6  -1  12  -1  14   1
M  END
> <DATABASE_ID>
MMDBc0048172

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H7NO4/c7-4(6(10)11)2-1-3-5(8)9/h1-3H,7H2,(H,8,9)(H,10,11)/p-1/b3-1+,4-2-

> <INCHI_KEY>
ZRHONLCTYUYMIQ-TZFCGSKZSA-M

> <FORMULA>
C6H6NO4

> <MOLECULAR_WEIGHT>
156.118

> <EXACT_MASS>
156.030231257

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
13.722856688153541

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z,4E)-2-azaniumylhexa-2,4-dienedioate

> <ALOGPS_LOGP>
-1.57

> <JCHEM_LOGP>
-3.076452598331282

> <ALOGPS_LOGS>
-1.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.8858930807360506

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.5823469052998527

> <JCHEM_PKA_STRONGEST_BASIC>
8.370806500114028

> <JCHEM_POLAR_SURFACE_AREA>
107.89999999999999

> <JCHEM_REFRACTIVITY>
71.51750000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.85e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z,4E)-2-ammoniohexa-2,4-dienedioate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  H   UNK     0       1.540   2.667   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM    4  H   UNK     0       4.620   0.000   0.000  0.00  0.00           H+0
HETATM    5  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.160   2.667   0.000  0.00  0.00           O-1
HETATM    7  O   UNK     0       3.850   4.001   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    9  H   UNK     0       2.310  -1.334   0.000  0.00  0.00           H+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.000  -2.667   0.000  0.00  0.00           O-1
HETATM   13  O   UNK     0      -2.310  -1.334   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0      -0.770   1.334   0.000  0.00  0.00           N+1
HETATM   15  H   UNK     0       0.564   2.104   0.000  0.00  0.00           H+0
HETATM   16  H   UNK     0      -1.540   2.667   0.000  0.00  0.00           H+0
HETATM   17  H   UNK     0      -2.104   0.564   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    2    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   10   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

Synonyms

Value	Source
(2Z,4E)-2-Aminomuconate	ChEBI
(2Z,4E)-2-Ammoniohexa-2,4-dienedioate	ChEBI
(2Z,4E)-2-Aminomuconic acid	Generator
(2Z,4E)-2-Ammoniohexa-2,4-dienedioic acid	Generator
(2Z,4E)-2-Ammoniomuconic acid(1-)	Generator

Molecular Formula

C₆H₆NO₄

Average Mass

156.118

Monoisotopic Mass

156.030231257

IUPAC Name

(2Z,4E)-2-azaniumylhexa-2,4-dienedioate

Traditional Name

(2Z,4E)-2-ammoniohexa-2,4-dienedioate

CAS Registry Number

4548-99-6

SMILES

[H]\C(=C(\[H])C([O-])=O)\C(\[H])=C(\C([O-])=O)[N+]([H])([H])[H]

InChI Identifier

InChI=1S/C6H7NO4/c7-4(6(10)11)2-1-3-5(8)9/h1-3H,7H2,(H,8,9)(H,10,11)/p-1/b3-1+,4-2-

InChI Key

ZRHONLCTYUYMIQ-TZFCGSKZSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents

Substituents

Alpha-amino acid
Medium-chain fatty acid
Amino fatty acid
Dicarboxylic acid or derivatives
Unsaturated fatty acid
Fatty acyl
Fatty acid
Carboxylic acid salt
Amino acid
Carboxylic acid
Organic salt
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Amine
Organic nitrogen compound
Organic anion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dicarboxylic acid monoanion (CHEBI:77859 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	5.85 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-3.1	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	2.58	ChemAxon
pKa (Strongest Basic)	8.37	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	107.9 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	71.52 m³·mol⁻¹	ChemAxon
Polarizability	13.72 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

Spectrum Type	Description	Deposition Date	View
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

Cytoplasm

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

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0000298	2-Aminomuconic acid	Oxoadipic acid	Not Available	2-Aminomuconate Reductase	VMH	30371894
MMDBr0002643	2-Aminomuconic acid semialdehyde	2-Aminomuconic acid	Not Available	2-Aminomuconate Semialdehyde:NAD+ 6-Oxidoreductase	VMH	30371894
MMDBr0013318	2-Aminomuconic acid semialdehyde	2-Aminomuconic acid	2-aminomuconic 6-semialdehyde dehydrogenase	Dehydrogenation	RHEA	34755880
MMDBr0014059	2-Aminomuconic acid	(3E)-2-oxohex-3-enedioate	2-aminomuconate deaminase	Deamination	RHEA	34755880
MMDBr0016451	2-Aminomuconic acid	(2Z,4E)-2-hydroxyhexa-2,4-dienedioic acid	2-amino-5-chloromuconate deaminase	Deamination	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	3	Human feces; Human ; Human supragingival plaque

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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

31150412

KEGG Compound ID

Not Available

BioCyc ID

2-AMINO-MUCONATE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

86289384

PDB ID

Not Available

ChEBI ID

77859

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 ]
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-Aminomuconic acid (MMDBc0048172)

MOL for #<Metabolite:0x000055d24ae17ce8>

3D MOL for #<Metabolite:0x000055d24ae17ce8>

3D SDF for #<Metabolite:0x000055d24ae17ce8>

3D-SDF for #<Metabolite:0x000055d24ae17ce8>

PDB for #<Metabolite:0x000055d24ae17ce8>

3D PDB for #<Metabolite:0x000055d24ae17ce8>

SMILES for #<Metabolite:0x000055d24ae17ce8>

INCHI for #<Metabolite:0x000055d24ae17ce8>

Structure for #<Metabolite:0x000055d24ae17ce8>

3D Structure for #<Metabolite:0x000055d24ae17ce8>