MiMeDB: Showing metabocard for 2-Amino-3-carboxymuconic acid semialdehyde (MMDBc0032953)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:28:41 UTC

Update Date

2022-12-15 22:51:52 UTC

Metabolite ID

MMDBc0032953

Metabolite Identification

Common Name

2-Amino-3-carboxymuconic acid semialdehyde

Description

2-Amino-3-carboxymuconic acid semialdehyde (CAS: 16597-58-3) is an intermediate metabolite of the tryptophan-niacin catabolic pathway. Current interest in the degradation of tryptophan is mostly due to the role of quinolinate and other metabolites in several neuropathological conditions. Quinolinate is a neurotoxin formed nonenzymatically from 2-amino-3-carboxymuconic semialdehyde in mammalian tissues. 2-Amino-3-carboxymuconic acid semialdehyde is enzymatically converted into 2-aminomuconate via 2-aminomuconic semialdehyde (PMID: 10510494 , 16267312 , 14275129 ).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305221920532D          

 13 12  0  0  0  0            999 V2000
    2.0625    0.7145    0.0000 C   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
    2.4750    1.4289    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
    0.0000    0.0000    0.0000 C   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
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 O   0  0  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
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  2  4  1  4  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  5  8  1  4  0  0  0
  9  3  2  0  0  0  0
 10  6  2  0  0  0  0
 11  6  1  0  0  0  0
 12  7  2  0  0  0  0
 13  7  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0032953

> <DATABASE_NAME>
MIME

> <SMILES>
NC(C(O)=O)=C(C=CC=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H7NO5/c8-5(7(12)13)4(6(10)11)2-1-3-9/h1-3H,8H2,(H,10,11)(H,12,13)

> <INCHI_KEY>
KACPVQQHDVBVFC-UHFFFAOYSA-N

> <FORMULA>
C7H7NO5

> <MOLECULAR_WEIGHT>
185.1342

> <EXACT_MASS>
185.032422339

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
16.012769133997885

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-3-(3-oxoprop-1-en-1-yl)but-2-enedioic acid

> <ALOGPS_LOGP>
-0.05

> <JCHEM_LOGP>
-3.668506936230873

> <ALOGPS_LOGS>
-2.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.4453592131045303

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.3791525915700023

> <JCHEM_PKA_STRONGEST_BASIC>
6.720078986530107

> <JCHEM_POLAR_SURFACE_AREA>
117.69

> <JCHEM_REFRACTIVITY>
43.624300000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.64e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-3-(3-oxoprop-1-en-1-yl)but-2-enedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-19         0                                  
HETATM    1  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.310   1.334   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       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -0.770   1.334   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0       6.160   2.667   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.540  -2.667   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       3.850  -1.334   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000  -2.667   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -2.310  -1.334   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    9                                                       
CONECT    4    2    5    6                                                  
CONECT    5    4    7    8                                                  
CONECT    6    4   10   11                                                  
CONECT    7    5   12   13                                                  
CONECT    8    5                                                            
CONECT    9    3                                                            
CONECT   10    6                                                            
CONECT   11    6                                                            
CONECT   12    7                                                            
CONECT   13    7                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

Synonyms

Value	Source
2-Amino-3-carboxymuconate semialdehyde	Generator

Molecular Formula

C₇H₇NO₅

Average Mass

185.1342

Monoisotopic Mass

185.032422339

IUPAC Name

2-amino-3-(3-oxoprop-1-en-1-yl)but-2-enedioic acid

Traditional Name

2-amino-3-(3-oxoprop-1-en-1-yl)but-2-enedioic acid

CAS Registry Number

16597-58-3

SMILES

NC(C(O)=O)=C(C=CC=O)C(O)=O

InChI Identifier

InChI=1S/C7H7NO5/c8-5(7(12)13)4(6(10)11)2-1-3-9/h1-3H,8H2,(H,10,11)(H,12,13)

InChI Key

KACPVQQHDVBVFC-UHFFFAOYSA-N

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
Branched fatty acid
Dicarboxylic acid or derivatives
Unsaturated fatty acid
Fatty acid
Fatty acyl
Vinylogous amide
Alpha,beta-unsaturated aldehyde
Enal
Amino acid
Carboxylic acid
Enamine
Organic oxide
Primary aliphatic amine
Organonitrogen compound
Organooxygen compound
Aldehyde
Primary amine
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Amine
Organic nitrogen compound
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

amino dicarboxylic acid (CHEBI:19448 )
non-proteinogenic alpha-amino acid (CHEBI:19448 )
oxo dicarboxylic acid (CHEBI:19448 )
muconic semialdehyde (CHEBI:19448 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.64 g/L	ALOGPS
logP	-0.05	ALOGPS
logP	-3.7	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	2.38	ChemAxon
pKa (Strongest Basic)	6.72	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	117.69 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	43.62 m³·mol⁻¹	ChemAxon
Polarizability	16.01 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	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-5900000000-5678760d98b1c1aef0dd	2016-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0076-1900000000-ac5d927ca2365b6ae1f5	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dl-5900000000-996af9cc34d138cdb97d	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kf-9200000000-ce06d4a9da9f0e145089	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-007o-2900000000-e08a15f38a790c0a8a8e	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dl-8900000000-f7aba3f0258e753f5128	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dl-9200000000-70dfc7f87c3079551557	2016-09-12	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

Cytoplasm

Biospecimen Locations

Brain
Feces
Kidney
Liver

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
MMDBr0000063	3-Hydroxyanthranilic acid	2-Amino-3-carboxymuconic acid semialdehyde	Not Available	3-Hydroxyanthranilate 3, 4-Dioxygenase	VMH	7514594
MMDBr0001893	2-Amino-3-carboxymuconic acid semialdehyde	2-Aminomuconic acid semialdehyde	Aminocarboxymuconate semialdehyde decarboxylase	Picolinic Acid Decarboxylase	VMH	30371894
MMDBr0002048	2-Amino-3-carboxymuconic acid semialdehyde	Hydrogen Ion	Not Available	Quinolinate Synthase (Eukaryotic)	VMH	30371894
MMDBr0019600	3-Hydroxyanthranilic acid	Hydrogen Ion	3-hydroxyanthranilate 3,4-dioxygenase	Oxygenation	PathBank	31602464

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
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown
Bacteria	Proteobacteria	7	Human feces; Human sputum; Human	Metabolic reconstruction
Bacteria	Firmicutes	5	Human feces	Metabolic reconstruction
Bacteria	Actinobacteria	5	Human feces; Human	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified				HMDB
Human Brain	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Kidney	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022559

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

PDB ID

Not Available

ChEBI ID

19448

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

He Z, Spain J: Preparation of 2-aminomuconate from 2-aminophenol by coupled enzymatic dioxygenation and dehydrogenation reactions. J Ind Microbiol Biotechnol. 1999 Aug;23(2):138-142. doi: 10.1038/sj.jim.2900705. [PubMed:10510494 ]
NISHIZUKA Y, ICHIYAMA A, GHOLSON RK, HAYAISHI O: STUDIES ON THE METABOLISM OF THE BENZENE RING OF TRYPTOPHAN IN MAMMALIAN TISSUES. I. ENZYMIC FORMATION OF GLUTARIC ACID FROM 3-HYDROXYANTHRANILIC ACID. J Biol Chem. 1965 Feb;240:733-9. [PubMed:14275129 ]
Ftukijwatari T, Murakami M, Ohta M, Kimura N, Jin-No Y, Sasaki R, Shibata K: Changes in the urinary excretion of the metabolites of the tryptophan-niacin pathway during pregnancy in Japanese women and rats. J Nutr Sci Vitaminol (Tokyo). 2004 Dec;50(6):392-8. doi: 10.3177/jnsv.50.392. [PubMed:15895513 ]
Colabroy KL, Begley TP: Tryptophan catabolism: identification and characterization of a new degradative pathway. J Bacteriol. 2005 Nov;187(22):7866-9. doi: 10.1128/JB.187.22.7866-7869.2005. [PubMed:16267312 ]

Showing metabocard for 2-Amino-3-carboxymuconic acid semialdehyde (MMDBc0032953)

MOL for #<Metabolite:0x000055d24ae635f8>

3D MOL for #<Metabolite:0x000055d24ae635f8>

3D SDF for #<Metabolite:0x000055d24ae635f8>

3D-SDF for #<Metabolite:0x000055d24ae635f8>

PDB for #<Metabolite:0x000055d24ae635f8>

3D PDB for #<Metabolite:0x000055d24ae635f8>

SMILES for #<Metabolite:0x000055d24ae635f8>

INCHI for #<Metabolite:0x000055d24ae635f8>

Structure for #<Metabolite:0x000055d24ae635f8>

3D Structure for #<Metabolite:0x000055d24ae635f8>