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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:35 UTC

HMDB ID

HMDB0001280

Secondary Accession Numbers

HMDB01280

Metabolite Identification

Common Name

2-Aminomuconic acid semialdehyde

Description

2-Aminomuconic acid semialdehyde 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). 2-Aminomuconic acid semialdehyde is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. A muconic semialdehyde having a 2-amino substituent. 2-Aminomuconic acid semialdehyde exists in all living organisms, ranging from bacteria to humans. Within humans, 2-aminomuconic acid semialdehyde participates in a number of enzymatic reactions. In particular, 2-aminomuconic acid semialdehyde can be biosynthesized from 2-amino-3-carboxymuconic acid semialdehyde through its interaction with the enzyme 2-amino-3-carboxymuconate-6-semialdehyde decarboxylase. In addition, 2-aminomuconic acid semialdehyde can be converted into 2-aminomuconic acid through the action of the enzyme 2-aminomuconate-semialdehyde dehydrogenase. In humans, 2-aminomuconic acid semialdehyde is involved in the metabolic disorder called 2-amino-3-carboxymuconate semialdehyde degradation.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Aminomuconate 6-semialdehyde	ChEBI
2-Aminomuconate semialdehyde	ChEBI
2-Aminomuconic semialdehyde	ChEBI
2-Aminomuconic acid 6-semialdehyde	Generator

Chemical Formula

C₆H₇NO₃

Average Molecular Weight

141.1247

Monoisotopic Molecular Weight

141.042593095

IUPAC Name

(2E,4Z)-2-amino-6-oxohexa-2,4-dienoic acid

Traditional Name

2-aminomuconic semialdehyde

CAS Registry Number

245128-91-0

SMILES

N\C(=C\C=C/C=O)C(O)=O

InChI Identifier

InChI=1S/C6H7NO3/c7-5(6(9)10)3-1-2-4-8/h1-4H,7H2,(H,9,10)/b2-1-,5-3+

InChI Key

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

alpha,beta-unsaturated monocarboxylic acid (CHEBI:15745 )
muconic semialdehyde (CHEBI:15745 )
Oxo fatty acids (LMFA01060191 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0001280)

Source

Endogenous

Endogenous (HMDB: HMDB0001280)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tryptophan Metabolism (PathBank: SMP0063693)
2-Amino-3-Carboxymuconate Semialdehyde Degradation (PathBank: SMP0121131)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.9 g/L	ALOGPS
logP	-0.14	ALOGPS
logP	-3.1	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	2.76	ChemAxon
pKa (Strongest Basic)	7.72	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	80.39 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	37.63 m³·mol⁻¹	ChemAxon
Polarizability	12.96 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	132.044	32859911
AllCCS	[M-H]-	126.725	32859911
DeepCCS	[M+H]+	127.456	30932474
DeepCCS	[M-H]-	123.627	30932474
DeepCCS	[M-2H]-	160.844	30932474
DeepCCS	[M+Na]+	136.119	30932474
AllCCS	[M+H]+	132.0	32859911
AllCCS	[M+H-H2O]+	127.9	32859911
AllCCS	[M+NH4]+	135.9	32859911
AllCCS	[M+Na]+	137.0	32859911
AllCCS	[M-H]-	126.7	32859911
AllCCS	[M+Na-2H]-	128.8	32859911
AllCCS	[M+HCOO]-	131.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Aminomuconic acid semialdehyde	N\C(=C\C=C/C=O)C(O)=O	2309.3	Standard polar	33892256
2-Aminomuconic acid semialdehyde	N\C(=C\C=C/C=O)C(O)=O	1267.8	Standard non polar	33892256
2-Aminomuconic acid semialdehyde	N\C(=C\C=C/C=O)C(O)=O	1622.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Aminomuconic acid semialdehyde,1TMS,isomer #1	C[Si](C)(C)OC(=O)/C(N)=C\C=C/C=O	1618.0	Semi standard non polar	33892256
2-Aminomuconic acid semialdehyde,1TMS,isomer #2	C[Si](C)(C)N/C(=C/C=C\C=O)C(=O)O	1721.6	Semi standard non polar	33892256
2-Aminomuconic acid semialdehyde,2TMS,isomer #1	C[Si](C)(C)N/C(=C/C=C\C=O)C(=O)O[Si](C)(C)C	1755.8	Semi standard non polar	33892256
2-Aminomuconic acid semialdehyde,2TMS,isomer #1	C[Si](C)(C)N/C(=C/C=C\C=O)C(=O)O[Si](C)(C)C	1693.3	Standard non polar	33892256
2-Aminomuconic acid semialdehyde,2TMS,isomer #1	C[Si](C)(C)N/C(=C/C=C\C=O)C(=O)O[Si](C)(C)C	2108.2	Standard polar	33892256
2-Aminomuconic acid semialdehyde,2TMS,isomer #2	C[Si](C)(C)N(/C(=C/C=C\C=O)C(=O)O)[Si](C)(C)C	1870.5	Semi standard non polar	33892256
2-Aminomuconic acid semialdehyde,2TMS,isomer #2	C[Si](C)(C)N(/C(=C/C=C\C=O)C(=O)O)[Si](C)(C)C	1668.9	Standard non polar	33892256
2-Aminomuconic acid semialdehyde,2TMS,isomer #2	C[Si](C)(C)N(/C(=C/C=C\C=O)C(=O)O)[Si](C)(C)C	2073.3	Standard polar	33892256
2-Aminomuconic acid semialdehyde,3TMS,isomer #1	C[Si](C)(C)OC(=O)/C(=C\C=C/C=O)N([Si](C)(C)C)[Si](C)(C)C	1876.3	Semi standard non polar	33892256
2-Aminomuconic acid semialdehyde,3TMS,isomer #1	C[Si](C)(C)OC(=O)/C(=C\C=C/C=O)N([Si](C)(C)C)[Si](C)(C)C	1692.2	Standard non polar	33892256
2-Aminomuconic acid semialdehyde,3TMS,isomer #1	C[Si](C)(C)OC(=O)/C(=C\C=C/C=O)N([Si](C)(C)C)[Si](C)(C)C	1814.3	Standard polar	33892256
2-Aminomuconic acid semialdehyde,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)/C(N)=C\C=C/C=O	1869.2	Semi standard non polar	33892256
2-Aminomuconic acid semialdehyde,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N/C(=C/C=C\C=O)C(=O)O	1961.5	Semi standard non polar	33892256
2-Aminomuconic acid semialdehyde,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N/C(=C/C=C\C=O)C(=O)O[Si](C)(C)C(C)(C)C	2238.0	Semi standard non polar	33892256
2-Aminomuconic acid semialdehyde,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N/C(=C/C=C\C=O)C(=O)O[Si](C)(C)C(C)(C)C	2138.1	Standard non polar	33892256
2-Aminomuconic acid semialdehyde,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N/C(=C/C=C\C=O)C(=O)O[Si](C)(C)C(C)(C)C	2219.8	Standard polar	33892256
2-Aminomuconic acid semialdehyde,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(/C(=C/C=C\C=O)C(=O)O)[Si](C)(C)C(C)(C)C	2332.6	Semi standard non polar	33892256
2-Aminomuconic acid semialdehyde,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(/C(=C/C=C\C=O)C(=O)O)[Si](C)(C)C(C)(C)C	2110.7	Standard non polar	33892256
2-Aminomuconic acid semialdehyde,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(/C(=C/C=C\C=O)C(=O)O)[Si](C)(C)C(C)(C)C	2154.1	Standard polar	33892256
2-Aminomuconic acid semialdehyde,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)/C(=C\C=C/C=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2549.1	Semi standard non polar	33892256
2-Aminomuconic acid semialdehyde,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)/C(=C\C=C/C=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2294.1	Standard non polar	33892256
2-Aminomuconic acid semialdehyde,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)/C(=C\C=C/C=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2105.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Aminomuconic acid semialdehyde GC-MS (Non-derivatized) - 70eV, Positive	splash10-014m-9200000000-6fd74f95ac9e06d815d8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Aminomuconic acid semialdehyde GC-MS (1 TMS) - 70eV, Positive	splash10-0002-9200000000-c20041baa79945f5d800	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Aminomuconic acid semialdehyde GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminomuconic acid semialdehyde 10V, Positive-QTOF	splash10-0095-7900000000-d57e751610237d25aaf4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminomuconic acid semialdehyde 20V, Positive-QTOF	splash10-002b-9100000000-82f13963addf5ffc0e16	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminomuconic acid semialdehyde 40V, Positive-QTOF	splash10-0gb9-9000000000-9c9844252423065aceda	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminomuconic acid semialdehyde 10V, Negative-QTOF	splash10-0006-1900000000-49ad8b8a0c9588a39938	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminomuconic acid semialdehyde 20V, Negative-QTOF	splash10-006x-6900000000-77aa0f01bf2a2c535794	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminomuconic acid semialdehyde 40V, Negative-QTOF	splash10-0006-9100000000-9bd7a5539e729542e8f1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminomuconic acid semialdehyde 10V, Positive-QTOF	splash10-0002-9100000000-7831b7cf7af8efc10bc2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminomuconic acid semialdehyde 20V, Positive-QTOF	splash10-017j-9000000000-1067cced8ab6220283a7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminomuconic acid semialdehyde 40V, Positive-QTOF	splash10-014i-9000000000-3febc896ed7c770666d0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminomuconic acid semialdehyde 10V, Negative-QTOF	splash10-0007-9500000000-770609a188bfdc543692	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminomuconic acid semialdehyde 20V, Negative-QTOF	splash10-014i-9100000000-8ede36ee93f2e80508d3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminomuconic acid semialdehyde 40V, Negative-QTOF	splash10-014l-9000000000-224bae95c47132912d4d	2021-09-23	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Tryptophan metabolism	Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

1445635

Wikipedia Link

Not Available

METLIN ID

6133

PubChem Compound

5280625

PDB ID

Not Available

ChEBI ID

15745

Food Biomarker Ontology

Not Available

VMH ID

AM6SA

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

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. [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 ]
Colabroy KL, Begley TP: Tryptophan catabolism: identification and characterization of a new degradative pathway. J Bacteriol. 2005 Nov;187(22):7866-9. [PubMed:16267312 ]

Enzymes

Enzyme Details

1. 2-amino-3-carboxymuconate-6-semialdehyde decarboxylase

General function:: Involved in catalytic activity
Specific function:: Converts alpha-amino-beta-carboxymuconate-epsilon-semialdehyde (ACMS) to alpha-aminomuconate semialdehyde (AMS). ACMS can be converted non-enzymatically to quinolate (QA), a key precursor of NAD, and a potent endogenous excitotoxin of neuronal cells which is implicated in the pathogenesis of various neurodegenerative disorders. In the presence of ACMSD, ACMS is converted to AMS, a benign catabolite. ACMSD ultimately controls the metabolic fate of tryptophan catabolism along the kynurenine pathway.
Gene Name:: ACMSD
Uniprot ID:: Q8TDX5
Molecular weight:: 38035.045

Reactions

2-Amino-3-carboxymuconic acid semialdehyde → 2-Aminomuconic acid semialdehyde + CO(2)	details
2-Amino-3-carboxymuconic acid semialdehyde → 2-Aminomuconic acid semialdehyde + Carbon dioxide	details

Showing metabocard for 2-Aminomuconic acid semialdehyde (HMDB0001280)

MOL for HMDB0001280 (2-Aminomuconic acid semialdehyde)

3D MOL for HMDB0001280 (2-Aminomuconic acid semialdehyde)

3D SDF for HMDB0001280 (2-Aminomuconic acid semialdehyde)

3D-SDF for HMDB0001280 (2-Aminomuconic acid semialdehyde)

PDB for HMDB0001280 (2-Aminomuconic acid semialdehyde)

3D PDB for HMDB0001280 (2-Aminomuconic acid semialdehyde)

SMILES for HMDB0001280 (2-Aminomuconic acid semialdehyde)

INCHI for HMDB0001280 (2-Aminomuconic acid semialdehyde)

Structure for HMDB0001280 (2-Aminomuconic acid semialdehyde)

3D Structure for HMDB0001280 (2-Aminomuconic acid semialdehyde)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra

Enzymes

Reactions