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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:23:09 UTC
HMDB IDHMDB0001280
Secondary Accession Numbers
  • HMDB01280
Metabolite Identification
Common Name2-Aminomuconic acid semialdehyde
Description2-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
Data?1582752189
Synonyms
ValueSource
2-Aminomuconate 6-semialdehydeChEBI
2-Aminomuconate semialdehydeChEBI
2-Aminomuconic semialdehydeChEBI
2-Aminomuconic acid 6-semialdehydeGenerator
Chemical FormulaC6H7NO3
Average Molecular Weight141.1247
Monoisotopic Molecular Weight141.042593095
IUPAC Name(2E,4Z)-2-amino-6-oxohexa-2,4-dienoic acid
Traditional Name2-aminomuconic semialdehyde
CAS Registry Number245128-91-0
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 KeyQCGTZPZKJPTAEP-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).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha 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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility5.9 g/LALOGPS
logP-0.14ALOGPS
logP-3.1ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)2.76ChemAxon
pKa (Strongest Basic)7.72ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.39 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity37.63 m³·mol⁻¹ChemAxon
Polarizability12.96 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+132.04432859911
AllCCS[M-H]-126.72532859911
DeepCCS[M+H]+127.45630932474
DeepCCS[M-H]-123.62730932474
DeepCCS[M-2H]-160.84430932474
DeepCCS[M+Na]+136.11930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Aminomuconic acid semialdehydeN\C(=C\C=C/C=O)C(O)=O2309.3Standard polar33892256
2-Aminomuconic acid semialdehydeN\C(=C\C=C/C=O)C(O)=O1267.8Standard non polar33892256
2-Aminomuconic acid semialdehydeN\C(=C\C=C/C=O)C(O)=O1622.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Aminomuconic acid semialdehyde,1TMS,isomer #1C[Si](C)(C)OC(=O)/C(N)=C\C=C/C=O1618.0Semi standard non polar33892256
2-Aminomuconic acid semialdehyde,1TMS,isomer #2C[Si](C)(C)N/C(=C/C=C\C=O)C(=O)O1721.6Semi standard non polar33892256
2-Aminomuconic acid semialdehyde,2TMS,isomer #1C[Si](C)(C)N/C(=C/C=C\C=O)C(=O)O[Si](C)(C)C1755.8Semi standard non polar33892256
2-Aminomuconic acid semialdehyde,2TMS,isomer #1C[Si](C)(C)N/C(=C/C=C\C=O)C(=O)O[Si](C)(C)C1693.3Standard non polar33892256
2-Aminomuconic acid semialdehyde,2TMS,isomer #1C[Si](C)(C)N/C(=C/C=C\C=O)C(=O)O[Si](C)(C)C2108.2Standard polar33892256
2-Aminomuconic acid semialdehyde,2TMS,isomer #2C[Si](C)(C)N(/C(=C/C=C\C=O)C(=O)O)[Si](C)(C)C1870.5Semi standard non polar33892256
2-Aminomuconic acid semialdehyde,2TMS,isomer #2C[Si](C)(C)N(/C(=C/C=C\C=O)C(=O)O)[Si](C)(C)C1668.9Standard non polar33892256
2-Aminomuconic acid semialdehyde,2TMS,isomer #2C[Si](C)(C)N(/C(=C/C=C\C=O)C(=O)O)[Si](C)(C)C2073.3Standard polar33892256
2-Aminomuconic acid semialdehyde,3TMS,isomer #1C[Si](C)(C)OC(=O)/C(=C\C=C/C=O)N([Si](C)(C)C)[Si](C)(C)C1876.3Semi standard non polar33892256
2-Aminomuconic acid semialdehyde,3TMS,isomer #1C[Si](C)(C)OC(=O)/C(=C\C=C/C=O)N([Si](C)(C)C)[Si](C)(C)C1692.2Standard non polar33892256
2-Aminomuconic acid semialdehyde,3TMS,isomer #1C[Si](C)(C)OC(=O)/C(=C\C=C/C=O)N([Si](C)(C)C)[Si](C)(C)C1814.3Standard polar33892256
2-Aminomuconic acid semialdehyde,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C(N)=C\C=C/C=O1869.2Semi standard non polar33892256
2-Aminomuconic acid semialdehyde,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N/C(=C/C=C\C=O)C(=O)O1961.5Semi standard non polar33892256
2-Aminomuconic acid semialdehyde,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N/C(=C/C=C\C=O)C(=O)O[Si](C)(C)C(C)(C)C2238.0Semi standard non polar33892256
2-Aminomuconic acid semialdehyde,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N/C(=C/C=C\C=O)C(=O)O[Si](C)(C)C(C)(C)C2138.1Standard non polar33892256
2-Aminomuconic acid semialdehyde,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N/C(=C/C=C\C=O)C(=O)O[Si](C)(C)C(C)(C)C2219.8Standard polar33892256
2-Aminomuconic acid semialdehyde,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(/C(=C/C=C\C=O)C(=O)O)[Si](C)(C)C(C)(C)C2332.6Semi standard non polar33892256
2-Aminomuconic acid semialdehyde,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(/C(=C/C=C\C=O)C(=O)O)[Si](C)(C)C(C)(C)C2110.7Standard non polar33892256
2-Aminomuconic acid semialdehyde,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(/C(=C/C=C\C=O)C(=O)O)[Si](C)(C)C(C)(C)C2154.1Standard polar33892256
2-Aminomuconic acid semialdehyde,3TBDMS,isomer #1CC(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)C2549.1Semi standard non polar33892256
2-Aminomuconic acid semialdehyde,3TBDMS,isomer #1CC(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)C2294.1Standard non polar33892256
2-Aminomuconic acid semialdehyde,3TBDMS,isomer #1CC(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)C2105.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Aminomuconic acid semialdehyde GC-MS (Non-derivatized) - 70eV, Positivesplash10-014m-9200000000-6fd74f95ac9e06d815d82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Aminomuconic acid semialdehyde GC-MS (1 TMS) - 70eV, Positivesplash10-0002-9200000000-c20041baa79945f5d8002017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Aminomuconic acid semialdehyde GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Aminomuconic acid semialdehyde 10V, Positive-QTOFsplash10-0095-7900000000-d57e751610237d25aaf42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Aminomuconic acid semialdehyde 20V, Positive-QTOFsplash10-002b-9100000000-82f13963addf5ffc0e162017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Aminomuconic acid semialdehyde 40V, Positive-QTOFsplash10-0gb9-9000000000-9c9844252423065aceda2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Aminomuconic acid semialdehyde 10V, Negative-QTOFsplash10-0006-1900000000-49ad8b8a0c9588a399382017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Aminomuconic acid semialdehyde 20V, Negative-QTOFsplash10-006x-6900000000-77aa0f01bf2a2c5357942017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Aminomuconic acid semialdehyde 40V, Negative-QTOFsplash10-0006-9100000000-9bd7a5539e729542e8f12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Aminomuconic acid semialdehyde 10V, Positive-QTOFsplash10-0002-9100000000-7831b7cf7af8efc10bc22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Aminomuconic acid semialdehyde 20V, Positive-QTOFsplash10-017j-9000000000-1067cced8ab6220283a72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Aminomuconic acid semialdehyde 40V, Positive-QTOFsplash10-014i-9000000000-3febc896ed7c770666d02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Aminomuconic acid semialdehyde 10V, Negative-QTOFsplash10-0007-9500000000-770609a188bfdc5436922021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Aminomuconic acid semialdehyde 20V, Negative-QTOFsplash10-014i-9100000000-8ede36ee93f2e80508d32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Aminomuconic acid semialdehyde 40V, Negative-QTOFsplash10-014l-9000000000-224bae95c47132912d4d2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022532
KNApSAcK IDC00007492
Chemspider ID4444230
KEGG Compound IDC03824
BioCyc IDNot Available
BiGG ID1445635
Wikipedia LinkNot Available
METLIN ID6133
PubChem Compound5280625
PDB IDNot Available
ChEBI ID15745
Food Biomarker OntologyNot Available
VMH IDAM6SA
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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

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 dioxidedetails