2-amino-3-(3-oxoprop-1-enyl)but-2-enedioate (YMDB00479)

Identification
YMDB IDYMDB00479
Name2-amino-3-(3-oxoprop-1-enyl)but-2-enedioate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description2-Amino-3-carboxymuconic acid semialdehyde, also known as 2-amino-3-(3-oxoprop-1-en-1-yl)but-2-enedioate or ACS, 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-Amino-3-carboxymuconic acid semialdehyde is a very strong basic compound (based on its pKa). 2-Amino-3-carboxymuconic acid semialdehyde exists in all living species, ranging from bacteria to humans. 2-amino-3-carboxymuconic acid semialdehyde can be biosynthesized from 3-hydroxyanthranilic acid; which is catalyzed by the enzyme 3-hydroxyanthranilate 3,4-dioxygenase. In yeast, 2-amino-3-carboxymuconic acid semialdehyde is involved in the metabolic pathway called the nad metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 2-Amino-3-(3-oxoprop-1-en-1-yl)but-2-enedioate
  • 2-Amino-3-(3-oxoprop-1-enyl)-but-2-enedioate
  • 2-Amino-3-carboxymuconate semialdehyde
  • 2-Amino-3-(3-oxoprop-1-en-1-yl)but-2-enedioic acid
  • 2-Amino-3-(3-oxoprop-1-enyl)-but-2-enedioic acid
  • 2-Amino-3-carboxymuconate-6-semialdehyde
  • ACS
  • Amino-3-(3-oxoprop-1-en-1-yl)but-2-enedioate
  • Amino-3-(3-oxoprop-1-en-1-yl)but-2-enedioic acid
CAS numberNot Available
WeightAverage: 185.1342
Monoisotopic: 185.032422339
InChI KeyKACPVQQHDVBVFC-UHFFFAOYSA-N
InChIInChI=1S/C7H7NO5/c8-5(7(12)13)4(6(10)11)2-1-3-9/h1-3H,8H2,(H,10,11)(H,12,13)
IUPAC Name(2Z)-2-amino-3-[(1Z)-3-oxoprop-1-en-1-yl]but-2-enedioic acid
Traditional IUPAC Name(2Z)-2-amino-3-[(1Z)-3-oxoprop-1-en-1-yl]but-2-enedioic acid
Chemical FormulaC7H7NO5
SMILES[H]C(=O)C([H])=C([H])C(C(O)=O)=C(N)C(O)=O
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
  • 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 FrameworkAliphatic acyclic compounds
External Descriptors
  • 2-amino-3-(3-oxoprop-1-enyl)but-2-enedioic acid (CHEBI:995 )
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.64 g/LALOGPS
logP-0.05ALOGPS
logP-3.7ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)2.38ChemAxon
pKa (Strongest Basic)6.72ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area117.69 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity43.62 m³·mol⁻¹ChemAxon
Polarizability15.75 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG Reactions
3-Hydroxyanthranilic acid + oxygen → 2-amino-3-(3-oxoprop-1-enyl)but-2-enedioate + hydron
2-amino-3-(3-oxoprop-1-enyl)but-2-enedioate → Quinolinic acid + water + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ox-4900000000-62ebd57b1dadb165bc36JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0300-8793000000-3b592a4ef216b8fdf12eJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00r6-0900000000-0a2ef2dbb21b597d6fc4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-4900000000-53b3810106e9c56f7d0aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-9100000000-fa0ffd8141b90a020246JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00ec-1900000000-590832d218cda44b13f8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0229-5900000000-74f5fb374736aa527071JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-9300000000-84211b6b70277d6fb146JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-5900000000-210673f89c9ac4437575JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01oy-8900000000-1eabc10d32130d827b37JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9200000000-3900709db9f9f0db1c3bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kf-0900000000-1ac99f0053d2cc748f29JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03kc-2900000000-f5ecf269380d030c89a9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066u-9100000000-df3d348bf5ff10948d70JSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Kucharczyk, R., Zagulski, M., Rytka, J., Herbert, C. J. (1998). "The yeast gene YJR025c encodes a 3-hydroxyanthranilic acid dioxygenase and is involved in nicotinic acid biosynthesis." FEBS Lett 424:127-130.9539135
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID19448
HMDB IDHMDB0001330
Pubchem Compound ID5280673
Kegg IDC04409
ChemSpider ID22
FOODB IDFDB022559
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. 3-hydroxyanthranilate 3,4-dioxygenase
General function:
Involved in 3-hydroxyanthranilate 3,4-dioxygenase activity
Specific function:
Catalyzes the oxidative ring opening of 3- hydroxyanthranilate to 2-amino-3-carboxymuconate semialdehyde, which spontaneously cyclizes to quinolinate
Gene Name:
BNA1
Uniprot ID:
P47096
Molecular weight:
20234.90039
Reactions
3-hydroxyanthranilate + O(2) → 2-amino-3-carboxymuconate semialdehyde.