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Showing NP-Card for 2-Aminomuconate semialdehyde (NP0054986)

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Record Information
Version2.0
Created at2022-04-28 01:10:18 UTC
Updated at2022-04-28 01:10:18 UTC
NP-MRD IDNP0054986
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Aminomuconate 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. 2-Aminomuconate semialdehyde is found in Pseudomonas pseudoalcaligenes. 2-Aminomuconate semialdehyde was first documented in 1999 (PMID: 10510494). In humans, 2-aminomuconic acid semialdehyde is involved in the metabolic disorder called 2-amino-3-carboxymuconate semialdehyde degradation.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0054986 (2-Aminomuconate semialdehyde)


  Mrv0541 02231219022D          

 10  9  0  0  0  0            999 V2000
    0.4715    0.7921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2602    1.1353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4715    0.1659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1882    1.0863    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0863    0.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0830   -0.1320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0939   -0.1659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0826   -0.6451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3621   -1.0524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3545   -1.8747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  2  0  0  0  0
  5  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
M  END
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3D MOL for NP0054986 (2-Aminomuconate semialdehyde)

     RDKit          3D

 17 16  0  0  0  0  0  0  0  0999 V2000
   -1.6972   -1.9271   -0.2085 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1837   -0.5832    0.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0964   -0.3765   -0.2163 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7826    0.8753   -0.0629 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0841    0.9405   -0.3203 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8328   -0.1959   -0.7471 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0873    0.0011   -0.9634 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0888    0.4481    0.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3136    0.1052    0.6131 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7007    1.7362    0.6622 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1503   -2.7813   -0.0333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6691   -2.0097   -0.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6332   -1.2865   -0.5449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2821    1.7903    0.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5487    1.9385   -0.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5196   -1.1993   -0.9197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0633    2.5243    0.1260 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  2  8  1  0
  8 10  1  0
  8  9  2  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  5 15  1  0
  6 16  1  0
 10 17  1  0
M  END
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3D SDF for NP0054986 (2-Aminomuconate semialdehyde)


  Mrv0541 02231219022D          

 10  9  0  0  0  0            999 V2000
    0.4715    0.7921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2602    1.1353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4715    0.1659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1882    1.0863    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0863    0.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0830   -0.1320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0939   -0.1659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0826   -0.6451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3621   -1.0524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3545   -1.8747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  2  0  0  0  0
  5  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0054986

> <DATABASE_NAME>
NP-MRD

> <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

> <FORMULA>
C6H7NO3

> <MOLECULAR_WEIGHT>
141.1247

> <EXACT_MASS>
141.042593095

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
12.955028553813651

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.14

> <JCHEM_LOGP>
-3.074032307631351

> <ALOGPS_LOGS>
-1.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.759990591792232

> <JCHEM_PKA_STRONGEST_BASIC>
7.719389495707983

> <JCHEM_POLAR_SURFACE_AREA>
80.39

> <JCHEM_REFRACTIVITY>
37.6251

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.90e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-aminomuconic semialdehyde

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0054986 (2-Aminomuconate semialdehyde)

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PDB for NP0054986 (2-Aminomuconate semialdehyde)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       0.880   1.479   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.486   2.119   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.880   0.310   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       2.218   2.028   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -2.028   1.288   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.155  -0.246   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       2.042  -0.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.021  -1.204   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.676  -1.964   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.662  -3.499   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6    7                                                  
CONECT    4    1                                                            
CONECT    5    2    8                                                       
CONECT    6    3                                                            
CONECT    7    3                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END

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3D PDB for NP0054986 (2-Aminomuconate semialdehyde)
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SMILES for NP0054986 (2-Aminomuconate semialdehyde)
N\C(=C\C=C/C=O)C(O)=O
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INCHI for NP0054986 (2-Aminomuconate semialdehyde)
InChI=1S/C6H7NO3/c7-5(6(9)10)3-1-2-4-8/h1-4H,7H2,(H,9,10)/b2-1-,5-3+
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View in JSmol
Synonyms
ValueSource
2-Aminomuconate 6-semialdehydeChEBI
2-Aminomuconate semialdehydeChEBI
2-Aminomuconic semialdehydeChEBI
2-Aminomuconic acid 6-semialdehydeGenerator
Chemical FormulaC6H7NO3
Average Mass141.1247 Da
Monoisotopic Mass141.04259 Da
IUPAC Name(2E,4Z)-2-amino-6-oxohexa-2,4-dienoic acid
Traditional Name2-aminomuconic semialdehyde
CAS Registry NumberNot Available
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
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Pseudomonas pseudoalcaligenesBacteria
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
HMDB IDHMDB0001280  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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  
Good Scents IDNot Available
References
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. doi: 10.1038/sj.jim.2900705. [PubMed:10510494  ]