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Showing NP-Card for Tricholomic acid (NP0045909)

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Record Information
Version1.0
Created at2022-03-17 19:45:14 UTC
Updated at2022-03-17 19:45:14 UTC
NP-MRD IDNP0045909
Secondary Accession NumbersNone
Natural Product Identification
Common NameTricholomic acid
DescriptionTricholomic acid, also known as tricholomate, 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). Tricholomic acid is a non-proteinogenic amino acid found in some mushrooms, including Tricholoma muscarium. Tricholomic acid is a very strong basic compound (based on its pKa). Outside of the human body, Tricholomic acid has been detected, but not quantified in, mushrooms. This could make tricholomic acid a potential biomarker for the consumption of these foods. Because glutamate receptors are thought to be responsible for the reception of umami taste, tricholomic acid and close analogs have been investigated as flavor enhancers. Tricholomic acid is found in Tricholoma muscarium. It has a chemical structure similar to glutamic acid, hence the synonym cycloglutamate, and it interacts with glutamate receptors.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0045909 (Tricholomic acid)


  Mrv0541 02241217212D          

 11 11  0  0  0  0            999 V2000
   -1.3607    0.1646    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5358    0.4121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1234   -0.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5358   -0.9070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3607   -0.6595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0207   -1.1545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7833    1.1545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0207    0.4121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1958    0.4946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7008   -0.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1958   -0.9895    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 10  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  9  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
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3D MOL for NP0045909 (Tricholomic acid)

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3D SDF for NP0045909 (Tricholomic acid)

  Mrv0541 02241217212D          

 11 11  0  0  0  0            999 V2000
   -1.3607    0.1646    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5358    0.4121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1234   -0.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5358   -0.9070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3607   -0.6595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0207   -1.1545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7833    1.1545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0207    0.4121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1958    0.4946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7008   -0.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1958   -0.9895    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 10  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  9  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045909

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(C1CC(=O)NO1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H8N2O4/c6-4(5(9)10)2-1-3(8)7-11-2/h2,4H,1,6H2,(H,7,8)(H,9,10)

> <INCHI_KEY>
NTHMUJMQOXQYBR-UHFFFAOYSA-N

> <FORMULA>
C5H8N2O4

> <MOLECULAR_WEIGHT>
160.128

> <EXACT_MASS>
160.048406754

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
13.866669744666781

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-2-(3-oxo-1,2-oxazolidin-5-yl)acetic acid

> <ALOGPS_LOGP>
-3.02

> <JCHEM_LOGP>
-4.027071544096645

> <ALOGPS_LOGS>
0.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.491786689106846

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.6934855592877343

> <JCHEM_PKA_STRONGEST_BASIC>
9.114422071688555

> <JCHEM_POLAR_SURFACE_AREA>
101.64999999999999

> <JCHEM_REFRACTIVITY>
32.303000000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.72e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
amino(3-oxo-1,2-oxazolidin-5-yl)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0045909 (Tricholomic acid)
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PDB for NP0045909 (Tricholomic acid)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  N   UNK     0      -2.540   0.307   0.000  0.00  0.00           N+0
HETATM    2  O   UNK     0      -1.000   0.769   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.230  -0.461   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.000  -1.693   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.540  -1.231   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -3.772  -2.155   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       1.462   2.155   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       3.772   0.769   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.232   0.923   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.308  -0.461   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       2.232  -1.847   0.000  0.00  0.00           N+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    1    4    6                                                  
CONECT    6    5                                                            
CONECT    7    9                                                            
CONECT    8    9                                                            
CONECT    9    7    8   10                                                  
CONECT   10    3    9   11                                                  
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0045909 (Tricholomic acid)
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SMILES for NP0045909 (Tricholomic acid)
NC(C1CC(=O)NO1)C(O)=O
Download
INCHI for NP0045909 (Tricholomic acid)
InChI=1S/C5H8N2O4/c6-4(5(9)10)2-1-3(8)7-11-2/h2,4H,1,6H2,(H,7,8)(H,9,10)
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View in JSmol
Synonyms
ValueSource
TricholomateGenerator
(2S)-Amino[(5S)-3-oxoisoxazolidin-5-yl]acetic acidHMDB
2-(3-oxo-5-Isoxazolidinyl)glycineHMDB
a-Amino-3-oxo-5-isoxazolidineacetic acid, 9ciHMDB
alpha-Amino-3-oxo-5-isoxazolidineacetic acidHMDB
alpha-Amino-3-oxo-5-isoxazolidineacetic acid, (r*,s*)-isomerHMDB
alpha-CycloglutamateHMDB
Amino-(3'-hydroxy-4',5'-dihydroisoxazol-5'-yl)acetic acidHMDB
gamma-CycloglutamateHMDB
2-Amino-2-(3-hydroxy-4,5-dihydro-1,2-oxazol-5-yl)acetateGenerator
Tricholomic acidMeSH
Chemical FormulaC5H8N2O4
Average Mass160.1280 Da
Monoisotopic Mass160.04841 Da
IUPAC Name2-amino-2-(3-oxo-1,2-oxazolidin-5-yl)acetic acid
Traditional Nameamino(3-oxo-1,2-oxazolidin-5-yl)acetic acid
CAS Registry Number2644-49-7
SMILES
NC(C1CC(=O)NO1)C(O)=O
InChI Identifier
InChI=1S/C5H8N2O4/c6-4(5(9)10)2-1-3(8)7-11-2/h2,4H,1,6H2,(H,7,8)(H,9,10)
InChI KeyNTHMUJMQOXQYBR-UHFFFAOYSA-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
Agaricus bisporusFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Pleurotus ostreatusFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Tricholoma muscariumFungi
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
    • 

  • Oxazolidinone
    • 

  • Isoxazolidine
    • 

  • Amino acid
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organoheterocyclic compound
    • 

  • Azacycle
    • 

  • Oxacycle
    • 

  • Primary amine
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic nitrogen compound
    • 

  • Primary aliphatic amine
    • 

  • Amine
    • 

  • Carbonyl group
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
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-3ALOGPS
logP-4ChemAxon
logS0.23ALOGPS
pKa (Strongest Acidic)1.69ChemAxon
pKa (Strongest Basic)9.11ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area101.65 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity32.3 m³·mol⁻¹ChemAxon
Polarizability13.87 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0030412  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB002274  
KNApSAcK IDC00001395  
Chemspider ID133122  
KEGG Compound IDC08298  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTricholomic acid  
METLIN IDNot Available
PubChem Compound151031  
PDB IDNot Available
ChEBI ID529821  
Good Scents IDNot Available
References
General ReferencesNot Available