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Showing NP-Card for stizolobate (NP0247129)

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Record Information
Version2.0
Created at2022-09-07 08:50:59 UTC
Updated at2022-09-07 08:50:59 UTC
NP-MRD IDNP0247129
Secondary Accession NumbersNone
Natural Product Identification
Common Namestizolobate
DescriptionAC1L9A4Y 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). AC1L9A4Y is a very strong basic compound (based on its pKa). stizolobate is found in Clitocybe acromelalga. AC1L9A4Y is a potentially toxic compound.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0247129 (stizolobate)


  Mrv0541 08291400592D          

 16 16  0  0  0  0            999 V2000
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  4  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  1  1  0  0  0  0
  6  2  2  0  0  0  0
  7  3  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  5  1  0  0  0  0
 11  7  2  0  0  0  0
 12  8  2  0  0  0  0
 13  8  1  0  0  0  0
 14  9  1  0  0  0  0
 15  9  2  0  0  0  0
 16  6  1  0  0  0  0
 16  7  1  0  0  0  0
M  END
Download

3D MOL for NP0247129 (stizolobate)

     RDKit          3D

 25 25  0  0  0  0  0  0  0  0999 V2000
   -2.0204   -0.4929    1.5373 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9320   -0.7711    0.1338 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2546    0.3808   -0.5708 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1063    0.6270   -0.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2101   -0.0003   -0.6459 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4801    0.2450   -0.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425   -0.3998   -0.7474 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4721   -1.2032   -1.7128 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9285   -0.2003   -0.3205 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6746    1.0714    0.8282 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6738    1.7027    1.4161 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9285    2.4837    2.3681 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3684    1.4849    0.9650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3007   -0.9243   -0.4215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3450   -0.8146    0.2872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4522   -1.1954   -1.7524 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7830   -1.0480    2.0182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2905    0.5068    1.6662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3815   -1.7187   -0.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2765    0.1796   -1.6797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8859    1.2842   -0.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0331   -0.6709   -1.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5622   -0.9726   -0.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4267    2.0034    1.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7313   -1.5571   -2.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4 13  2  0
 13 11  1  0
 11 12  2  0
 11 10  1  0
 10  6  1  0
  6  5  2  0
  6  7  1  0
  7  9  1  0
  7  8  2  0
  2 14  1  0
 14 16  1  0
 14 15  2  0
  5  4  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  1
  3 20  1  0
  3 21  1  0
 13 24  1  0
  5 22  1  0
  9 23  1  0
 16 25  1  0
M  END
Download

3D SDF for NP0247129 (stizolobate)


  Mrv0541 08291400592D          

 16 16  0  0  0  0            999 V2000
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  4  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  1  1  0  0  0  0
  6  2  2  0  0  0  0
  7  3  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  5  1  0  0  0  0
 11  7  2  0  0  0  0
 12  8  2  0  0  0  0
 13  8  1  0  0  0  0
 14  9  1  0  0  0  0
 15  9  2  0  0  0  0
 16  6  1  0  0  0  0
 16  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0247129

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(CC1=CC(=O)OC(=C1)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H9NO6/c10-5(8(12)13)1-4-2-6(9(14)15)16-7(11)3-4/h2-3,5H,1,10H2,(H,12,13)(H,14,15)

> <INCHI_KEY>
KQZBVNZAEQASKU-UHFFFAOYSA-N

> <FORMULA>
C9H9NO6

> <MOLECULAR_WEIGHT>
227.1709

> <EXACT_MASS>
227.042987025

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
20.146931662350347

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-(2-amino-2-carboxyethyl)-2-oxo-2H-pyran-6-carboxylic acid

> <ALOGPS_LOGP>
-2.86

> <JCHEM_LOGP>
-3.2082915826798972

> <ALOGPS_LOGS>
-2.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.4038581050267305

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.603347025550529

> <JCHEM_PKA_STRONGEST_BASIC>
9.463679570296335

> <JCHEM_POLAR_SURFACE_AREA>
126.92

> <JCHEM_REFRACTIVITY>
51.69990000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.78e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
stizolobate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0247129 (stizolobate)

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PDB for NP0247129 (stizolobate)
HEADER    PROTEIN                                 29-AUG-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-AUG-14         0                                  
HETATM    1  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -1.334   3.850   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1    4    5                                                       
CONECT    2    4    6                                                       
CONECT    3    4    7                                                       
CONECT    4    1    2    3                                                  
CONECT    5    1    8   10                                                  
CONECT    6    2    9   16                                                  
CONECT    7    3   11   16                                                  
CONECT    8    5   12   13                                                  
CONECT    9    6   14   15                                                  
CONECT   10    5                                                            
CONECT   11    7                                                            
CONECT   12    8                                                            
CONECT   13    8                                                            
CONECT   14    9                                                            
CONECT   15    9                                                            
CONECT   16    6    7                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

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3D PDB for NP0247129 (stizolobate)
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SMILES for NP0247129 (stizolobate)
NC(CC1=CC(=O)OC(=C1)C(O)=O)C(O)=O
Download
INCHI for NP0247129 (stizolobate)
InChI=1S/C9H9NO6/c10-5(8(12)13)1-4-2-6(9(14)15)16-7(11)3-4/h2-3,5H,1,10H2,(H,12,13)(H,14,15)
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View in JSmol
Synonyms
ValueSource
4-(2-Amino-2-carboxyethyl)-2-oxo-2H-pyran-6-carboxylateGenerator
Chemical FormulaC9H9NO6
Average Mass227.1709 Da
Monoisotopic Mass227.04299 Da
IUPAC Name4-(2-amino-2-carboxyethyl)-2-oxo-2H-pyran-6-carboxylic acid
Traditional Namestizolobate
CAS Registry NumberNot Available
SMILES
NC(CC1=CC(=O)OC(=C1)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C9H9NO6/c10-5(8(12)13)1-4-2-6(9(14)15)16-7(11)3-4/h2-3,5H,1,10H2,(H,12,13)(H,14,15)
InChI KeyKQZBVNZAEQASKU-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Clitocybe acromelalgaLOTUS Database
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
    • 

  • Pyranone
    • 

  • Aralkylamine
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Pyran
    • 

  • Heteroaromatic compound
    • 

  • Amino acid
    • 

  • Lactone
    • 

  • Carboxylic acid
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Organic oxygen compound
    • 

  • Primary amine
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Primary aliphatic amine
    • 

  • Hydrocarbon derivative
    • 

  • Organic nitrogen compound
    • 

  • Organic oxide
    • 

  • Carbonyl group
    • 

  • Amine
    • 

  • Organopnictogen compound
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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-2.9ALOGPS
logP-3.2ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)1.6ChemAxon
pKa (Strongest Basic)9.46ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area126.92 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity51.7 m³·mol⁻¹ChemAxon
Polarizability20.15 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC06047  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440896  
PDB IDNot Available
ChEBI ID9274  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]