Np mrd loader

Showing NP-Card for Quisqualic acid (NP0050685)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-04-27 22:01:59 UTC
Updated at2022-04-27 22:01:59 UTC
NP-MRD IDNP0050685
Secondary Accession NumbersNone
Natural Product Identification
Common NameQuisqualic acid
DescriptionQuisqualic acid, also known as quisqualate, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Quisqualic acid is thought to mimic L-glutamic acid, which is a neurotransmitter in the insect neuromuscular junction and mammalian central nervous system. It causes excitotoxicity and is used in neuroscience to selectively destroy neurons in the brain or spinal cord. Quisqualic acid is a very strong basic compound (based on its pKa). Research conducted by the USDA Agricultural Research Service, has demonstrated quisqualic acid is also present within the flower petals of zonal geranium (Pelargonium x hortorum) and is responsible for causing rigid paralysis of the Japanese beetle. Quisqualic acid occurs naturally in the seeds of Quisqualis species. It is one of the most potent AMPA receptor agonists known. Quisqualic acid is found in Apis cerana, Quisqualis fructus and Quisqualis indica . Quisqualic acid is an agonist of the AMPA, kainate, and group I metabotropic glutamate receptors.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0050685 (Quisqualic acid)


  Mrv0541 02231216372D          

 13 13  0  0  1  0            999 V2000
    1.5783    2.2433    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1913    1.6913    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9760    1.9462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1475    2.7532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5891    1.3942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  2  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
M  END
Download

3D MOL for NP0050685 (Quisqualic acid)

Download
3D SDF for NP0050685 (Quisqualic acid)

  Mrv0541 02231216372D          

 13 13  0  0  1  0            999 V2000
    1.5783    2.2433    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1913    1.6913    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9760    1.9462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1475    2.7532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5891    1.3942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  2  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0050685

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@@H](CN1OC(=O)NC1=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H7N3O5/c6-2(3(9)10)1-8-4(11)7-5(12)13-8/h2H,1,6H2,(H,9,10)(H,7,11,12)/t2-/m0/s1

> <INCHI_KEY>
ASNFTDCKZKHJSW-REOHCLBHSA-N

> <FORMULA>
C5H7N3O5

> <MOLECULAR_WEIGHT>
189.1262

> <EXACT_MASS>
189.038570349

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
15.393163589413179

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-3-(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)propanoic acid

> <ALOGPS_LOGP>
-2.69

> <JCHEM_LOGP>
-3.6865236566092165

> <ALOGPS_LOGS>
-0.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.433048314840663

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4555189354790445

> <JCHEM_PKA_STRONGEST_BASIC>
8.556654742157054

> <JCHEM_POLAR_SURFACE_AREA>
121.96000000000001

> <JCHEM_REFRACTIVITY>
36.51180000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.36e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
quisqualate

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0050685 (Quisqualic acid)
Download
PDB for NP0050685 (Quisqualic acid)
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  N   UNK     0       2.946   4.187   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       4.090   3.157   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.770   1.651   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       2.306   1.175   0.000  0.00  0.00           N+0
HETATM    5  O   UNK     0       1.830  -0.290   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.615  -1.536   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      -0.186   1.175   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.060   3.620   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.555   3.633   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.875   5.139   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       6.700   2.603   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8    4   10                                                  
CONECT   10    9                                                            
CONECT   11    2   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

Download
3D PDB for NP0050685 (Quisqualic acid)
Download
SMILES for NP0050685 (Quisqualic acid)
N[C@@H](CN1OC(=O)NC1=O)C(O)=O
Download
INCHI for NP0050685 (Quisqualic acid)
InChI=1S/C5H7N3O5/c6-2(3(9)10)1-8-4(11)7-5(12)13-8/h2H,1,6H2,(H,9,10)(H,7,11,12)/t2-/m0/s1
Download
View in JSmol
Synonyms
ValueSource
QuisqualateGenerator
Quisqualic acidChEMBL, Generator
(2S)-2-Amino-3-(3-hydroxy-5-oxo-2,5-dihydro-1,2,4-oxadiazol-2-yl)propanoateGenerator
Chemical FormulaC5H7N3O5
Average Mass189.1262 Da
Monoisotopic Mass189.03857 Da
IUPAC Name(2S)-2-amino-3-(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)propanoic acid
Traditional Namequisqualate
CAS Registry NumberNot Available
SMILES
N[C@@H](CN1OC(=O)NC1=O)C(O)=O
InChI Identifier
InChI=1S/C5H7N3O5/c6-2(3(9)10)1-8-4(11)7-5(12)13-8/h2H,1,6H2,(H,9,10)(H,7,11,12)/t2-/m0/s1
InChI KeyASNFTDCKZKHJSW-REOHCLBHSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Apis ceranaLOTUS Database
Quisqualis fructusPlant
Quisqualis indicaPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentL-alpha-amino acids  
Alternative Parents
Substituents
  • L-alpha-amino acid
    • 

  • 1,2,4-oxadiazole
    • 

  • Azole
    • 

  • Oxadiazole
    • 

  • Heteroaromatic compound
    • 

  • Amino acid
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organoheterocyclic compound
    • 

  • Azacycle
    • 

  • Oxacycle
    • 

  • Primary amine
    • 

  • Organopnictogen compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Amine
    • 

  • Primary aliphatic amine
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • 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-2.7ALOGPS
logP-3.7ChemAxon
logS-0.55ALOGPS
pKa (Strongest Acidic)1.46ChemAxon
pKa (Strongest Basic)8.56ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area121.96 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity36.51 m³·mol⁻¹ChemAxon
Polarizability15.39 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDDB02999  
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00001391  
Chemspider IDNot Available
KEGG Compound IDC08296  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkQuisqualic acid  
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available