Np mrd loader

Record Information
Version2.0
Created at2022-09-02 10:00:40 UTC
Updated at2025-02-11 15:45:12 UTC
NP-MRD IDNP0153363
Natural Product DOIhttps://doi.org/10.57994/2413
Secondary Accession NumbersNone
Natural Product Identification
Common Namekainic acid
DescriptionKainic acid, also known as kainate or acide kainique, belongs to the class of organic compounds known as kainoids. These are non-proteigenous amino acids with a structure characterized by the presence of a pyrrolidine ring bearing two dicarboxylic acid groups. Glutamate is produced by the cell's metabolic processes and there are four major classifications of glutamate receptors: NMDA receptors, AMPA receptors, kainate receptors, and the metabotropic glutamate receptors. Kainic acid is a very strong basic compound (based on its pKa). Such damage and death of neurons is referred to as an excitotoxic lesion. It is important to note that both chemical and electrical lesions potentially cause additional damage to the brain due to the very nature of the inserted electrode or cannula. In addition to inducing seizures, kainic acid is excitotoxic and epileptogenic. Called "Kainin-sou" or "Makuri" in Japan. kainic acid is found in Apis cerana, Chondria armata and Digenea simplex. Kainate receptors likely control a sodium channel that produces excitatory postsynaptic potentials (EPSPs) when glutamate binds.
Structure
Thumb
Synonyms
ValueSource
(2S-(2alpha,3beta,4beta))-2-Carboxy-4-(1-methylethenyl)-3-pyrrolidineacetic acidChEBI
Acide kainiqueChEBI
Acido kainicoChEBI
Acidum kainicumChEBI
alpha- Kainic acidChEBI
alpha-Kainic acidChEBI
Digenic acidChEBI
DigeninChEBI
DigensaeureChEBI
HelminalChEBI
KainsaeureChEBI
L-alpha-Kainic acidChEBI
KainateKegg
(2S-(2a,3b,4b))-2-Carboxy-4-(1-methylethenyl)-3-pyrrolidineacetateGenerator
(2S-(2a,3b,4b))-2-Carboxy-4-(1-methylethenyl)-3-pyrrolidineacetic acidGenerator
(2S-(2alpha,3beta,4beta))-2-Carboxy-4-(1-methylethenyl)-3-pyrrolidineacetateGenerator
(2S-(2Α,3β,4β))-2-carboxy-4-(1-methylethenyl)-3-pyrrolidineacetateGenerator
(2S-(2Α,3β,4β))-2-carboxy-4-(1-methylethenyl)-3-pyrrolidineacetic acidGenerator
a- KainateGenerator
a- Kainic acidGenerator
alpha- KainateGenerator
Α- kainateGenerator
Α- kainic acidGenerator
a-KainateGenerator
a-Kainic acidGenerator
alpha-KainateGenerator
Α-kainateGenerator
Α-kainic acidGenerator
DigenateGenerator
L-a-KainateGenerator
L-a-Kainic acidGenerator
L-alpha-KainateGenerator
L-Α-kainateGenerator
L-Α-kainic acidGenerator
Acid, digenicMeSH
Acid, kainicMeSH
Chemical FormulaC10H15NO4
Average Mass213.2304 Da
Monoisotopic Mass213.10011 Da
IUPAC Name(2S,3S,4S)-3-(carboxymethyl)-4-(prop-1-en-2-yl)pyrrolidine-2-carboxylic acid
Traditional Namekainic acid
CAS Registry NumberNot Available
SMILES
[H][C@@]1(CN[C@]([H])(C(O)=O)[C@@]1([H])CC(O)=O)C(C)=C
InChI Identifier
InChI=1S/C10H15NO4/c1-5(2)7-4-11-9(10(14)15)6(7)3-8(12)13/h6-7,9,11H,1,3-4H2,2H3,(H,12,13)(H,14,15)/t6-,7+,9-/m0/s1
InChI KeyVLSMHEGGTFMBBZ-OOZYFLPDSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HMBC NMR[1H, 13C] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)[email protected]Not AvailableNot Available2024-05-09View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)[email protected]Not AvailableNot Available2024-05-09View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)[email protected]Not AvailableNot Available2024-05-09View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)[email protected]Not AvailableNot Available2024-05-09View Spectrum
HOMO2DJ NMR[1H, 1H] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)[email protected]Not AvailableNot Available2024-05-09View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, C2D6OS, experimental)[email protected]Not AvailableNot Available2024-05-09View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, C2D6OS, experimental)[email protected]Not AvailableNot Available2024-05-09View Spectrum
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
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 499.83, C2D6OS, simulated)[email protected]Not AvailableNot Available2024-05-09View Spectrum
Species
Species of Origin
Species NameSourceReference
Apis ceranaLOTUS Database
Chondria armataLOTUS Database
Digenea simplexLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as kainoids. These are non-proteigenous amino acids with a structure characterized by the presence of a pyrrolidine ring bearing two dicarboxylic acid groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentKainoids
Alternative Parents
Substituents
  • Kainoid skeleton
  • Proline or derivatives
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Pyrrolidine carboxylic acid
  • Pyrrolidine carboxylic acid or derivatives
  • Dicarboxylic acid or derivatives
  • Pyrrolidine
  • Amino acid
  • Carboxylic acid
  • Secondary aliphatic amine
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Amine
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic 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-1.2ALOGPS
logP-2.4ChemAxon
logS-0.78ALOGPS
pKa (Strongest Acidic)1.74ChemAxon
pKa (Strongest Basic)11.59ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.63 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity52.2 m³·mol⁻¹ChemAxon
Polarizability21.02 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 IDC12819
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkKainic acid
METLIN IDNot Available
PubChem Compound10255
PDB IDNot Available
ChEBI ID31746
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]