Acromelic acid A (CHEM003092)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2014-08-29 05:29:26 UTC
Update Date2026-04-05 15:27:24 UTC
Accession NumberCHEM003092
Identification
Common NameAcromelic acid A
ClassSmall Molecule
DescriptionAcromelic acid A, one of the kainoids of natural origin, is a unique and potent excitotoxic glutamate analogue. It has also been shown to directly activate non-N-methyl-D-aspartate receptors on cultured spinal neurons to induce neuronal death (1).
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Amine
  • Animal Toxin
  • Ester
  • Fungal Toxin
  • Human Neurotoxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Acromelate aGenerator
Chemical FormulaC13H14N2O7
Average Molecular Mass310.260 g/mol
Monoisotopic Mass310.080 g/mol
CAS Registry Number86630-09-3
IUPAC NameNot Available
Traditional Name5-[(3S,4S,5S)-5-carboxy-4-(carboxymethyl)pyrrolidin-3-yl]-6-hydroxypyridine-2-carboxylic acid
SMILES[H][C@@]1(NC[C@]([H])(C2=C(O)N=C(C=C2)C(O)=O)[C@]1([H])CC(O)=O)C(O)=O
InChI IdentifierInChI=1S/C13H14N2O7/c16-9(17)3-6-7(4-14-10(6)13(21)22)5-1-2-8(12(19)20)15-11(5)18/h1-2,6-7,10,14H,3-4H2,(H,15,18)(H,16,17)(H,19,20)(H,21,22)/t6-,7+,10-/m0/s1
InChI KeyCWXNEBSQRIECMV-PJKMHFRUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolides and analogues
Sub ClassNot Available
Direct ParentMacrolides and analogues
Alternative Parents
Substituents
  • Macrolide
  • Benzylether
  • 2-bromophenol
  • 2-halophenol
  • 4-halophenol
  • 4-bromophenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Ketal
  • Bromobenzene
  • Halobenzene
  • Phenol
  • Oxane
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl bromide
  • Carboxylic acid ester
  • Secondary alcohol
  • Hemiacetal
  • Lactone
  • Ether
  • Dialkyl ether
  • Acetal
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Organooxygen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organobromide
  • Organohalogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cell surface
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.77 g/LALOGPS
logP-1.2ALOGPS
logP-2.5ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)0.71ChemAxon
pKa (Strongest Basic)11.93ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area157.05 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity70.39 m³·mol⁻¹ChemAxon
Polarizability28.39 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02td-0091000000-de71af5e29036d0557d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0190000000-792200eb94a1f330fa85Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06di-2890000000-6716c34cc744126907b6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-066r-0093000000-08244baf3af4047e40eeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0091000000-9dcf70b9abb364723b7bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-8290000000-7b869b76c0cd1ac7ee02Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID134690
PubChem Compound ID108086
Kegg Compound IDC19949
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12882485
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=1341901
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=1359719
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=1375859
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=15560485
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=16480870
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=1687368
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=1817797
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=1890926
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=19429136
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=1963751
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=21354794
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=23124023
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=2574623
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=25861935
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=2881596
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=7477968
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=7595634
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=7821331
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=8317271
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=8846097