Acivicin (CHEM018691)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:27:35 UTC
Update Date2016-11-09 01:15:51 UTC
Accession NumberCHEM018691
Identification
Common NameAcivicin
ClassSmall Molecule
DescriptionAn L-alpha-amino acid that is L-alanine in which the methyl group is replaced by a (5S)-3-chloro-4,5-dihydro-1,2-oxazol-5-yl group. A glutamine analogue antimetabolite, it interferes with glutamate metabolism and several glutamate-dependent synthetic enzymes. It is obtained as a fermentation product of Streptomyces sviceus bacteria.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(alpha-S,5S)-alpha-Amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acidChEBI
(AlphaS,5S)-alpha-amino-3-chloro-2-isoxazoline-5-acetic acidChEBI
AcivicineChEBI
AcivicinoChEBI
AcivicinumChEBI
Antibiotic at 125ChEBI
AT 125ChEBI
AT-125ChEBI
NSC 163501ChEBI
NSC-163501ChEBI
U 42126ChEBI
U-42,126ChEBI
(a-S,5S)-a-Amino-3-chloro-4,5-dihydro-5-isoxazoleacetateGenerator
(a-S,5S)-a-Amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acidGenerator
(alpha-S,5S)-alpha-Amino-3-chloro-4,5-dihydro-5-isoxazoleacetateGenerator
(Α-S,5S)-α-amino-3-chloro-4,5-dihydro-5-isoxazoleacetateGenerator
(Α-S,5S)-α-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acidGenerator
(AlphaS,5S)-a-amino-3-chloro-2-isoxazoline-5-acetateGenerator
(AlphaS,5S)-a-amino-3-chloro-2-isoxazoline-5-acetic acidGenerator
(AlphaS,5S)-alpha-amino-3-chloro-2-isoxazoline-5-acetateGenerator
(AlphaS,5S)-α-amino-3-chloro-2-isoxazoline-5-acetateGenerator
(AlphaS,5S)-α-amino-3-chloro-2-isoxazoline-5-acetic acidGenerator
L-(AlphaS,5S)-alpha-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acidMeSH
alpha-S,5S-alpha-amino-3-chloro-2-Isoxazoline-5-acetic acidMeSH
alpha-amino-3-chloro-4,5-dihydro-5-Isoxazoleacetic acidMeSH
Chemical FormulaC5H7ClN2O3
Average Molecular Mass178.574 g/mol
Monoisotopic Mass178.015 g/mol
CAS Registry Number42228-92-2
IUPAC Name(2S)-2-amino-2-[(5S)-3-chloro-4,5-dihydro-1,2-oxazol-5-yl]acetic acid
Traditional Nameacivicin
SMILES[H][C@@](N)(C(O)=O)[C@]1([H])CC(Cl)=NO1
InChI IdentifierInChI=1S/C5H7ClN2O3/c6-3-1-2(11-8-3)4(7)5(9)10/h2,4H,1,7H2,(H,9,10)/t2-,4-/m0/s1
InChI KeyQAWIHIJWNYOLBE-OKKQSCSOSA-N
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
  • Isoxazoline
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility11.5 g/LALOGPS
logP-2.6ALOGPS
logP-2.7ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)1.4ChemAxon
pKa (Strongest Basic)8.59ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area84.91 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity36.4 m³·mol⁻¹ChemAxon
Polarizability14.96 ųChemAxon
Number of Rings1ChemAxon
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, Positivesplash10-01u0-2900000000-76e795e9bd82e5e43967Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-2900000000-a228ee07a7380aa3da3bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-9200000000-54e3b8fb1dc803d75f8fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1900000000-81c845867113a4174dfcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-3900000000-e5a8dbb10849b5f0fc08Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-6cb45d6cb526b41df671Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
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 IDCPD0-1036
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAcivicin
Chemspider IDNot Available
ChEBI ID74545
PubChem Compound ID294641
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11478776
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=14586123
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=2383250
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=2894949
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=3112985
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=3165971
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=3710919
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=3915184
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=6102405
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=7026076
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=7150366
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=8060335
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=9829740