Azaserine (CHEM004158)

Record Information
Version1.0
Creation Date2016-05-19 01:36:09 UTC
Update Date2026-08-23 01:13:11 UTC
Accession NumberCHEM004158
Identification
Common NameAzaserine
ClassSmall Molecule
Description
A carboxylic ester resulting from the formal condensation of the carboxy group of diazoacetic acid with the alcoholic hydroxy group of L-serine. An antibiotic produced by a Streptomyces species.
Contaminant Sources
  • Clean Air Act Chemicals
  • IARC Carcinogens Group 2B
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
MOLSDF3D SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
AzaserinaChEBI
AzaserinumChEBI
L-AzaserineChEBI
L-beta-(Diazoacetoxy)alaninChEBI
L-beta-(Diazoacetoxy)alanineChEBI
L-Serine diazoacetateChEBI
L-Serine diazoacetate esterChEBI
L-b-(Diazoacetoxy)alaninGenerator
L-Β-(diazoacetoxy)alaninGenerator
L-b-(Diazoacetoxy)alanineGenerator
L-Β-(diazoacetoxy)alanineGenerator
L-Serine diazoacetic acidGenerator
L-Serine diazoacetic acid esterGenerator
AzeserineMeSH
O Diazoacetyl L serineMeSH
O-Diazoacetyl-L-serineMeSH
Chemical FormulaC5H7N3O4
Average Molecular Mass173.127 g/mol
Monoisotopic Mass173.044 g/mol
CAS Registry Number115-02-6
IUPAC Name(2S)-2-amino-3-[(2-diazoacetyl)oxy]propanoic acid
Traditional Nameazaserine
SMILES[H][C@](N)(COC(=O)C=[N+]=[N-])C(O)=O
InChI IdentifierInChI=1S/C5H7N3O4/c6-3(5(10)11)2-12-4(9)1-8-7/h1,3H,2,6H2,(H,10,11)/t3-/m0/s1
InChI KeyMZZGOOYMKKIOOX-VKHMYHEASA-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
  • Alpha-diazo ester
  • Dicarboxylic acid or derivatives
  • Carboxylic acid ester
  • Amino acid
  • Diazo compound
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organic zwitterion
  • Organic nitrogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxide
  • Carbonyl group
  • Amine
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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 Solubility19.4 g/LALOGPS
logP-1.3ALOGPS
logP-4.6ChemAxon
logS-0.95ALOGPS
pKa (Strongest Acidic)1.55ChemAxon
pKa (Strongest Basic)8.38ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area106.69 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity34.75 m³·mol⁻¹ChemAxon
Polarizability14.6 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
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
External Links
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDL-AZASERINE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAzaserine
Chemspider IDNot Available
ChEBI ID74846
PubChem Compound ID460129
Kegg Compound IDC19194
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=19136606
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23101568
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23301939
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=4951003
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=7048085
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=791808