Compound: azaserine
SMILES: O=C(OC[C@H](N)C(=O)O)C=[N+]=[N-]
InChIKey: MZZGOOYMKKIOOX-VKHMYHEASA-N
Synonyms: azaserine, 115-02-6, O-Diazoacetyl-L-serine, L-azaserine, Azaserina, L-Serine, diazoacetate (ester), Azaserinum, Diazoacetate (ester) L-serine, CL 337, L-beta-(Diazoacetoxy)alanin, NSC-742, CN-15,757, P-165, CN 15757, Serine, diazoacetate (ester), L-, Acetic acid, diazo-, ester with serine, CL-337, NSC742, CN-15757, DTXSID9020118, 87299V3Q9W, DTXCID70118, CHEBI:74846, (2S)-2-amino-3-(2-diazoacetyl)oxypropanoic acid, Azeserine, L-serine diazoacetate (ester), Serine Diazoacetate, O Diazoacetyl L serine, RefChem:560455, Diazoacetic Acid Ester with Serine, L-DIAZOACETATE (ESTER) SERINE, (2S)-2-amino-3-((2E)-2-diazoacetyl)oxypropanoic acid, 204-061-6, Diazoacetate(ester) L-serine, Diazoacetylserine, L-Diazoacetate(ester) serine, Azaserin, L-Serine, O-(2-diazoacetyl)-, O-(diazoacetyl)-L-serine, RCRA waste number U015, CCRIS 61, HSDB 5093, (2S)-2-amino-3-[(2-diazoacetyl)oxy]propanoic acid, AI3-25016, AZS, MLS000028392, SMR000058638, (2S)-2-amino-3-(2-diazoacetyl)oxy-propanoic acid, Azaserine [USAN:INN], Azaserinum [INN-Latin], Azaserina [INN-Spanish], CAS-115-02-6, NSC 742, EINECS 204-061-6, RCRA waste no. U015, UNII-87299V3Q9W, NCGC00018164-02, CI-337;O-Diazoacetyl-L-serine;P-165, ASASERINE, L-serine diazoacetate, AZASERINE [INN], Opera_ID_431, AZASERINE [MI], Azaserine (USAN/INN), AZASERINE [HSDB], AZASERINE [IARC], AZASERINE [USAN], (S)-2-amino-3-(2-diazoacetoxy)propanoic acid, L-serine diazoacetate ester, NCIMech_000844, SCHEMBL8861, L-beta-(diazoacetoxy)alanine, L-serine, O-(diazoacetyl)-, CHEMBL442607, orb1296166, CHEMBL1095699, O-(2-11Diazoacetyl)-L-serine, MZZGOOYMKKIOOX-VKHMYHEASA-N, GLXC-20291, HMS2232J04, HY-B0919, Tox21_110833, Tox21_302892, MFCD00036802, Tox21_110833_1, EBC-536096, NCGC00021876-03, NCGC00021876-04, NCGC00256571-01, AC-37858, AS-80005, FD145614, DB-229831, C19194, D03032, F787600, Q4832281
Theoretical properties:
molecular_formula: C5H7N3O4
molecular_weight: 173.13 g/mol
exact_mass: 173.04365571 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 6
rotatable_bond_count: 5
heavy_atom_count: 12
topological_polar_surface_area: 91.6 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: ORTHORHOMBIC, PALE YELLOW TO GREEN CRYSTALS FROM 90% ETHANOL.
color: ORTHORHOMBIC, PALE YELLOW TO GREEN CRYSTALS FROM 90% ETHANOL.
melting_point: About 157 deg
solubility: SLIGHTLY SOL IN METHANOL, ABSOLUTE ETHANOL ACETONE; SOL IN WARM AQ SOLN OF METHANOL, ABSOLUTE ETHANOL ACETONE
vapor_pressure: 1.53X10-10 mmHg at 25 °C.
Descriptions:
pubchem: Azaserine can cause cancer according to an independent committee of scientific and health experts.
chebi: A carboxylic ester resulting from the formal condensation of the carboxy group of diazoacetic acid with the alcoholic hydroxy group of <small>L</small>-serine. An antibiotic produced by a <em>Streptomyces</em> species.
chembl: AZASERINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: Azaserine is a naturally occurring toxic serine derivative diazo compound with antineoplastic and antibiotic properties deriving from its action as a purinergic antagonist and structural similarity to glutamine.  Azaserine acts by competitively inhibiting glutamine amidotransferase, a key enzyme responsible for glutamine metabolism.