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CHEBI:2255 - 7β-aminocephalosporanic acid

Default Structure
ChEBI IDCHEBI:2255
ChEBI Name7β-aminocephalosporanic acid
Stars
ASCII Name7beta-aminocephalosporanic acid
DefinitionThe α,β-unsaturated monocarboxylic acid that is the active nucleus for the synthesis of cephalosporins and intermediates.
Last Modified21 November 2019
DownloadsMolfile
FormulaC10H12N2O5S
Net Charge0
Average Mass272.282
Monoisotopic Mass272.04669
SMILES[H][C@]12SCC(COC(C)=O)=C(C(=O)O)N1C(=O)[C@H]2N
InChIInChI=1S/C10H12N2O5S/c1-4(13)17-2-5-3-18-9-6(11)8(14)12(9)7(5)10(15)16/h6,9H,2-3,11H2,1H3,(H,15,16)/t6-,9-/m1/s1
InChIKeyHSHGZXNAXBPPDL-HZGVNTEJSA-N
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
ChEBI Ontology
Outgoing Relation(s)
7β-aminocephalosporanic acid (CHEBI:2255) has functional parent cephalosporanic acid (CHEBI:23064)
7β-aminocephalosporanic acid (CHEBI:2255) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
7β-aminocephalosporanic acid (CHEBI:2255) is tautomer of 7β-aminocephalosporanic acid zwitterion (CHEBI:58501)
Incoming Relation(s)
7β-aminocephalosporanic acid zwitterion (CHEBI:58501) is tautomer of 7β-aminocephalosporanic acid (CHEBI:2255)
IUPAC Names 
3-acetoxymethyl-7β-amino-3,4-didehydrocepham-4-carboxylic acid
(6R,7R)-3-(acetoxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Synonyms  Source
7-ACAKEGG COMPOUND
7-Aminocephalosporanic acidKEGG COMPOUND
7-Aminocephalosporinic acidKEGG COMPOUND
(7R)-7-AminocephalosporanateKEGG COMPOUND
Manual XrefsDatabases
4KRPDBeChem
C07756KEGG COMPOUND
LSM-5737LINCS
Registry NumbersSources
Reaxys:622638Reaxys
Beilstein:8919572Beilstein
CAS:957-68-6ChemIDplus
CAS:957-68-6KEGG COMPOUND
Citations