CHEBI:47325 - α-N-dichloroacetyl-p-aminophenylserinol

ChEBI IDCHEBI:47325
ChEBI Nameα-N-dichloroacetyl-p-aminophenylserinol
Stars
ASCII Namealpha-N-dichloroacetyl-p-aminophenylserinol
DefinitionA secondary carboxamide resulting from the formal condensation of the amino group of (1R,2R)-2-amino-1-(4-aminophenyl)propane-1,3-diol with the carboxy group of dichloroacetic acid. It is an intermediate used in the biosynthesis pathway of the antibiotic, chloramphenicol.
Last Modified10 January 2019
DownloadsMolfile
FormulaC11H14Cl2N2O3
Net Charge0
Average Mass293.150
Monoisotopic Mass292.03815
SMILESNc1ccc([C@@H](O)[C@@H](CO)NC(=O)C(Cl)Cl)cc1
InChIInChI=1S/C11H14Cl2N2O3/c12-10(13)11(18)15-8(5-16)9(17)6-1-3-7(14)4-2-6/h1-4,8-10,16-17H,5,14H2,(H,15,18)/t8-,9-/m1/s1
InChIKeyBFLNGKUCFYKCFZ-RKDXNWHRSA-N
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Application:
prodrug  A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
ChEBI Ontology
Outgoing Relation(s)
α-N-dichloroacetyl-p-aminophenylserinol (CHEBI:47325) has role prodrug (CHEBI:50266)
α-N-dichloroacetyl-p-aminophenylserinol (CHEBI:47325) is a diol (CHEBI:23824)
α-N-dichloroacetyl-p-aminophenylserinol (CHEBI:47325) is a organochlorine compound (CHEBI:36683)
α-N-dichloroacetyl-p-aminophenylserinol (CHEBI:47325) is a secondary carboxamide (CHEBI:140325)
α-N-dichloroacetyl-p-aminophenylserinol (CHEBI:47325) is a substituted aniline (CHEBI:48975)
IUPAC Name 
N-[(1R,2R)-1-(4-aminophenyl)-1,3-dihydroxypropan-2-yl]-2,2-dichloroacetamide
Synonyms  Source
N-[(1R,2R)-2-(4-aminophenyl)-2-hydroxy-1-(hydroxymethyl)ethyl]-2,2-dichloroacetamidePDBeChem
α-N-dichloroacetyl-p-aminophenylserinolPDBeChem
(1R,2R)-1-(4-aminophenyl)-2-(dichloroacetylamino)-1,3-propanediolChEBI
UniProt Name  Source
α-N-dichloroacetyl-p-aminophenylserinolUniProt
Manual XrefsDatabases
CLKPDBeChem
CPD-21781MetaCyc
DB04411DrugBank
Registry NumbersSources
CAS:7411-64-5ChEBI
Citations