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

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ChEBI Name α-N-dichloroacetyl-p-aminophenylserinol
ChEBI ID CHEBI:47325
ChEBI ASCII Name alpha-N-dichloroacetyl-p-aminophenylserinol
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C11H14Cl2N2O3
Net Charge 0
Average Mass 293.147
Monoisotopic Mass 292.03815
InChI InChI=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
InChIKey BFLNGKUCFYKCFZ-RKDXNWHRSA-N
SMILES C1=C([C@H]([C@H](NC(C(Cl)Cl)=O)CO)O)C=CC(=C1)N
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Application(s): 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.
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ChEBI Ontology
Outgoing 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 Sources
(1R,2R)-1-(4-aminophenyl)-2-(dichloroacetylamino)-1,3-propanediol ChEBI
α-N-dichloroacetyl-p-aminophenylserinol UniProt
α-N-dichloroacetyl-p-aminophenylserinol PDBeChem
N-[(1R,2R)-2-(4-aminophenyl)-2-hydroxy-1-(hydroxymethyl)ethyl]-2,2-dichloroacetamide PDBeChem
Manual Xrefs Databases
CLK PDBeChem
CPD-21781 MetaCyc
DB04411 DrugBank
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Registry Number Type Source
7411-64-5 CAS Registry Number ChEBI
Citations Waiting for Citations Types Sources
11468347 PubMed citation Europe PMC
24347692 PubMed citation Europe PMC
25267678 PubMed citation Europe PMC
25564306 PubMed citation Europe PMC
28823151 PubMed citation Europe PMC
Last Modified
10 January 2019