CHEBI:63200 - N2-[(R)-2-amino-2-(4-hydroxyphenyl)acetyl]-N-butyl-L-serinamide

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ChEBI Name N2-[(R)-2-amino-2-(4-hydroxyphenyl)acetyl]-N-butyl-L-serinamide
ChEBI ID CHEBI:63200
ChEBI ASCII Name N(2)-[(R)-2-amino-2-(4-hydroxyphenyl)acetyl]-N-butyl-L-serinamide
Definition A dipeptide consisting of N-butyl-L-serinamide having an (R)-2-amino-2-(4-hydroxyphenyl)acetyl residue attached to its α-amino nitrogen. A synthetic determinant of cefadroxil, it is a promising tool for determining in vitro cross-reactivity to cefadroxil in amoxicillin-allergic patients.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C15H23N3O4
Net Charge 0
Average Mass 309.36080
Monoisotopic Mass 309.16886
InChI InChI=1S/C15H23N3O4/c1-2-3-8-17-14(21)12(9-19)18-15(22)13(16)10-4-6-11(20)7-5-10/h4-7,12-13,19-20H,2-3,8-9,16H2,1H3,(H,17,21)(H,18,22)/t12-,13+/m0/s1
InChIKey KYIHERVMDNDRBE-QWHCGFSZSA-N
SMILES CCCCNC(=O)[C@H](CO)NC(=O)[C@H](N)c1ccc(O)cc1
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing N2-[(R)-2-amino-2-(4-hydroxyphenyl)acetyl]-N-butyl-L-serinamide (CHEBI:63200) has parent hydride Gly-Ser (CHEBI:73516)
N2-[(R)-2-amino-2-(4-hydroxyphenyl)acetyl]-N-butyl-L-serinamide (CHEBI:63200) is a L-serine derivative (CHEBI:84135)
N2-[(R)-2-amino-2-(4-hydroxyphenyl)acetyl]-N-butyl-L-serinamide (CHEBI:63200) is a dipeptide (CHEBI:46761)
IUPAC Name
N2-[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]-N-butyl-L-serinamide
Synonyms Sources
(αR)-α-amino-N-[(1S)-2-(butylamino)-1-(hydroxymethyl)-2-oxoethyl]-4-hydroxybenzeneacetamide ChEBI
2-[4-(HO)-C6H4]-Gly-SerNHBu ChEBI
HOPhG-Ser-Bu ChEBI
Citations Waiting for Citations Types Sources
21425867 PubMed citation Europe PMC
33292516 PubMed citation Europe PMC
Last Modified
12 January 2021