CHEBI:156046 - benzoyl-AMP

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ChEBI Name benzoyl-AMP
ChEBI ID CHEBI:156046
Definition A purine ribonucleoside 5'-monophosphate that is adenosine 5'-monophosphate in which one of the hydroxy groups of the phosphate has been condensed with the carboxylic acid group of benzoic acid.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ZINC000004097115
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Formula C17H18N5O8P
Net Charge 0
Average Mass 451.332
Monoisotopic Mass 451.08930
InChI InChI=1S/C17H18N5O8P/c18-14-11-15(20-7-19-14)22(8-21-11)16-13(24)12(23)10(29-16)6-28-31(26,27)30-17(25)9-4-2-1-3-5-9/h1-5,7-8,10,12-13,16,23-24H,6H2,(H,26,27)(H2,18,19,20)/t10-,12-,13-,16-/m1/s1
InChIKey PTJTVELTWZMHPG-XNIJJKJLSA-N
SMILES NC1=NC=NC2=C1N=CN2[C@@H]3O[C@H](COP(=O)(OC(C4=CC=CC=C4)=O)O)[C@@H](O)[C@H]3O
ChEBI Ontology
Outgoing benzoyl-AMP (CHEBI:156046) has functional parent adenosine 5'-monophosphate (CHEBI:16027)
benzoyl-AMP (CHEBI:156046) is a benzoate ester (CHEBI:36054)
benzoyl-AMP (CHEBI:156046) is a purine ribonucleoside 5'-monophosphate (CHEBI:37021)
benzoyl-AMP (CHEBI:156046) is conjugate acid of benzoyl-AMP(1−) (CHEBI:149705)
Incoming benzoyl-AMP(1−) (CHEBI:149705) is conjugate base of benzoyl-AMP (CHEBI:156046)
IUPAC Name
5'-O-[(benzoyloxy)(hydroxy)phosphoryl]adenosine
Synonyms Sources
5'-adenylic acid benzoyl ester ChEBI
5'-benzoylphosphoadenosine KEGG COMPOUND
benzoic acid AMP ester ChEBI
benzoyl adenylate ChEBI
benzoyl-AMP ChEBI
Bz-AMP ChEBI
Manual Xrefs Databases
C06433 KEGG COMPOUND
OOB PDBeChem
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Citations
Tripathi A, Park SR, Sikkema AP, Cho HJ, Wu J, Lee B, Xi C, Smith JL, Sherman DH (2018)
A Defined and Flexible Pocket Explains Aryl Substrate Promiscuity of the Cahuitamycin Starter Unit-Activating Enzyme CahJ.
Chembiochem : a European journal of chemical biology 19, 1595-1600 [PubMed:29742306]
[show Abstract]
Thornburg CK, Wortas-Strom S, Nosrati M, Geiger JH, Walker KD (2015)
Kinetically and Crystallographically Guided Mutations of a Benzoate CoA Ligase (BadA) Elucidate Mechanism and Expand Substrate Permissivity.
Biochemistry 54, 6230-6242 [PubMed:26378464]
[show Abstract]
Knights KM, Sykes MJ, Miners JO (2007)
Amino acid conjugation: contribution to the metabolism and toxicity of xenobiotic carboxylic acids.
Expert opinion on drug metabolism & toxicology 3, 159-168 [PubMed:17428148]
[show Abstract]
Li T, Rosazza JP (1998)
NMR identification of an acyl-adenylate intermediate in the aryl-aldehyde oxidoreductase catalyzed reaction.
The Journal of biological chemistry 273, 34230-34233 [PubMed:9852085]
[show Abstract]
KELLERMAN GM (1959)
Isolation and characteristics of the enzyme acyl 5'-nucleotidase.
Biochimica et biophysica acta 33, 101-105 [PubMed:13651188]
KELLERMAN GM (1958)
Benzoyl adenylate and hippuryl adenylate: preparation, properties, and relationship to the synthesis and transport of hippurate.
The Journal of biological chemistry 231, 427-443 [PubMed:13538981]
Last Modified
01 July 2020