benzoyl-AMP (CHEBI:156046)

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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

Download	Molfile XML SDF

more structures >>

Molfile

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The Resolver thinks Mol

OOB - Ideal conformer

RDKit 3D

starting HoverWatcher_5

Time for openFile(OOB - Ideal conformer

RDKit 3D

49 52 0 0 0 0 0 0 0 0999 V2000

-5.1290 0.0680 0.3830 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.8450 -0.0080 -0.0170 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.9150 -1.0990 0.7150 P 0 0 1 0 0 5 0 0 0 0 0 0

-2.7530 -0.7100 2.2690 O 0 0 0 0 0 0 0 0 0 0 0 0

-3.5410 -2.4350 0.6040 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.4650 -1.1250 0.0150 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.4470 -2.0620 0.3690 C 0 0 0 0 0 0 0 0 0 0 0 0

0.7980 -1.8100 -0.4850 C 0 0 2 0 0 0 0 0 0 0 0 0

1.8820 -2.8670 -0.1800 C 0 0 1 0 0 0 0 0 0 0 0 0

1.8610 -3.9040 -1.1630 O 0 0 0 0 0 0 0 0 0 0 0 0

3.2080 -2.0770 -0.2560 C 0 0 1 0 0 0 0 0 0 0 0 0

4.0460 -2.6020 -1.2870 O 0 0 0 0 0 0 0 0 0 0 0 0

2.7670 -0.6360 -0.5970 C 0 0 1 0 0 0 0 0 0 0 0 0

1.4010 -0.5460 -0.1340 O 0 0 0 0 0 0 0 0 0 0 0 0

3.6100 0.3350 0.1050 N 0 0 0 0 0 0 0 0 0 0 0 0

4.8240 0.8120 -0.3190 C 0 0 0 0 0 0 0 0 0 0 0 0

5.2520 1.7140 0.6710 C 0 0 0 0 0 0 0 0 0 0 0 0

4.2950 1.7390 1.6290 N 0 0 0 0 0 0 0 0 0 0 0 0

3.3280 0.9350 1.2960 C 0 0 0 0 0 0 0 0 0 0 0 0

5.5960 0.6050 -1.3810 N 0 0 0 0 0 0 0 0 0 0 0 0

6.7460 1.2320 -1.5080 C 0 0 0 0 0 0 0 0 0 0 0 0

7.1900 2.0880 -0.6050 N 0 0 0 0 0 0 0 0 0 0 0 0

6.4900 2.3560 0.4920 C 0 0 0 0 0 0 0 0 0 0 0 0

6.9630 3.2540 1.4320 N 0 0 0 0 0 0 0 0 0 0 0 0

-5.5370 -0.6690 1.2590 O 0 0 0 0 0 0 0 0 0 0 0 0

-6.0400 1.0500 -0.2400 C 0 0 0 0 0 0 0 0 0 0 0 0

-5.5760 1.8940 -1.2510 C 0 0 0 0 0 0 0 0 0 0 0 0

-6.4340 2.8050 -1.8320 C 0 0 0 0 0 0 0 0 0 0 0 0

-7.7510 2.8840 -1.4150 C 0 0 0 0 0 0 0 0 0 0 0 0

-8.2170 2.0500 -0.4140 C 0 0 0 0 0 0 0 0 0 0 0 0

-7.3710 1.1350 0.1760 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.3480 0.1560 2.4180 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.1940 -1.9430 1.4230 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.8080 -3.0760 0.1940 H 0 0 0 0 0 0 0 0 0 0 0 0

0.5390 -1.8260 -1.5440 H 0 0 0 0 0 0 0 0 0 0 0 0

1.7400 -3.2840 0.8170 H 0 0 0 0 0 0 0 0 0 0 0 0

2.5230 -4.5950 -1.0200 H 0 0 0 0 0 0 0 0 0 0 0 0

3.7230 -2.1030 0.7040 H 0 0 0 0 0 0 0 0 0 0 0 0

4.3030 -3.5240 -1.1530 H 0 0 0 0 0 0 0 0 0 0 0 0

2.8120 -0.4710 -1.6740 H 0 0 0 0 0 0 0 0 0 0 0 0

2.4360 0.7630 1.8810 H 0 0 0 0 0 0 0 0 0 0 0 0

7.3480 1.0400 -2.3830 H 0 0 0 0 0 0 0 0 0 0 0 0

7.8160 3.6960 1.2950 H 0 0 0 0 0 0 0 0 0 0 0 0

6.4430 3.4420 2.2290 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.5480 1.8340 -1.5770 H 0 0 0 0 0 0 0 0 0 0 0 0

-6.0760 3.4580 -2.6150 H 0 0 0 0 0 0 0 0 0 0 0 0

-8.4180 3.5990 -1.8730 H 0 0 0 0 0 0 0 0 0 0 0 0

-9.2460 2.1170 -0.0930 H 0 0 0 0 0 0 0 0 0 0 0 0

-7.7370 0.4820 0.9540 H 0 0 0 0 0 0 0 0 0 0 0 0

24 23 1 0

23 22 1 0

23 17 2 0

29 28 1 0

29 30 2 0

22 21 2 0

28 27 2 0

17 18 1 0

17 16 1 0

18 19 2 0

30 31 1 0

27 26 1 0

21 20 1 0

16 20 2 0

16 15 1 0

26 31 2 0

26 1 1 0

19 15 1 0

15 13 1 0

1 25 2 0

1 2 1 0

13 11 1 0

13 14 1 0

3 2 1 6

11 9 1 0

11 12 1 0

9 8 1 0

9 10 1 0

14 8 1 0

7 8 1 0

7 6 1 0

6 3 1 0

3 5 2 0

3 4 1 0

4 32 1 0

7 33 1 0

7 34 1 0

8 35 1 6

9 36 1 1

10 37 1 0

11 38 1 1

12 39 1 0

13 40 1 6

19 41 1 0

21 42 1 0

24 43 1 0

24 44 1 0

27 45 1 0

28 46 1 0

29 47 1 0

30 48 1 0

31 49 1 0

M END): 16 ms

reading 49 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

49 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Formula

C17H18N5O8P

Net Charge

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
View more database links

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]
A benzoate CoA ligase (BadA), isolated from the bacterium Rhodopseudomonas palustris, catalyzes the conversion of benzoate to benzoyl CoA on the catabolic pathway of aromatic carboxylic acids. Herein, apparent Michaelis constants K(app)cat and K(app)M were determined for an expanded array of 31 substrates chosen to systematically probe the active site architecture of the enzyme and provide a baseline for expansion of wild-type substrate specificity. Acyl CoA products were observed for 25 of the 31 substrates; in general, BadA converted ortho-substituted substrates better than the corresponding meta and para regioisomers, and the turnover number was more affected by steric rather than electronic effects. The kinetic data are interpreted in relation to six crystal structures of BadA in complex with several substrates and a benzoyl-AMP reaction intermediate. In contrast to other known natural substrate-bound benzoate ligase structures, all substrate-bound BadA structures adopted the thiolation conformation instead of the adenylation conformation. We also observed all the aryl carboxylates to be uniquely oriented within the active site, relative to other structures. Together, the kinetics and structural data suggested a mechanism that involves substrate binding in the thiolation conformation, followed by substrate rotation to an active orientation upon the transition to the adenylation conformation. On the basis of this hypothesis and the structural data, sterically demanding active site residues were mutated, and the substrate specificity was expanded substantially versus that of BadA. Novel activities were seen for substrates with larger substituents, including phenyl acetate. Additionally, the mutant Lys427Ala identified this nonconserved residue as essential for the thiolation step of BadA, but not adenylation. These variously acylated CoAs can serve as novel substrates of acyl CoA-dependent acyltransferases in coupled enzyme assays to produce analogues of bioactive natural products.

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

CHEBI:156046 - benzoyl-AMP

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