Record Information
Version2.0
Creation Date2012-05-31 14:03:38 -0600
Update Date2015-06-03 15:54:41 -0600
Secondary Accession Numbers
  • ECMDB04053
Identification
Name:(2,3-Dihydroxybenzoyl)adenylic acid
Description(2,3-dihydroxybenzoyl)adenylate is a member of the chemical class known as Purine Ribonucleoside Monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.
Structure
Thumb
Synonyms:
  • (2,3-Dihydroxybenzoyl)adenylate
  • 2,3-Dihydroxybenzoyl adenylate
  • 2,3-Dihydroxybenzoyl adenylic acid
Chemical Formula:C17H18N5O10P
Weight:Average: 483.3261
Monoisotopic: 483.079128333
InChI Key:ULPVJDOMCRTJSN-RVXWVPLUSA-N
InChI:InChI=1S/C17H18N5O10P/c18-14-10-15(20-5-19-14)22(6-21-10)16-13(26)12(25)9(31-16)4-30-33(28,29)32-17(27)7-2-1-3-8(23)11(7)24/h1-3,5-6,9,12-13,16,23-26H,4H2,(H,28,29)(H2,18,19,20)/t9-,12-,13-,16-/m1/s1
CAS number:Not Available
IUPAC Name:{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(2,3-dihydroxybenzoyloxy)phosphinic acid
Traditional IUPAC Name:[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(2,3-dihydroxybenzoyloxy)phosphinic acid
SMILES:[H][C@]1(COP(O)(=O)OC(=O)C2=C(O)C(O)=CC=C2)O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])O
Chemical Taxonomy
Description belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine ribonucleotides
Direct ParentPurine ribonucleoside monophosphates
Alternative Parents
Substituents
  • Purine ribonucleoside monophosphate
  • Pentose-5-phosphate
  • Pentose phosphate
  • N-glycosyl compound
  • Glycosyl compound
  • Salicylic acid or derivatives
  • 6-aminopurine
  • Pentose monosaccharide
  • Monosaccharide phosphate
  • Imidazopyrimidine
  • Purine
  • Benzoic acid or derivatives
  • Catechol
  • Benzoyl
  • Acyl phosphate
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Monocyclic benzene moiety
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Imidolactam
  • Benzenoid
  • Alkyl phosphate
  • Phosphoric acid ester
  • Pyrimidine
  • Azole
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Imidazole
  • Vinylogous acid
  • Secondary alcohol
  • Amino acid or derivatives
  • 1,2-diol
  • Carboxylic acid salt
  • Azacycle
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organonitrogen compound
  • Amine
  • Organic salt
  • Organooxygen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility1.78 g/LALOGPS
logP-0.59ALOGPS
logP-2.6ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)0.78ChemAxon
pKa (Strongest Basic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area232.6 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity107.85 m³·mol⁻¹ChemAxon
Polarizability42.45 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Biosynthesis of siderophore group nonribosomal peptidesPW000760 ThumbThumb?image type=greyscaleThumb?image type=simple
Enterobactin BiosynthesisPW002048 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Biosynthesis of siderophore group nonribosomal peptides ec01053
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_4_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0910100000-6cc966e42959845ce140View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-cac72a96ea912fac0134View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-3900000000-33d698b4dd44287997c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-003r-2897700000-96e367950f88d2ffbae6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-3910000000-2730f7b44e981db61411View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-9600000000-b9455f923a6c6d2e397bView in MoNA
MSMass Spectrum (Electron Ionization)Not AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID5572
HMDB IDNot Available
Pubchem Compound ID440201
Kegg IDC04030
ChemSpider ID389188
Wikipedia IDNot Available
BioCyc IDCPD-62
EcoCyc IDCPD-62

Enzymes

General function:
Involved in isochorismatase activity
Specific function:
Required for production of 2,3-DHB. Also serves as an aryl carrier protein and plays a role in enterobactin assembly
Gene Name:
entB
Uniprot ID:
P0ADI4
Molecular weight:
32554
Reactions
Isochorismate + H(2)O = 2,3-dihydroxy-2,3-dihydrobenzoate + pyruvate.
General function:
Involved in catalytic activity
Specific function:
Activates the carboxylate group of 2,3-dihydroxy- benzoate (2,3-DHB), via ATP-dependent PPi exchange reactions, to the acyladenylate. Then, catalyzes the acylation of holo-entB with 2,3-DHB adenylate, preparing that molecule for amide bond formation with L-serine
Gene Name:
entE
Uniprot ID:
P10378
Molecular weight:
59112
Reactions
ATP + 2,3-dihydroxybenzoate = diphosphate + (2,3-dihydroxybenzoyl)adenylate.
(2,3-dihydroxybenzoyl)adenylate + holo-entB = adenosine 5'-monophosphate + acyl-holo-entB.
General function:
Involved in ligase activity
Specific function:
Activates the carboxylate group of L-serine via ATP- dependent PPi exchange reactions to the aminoacyladenylate, preparing that molecule for the final stages of enterobactin synthesis. Holo-entF acts as the catalyst for the formation of the three amide and three ester bonds present in the cyclic (2,3- dihydroxybenzoyl)serine trimer enterobactin, using seryladenylate and acyl-holo-entB (acylated with 2,3-dihydroxybenzoate by entE)
Gene Name:
entF
Uniprot ID:
P11454
Molecular weight:
141990
Reactions
ATP + L-serine = diphosphate + L-serine-adenylate.
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the transfer of the 4'-phosphopantetheine moiety from coenzyme A to apo-domains of both entB (an ArCP domain) and entF (a PCP domain). Plays an essential role in the assembly of the enterobactin
Gene Name:
entD
Uniprot ID:
P19925
Molecular weight:
23604
Reactions
CoA + apo-EntB/F = adenosine 3',5'-bisphosphate + holo-EntB/F.