N-(5-phosphoribosyl)-anthranilate (ECMDB24200) (M2MDB006317)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (2)
Record Information
Version2.0
Creation Date2015-09-08 17:50:02 -0600
Update Date2015-09-14 16:46:10 -0600
Secondary Accession Numbers
  • ECMDB24200
Identification
Name: N-(5-phosphoribosyl)-anthranilate
DescriptionN-(5-Phosphoribosyl)-anthranilate is a member of the chemical class known as Pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. N-(5-phosphoribosyl)-anthranilate is invovled in tryptophan biosynthesis. N-(5'-Phosphoribosyl)anthranilate isomerase-indole-3-glycerol-phosphate synthase from Escherichia coli is a monomeric bifunctional enzyme of Mr 49,500 that catalyzes two sequential reactions in the biosynthesis of tryptophan. (PMID 3303031) Phosphoribosyl anthranilate isomerase from Thermotoga maritima is an extremely stable and active homodimer. (PMID 8897600)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • N-(5-Phosphoribosyl)-anthranilic acid
Chemical Formula:C12H13NO9P
Weight:Average: 346.209
Monoisotopic: 346.03443874
InChI Key:PMFMJXPRNJUYMB-UHFFFAOYSA-K
InChI:InChI=1S/C12H16NO9P/c14-9-8(5-21-23(18,19)20)22-11(10(9)15)13-7-4-2-1-3-6(7)12(16)17/h1-4,8-11,13-15H,5H2,(H,16,17)(H2,18,19,20)/p-3
CAS number:Not Available
IUPAC Name:2-({3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}amino)benzoate
Traditional IUPAC Name:2-({3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}amino)benzoate
SMILES:OC1C(O)C(NC2=C(C=CC=C2)C([O-])=O)OC1COP([O-])([O-])=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentose phosphates
Alternative Parents
Substituents
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Benzoic acid or derivatives
  • Benzoic acid
  • Benzoyl
  • Phenylalkylamine
  • Aniline or substituted anilines
  • Secondary aliphatic/aromatic amine
  • Monocyclic benzene moiety
  • Organic phosphoric acid derivative
  • Benzenoid
  • Alkyl phosphate
  • Phosphoric acid ester
  • Vinylogous amide
  • Tetrahydrofuran
  • Secondary alcohol
  • Amino acid or derivatives
  • Amino acid
  • 1,2-diol
  • Secondary amine
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Alcohol
  • Amine
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic anion
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility21.5 g/LALOGPS
logP0.09ALOGPS
logP-0.15ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)1.23ChemAxon
pKa (Strongest Basic)-2.1ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area174.27 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity84.67 m³·mol⁻¹ChemAxon
Polarizability29.01 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
2-Aminobenzoic acid + Phosphoribosyl pyrophosphate > Pyrophosphate + N-(5-phosphoribosyl)-anthranilate + N-(5-phosphoribosyl)-anthranilate
N-(5-phosphoribosyl)-anthranilate + N-(5-phosphoribosyl)-anthranilate > 1-(o-carboxyphenylamino)-1'-deoxyribulose 5'-phosphate + 1-(o-carboxyphenylamino)-1'-deoxyribulose 5'-phosphate
N-(5-phosphoribosyl)-anthranilate + N-(5-phosphoribosyl)-anthranilate > 1-(2-Carboxyphenylamino)-1'-deoxyribulose-5'-phosphate
SMPDB Pathways:
Tryptophan metabolismPW000815 ThumbThumb?image type=greyscaleThumb?image type=simple
tryptophan metabolism IIPW001916 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-ba91d10082bd2fb49789View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-0009000000-be942d0b329937457b73View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fu-7900000000-8a15ea25fd2c2ed717dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-69e13688e52695febbe4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-1009000000-778c77e3318e670312afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003s-9200000000-3dd565bffbe85a3ee03fView in MoNA
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:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID25245690
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Anthranilate synthase component II
General function:
Involved in anthranilate phosphoribosyltransferase activity
Specific function:
Chorismate + L-glutamine = anthranilate + pyruvate + L-glutamate
Gene Name:
trpD
Uniprot ID:
P00904
Molecular weight:
56869
Reactions
Chorismate + L-glutamine = anthranilate + pyruvate + L-glutamate.
N-(5-phospho-D-ribosyl)-anthranilate + diphosphate = anthranilate + 5-phospho-alpha-D-ribose 1-diphosphate.
Protein Details
2. Tryptophan biosynthesis protein trpCF
General function:
Involved in catalytic activity
Specific function:
Bifunctional enzyme that catalyzes two sequential steps of tryptophan biosynthetic pathway. The first reaction is catalyzed by the isomerase, coded by the trpF domain; the second reaction is catalyzed by the synthase, coded by the trpC domain
Gene Name:
trpC
Uniprot ID:
P00909
Molecular weight:
49361
Reactions
N-(5-phospho-beta-D-ribosyl)anthranilate = 1-(2-carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate.
1-(2-carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate = 1-C-(3-indolyl)-glycerol 3-phosphate + CO(2) + H(2)O.