P. aeruginosa Metabolome Database: N-(5-Phospho-D-ribosyl)anthranilate (PAMDB001021)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB001021

Identification

Name:

N-(5-Phospho-D-ribosyl)anthranilate

Description:

N-(5-phospho-D-ribosyl)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-Phospho-D-ribosyl)anthranilate is invovled in tryptophan biosynthesis. N-(5'-Phosphoribosyl)anthranilate isomerase-indole-3-glycerol-phosphate synthase from Pseudomonas aeruginosa 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

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

5'-P-Ribosyl-anthranilate
5'-P-Ribosyl-anthranilic acid
5'-Phosphoribosyl-anthranilate
5'-Phosphoribosyl-anthranilic acid
5-P-Ribosyl-anthranilate
5-P-Ribosyl-anthranilic acid
5-Phosphoribosyl-anthranilate
5-Phosphoribosyl-anthranilic acid
N-(5-phospho-β-D-ribosyl)-anthranilate
N-(5-phospho-D-ribosyl)-anthranilate
N-(5-phosphoribosyl)-anthranilate
N-(5'-Phosphoribosyl)anthranilate
N-(5'-Phosphoribosyl)anthranilic acid
n-(5-phospho-β-D-ribosyl)-anthranilate
n-(5-phospho-β-D-ribosyl)-anthranilic acid
N-(5-phospho-b-D-Ribosyl)-anthranilate
N-(5-phospho-b-D-Ribosyl)-anthranilic acid
N-(5-phospho-b-D-Ribosyl)anthranilate
N-(5-phospho-b-D-Ribosyl)anthranilic acid
N-(5-Phospho-beta-D-ribosyl)-anthranilate
N-(5-Phospho-beta-D-ribosyl)-anthranilic acid
N-(5-Phospho-beta-D-ribosyl)anthranilate
N-(5-Phospho-beta-D-ribosyl)anthranilic acid
N-(5-Phospho-D-ribosyl)-anthranilate
N-(5-Phospho-D-ribosyl)-anthranilic acid
N-(5-Phospho-D-ribosyl)anthranilic acid
N-(5-phospho-β-D-Ribosyl)-anthranilate
N-(5-phospho-β-D-Ribosyl)-anthranilic acid
N-(5-phospho-β-D-Ribosyl)anthranilate
N-(5-phospho-β-D-Ribosyl)anthranilic acid
N-(5-Phosphoribosyl)-anthranilate
N-(5-Phosphoribosyl)-anthranilic acid
N-(5-Phosphoribosyl)anthranilate
N-(5-Phosphoribosyl)anthranilic acid
Nprat
PRAnth

Chemical Formula:

C₁₂H₁₆NO₉P

Average Molecular Weight:

349.2305

Monoisotopic Molecular Weight:

349.056267627

InChI Key:

XUNHMFBIFPPJDL-NAORZKMKSA-N

InChI:

InChI=1S/C12H16NO9P/c14-7-8(15)10(22-9(7)12(18)23(19,20)21)13-6-4-2-1-3-5(6)11(16)17/h1-4,7-10,12-15,18H,(H,16,17)(H2,19,20,21)/t7-,8+,9-,10?,12?/m0/s1

CAS number:

4220-99-9

IUPAC Name:

2-{[(3R,4S,5S)-3,4-dihydroxy-5-[hydroxy(phosphono)methyl]oxolan-2-yl]amino}benzoic acid

Traditional IUPAC Name:

2-{[(3R,4S,5S)-3,4-dihydroxy-5-[hydroxy(phosphono)methyl]oxolan-2-yl]amino}benzoic acid

SMILES:

[H]C(O)([C@@]1([H])OC([H])(NC2=CC=CC=C2C(O)=O)[C@]([H])(O)[C@]1([H])O)P(O)(O)=O

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as glycosylamines. These are compounds consisting of an?amine?with a?beta-N-glycosidic bond?to a carbohydrate, thus forming a cyclic?hemiaminal ether?bond (alpha-amino ether).

Kingdom

Organic compounds

Super Class

Organooxygen compounds

Class

Carbohydrates and carbohydrate conjugates

Sub Class

Glycosyl compounds

Direct Parent

Glycosylamines

Alternative Parents

Substituents

N-glycosyl compound
Aminobenzoic acid or derivatives
Aminobenzoic acid
Benzoic acid
Benzoic acid or derivatives
Phenylalkylamine
Benzoyl
Secondary aliphatic/aromatic amine
Benzenoid
Monosaccharide
Monocyclic benzene moiety
Vinylogous amide
Oxolane
Organophosphonic acid derivative
Organophosphonic acid
Secondary alcohol
1,2-diol
Oxacycle
Organoheterocyclic compound
Secondary amine
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organophosphorus compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Not Available

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	7.28 mg/mL	ALOGPS
logP	-0.92	ALOGPS
logP	-1.2	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	1.25	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	176.78 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	75.62 m³·mol^-1	ChemAxon
Polarizability	30.25 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

N-(5-Phospho-D-ribosyl)anthranilate > 1-(2-Carboxyphenylamino)-1'-deoxy-D-ribulose 5'-phosphate
N-(5-Phospho-D-ribosyl)anthranilate + Pyrophosphate < 2-Aminobenzoic acid + Phosphoribosyl pyrophosphate

Pathways:

Phenylalanine, tyrosine and tryptophan biosynthesis pae00400

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uyi-0819000000-95763a6f1989f32a6dfc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9433000000-4e0c9f04cee4b88d0d04	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fe0-2900000000-e8ee92a0ccd03173d26e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-003r-2914000000-4ff300d6805ac0d243b3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f8i-9875000000-1c37f28497b620c1a45b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-005l-8900000000-9b8b58fda98d39398bd4	View in MoNA

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
Priestle, J. P., Grutter, M. G., White, J. L., Vincent, M. G., Kania, M., Wilson, E., Jardetzky, T. S., Kirschner, K., Jansonius, J. N. (1987). "Three-dimensional structure of the bifunctional enzyme N-(5'-phosphoribosyl)anthranilate isomerase-indole-3-glycerol-phosphate synthase from Escherichia coli." Proc Natl Acad Sci U S A 84:5690-5694. Pubmed: 3303031
Sterner, R., Kleemann, G. R., Szadkowski, H., Lustig, A., Hennig, M., Kirschner, K. (1996). "Phosphoribosyl anthranilate isomerase from Thermotoga maritima is an extremely stable and active homodimer." Protein Sci 5:2000-2008. Pubmed: 8897600

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	18277
HMDB ID	Not Available
Pubchem Compound ID	440289
Kegg ID	C04302
ChemSpider ID	389264
Wikipedia ID	Not Available
BioCyc ID	N-5-PHOSPHORIBOSYL-ANTHRANILATE
EcoCyc ID	N-5-PHOSPHORIBOSYL-ANTHRANILATE

N-(5-Phospho-D-ribosyl)anthranilate (PAMDB001021)

Structure for N-(5-Phospho-D-ribosyl)anthranilate (PAMDB001021)