N-(5-phospho-beta-D-ribosyl)anthranilic acid (YMDB00054)

Identification

YMDB ID

YMDB00054

Name

N-(5-phospho-beta-D-ribosyl)anthranilic acid

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

N-(5-phospho-beta-D-ribosyl)anthranilic acid, also known as NPRAT, 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. N-(5-phospho-beta-D-ribosyl)anthranilic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). N-(5-phospho-beta-D-ribosyl)anthranilic acid exists in both E. coli (prokaryote) and yeast (eukaryote).

Structure

MOL SDF PDB SMILES InChI

Synonyms

N-(2-carboxylatophenyl)-5-O-phosphonato-beta-D-ribofuranosylamine
N-(5-Phospho-beta-D-ribosyl)anthranilate
N-(5-Phospho-D-ribosyl)anthranilate
N-(5-Phosphoribosyl)anthranilate
N-(5-Phosphoribosyl)anthranilic acid
N-(5'-Phosphoribosyl)anthranilate
N-(5'-Phosphoribosyl)anthranilic acid
NPRAT
N-(5-Phospho-b-D-ribosyl)anthranilate
N-(5-Phospho-b-D-ribosyl)anthranilic acid
N-(5-Phospho-β-D-ribosyl)anthranilate
N-(5-Phospho-β-D-ribosyl)anthranilic acid
N-(5-phospho-D-Ribosyl)anthranilic acid
N-(5-Phospho-beta-D-ribosyl)anthranilic acid

CAS number

Not Available

Weight

Average: 349.2305
Monoisotopic: 349.056267627

InChI Key

PMFMJXPRNJUYMB-GWOFURMSSA-N

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)/t8-,9-,10-,11-/m1/s1

IUPAC Name

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

Traditional IUPAC Name

nprat

Chemical Formula

C₁₂H₁₆NO₉P

SMILES

O[C@H]1[C@@H](O)[C@H](NC2=CC=CC=C2C(O)=O)O[C@@H]1COP(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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Pentose phosphates

Alternative Parents

Substituents

Pentose-5-phosphate
Pentose phosphate
N-glycosyl compound
Glycosyl compound
Monosaccharide phosphate
Benzoic acid
Benzoic acid or derivatives
Phenylalkylamine
Aniline or substituted anilines
Benzoyl
Monoalkyl phosphate
Secondary aliphatic/aromatic amine
Phosphoric acid ester
Organic phosphoric acid derivative
Benzenoid
Alkyl phosphate
Monocyclic benzene moiety
Vinylogous amide
Tetrahydrofuran
Secondary alcohol
Amino acid or derivatives
1,2-diol
Amino acid
Secondary amine
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Monocarboxylic acid or derivatives
Organic oxide
Organopnictogen compound
Alcohol
Amine
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

N-glycosyl compound (CHEBI:7091 )
ribose monophosphate (CHEBI:7091 )

Physical Properties

State

Not Available

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	3.5 g/L	ALOGPS
logP	-1	ALOGPS
logP	-0.15	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	1.23	ChemAxon
pKa (Strongest Basic)	-2.1	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	165.78 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	76.08 m³·mol⁻¹	ChemAxon
Polarizability	30.59 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

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Phenylalanine, tyrosine and tryptophan biosynthesis

ec00400

SMPDB Reactions

Not Available

KEGG Reactions

2-Aminobenzoic acid + Phosphoribosyl pyrophosphate → Pyrophosphate + N-(5-phospho-beta-D-ribosyl)anthranilic acid

N-(5-phospho-beta-D-ribosyl)anthranilic acid → 1-(2-carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_10) - 70eV, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-1539000000-afa303df223fc236b2a8	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uej-6796000000-d8aec7db3c63af996744	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-2910000000-a2f91d8bb4e2ccda7cd1	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-005a-3904000000-63d42279e1736d1159fd	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9201000000-2cfcddd5b31d906f0cb2	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-b5c17b0df8b3db541b9e	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Hommel, U., Lustig, A., Kirschner, K. (1989). "Purification and characterization of yeast anthranilate phosphoribosyltransferase." Eur J Biochem 180:33-40.2651124
Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Miozzari, G., Niederberger, P., Hutter, R. (1978). "Tryptophan biosynthesis in Saccharomyces cerevisiae: control of the flux through the pathway." J Bacteriol 134:48-59.348687

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	7091
HMDB ID	Not Available
Pubchem Compound ID	440289
Kegg ID	C04302
ChemSpider ID	389264
FOODB ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. Anthranilate phosphoribosyltransferase

General function:: Involved in anthranilate phosphoribosyltransferase activity
Specific function:: N-(5-phospho-D-ribosyl)-anthranilate + diphosphate = anthranilate + 5-phospho-alpha-D-ribose 1- diphosphate
Gene Name:: TRP4
Uniprot ID:: P07285
Molecular weight:: 41374.0

Reactions

N-(5-phospho-D-ribosyl)-anthranilate + diphosphate → anthranilate + 5-phospho-alpha-D-ribose 1-diphosphate.

Protein Details

2. N-(5'-phosphoribosyl)anthranilate isomerase

General function:: Involved in catalytic activity
Specific function:: N-(5-phospho-beta-D-ribosyl)anthranilate = 1- (2-carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate
Gene Name:: TRP1
Uniprot ID:: P00912
Molecular weight:: 24144.30078

Reactions

N-(5-phospho-beta-D-ribosyl)anthranilate → 1-(2-carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate.

N-(5-phospho-beta-D-ribosyl)anthranilic acid (YMDB00054)

Structure for #<Compound:0xb1d087b4>

Enzymes

Reactions

Reactions