ECMDB: 1-(2-Carboxyphenylamino)-1'-deoxy-D-ribulose 5'-phosphate (ECMDB20019) (M2MDB000868)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (1)XML

Proteins (725)

Record Information

Version

2.0

Creation Date

2012-05-31 14:23:12 -0600

Update Date

2015-06-03 17:19:08 -0600

Secondary Accession Numbers

ECMDB20019

Identification

Name:

1-(2-Carboxyphenylamino)-1'-deoxy-D-ribulose 5'-phosphate

Description

1-(2-carboxyphenylamino)-1'-deoxy-D-ribulose 5'-phosphate is a pentose phosphate derivative. It is a substrate for indole-3-glycerol-phosphate synthase (IPGS) (EC 4.1.1.48)which is an enzyme that catalyzes the chemical reaction: 1-(2-carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate ightleftharpoons 1-C-(indol-3-yl)-glycerol 3-phosphate + CO2 + H2O

Structure

MOL SDF PDB SMILES InChI

Synonyms:

1-(2-carboxyphenylamino)-1'-Deoxy-D-ribulose 5'-phosphoric acid
1-(2-Carboxyphenylamino)-1-deoxy-D-ribulose-5-P
1-(2-Carboxyphenylamino)-1-deoxy-D-ribulose-5-phosphate
1-(2-carboxyphenylamino)-1-Deoxy-D-ribulose-5-phosphoric acid
1-(O-Carboxyphenylamino)-1'-deoxyribulose-5'-P
1-(O-Carboxyphenylamino)-1'-deoxyribulose-5'-phosphate
1-(O-carboxyphenylamino)-1'-Deoxyribulose-5'-phosphoric acid
Carboxyphenylamino-deoxyribulose-p
CPADRP

Chemical Formula:

C₁₂H₁₆NO₉P

Weight:

Average: 349.2305
Monoisotopic: 349.056267627

InChI Key:

QKMBYNRMPRKVTO-MNOVXSKESA-N

InChI:

InChI=1S/C12H16NO9P/c14-9(11(16)10(15)6-22-23(19,20)21)5-13-8-4-2-1-3-7(8)12(17)18/h1-4,10-11,13,15-16H,5-6H2,(H,17,18)(H2,19,20,21)/t10-,11+/m1/s1

CAS number:

Not Available

IUPAC Name:

2-{[(3R,4R)-3,4-dihydroxy-2-oxo-5-(phosphonooxy)pentyl]amino}benzoic acid

Traditional IUPAC Name:

2-{[(3R,4R)-3,4-dihydroxy-2-oxo-5-(phosphonooxy)pentyl]amino}benzoic acid

SMILES:

O[C@H](COP(O)(O)=O)[C@@H](O)C(=O)CNC1=C(C=CC=C1)C(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
Aminobenzoic acid or derivatives
Aminobenzoic acid
Monosaccharide phosphate
Benzoic acid
Benzoic acid or derivatives
Benzoyl
Phenylalkylamine
Aniline or substituted anilines
Monoalkyl phosphate
Secondary aliphatic/aromatic amine
Alkyl phosphate
Beta-hydroxy ketone
Phosphoric acid ester
Monocyclic benzene moiety
Organic phosphoric acid derivative
Benzenoid
Acyloin
Alpha-hydroxy ketone
Alpha-aminoketone
1,3-aminoalcohol
Vinylogous amide
Ketone
Amino acid or derivatives
Secondary alcohol
Amino acid
1,2-diol
Secondary amine
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organopnictogen compound
Organonitrogen compound
Amine
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

deoxyribulose phosphate (CHEBI:29112 )

Physical Properties

State:

Not Available

Charge:

-3

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	1.55 g/L	ALOGPS
logP	-0.91	ALOGPS
logP	-0.5	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	1.48	ChemAxon
pKa (Strongest Basic)	0.27	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	173.62 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	77.72 m³·mol⁻¹	ChemAxon
Polarizability	30.76 Å³	ChemAxon
Number of Rings	1	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:

SMPDB Pathways:

Not Available

KEGG Pathways:

Metabolic pathways eco01100
Phenylalanine, tyrosine and tryptophan biosynthesis ec00400

EcoCyc Pathways:

tryptophan biosynthesis TRPSYN-PWY

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0005-5911000000-37b09c66588c632153be	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ue9-0339000000-69722cac0a11d3f77f39	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udm-1921000000-c609a3aa34bcb82cfcfd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zfr-3900000000-a5ab2361731c8e108c8d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a6s-4955000000-a019a420bd68acd6c195	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9410000000-f6a1776a0ae271fef65d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-6a98c0c5e5f9775e0b22	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View 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
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	29112
HMDB ID	Not Available
Pubchem Compound ID	287
Kegg ID	C01302
ChemSpider ID	394132
Wikipedia ID	Not Available
BioCyc ID	CARBOXYPHENYLAMINO-DEOXYRIBULOSE-P
EcoCyc ID	CARBOXYPHENYLAMINO-DEOXYRIBULOSE-P

Enzymes

Protein Details

1. 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.

1-(2-Carboxyphenylamino)-1'-deoxy-D-ribulose 5'-phosphate (ECMDB20019) (M2MDB000868)

Structure for #<Compound:0xae2e5c58>

Enzymes

Reactions