ECMDB: 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate (ECMDB06273) (M2MDB000663)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (2)XML

Proteins (823)

Record Information

Version

2.0

Creation Date

2012-05-31 14:07:58 -0600

Update Date

2015-06-03 15:54:51 -0600

Secondary Accession Numbers

ECMDB06273

Identification

Name:

5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate

Description

5-amino-1-(5-phospho-D-ribosyl) imidazole-4-carboxylate is an intermediate in purine metabolism. 5-amino-1-(5-phospho-D-ribosyl) imidazole-4-carboxylate is converted from aminoimidazole ribotide via phosphoribosylaminoimidazole carboxylase [EC: 4.1.1.21].

Structure

MOL SDF PDB SMILES InChI

Synonyms:

1-(5'-Phosphoribosyl)-4-carboxy-5-aminoimidazole
1-(5'-Phosphoribosyl)-5-amino-4-carboxyimidazole
1-(5'-Phosphoribosyl)-5-amino-4-imidazole carboxylate
1-(5'-Phosphoribosyl)-5-amino-4-imidazole carboxylic acid
1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxylate
1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxylic acid
1-(5-Phospho-D-ribosyl)-5-amino-4-imidazolecarboxylate
1-(5-Phospho-D-ribosyl)-5-amino-4-imidazolecarboxylic acid
1-(5-Phosphoribosyl)-4-carboxy-5-aminoimidazole
4-Carboxy-5-aminoimidazole ribonucleotide
4-Carboxyaminoimidazole ribonucleotide
5'-P-Ribosyl-4-carboxy-5-aminoimidazole
5'-Phosphoribosyl-4-carboxy-5-aminoimidazole
5'-Phosphoribosyl-5-amino-4-imidazolecarboxylate
5'-Phosphoribosyl-5-amino-4-imidazolecarboxylic acid
5'Phosphoribosyl-4-carboxy-5-aminoimidazole
5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate
5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid
5-Amino-4-carboxyimidazole ribonucleotide
5-Amino-4-imidazolecarboxylate ribonucleotide
5-Amino-4-imidazolecarboxylic acid ribonucleotide
5-Aminoimidazole carboxilate ribonucleotice
5-Aminoimidazole carboxilic acid ribonucleotice
5-Aminoimidazole-4-carboxilate ribonucleotide
5-Aminoimidazole-4-carboxilic acid ribonucleotide
5-Phosphoribosyl-4-carboxy-5-aminoimidazole
CAIR
Carboxyaminoimidazole ribonucleotide
Phosphoribosyl-carboxy-aminoimidazole

Chemical Formula:

C₉H₁₄N₃O₉P

Weight:

Average: 339.1959
Monoisotopic: 339.046765573

InChI Key:

XFVULMDJZXYMSG-ZIYNGMLESA-N

InChI:

InChI=1S/C9H14N3O9P/c10-7-4(9(15)16)11-2-12(7)8-6(14)5(13)3(21-8)1-20-22(17,18)19/h2-3,5-6,8,13-14H,1,10H2,(H,15,16)(H2,17,18,19)/t3-,5-,6-,8-/m1/s1

CAS number:

Not Available

IUPAC Name:

5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1H-imidazole-4-carboxylic acid

Traditional IUPAC Name:

5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]imidazole-4-carboxylic acid

SMILES:

NC1=C(N=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O)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 phosphate
Pentose-5-phosphate
Imidazole ribonucleoside
N-glycosyl compound
Glycosyl compound
Monosaccharide phosphate
Monoalkyl phosphate
Imidazole-4-carbonyl group
Alkyl phosphate
Phosphoric acid ester
Aminoimidazole
Organic phosphoric acid derivative
N-substituted imidazole
Azole
Vinylogous amide
Tetrahydrofuran
Imidazole
Heteroaromatic compound
1,2-diol
Secondary alcohol
Amino acid
Amino acid or derivatives
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
Amine
Organopnictogen compound
Organic oxide
Primary amine
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

1-(phosphoribosyl)imidazole (CHEBI:28413 )
aminoimidazole (CHEBI:28413 )
imidazole-4-carboxylic acid (CHEBI:28413 )

Physical Properties

State:

Solid

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	2.81 g/L	ALOGPS
logP	-2	ALOGPS
logP	-3.7	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	1.18	ChemAxon
pKa (Strongest Basic)	7.11	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	197.59 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	67.32 m³·mol⁻¹	ChemAxon
Polarizability	28.49 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:

SMPDB Pathways:

purine nucleotides de novo biosynthesis	PW000910
purine nucleotides de novo biosynthesis 1435709748	PW000960
purine nucleotides de novo biosynthesis 2	PW002033

KEGG Pathways:

Metabolic pathways eco01100
Purine metabolism ec00230

EcoCyc Pathways:

inosine-5'-phosphate biosynthesis I PWY-6123

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9613000000-2a087bcb710ee7b50b52	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-00lu-2923230000-25e41df497cf1b5c9281	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0914000000-87d6bac417ced888900f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01t9-1900000000-e298883e772e11c253f0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-8900000000-82583bffa17f1262d918	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004r-8928000000-d296c2812c7b06149794	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9400000000-76793052d8d2699d70dd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-a8b367167e97f6df3690	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0539000000-deee029059e464053ab9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-2900000000-c7cafadad92d61fbb8a1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01u0-7900000000-97962f3ed9f96ac07b6a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-3009000000-ff79299d0fd8156f9b05	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-a211e114c93b066eaf36	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9100000000-bfdd206a6413421623ed	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
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
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	28413
HMDB ID	HMDB06273
Pubchem Compound ID	165388
Kegg ID	C04751
ChemSpider ID	144983
Wikipedia ID	Not Available
BioCyc ID	PHOSPHORIBOSYL-CARBOXY-AMINOIMIDAZOLE
EcoCyc ID	PHOSPHORIBOSYL-CARBOXY-AMINOIMIDAZOLE
Ligand Expo	C2R

Enzymes

Protein Details

1. Phosphoribosylaminoimidazole-succinocarboxamide synthase

General function:: Involved in ATP binding
Specific function:: ATP + 5-amino-1-(5-phospho-D- ribosyl)imidazole-4-carboxylate + L-aspartate = ADP + phosphate + (S)-2-(5-amino-1-(5-phospho-D-ribosyl)imidazole-4- carboxamido)succinate
Gene Name:: purC
Uniprot ID:: P0A7D7
Molecular weight:: 26995

Reactions

ATP + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-aspartate = ADP + phosphate + (S)-2-(5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido)succinate.

Protein Details

2. Phosphoribosylaminoimidazole carboxylase catalytic subunit

General function:: Involved in 5-(carboxyamino)imidazole ribonucleotide mutase activity
Specific function:: This subunit can alone transform AIR to CAIR, but in association with purK, which possesses an ATPase activity, an enzyme complex is produced which is capable of converting AIR to CAIR efficiently under physiological condition
Gene Name:: purE
Uniprot ID:: P0AG18
Molecular weight:: 17780

Reactions

5-carboxyamino-1-(5-phospho-D-ribosyl)imidazole = 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate.

5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate (ECMDB06273) (M2MDB000663)

Structure for #<Compound:0x5e78eed0>

Enzymes

Reactions

Reactions