P. aeruginosa Metabolome Database: Phosphoribosyl formamidocarboxamide (PAMDB000388)

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

PAMDB000388

Identification

Name:

Phosphoribosyl formamidocarboxamide

Description:

Phosphoribosyl formamidocarboxamide is an intermediate in purine metabolism, where it is the byproduct of phosphoribosylaminoimidazolecarboxamide formyltransferase (EC 2.1.2.3) and IMP cyclohydrolase (EC 3.5.4.10). It is also a byproduct of Ligases (EC 6.3.4.-).

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

5'-p-Ribosyl-5-formamido-4-imidazole carboxamide
5'-p-Ribosyl-5-formamido-4-imidazolecarboxamide
5'-Phosphoribosyl-5-formamido-4-imidazole carboxamide
5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide
5-Formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide
5-Formamido-1-(5-phosphoribosyl)-imidazole-4-carboxamide
5-Formylamidoimidazole-4-carboxamide ribonucleotide
5-Phosphoribosyl-5-formamido-4-imid-carboxamide
FAICAR
Phosphoribosyl-formamido-carboxamide

Chemical Formula:

C₁₀H₁₅N₄O₉P

Average Molecular Weight:

366.2213

Monoisotopic Molecular Weight:

366.05766461

InChI Key:

ABCOOORLYAOBOZ-KQYNXXCUSA-N

InChI:

InChI=1S/C10H15N4O9P/c11-8(18)5-9(13-3-15)14(2-12-5)10-7(17)6(16)4(23-10)1-22-24(19,20)21/h2-4,6-7,10,16-17H,1H2,(H2,11,18)(H,13,15)(H2,19,20,21)/t4-,6-,7-,10-/m1/s1

CAS number:

Not Available

IUPAC Name:

{[(2R,3S,4R,5R)-5-(4-carbamoyl-5-formamido-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid

Traditional IUPAC Name:

[(2R,3S,4R,5R)-5-(4-carbamoyl-5-formamidoimidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid

SMILES:

NC(=O)C1=C(NC=O)N(C=N1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as 1-phosphoribosyl-imidazolecarboxamides. These are organic compounds containing the imidazolecarboxamide linked to a ribose phosphate through a 1-2 bond.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Imidazole ribonucleosides and ribonucleotides

Sub Class

1-ribosyl-imidazolecarboxamides

Direct Parent

1-phosphoribosyl-imidazolecarboxamides

Alternative Parents

Substituents

1-phosphoribosyl-imidazolecarboxamide
1-phosphoribosyl-imidazole
N-glycosyl compound
Glycosyl compound
Monosaccharide phosphate
Monoalkyl phosphate
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Organic phosphate
N-substituted imidazole
Monosaccharide
Saccharide
Aminoimidazole
Heteroaromatic compound
Vinylogous amide
Oxolane
Imidazole
Azole
Secondary carboxylic acid amide
Secondary alcohol
Primary carboxylic acid amide
Carboxamide group
1,2-diol
Oxacycle
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid amide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

1-(phosphoribosyl)imidazolecarboxamide (CHEBI:18381 )

Physical Properties

State:

Solid

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	2.14 mg/mL	ALOGPS
logP	-1.8	ALOGPS
logP	-4.1	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	1.21	ChemAxon
pKa (Strongest Basic)	6.25	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	206.46 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	74.81 m³·mol^-1	ChemAxon
Polarizability	30.52 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	0	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:

Pathways:

Metabolic pathways pae01100
One carbon pool by folate pae00670
Purine metabolism pae00230

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ar0-0914000000-1d61e2aa1204766a006e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-0900000000-051245189eb5cd0ff26f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056r-1900000000-f18e08c70bdaa9aa6913	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0gdj-8809000000-e71e875c5ef95845f25d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fb9-9700000000-1930562d45d841bd928d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9100000000-5b37e0fb5e34ee3423f0	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
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

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	18381
HMDB ID	HMDB01439
Pubchem Compound ID	1011
Kegg ID	C04734
ChemSpider ID	145893
Wikipedia ID	Not Available
BioCyc ID	PHOSPHORIBOSYL-FORMAMIDO-CARBOXAMIDE
EcoCyc ID	PHOSPHORIBOSYL-FORMAMIDO-CARBOXAMIDE
Ligand Expo	FAI

Phosphoribosyl formamidocarboxamide (PAMDB000388)

Structure for Phosphoribosyl formamidocarboxamide (PAMDB000388)