ECMDB: SAICAR (ECMDB00797) (M2MDB000186)

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

Proteins (850)

Record Information

Version

2.0

Creation Date

2012-05-31 13:01:12 -0600

Update Date

2015-09-17 15:41:06 -0600

Secondary Accession Numbers

ECMDB00797

Identification

Name:

SAICAR

Description

SAICAR (or (S)-2-[5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinate) is a substrate for the multifunctional protein ADE2. SAICAR is an intermediate in purine metabolism. (S)-2-[5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinate is converted from 5-Amino-1-(5-phospho-D-ribosyl) imidazole-4-carboxylate via phosphoribosylaminoimidazole-succinocarboxamide synthase [EC: 6.3.2.6] or SAICAR synthase. This enzyme catalyses the seventh step out of ten in the biosynthesis of purine nucleotides. (Wikipedia)

Structure

MOL SDF PDB SMILES InChI

Synonyms:

(S)-2-[5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinate
(S)-2-(5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido)succinate
(S)-2-(5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido)succinic acid
(S)-2-(5-amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido)succinate
(S)-2-(5-amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido)succinic acid
(S)-2-(5-amino-1-(5-phospho-δ-Ribosyl)imidazole-4-carboxamido)succinate
(S)-2-(5-amino-1-(5-phospho-δ-Ribosyl)imidazole-4-carboxamido)succinic acid
(S)-2-[5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinate
(S)-2-[5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinic acid
(S)-2-[5-Amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido]succinate
(S)-2-[5-Amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido]succinic acid
(S)-2-[5-amino-1-(5-phospho-δ-Ribosyl)imidazole-4-carboxamido]succinate
(S)-2-[5-amino-1-(5-phospho-δ-Ribosyl)imidazole-4-carboxamido]succinic acid
1-(5'-Phosphoribosyl)-4-(N-succino-carboxamide)-5-aminoimidazole
1-(5'-Phosphoribosyl)-4-(N-succinocarboxamide)-5-aminoimidazole
1-(5'-Phosphoribosyl)-5-amino-4-(N-succinocarboxamide)-imidazole
1-(5'-Phosphoribosyl)-5-amino-4-(N-succinocarboxamide)-imidazole' 1-(5'-Phosphoribosyl)-4-(N-succinocarboxamide)-5-aminoimidazole
1-(5-Phosphoribosyl)-4-(N-succino-carboxamide)-5-aminoimidazole
5'-p-Ribosyl-4-(N-succinocarboxamide)-5-amino imidazole
5'-P-Ribosyl-4-(N-succinocarboxamide)-5-aminoimidazole
5'-Phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole
5'-Phosphoribosyl-4-(N-succinocarbozamide)-5-aminoimidazole
5-Amino-4-imidazole-N-succinocarboxamide ribonucleotide
L-N-[(5-Amino-1-b-D-ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphate)
L-N-[(5-amino-1-b-D-Ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphoric acid)
L-N-[(5-amino-1-b-delta-Ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphate)
L-N-[(5-amino-1-b-delta-Ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphoric acid)
L-N-[(5-amino-1-b-δ-Ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphate)
L-N-[(5-amino-1-b-δ-Ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphoric acid)
L-N-[(5-Amino-1-beta-delta-ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphate)
L-N-[(5-amino-1-beta-delta-Ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphoric acid)
L-N-[(5-amino-1-β-δ-Ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphate)
L-N-[(5-amino-1-β-δ-Ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphoric acid)
N-(5-Amino-1-ribofuranosylimidazol-4-ylcarbonyl)aspartate 5'-phosphate
N-(5-Amino-1-ribofuranosylimidazol-4-ylcarbonyl)aspartic acid 5'-phosphate
N-(5-amino-1-Ribofuranosylimidazol-4-ylcarbonyl)aspartic acid 5'-phosphoric acid
N-[5-Amino-1-(5'-phosphoribofuranosyl)-4-imidazolecarbonyl]aspartate
N-[5-Amino-1-(5'-phosphoribofuranosyl)-4-imidazolecarbonyl]aspartic acid
Phosphoribosylaminoimidazolesuccinocarboxamide
SAICAR
SAICAriboside
Succino-AICAR
Succinylaminoimidazole carboxamide riboside

Chemical Formula:

C₁₃H₁₉N₄O₁₂P

Weight:

Average: 454.2833
Monoisotopic: 454.073708604

InChI Key:

NAQGHJTUZRHGAC-ZZZDFHIKSA-N

InChI:

InChI=1S/C13H19N4O12P/c14-10-7(11(22)16-4(13(23)24)1-6(18)19)15-3-17(10)12-9(21)8(20)5(29-12)2-28-30(25,26)27/h3-5,8-9,12,20-21H,1-2,14H2,(H,16,22)(H,18,19)(H,23,24)(H2,25,26,27)/t4-,5+,8+,9+,12+/m0/s1

CAS number:

3031-95-6

IUPAC Name:

(2S)-2-[({5-amino-1-[(3R,4S,5S)-3,4-dihydroxy-5-[hydroxy(phosphono)methyl]oxolan-2-yl]-1H-imidazol-4-yl}(hydroxy)methylidene)amino]butanedioic acid

Traditional IUPAC Name:

(2S)-2-[({5-amino-1-[(3R,4S,5S)-3,4-dihydroxy-5-[hydroxy(phosphono)methyl]oxolan-2-yl]imidazol-4-yl}(hydroxy)methylidene)amino]butanedioic acid

SMILES:

NC1=C(N=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O)C(=O)N[C@@H](CC(O)=O)C(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Aspartic acid and derivatives

Alternative Parents

Substituents

Aspartic acid or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Imidazole ribonucleoside
N-glycosyl compound
Glycosyl compound
Imidazolyl carboxylic acid derivative
N-substituted imidazole
Dicarboxylic acid or derivatives
Aminoimidazole
Heteroaromatic compound
Tetrahydrofuran
Organophosphonic acid derivative
Organophosphonic acid
Imidazole
Azole
Amino acid
Secondary alcohol
1,2-diol
Oxacycle
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboxylic acid
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organophosphorus compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Solid

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	4.72 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-5.9	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	1.25	ChemAxon
pKa (Strongest Basic)	7.08	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	278.48 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	90.71 m³·mol⁻¹	ChemAxon
Polarizability	38.81 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:

SAICAR <> Phosphoribosyl formamidocarboxamide + Fumaric acid
5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-Aspartic acid + Adenosine triphosphate <> SAICAR + ADP + Hydrogen ion + Phosphate
SAICAR <> Fumaric acid + AICAR
Adenosine triphosphate + 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-Aspartic acid <> ADP + Phosphate + SAICAR
SAICAR > Fumaric acid + AICAR
Adenosine triphosphate + 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-Aspartic acid > Hydrogen ion + ADP + Phosphate + SAICAR
Adenosine triphosphate + 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-Aspartic acid > ADP + Inorganic phosphate + SAICAR
Adenylsuccinic acid + SAICAR <> Fumaric acid + Adenosine monophosphate + AICAR
5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-Aspartic acid + Adenosine triphosphate + L-Aspartic acid > SAICAR + Phosphate + Adenosine diphosphate + Hydrogen ion + SAICAR + ADP
SAICAR + SAICAR > AICAR + Fumaric acid
5 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-Aspartic acid + Adenosine triphosphate <> SAICAR + ADP + Hydrogen ion + Phosphate
SAICAR <> Fumaric acid + AICAR
5 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-Aspartic acid + Adenosine triphosphate <> SAICAR + ADP + Hydrogen ion + Phosphate

SMPDB Pathways:

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

KEGG Pathways:

Alanine, aspartate and glutamate metabolism ec00250
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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004u-0490700000-86a0d53f872d386acc0b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-6960000000-f6a547b69124d08116b3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001l-4940000000-fd3462a73fc305a5d0f3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f7c-2293800000-83e319c3c83a959d977a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000x-3390100000-d322d060609e295ccfa2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-003u-9420000000-980569ce0c7a7ec24733	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
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:

Shaw, Gordon; Thomas, Peter S.; Patey, Carole A. H.; Thomas, Susan E. Purines, pyrimidines and imidazoles. Part 50. Inhibition of adenylosuccinate AMP-lyase no. 4.3.2.2. by derivatives of N-(5-amino-1-b-D-ribofuranosylimidazole-4-carbonyl)-L-aspartic a

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	18319
HMDB ID	HMDB00797
Pubchem Compound ID	160666
Kegg ID	C04823
ChemSpider ID	141175
Wikipedia ID	Phosphoribosylaminoimidazolesuccinocarboxamide
BioCyc ID	P-RIBOSYL-4-SUCCCARB-AMINOIMIDAZOLE
EcoCyc ID	P-RIBOSYL-4-SUCCCARB-AMINOIMIDAZOLE

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. Adenylosuccinate lyase

General function:: Involved in N6-(1,2-dicarboxyethyl)AMP AMP-lyase (fumarate-forming) activity
Specific function:: N(6)-(1,2-dicarboxyethyl)AMP = fumarate + AMP
Gene Name:: purB
Uniprot ID:: P0AB89
Molecular weight:: 51542

Reactions

N(6)-(1,2-dicarboxyethyl)AMP = fumarate + AMP.
(S)-2-(5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido)succinate = fumarate + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide.

SAICAR (ECMDB00797) (M2MDB000186)

Structure for #<Compound:0xa6eccac4>

Enzymes

Reactions

Reactions