ChemFOnt: Showing chemical card for 5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole (CFc000337636)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:31:33 UTC

Chemfont ID

CFc000337636

Molecule Identification

Common Name

5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole

Definition

5'-phosphoribosyl-4-(n-succinocarboxamide)-5-aminoimidazole, also known as saica riboside or succino-aicar, is a member of the class of compounds known as 1-ribosyl-imidazolecarboxamides. 1-ribosyl-imidazolecarboxamides are organic compounds containing the imidazole ring linked to a ribose ring through a 1-2 bond. 5'-phosphoribosyl-4-(n-succinocarboxamide)-5-aminoimidazole is slightly soluble (in water) and a moderately acidic compound (based on its pKa). 5'-phosphoribosyl-4-(n-succinocarboxamide)-5-aminoimidazole can be found in a number of food items such as common persimmon, natal plum, spearmint, and pepper (spice), which makes 5'-phosphoribosyl-4-(n-succinocarboxamide)-5-aminoimidazole a potential biomarker for the consumption of these food products. 5'-phosphoribosyl-4-(n-succinocarboxamide)-5-aminoimidazole can be found primarily in cerebrospinal fluid (CSF) and urine, as well as in human fibroblasts and intestine tissues. 5'-phosphoribosyl-4-(n-succinocarboxamide)-5-aminoimidazole exists in all eukaryotes, ranging from yeast to humans. In humans, 5'-phosphoribosyl-4-(n-succinocarboxamide)-5-aminoimidazole is involved in few metabolic pathways, which include azathioprine action pathway, mercaptopurine action pathway, purine metabolism, and thioguanine action pathway. 5'-phosphoribosyl-4-(n-succinocarboxamide)-5-aminoimidazole is also involved in several metabolic disorders, some of which include gout or kelley-seegmiller syndrome, myoadenylate deaminase deficiency, xanthinuria type II, and adenosine deaminase deficiency. Moreover, 5'-phosphoribosyl-4-(n-succinocarboxamide)-5-aminoimidazole is found to be associated with aTIC deficiency. 5'-phosphoribosyl-4-(n-succinocarboxamide)-5-aminoimidazole is a non-carcinogenic (not listed by IARC) potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S)-2-[5-Amino-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamido]succinic acid	ChEBI
(S)-2-[5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinate	ChEBI
1-(5'-Phosphoribosyl)-4-(N-succinocarboxamide)-5-aminoimidazole	ChEBI
1-(5'-Phosphoribosyl)-5-amino-4-(N-succinocarboxamide)-imidazole	ChEBI
5'-Phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole	ChEBI
Succino-aicar	ChEBI
Succinyl-5-aminoimidazole-4-carboxamide-1-ribose-5-phosphate	ChEBI
Succinylaminoimidazolecarboxamide ribose-5'-phosphate	ChEBI
(2S)-2-[5-Amino-1-(5-phospho-b-D-ribosyl)imidazole-4-carboxamido]succinate	Generator
(2S)-2-[5-Amino-1-(5-phospho-b-D-ribosyl)imidazole-4-carboxamido]succinic acid	Generator
(2S)-2-[5-Amino-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamido]succinate	Generator
(2S)-2-[5-Amino-1-(5-phospho-β-D-ribosyl)imidazole-4-carboxamido]succinate	Generator
(2S)-2-[5-Amino-1-(5-phospho-β-D-ribosyl)imidazole-4-carboxamido]succinic acid	Generator
(S)-2-[5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinic acid	Generator
Succinyl-5-aminoimidazole-4-carboxamide-1-ribose-5-phosphoric acid	Generator
Succinylaminoimidazolecarboxamide ribose-5'-phosphoric acid	Generator
(S)-2-(5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido)succinate	HMDB
(S)-2-(5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido)succinic acid	HMDB
(S)-2-(5-Amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido)succinate	HMDB
(S)-2-(5-Amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido)succinic acid	HMDB
(S)-2-[5-Amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido]succinate	HMDB
1-(5'-Phosphoribosyl)-5-amino-4-(N-succinocarboxamide)-imidazole' 1-(5'-phosphoribosyl)-4-(N-succinocarboxamide)-5-aminoimidazole	HMDB
5'-Phosphoribosyl-4-(N-succinocarbozamide)-5-aminoimidazole	HMDB
5-Amino-4-imidazole-N-succinocarboxamide ribonucleotide	HMDB
L-N-[(5-Amino-1-b-D-ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphate)	HMDB
L-N-[(5-Amino-1-beta-delta-ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphate)	HMDB
N-(5-Amino-1-ribofuranosylimidazol-4-ylcarbonyl)aspartic acid 5'-phosphate	HMDB
N-[5-Amino-1-(5'-phosphoribofuranosyl)-4-imidazolecarbonyl]aspartate	HMDB
N-[5-Amino-1-(5'-phosphoribofuranosyl)-4-imidazolecarbonyl]aspartic acid	HMDB
Phosphoribosylaminoimidazolesuccinocarboxamide	HMDB
N-(5-Amino-1-beta-D-ribofuranosylimidazole-4-carbonyl)-L-aspartic acid 5'-phosphate	HMDB
5'-Phosphoribosyl-4-(N-succinylcarboxamide)-5-aminoimidazole	HMDB
SAICAR, (D)-isomer	HMDB
SAICAribotide	HMDB
Succinylaminoimidazole carboxamide ribotide	HMDB
SAICA ribotide	HMDB
Succinylaminoimidazolecarboxamide ribose-5’-phosphate	HMDB

Chemical Formula

C₁₃H₁₉N₄O₁₂P

Average Molecular Weight

454.2833

Monoisotopic Molecular Weight

454.073708604

IUPAC Name

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

Traditional Name

saicar

CAS Registry Number

3031-95-6

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

InChI Identifier

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

InChI Key

NAQGHJTUZRHGAC-ZZZDFHIKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-ribosyl-imidazolecarboxamides. These are organic compounds containing the imidazole ring linked to a ribose ring 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-ribosyl-imidazolecarboxamides

Alternative Parents

Substituents

1-ribosyl-imidazolecarboxamide
Pentose-5-phosphate
Pentose phosphate
Aspartic acid or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Glycosyl compound
N-glycosyl compound
Monosaccharide phosphate
Alpha-amino acid or derivatives
Pentose monosaccharide
2-heteroaryl carboxamide
Imidazolyl carboxylic acid derivative
Imidazole-4-carbonyl group
Monoalkyl phosphate
N-substituted imidazole
Organic phosphoric acid derivative
Alkyl phosphate
Dicarboxylic acid or derivatives
Phosphoric acid ester
Aminoimidazole
Monosaccharide
Imidazole
Heteroaromatic compound
Azole
Vinylogous amide
Tetrahydrofuran
Amino acid or derivatives
Carboxamide group
Amino acid
1,2-diol
Secondary carboxylic acid amide
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Alcohol
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Amine
Primary amine
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

1-(phosphoribosyl)imidazolecarboxamide (CHEBI:18319 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0000797)

Herbs and Spices (FooDB: FOOD00866)

Nut

Almond (FooDB: FOOD00148)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)
Hazelnut (FooDB: FOOD00376)
Peanut (FooDB: FOOD00016)
Pecan nut (FooDB: FOOD00044)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Walnut (FooDB: FOOD00608)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Macadamia nut (FooDB: FOOD00525)
Mixed nuts (FooDB: FOOD00771)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Japanese chestnut (FooDB: FOOD00385)
Common hazelnut (FooDB: FOOD00062)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Nuts (FooDB: FOOD00869)

Fruit

Pome

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)
Common chokecherry (FooDB: FOOD00562)
Peach (var.) (FooDB: FOOD00230)

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)
Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Ohelo berry (FooDB: FOOD00419)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)
Jujube (FooDB: FOOD00388)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Persian lime (FooDB: FOOD00543)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Vegetable

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Mexican groundcherry (FooDB: FOOD00491)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Garden tomato (var.) (FooDB: FOOD00173)
Cherry tomato (FooDB: FOOD00172)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. frutescens) (FooDB: FOOD00428)
Pepper (C. pubescens) (FooDB: FOOD00849)
Orange bell pepper (FooDB: FOOD00879)

Root vegetable

Cabbage

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Swiss chard (FooDB: FOOD00237)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)
Spinach (FooDB: FOOD00178)
Common beet (FooDB: FOOD00025)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Yautia (FooDB: FOOD00510)
Romaine lettuce (FooDB: FOOD00888)
Rocket salad (FooDB: FOOD00244)
Chicory leaves (FooDB: FOOD00250)
Corn salad (FooDB: FOOD00340)
Malabar spinach (FooDB: FOOD00404)
Ostrich fern (FooDB: FOOD00556)
Green vegetables (FooDB: FOOD00872)

Mushroom

Tuber

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)
Shallot (FooDB: FOOD00243)
Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Other vegetable

Okra (FooDB: FOOD00420)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Tree fern (FooDB: FOOD00797)
Chinese water chestnut (FooDB: FOOD00332)
Nopal (FooDB: FOOD00416)
Carob (FooDB: FOOD00321)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Giant butterbur (FooDB: FOOD00314)
Sesbania flower (FooDB: FOOD00469)

Stalk vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

White lupine (FooDB: FOOD00403)
Lupine (FooDB: FOOD00104)

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Other soy product (FooDB: FOOD00271)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.73 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-4.8	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	1.22	ChemAxon
pKa (Strongest Basic)	4.54	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	263.99 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	90.65 m³·mol⁻¹	ChemAxon
Polarizability	38.5 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000797

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022251

KNApSAcK ID

Not Available

Chemspider ID

141175

KEGG Compound ID

C04823

BioCyc ID

P-RIBOSYL-4-SUCCCARB-AMINOIMIDAZOLE

BiGG ID

44624

Wikipedia Link

Phosphoribosylaminoimidazolesuccinocarboxamide

METLIN ID

5762

PubChem Compound

160666

PDB ID

Not Available

ChEBI ID

18319

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole (CFc000337636)

MOL for CFc000337636 (5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole)

3D MOL for CFc000337636 (5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole)

3D SDF for CFc000337636 (5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole)

3D-SDF for CFc000337636 (5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole)

PDB for CFc000337636 (5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole)

3D PDB for CFc000337636 (5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole)

SMILES for CFc000337636 (5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole)

INCHI for CFc000337636 (5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole)

Structure for CFc000337636 (5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole)

3D Structure for CFc000337636 (5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole)