PRP

1-O-pyrophosphono-5-O-phosphono-alpha-D-ribofuranose

Created:	1999-07-08
Last modified:	2020-07-17

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87 entries where PRP is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	35
Chiral Atom Count	5
Bond Count	35
Aromatic Bond Count	0

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Chemical Component Summary
Name	1-O-pyrophosphono-5-O-phosphono-alpha-D-ribofuranose
Synonyms	ALPHA-PHOSPHORIBOSYLPYROPHOSPHORIC ACID; 1-O-pyrophosphono-5-O-phosphono-alpha-D-ribose; 1-O-pyrophosphono-5-O-phosphono-D-ribose; 1-O-pyrophosphono-5-O-phosphono-ribose
Systematic Name (OpenEye OEToolkits)	[(2R,3R,4S,5R)-3,4-dihydroxy-5-(phosphonooxymethyl)oxolan-2-yl] phosphono hydrogen phosphate
Formula	C₅ H₁₃ O₁₄ P₃
Molecular Weight	390.07
Type	D-SACCHARIDE

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	O=P(OC1OC(C(O)C1O)COP(=O)(O)O)(O)OP(=O)(O)O
SMILES	CACTVS	3.341	O[CH]1[CH](O)[CH](O[CH]1CO[P](O)(O)=O)O[P](O)(=O)O[P](O)(O)=O
SMILES	OpenEye OEToolkits	1.5.0	C(C1C(C(C(O1)OP(=O)(O)OP(=O)(O)O)O)O)OP(=O)(O)O
Canonical SMILES	CACTVS	3.341	O[C@H]1[C@@H](O)[C@H](O[C@@H]1CO[P](O)(O)=O)O[P@](O)(=O)O[P](O)(O)=O
Canonical SMILES	OpenEye OEToolkits	1.5.0	C([C@@H]1[C@H]([C@H]([C@H](O1)O[P@@](=O)(O)OP(=O)(O)O)O)O)OP(=O)(O)O
InChI	InChI	1.03	InChI=1S/C5H13O14P3/c6-3-2(1-16-20(8,9)10)17-5(4(3)7)18-22(14,15)19-21(11,12)13/h2-7H,1H2,(H,14,15)(H2,8,9,10)(H2,11,12,13)/t2-,3-,4-,5-/m1/s1
InChIKey	InChI	1.03	PQGCEDQWHSBAJP-TXICZTDVSA-N

Drug Info: DrugBank

DrugBank ID	DB01632
Name	5-O-phosphono-alpha-D-ribofuranosyl diphosphate
Groups	investigational approved experimental
Description	The key substance in the biosynthesis of histidine, tryptophan, and purine and pyrimidine nucleotides.
Synonyms	5-O-phosphono-α-D-ribofuranosyl diphosphate PRPP Phosphoribosylpyrophosphate 5-Phosphoribosyl 1-pyrophosphate α-D-ribofuranose 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate) 5-O-phosphono-alpha-D-ribofuranosyl diphosphate Phosphoribosyl pyrophosphate 5-Phospho-alpha-D-ribose 1-diphosphate PRib-PP 5-Phosphoribosyl diphosphate
Categories	Carbohydrates Pentosephosphates Sugar Phosphates
CAS number	13270-65-0

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Hypoxanthine-guanine phosphoribosyltransferase	MATRSPGVVISDDEPGYDLDLFCIPNHYAEDLERVFIPHGLIMDRTERLA...	unknown
Orotate phosphoribosyltransferase	MKPYQRQFIEFALNKQVLKFGEFTLKSGRKSPYFFNAGLFNTGRDLALLG...	unknown	substrate
Uridine-cytidine kinase-like 1	MAAPPARADADPSPTSPPTARDTPGRQAEKSETACEDRSNAESLDRLLPP...	unknown
Hypoxanthine-guanine phosphoribosyltransferase	MPREYEFAEKILFTEEEIRTRIMEVAKRIADDYKGKGLRPYVNPLVLISV...	unknown
Adenine phosphoribosyltransferase	MADSELQLVEQRIRSFPDFPTPGVVFRDISPVLKDPASFRAAIGLLARHL...	unknown
Anthranilate phosphoribosyltransferase	MQATLIKPTIFTHQPILEKLFKSQSMTQEESHQLFAAIVRGELEDSQLAA...	unknown
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682