GCP

PHOSPHOMETHYLPHOSPHONIC ACID GUANYLATE ESTER

Created:	1999-07-08
Last modified:	2024-09-27

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152 entries where GCP is found as a standalone ligand7 entries where GCP is covalently linked to polymer or other heterogen groups 2 entries where GCP is found in a polymer sequence

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Chemical Details
Formal Charge	0
Atom Count	50
Chiral Atom Count	6
Bond Count	52
Aromatic Bond Count	10

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Chemical Component Summary
Name	PHOSPHOMETHYLPHOSPHONIC ACID GUANYLATE ESTER
Systematic Name (OpenEye OEToolkits)	[[[(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]methylphosphonic acid
Formula	C₁₁ H₁₈ N₅ O₁₃ P₃
Molecular Weight	521.208
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	O=P(O)(O)CP(=O)(O)OP(=O)(O)OCC3OC(n2cnc1c2N=C(N)NC1=O)C(O)C3O
SMILES	CACTVS	3.341	NC1=Nc2n(cnc2C(=O)N1)[CH]3O[CH](CO[P](O)(=O)O[P](O)(=O)C[P](O)(O)=O)[CH](O)[CH]3O
SMILES	OpenEye OEToolkits	1.5.0	c1nc2c(n1C3C(C(C(O3)COP(=O)(O)OP(=O)(CP(=O)(O)O)O)O)O)N=C(NC2=O)N
Canonical SMILES	CACTVS	3.341	NC1=Nc2n(cnc2C(=O)N1)[C@@H]3O[C@H](CO[P@@](O)(=O)O[P@@](O)(=O)C[P](O)(O)=O)[C@@H](O)[C@H]3O
Canonical SMILES	OpenEye OEToolkits	1.5.0	c1nc2c(n1[C@H]3[C@@H]([C@@H]([C@H](O3)CO[P@](=O)(O)O[P@@](=O)(CP(=O)(O)O)O)O)O)N=C(NC2=O)N
InChI	InChI	1.03	InChI=1S/C11H18N5O13P3/c12-11-14-8-5(9(19)15-11)13-2-16(8)10-7(18)6(17)4(28-10)1-27-32(25,26)29-31(23,24)3-30(20,21)22/h2,4,6-7,10,17-18H,1,3H2,(H,23,24)(H,25,26)(H2,20,21,22)(H3,12,14,15,19)/t4-,6-,7-,10-/m1/s1
InChIKey	InChI	1.03	PHBDHXOBFUBCJD-KQYNXXCUSA-N

Drug Info: DrugBank

DrugBank ID	DB03725
Name	5'-Guanylylmethylenebisphosphonate
Groups	experimental
Synonyms	5'-Guanylylmethylenebisphosphonate guanosine 5'-[beta,gamma-methylene]triphosphate 5'-Guanylylmethylenediphosphonate GppCp 5'-Guanosyl-methylene-triphosphate
Categories	Anti-Infective Agents Antiviral Agents Guanine Nucleotides Heterocyclic Compounds, Fused-Ring Nucleic Acids, Nucleotides, and Nucleosides Nucleotides Purine Nucleotides Purines Ribonucleotides
CAS number	13912-93-1

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Phosphoenolpyruvate carboxykinase, cytosolic [GTP]	MPPQLQNGLNLSAKVVQGSLDSLPQAVREFLENNAELCQPDHIHICDGSE...	unknown

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