A12

PHOSPHOMETHYLPHOSPHONIC ACID ADENOSYL ESTER

Created:	2000-12-15
Last modified:	2020-06-05

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12 entries where A12 is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	44
Chiral Atom Count	5
Bond Count	46
Aromatic Bond Count	10

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Chemical Component Summary
Name	PHOSPHOMETHYLPHOSPHONIC ACID ADENOSYL ESTER
Synonyms	ALPHA,BETA-METHYLENEADENOSINE-5'-DIPHOSPHATE
Systematic Name (OpenEye OEToolkits)	[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]methylphosphonic acid
Formula	C₁₁ H₁₇ N₅ O₉ P₂
Molecular Weight	425.228
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	O=P(O)(O)CP(=O)(O)OCC3OC(n2cnc1c(ncnc12)N)C(O)C3O
SMILES	CACTVS	3.341	Nc1ncnc2n(cnc12)[CH]3O[CH](CO[P](O)(=O)C[P](O)(O)=O)[CH](O)[CH]3O
SMILES	OpenEye OEToolkits	1.5.0	c1nc(c2c(n1)n(cn2)C3C(C(C(O3)COP(=O)(CP(=O)(O)O)O)O)O)N
Canonical SMILES	CACTVS	3.341	Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO[P@](O)(=O)C[P](O)(O)=O)[C@@H](O)[C@H]3O
Canonical SMILES	OpenEye OEToolkits	1.5.0	c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO[P@](=O)(CP(=O)(O)O)O)O)O)N
InChI	InChI	1.03	InChI=1S/C11H17N5O9P2/c12-9-6-10(14-2-13-9)16(3-15-6)11-8(18)7(17)5(25-11)1-24-27(22,23)4-26(19,20)21/h2-3,5,7-8,11,17-18H,1,4H2,(H,22,23)(H2,12,13,14)(H2,19,20,21)/t5-,7-,8-,11-/m1/s1
InChIKey	InChI	1.03	OLCWZBFDIYXLAA-IOSLPCCCSA-N

Drug Info: DrugBank

DrugBank ID	DB03148
Name	Adenosine 5'-methylenediphosphate
Groups	experimental
Synonyms	Adenosine, 5'-(trihydrogen methylenebis(phosphonate)) Adenosine 5'-methylenediphosphate Phosphomethylphosphonic acid adenosyl ester Adenosine 5'-(hydrogen (phosphonomethyl)phosphonate)
Categories	5'-Nucleotidase, antagonists & inhibitors Adenine Nucleotides Enzyme Inhibitors Heterocyclic Compounds, Fused-Ring Nucleic Acids, Nucleotides, and Nucleosides Nucleotides Purine Nucleotides Purines Ribonucleotides
CAS number	3768-14-7

Drug Targets

Name	Target Sequence	Pharmacological Action
DNA	-	unknown
Ribose-phosphate pyrophosphokinase	MSNQYGDKNLKIFSLNSNPELAKEIADIVGVQLGKCSVTRFSDGEVQINI...	unknown
MutT/nudix family protein	MAEHDFETISSETLHTGAIFALRRDQVRMPGGGIVTREVVEHFGAVAIVA...	unknown
Protein UshA	MKLLQRGVALALLTTFTLASETALAYEQDKTYKITVLHTNDHHGHFWRNE...	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