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Record Information
Version	2.0
Creation Date	2012-07-30 14:55:16 -0600
Update Date	2015-06-03 17:21:08 -0600
Secondary Accession Numbers	ECMDB21307
Identification
Name:	Adenylated molybdopterin
Description	Adenylated molybdopterin is a member of the chemical class known as Purine Ribonucleoside Diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety. MPT-AMP is the reaction product of Cnx1G. Catalytically inactive Cnx1G mutant variants showed impaired MPT adenylation confirming that MPT-AMP is the reaction product of Cnx1G. (PMID 15504727)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xafa8bb8c> Close
Synonyms:	5'-O-[{[{[(5aR,8R,9aR)-2-amino-4-oxo-6,7-disulfanyl-3,5,5a,8,9a,10-hexahydro-4H-pyrano[3,2-g]pteridin-8-yl]methoxy}(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl]adenosine 5'-O-[{[{[(5aR,8R,9aR)-2-amino-4-oxo-6,7-disulphanyl-3,5,5a,8,9a,10-hexahydro-4H-pyrano[3,2-g]pteridin-8-yl]methoxy}(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl]adenosine Adenylated molybdopterin Adenylyl-molybdopterin H2Dtpp-mADP Molybdopterin-AMP MPT-AMP
Chemical Formula:	C20H26N10O12P2S2
Weight:	Average: 724.558 Monoisotopic: 724.06483075
InChI Key:	XJXFAXLUOKQPAQ-UHFFFAOYSA-N
InChI:	InChI=1S/C20H26N10O12P2S2/c21-14-8-16(24-3-23-14)30(4-25-8)19-11(32)10(31)5(41-19)1-38-43(34,35)42-44(36,37)39-2-6-12(45)13(46)7-18(40-6)27-15-9(26-7)17(33)29-20(22)28-15/h3-7,10-11,18-19,26,31-32,45-46H,1-2H2,(H,34,35)(H,36,37)(H2,21,23,24)(H4,22,27,28,29,33)
CAS number:	Not Available
IUPAC Name:	({2-amino-4-oxo-6,7-disulfanyl-3H,4H,5H,5aH,8H,9aH,10H-pyrano[3,2-g]pteridin-8-yl}methoxy)[({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphinic acid
Traditional IUPAC Name:	{2-amino-4-oxo-6,7-disulfanyl-3H,5H,5aH,8H,9aH,10H-pyrano[3,2-g]pteridin-8-yl}methoxy({[5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy)phosphinic acid
SMILES:	NC1=NC2=C(NC3C(N2)OC(COP(O)(=O)OP(O)(=O)OCC2OC(C(O)C2O)N2C=NC4=C2N=CN=C4N)C(S)=C3S)C(=O)N1
Chemical Taxonomy
Description	belongs to the class of organic compounds known as molybdopterin dinucleotides. These are a dinucleotide that is made up of a molybdopterin and a purine or pyrimidine base linked to each other through a phosphate chain.
Kingdom	Organic compounds
Super Class	Nucleosides, nucleotides, and analogues
Class	Molybdopterin dinucleotides
Sub Class	Not Available
Direct Parent	Molybdopterin dinucleotides
Alternative Parents	Purine ribonucleoside diphosphates Molybdopterins Purine ribonucleoside monophosphates Pentose phosphates Pyranopterins and derivatives Glycosylamines 6-aminopurines Monosaccharide phosphates Organic pyrophosphates Secondary alkylarylamines Pyrimidones Aminopyrimidines and derivatives Monoalkyl phosphates Pyrans Imidolactams N-substituted imidazoles Tetrahydrofurans Vinylogous amides Heteroaromatic compounds Secondary alcohols 1,2-diols Thioenols Azacyclic compounds Oxacyclic compounds Alkylthiols Organopnictogen compounds Hydrocarbon derivatives Primary amines Organic oxides
Substituents	Molybdopterin dinucleotide Purine ribonucleoside diphosphate Molybdopterin Purine ribonucleoside monophosphate Pentose phosphate Pentose-5-phosphate Pyranopterin Pterin Glycosyl compound N-glycosyl compound 6-aminopurine Monosaccharide phosphate Organic pyrophosphate Pentose monosaccharide Pteridine Imidazopyrimidine Purine Secondary aliphatic/aromatic amine Pyrimidone Aminopyrimidine Monoalkyl phosphate Monosaccharide N-substituted imidazole Pyrimidine Pyran Organic phosphoric acid derivative Alkyl phosphate Imidolactam Phosphoric acid ester Tetrahydrofuran Imidazole Azole Heteroaromatic compound Vinylogous amide 1,2-diol Secondary alcohol Azacycle Secondary amine Thioenol Oxacycle Alkylthiol Organoheterocyclic compound Amine Organopnictogen compound Alcohol Organic oxygen compound Organic nitrogen compound Organonitrogen compound Organooxygen compound Organosulfur compound Organic oxide Hydrocarbon derivative Primary amine Aromatic heteropolycyclic compound
Molecular Framework	Aromatic heteropolycyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Not Available
Charge:	-3
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 2.72 g/L ALOGPS logP -0.36 ALOGPS logP -5.5 ChemAxon logS -2.4 ALOGPS pKa (Strongest Acidic) 1.85 ChemAxon pKa (Strongest Basic) 4.01 ChemAxon Physiological Charge -3 ChemAxon Hydrogen Acceptor Count 17 ChemAxon Hydrogen Donor Count 11 ChemAxon Polar Surface Area 322.37 Ų ChemAxon Rotatable Bond Count 9 ChemAxon Refractivity 169.25 m³·mol⁻¹ ChemAxon Polarizability 62.78 ų ChemAxon Number of Rings 6 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:	Adenosine triphosphate + Hydrogen ion + Molybdopterin <> Adenylated molybdopterin + Pyrophosphate Molybdopterin + Adenylated molybdopterin > Adenosine monophosphate + bis-molybdenum cofactor + Copper Adenylated molybdopterin + tungsten binding cofactor > Adenosine monophosphate + tungsten bispterin cofactor + Copper 2 Hydrogen ion + Molybdate + Adenylated molybdopterin > Adenosine monophosphate + Copper + Water + Molybdopterin 2 Hydrogen ion + Adenylated molybdopterin + Tungstate > Adenosine monophosphate + Copper + Water + tungsten binding cofactor Adenosine triphosphate + Molybdopterin <> Pyrophosphate + Adenylated molybdopterin Adenylated molybdopterin + Molybdate <> Molybdoenzyme molybdenum cofactor + Adenosine monophosphate + Water + Molybdoenzyme molybdenum cofactor Hydrogen ion + Molybdopterin + Adenosine triphosphate > Adenylated molybdopterin + Pyrophosphate Adenylated molybdopterin + Molybdate > molybdenum cofactor + Adenosine monophosphate + Water
SMPDB Pathways:	Not Available
KEGG Pathways:	Sulfur relay system ec04122
EcoCyc Pathways:	molybdenum cofactor biosynthesis PWY-6823
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-004l-1723920100-bb1613d2f84a938b7a7e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-000i-0931101300-8d586fe7752001dd24cb View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-000i-0911000000-b051063e6b7a0a63f1f6 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-000i-1910000000-34bc9592e93856ccd5c2 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-08n9-1790232100-43f0c1f38049a8fdaf61 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-001i-0910600000-682c0ffebbb9af7a0134 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a7i-3900000000-6aece1e85f04e32c2771 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-004i-0001000900-ffa1a59ff1824e74917a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-002b-0393011600-d5404022df3e8fd231bf View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-000i-0923000000-b412c4768c1614066341 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-00di-0000002900-a1df204dd3a6582fbd67 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-00gr-9502308500-32959dd120e465001372 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a4i-4905805200-c9d6b2442ad99b0bcf05 View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	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 Llamas, A., Mendel, R. R., Schwarz, G. (2004). "Synthesis of adenylated molybdopterin: an essential step for molybdenum insertion." J Biol Chem 279:55241-55246. Pubmed: 15504727
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 62728 HMDB ID HMDB0012262 Pubchem Compound ID 25245677 Kegg ID C19848 ChemSpider ID 35032425 Wikipedia ID Not Available BioCyc ID CPD-8122 EcoCyc ID CPD-8122

Enzymes