ECMDB: Molybdopterin guanine dinucleotide (ECMDB20281) (M2MDB001121)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (2)XML

Proteins (2)

Record Information

Version

2.0

Creation Date

2012-05-31 14:37:02 -0600

Update Date

2015-06-03 17:19:42 -0600

Secondary Accession Numbers

ECMDB20281

Identification

Name:

Molybdopterin guanine dinucleotide

Description

Molybdopterin guanine dinucleotide is a member of the chemical class known as Purine Ribonucleoside Diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety. It appears that the molybdopterin present in the nitrate reductase of a chlB mutant is converted to molybdopterin guanine dinucleotide during activation. (PMID 1459941) We propose therefore that MobB is an adapter protein that acts in concert with MobA to achieve the efficient biosynthesis and utilization of molybdopterin guanine dinucleotide. (PMID 12682065)

Structure

MOL SDF PDB SMILES InChI

Synonyms:

bis-molybdopterin guanine dinucleotide
Bis-molybdopterin guanine dinucleotide
MGD
Molybdopterin guanine dinucleotide
Molybdopteringuaninedinucleotide
MoO2(OH)Dtpp-mGDP
MoO₂(OH)Dtpp-mGDP
MPT-GMP

Chemical Formula:

C₂₀H₂₄N₁₀O₁₃P₂S₂

Weight:

Average: 738.541
Monoisotopic: 738.044095308

InChI Key:

MNEQOJMCKOBWNR-UHFFFAOYSA-N

InChI:

InChI=1S/C20H24N10O13P2S2/c21-19-26-14-8(16(34)28-19)25-5(1-23-14)12(46)13(47)6(31)2-40-44(36,37)43-45(38,39)41-3-7-10(32)11(33)18(42-7)30-4-24-9-15(30)27-20(22)29-17(9)35/h1,4,6-7,10-11,18,25,31-33H,2-3H2,(H,36,37)(H,38,39)(H3,22,27,29,35)(H4,21,23,26,28,34)

CAS number:

128007-95-4

IUPAC Name:

[({[3,4-dihydroxy-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy][2-hydroxy-4-(4-hydroxy-2-imino-1,2,5,8-tetrahydropteridin-6-yl)-3,4-disulfanylidenebutoxy]phosphinic acid

Traditional IUPAC Name:

{[3,4-dihydroxy-5-(6-hydroxy-2-imino-3H-purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(2-hydroxy-4-(4-hydroxy-2-imino-5,8-dihydro-1H-pteridin-6-yl)-3,4-disulfanylidenebutoxy)phosphinic acid

SMILES:

OC(COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1O)N1C=NC2=C1NC(=N)N=C2O)C(=S)C(=S)C1=CNC2=C(N1)C(O)=NC(=N)N2

Chemical Taxonomy

Description

belongs to the class of organic compounds known as purine ribonucleoside diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine ribonucleotides

Direct Parent

Purine ribonucleoside diphosphates

Alternative Parents

Substituents

Purine ribonucleoside diphosphate
Purine ribonucleoside monophosphate
Pentose phosphate
Pentose-5-phosphate
Pterin
Glycosyl compound
N-glycosyl compound
6-oxopurine
Hypoxanthine
Monosaccharide phosphate
Organic pyrophosphate
Pentose monosaccharide
Pteridine
Purine
Imidazopyrimidine
Secondary aliphatic/aromatic amine
Aminopyrimidine
Pyrimidone
Monoalkyl phosphate
Monosaccharide
N-substituted imidazole
Organic phosphoric acid derivative
Pyrimidine
Alkyl phosphate
Phosphoric acid ester
Tetrahydrofuran
Imidazole
Heteroaromatic compound
Azole
Vinylogous amide
Thioketone
Secondary alcohol
Enamine
Azacycle
Secondary amine
Organoheterocyclic compound
Oxacycle
Thiocarbonyl group
Amine
Organonitrogen compound
Organooxygen compound
Alcohol
Organic oxygen compound
Organic nitrogen compound
Organosulfur compound
Organopnictogen compound
Organic oxide
Primary amine
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Not Available

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.25 g/L	ALOGPS
logP	-0.46	ALOGPS
logP	-3	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	-4.5	ChemAxon
pKa (Strongest Basic)	15	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	351.03 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	195.57 m³·mol⁻¹	ChemAxon
Polarizability	64.66 Å³	ChemAxon
Number of Rings	5	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:

Guanosine triphosphate + Hydrogen ion + Molybdopterin > Molybdopterin guanine dinucleotide + Pyrophosphate
Hydrogen ion + molybdenum cofactor + Guanosine triphosphate <> Molybdopterin guanine dinucleotide + Pyrophosphate
Bis-molybdopterin guanine dinucleotide + Guanosine triphosphate + Hydrogen ion + Molybdopterin guanine dinucleotide > Guanylyl molybdenum cofactor + Pyrophosphate

SMPDB Pathways:

guanylyl molybdenum cofactor biosynthesis

PW002032

KEGG Pathways:

Not Available

EcoCyc Pathways:

guanylyl molybdenum cofactor biosynthesis PWY-5964

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0930100400-d7d4d0a58c184123438b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0911000000-1fdeb76e4ff24e3c3b47	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-2920000000-95390e018955c5db8898	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udr-0610311900-9228ca763e6b55205fb0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-1920200000-6a75b94d4c73e6089e93	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pdi-3900000000-6295a32e18f9af17c4c4	View in MoNA
MS	Mass Spectrum (Electron Ionization)	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
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
McLuskey, K., Harrison, J. A., Schuttelkopf, A. W., Boxer, D. H., Hunter, W. N. (2003). "Insight into the role of Escherichia coli MobB in molybdenum cofactor biosynthesis based on the high resolution crystal structure." J Biol Chem 278:23706-23713. Pubmed: 12682065
Santini, C. L., Iobbi-Nivol, C., Romane, C., Boxer, D. H., Giordano, G. (1992). "Molybdoenzyme biosynthesis in Escherichia coli: in vitro activation of purified nitrate reductase from a chlB mutant." J Bacteriol 174:7934-7940. Pubmed: 1459941
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	30404
HMDB ID	Not Available
Pubchem Compound ID	5486686
Kegg ID	Not Available
ChemSpider ID	4589022
Wikipedia ID	Not Available
BioCyc ID	CPD-582
EcoCyc ID	CPD-582

Enzymes

Protein Details

1. Molybdopterin-guanine dinucleotide biosynthesis protein A

General function:: Involved in catalytic activity
Specific function:: Links a guanosine 5'-phosphate to molydopterin (MPT) forming molybdopterin guanine dinucleotide (MGD)
Gene Name:: mobA
Uniprot ID:: P32173
Molecular weight:: 21643

Reactions

GTP + molybdenum cofactor = diphosphate + guanylyl molybdenum cofactor.

Protein Details

2. Molybdopterin-guanine dinucleotide biosynthesis protein B

General function:: Involved in GTP binding
Specific function:: May bind the guanine nucleotide required for the synthesis of molybdopterin guanine dinucleotide
Gene Name:: mobB
Uniprot ID:: P32125
Molecular weight:: 19363

Molybdopterin guanine dinucleotide (ECMDB20281) (M2MDB001121)

Structure for #<Compound:0x99ca2ae4>

Enzymes

Reactions