P. aeruginosa Metabolome Database: Molybdopterin (PAMDB000446)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB000446

Identification

Name:

Molybdopterin

Description:

Molybdopterins are a class of biochemical cofactor that are used in many different enzymes. The simplest structure of molybdopterin contains a pyranopterin coordinated to molybdenum. The pyranopterin structure is a fused ring system containing a pyran fused to pterin. In addition, the pyran ring is substituted with two thiols and an alkyl phosphate. In molybdopterin, the thiols coordinate to molybdenum. In some cases, the alkyl phosphate group is replaced by an alkyl diphosphate nucleotide. -- Wikipedia

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

Ene-dithiol pyranopterin
H2Dtpp-mP
H₂Dtpp-mP
MoCo
Molybdenum cofactor
Molybdenum enzyme molybdenum cofactor
Molybdoenzyme molybdenum-containing cofactor
MPT
Nitrate reductase molybdenum cofactor
Nitric acid reductase molybdenum cofactor
Pterin molybdenum cofactor
Pyranopterin-dithiolate
Pyranopterin-dithiolic acid
[(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]methyl dihydrogen phosphate
[(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]methyl dihydrogen phosphoric acid
[(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]methyl dihydrogen phosphate
[(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]methyl dihydrogen phosphoric acid

Chemical Formula:

C₁₀H₁₂MoN₅O₈PS₂

Average Molecular Weight:

521.27

Monoisotopic Molecular Weight:

522.891898123

InChI Key:

HDAJUGGARUFROU-UHFFFAOYSA-L

InChI:

InChI=1S/C10H14N5O6PS2.Mo.2O/c11-10-14-7-4(8(16)15-10)12-3-6(24)5(23)2(21-9(3)13-7)1-20-22(17,18)19;;;/h2-3,9,12,23-24H,1H2,(H2,17,18,19)(H4,11,13,14,15,16);;;/q;+2;;/p-2

CAS number:

73508-07-3

IUPAC Name:

({4-hydroxy-2-imino-6,7-disulfanyl-1H,2H,5H,5aH,8H,9aH,10H-pyrano[3,2-g]pteridin-8-yl}methoxy)phosphonic acid

Traditional IUPAC Name:

molybdopterin cofactor

SMILES:

NC1=NC2=C(NC3C(N2)OC(COP(O)(O)=O)C2=C3S[Mo](=O)(=O)S2)C(=O)N1

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as molybdopterins. These are cofactors or analogs thereof, with a structure based on a furan ring fused to a pterin. In addition, the pyran ring features two thiolates, which serve as ligands in molybdo- and tungstoenzymes. In some cases, the alkyl phosphate group is replaced by an alkyl diphosphate nucleotide.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Pterins and derivatives

Direct Parent

Molybdopterins

Alternative Parents

Substituents

Molybdopterin
Pyranopterin
Monoalkyl phosphate
Secondary aliphatic/aromatic amine
Pyrimidone
Imidolactam
Alkyl phosphate
Pyrimidine
Pyran
Primary aromatic amine
Phosphoric acid ester
Organic phosphoric acid derivative
Organic phosphate
Heteroaromatic compound
Vinylogous amide
Lactam
Oxacycle
Azacycle
Thioenol
Secondary amine
Alkylthiol
Hydrocarbon derivative
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Not Available

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.212 mg/mL	ALOGPS
logP	-0.04	ALOGPS
logP	-5	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	-4.1	ChemAxon
pKa (Strongest Basic)	15	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	168.52 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	109.78 m³·mol^-1	ChemAxon
Polarizability	34.81 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	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:

Cyclic pyranopterin monophosphate + Copper + 2 MoaD Protein with thiocarboxylate >5 Hydrogen ion +2 MoaD Protein with carboxylate + Molybdopterin
Guanosine triphosphate + Hydrogen ion + Molybdopterin > Molybdopterin guanine dinucleotide + Pyrophosphate
Adenosine triphosphate + Hydrogen ion + Molybdopterin <> Adenylated molybdopterin + Pyrophosphate
Molybdopterin + Adenylated molybdopterin > Adenosine monophosphate + bis-molybdenum cofactor + Copper
2 Hydrogen ion + Molybdate + Adenylated molybdopterin > Adenosine monophosphate + Copper + Water + Molybdopterin
Cytidine triphosphate + Hydrogen ion + Molybdopterin > Molybdopterin cytosine dinucleotide + Pyrophosphate
Cyclic pyranopterin monophosphate + 2 Sulfur donor <> Molybdopterin
Adenosine triphosphate + Molybdopterin <> Pyrophosphate + Adenylated molybdopterin
Cyclic pyranopterin monophosphate + Water + Thiocarboxylated-MPT-synthases > Molybdopterin + MPT-Synthases
Cyclic pyranopterin monophosphate + Water + thiocarboxylated small subunit of molybdopterin synthase >4 Hydrogen ion +2 thiocarboxylated small subunit of molybdopterin synthase + Molybdopterin + Molybdopterin
Molybdopterin + Adenosine triphosphate + Hydrogen ion + Molybdopterin > Pyrophosphate + Adenylyl-molybdopterin + Adenylyl-molybdopterin

Pathways:

Folate biosynthesis pae00790
Sulfur relay system pae04122

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0039000000-84cf32f404eeb78b5691	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kb-5971000000-199db225c024b4165ff2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-6950000000-5b6c74baa781ba9844c2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-053r-4973000000-330fc1913c91eda018ef	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00os-9400000000-c006fe4a32c3257f786b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-98d79a714310b9150084	View in MoNA

References

References:

Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
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
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
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	21437
HMDB ID	HMDB02206
Pubchem Compound ID	459
Kegg ID	C05924
ChemSpider ID	446
Wikipedia	Molybdopterin
BioCyc ID	CPD-4
EcoCyc ID	CPD-4

Molybdopterin (PAMDB000446)

Structure for Molybdopterin (PAMDB000446)