ECMDB: Cyclic pyranopterin monophosphate (ECMDB20601) (M2MDB001401)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (4)XML

Proteins (1162)

Record Information

Version

2.0

Creation Date

2012-05-31 14:52:51 -0600

Update Date

2015-06-03 17:20:22 -0600

Secondary Accession Numbers

ECMDB20601

Identification

Name:

Cyclic pyranopterin monophosphate

Description

Cyclic pyranopterin monophosphate is a member of the chemical class known as Pterins and Derivatives. These are polycyclic aromatic compounds containing a pterin moeity, which consist of a pteridine ring bearing a ketone and an amine group to form 2-aminopteridin-4(3H)-one. cPMP is a precursor to molybdenum cofactor, which is required for the enyzme activity of sulfite oxidase, xanthine dehydrogenase/oxidase and aldehyde oxidase. The transition element molybdenum (Mo) has been long known as an essential micronutrient across the kingdoms of plants, animals, fungi and bacteria. However, molybdate itself is catalytically inactive and, with the exception of bacterial nitrogenase, needs to be activated through complexation by a special cofactor. There are several molybdenum cofactors, including molybdopterin (MPT), guanylyl molybdenum cofactor (MGD), cytidylyl molybdenum cofactor, or others. In Escherichia coli, the MoaD protein plays a central role in the conversion of precursor Z to molybdopterin (MPT) during molybdenum cofactor biosynthesis. (PMID 17223713) In Escherichia coli, MPT is formed by incorporation of two sulfur atoms into precursor Z, which is catalyzed by MPT synthase. (PMID 11459846)

Structure

MOL SDF PDB SMILES InChI

Synonyms:

8-Amino-2,12,12-trihydroxy-4,4a,5a,6,9,10,11,11a,12,12a-decahydro-[1,3,2]dioxaphosphinino[4',5':5,6]pyrano[3,2-g]pteridine 2-oxide
8-Amino-2,12,12-trihydroxy-4a,5a,6,9,11,11a,12,12a-octahydro[1,3,2]dioxaphosphinino[4',5':5,6]pyrano[3,2-g]pteridin-10(4H)-one 2-oxide
CPMP
Cyclic pyranopterin monophosphate
Cyclic pyranopterin monophosphoric acid
Precursor z
Precursor-Z

Chemical Formula:

C₁₀H₁₄N₅O₈P

Weight:

Average: 363.2206
Monoisotopic: 363.057998961

InChI Key:

CZAKJJUNKNPTTO-AJFJRRQVSA-N

InChI:

InChI=1S/C10H14N5O8P/c11-9-14-6-3(7(16)15-9)12-4-8(13-6)22-2-1-21-24(19,20)23-5(2)10(4,17)18/h2,4-5,8,12,17-18H,1H2,(H,19,20)(H4,11,13,14,15,16)/t2-,4-,5+,8-/m1/s1

CAS number:

Not Available

IUPAC Name:

(4aR,5aR,11aR,12aS)-2,10,12,12-tetrahydroxy-8-imino-4,4a,5a,6,7,8,11,11a,12,12a-decahydro-2H-1,3,5-trioxa-6,7,9,11-tetraaza-2lambda5-phosphatetracen-2-one

Traditional IUPAC Name:

(4aR,5aR,11aR,12aS)-2,10,12,12-tetrahydroxy-8-imino-4,4a,5a,6,7,11,11a,12a-octahydro-1,3,5-trioxa-6,7,9,11-tetraaza-2lambda5-phosphatetracen-2-one

SMILES:

[H][C@@]12COP(O)(=O)O[C@]1([H])C(O)(O)[C@]1([H])NC3=C(NC(=N)N=C3O)N[C@]1([H])O2

Chemical Taxonomy

Description

belongs to the class of organic compounds known as pyranopterins and derivatives. These are pterin derivatives in which a pyran ring is fused either to the pyrimidine ring or the pyrazine ring of the pterin moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Pterins and derivatives

Direct Parent

Pyranopterins and derivatives

Alternative Parents

Substituents

Pyranopterin
Aminopyrimidine
Pyrimidone
Secondary aliphatic/aromatic amine
Monosaccharide
Organic phosphoric acid derivative
Oxane
Pyrimidine
Heteroaromatic compound
Vinylogous amide
Carbonyl hydrate
Polyol
Oxacycle
Azacycle
Secondary amine
Organic nitrogen compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Primary amine
Hydrocarbon derivative
Amine
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heterotetracyclic compound (CHEBI:60210 )
oxacycle (CHEBI:60210 )
organonitrogen heterocyclic compound (CHEBI:60210 )
ketone hydrate (CHEBI:60210 )

Physical Properties

State:

Not Available

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	9.05 g/L	ALOGPS
logP	-2	ALOGPS
logP	-3.2	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	1.8	ChemAxon
pKa (Strongest Basic)	3.96	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	197.98 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	93.04 m³·mol⁻¹	ChemAxon
Polarizability	29.91 Å³	ChemAxon
Number of Rings	4	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:

SMPDB Pathways:

Folate biosynthesis	PW000908
GTP degradation	PW001888

KEGG Pathways:

Folate biosynthesis ec00790
Metabolic pathways eco01100

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	splash10-03yi-0954000000-c0c03f7b7051e69aa940	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0h50-7792680000-b9bc8825f210f215306e	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0009000000-409073732cecfccd1306	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01qa-1069000000-41d8aad4b65debf6b22f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0560-5970000000-c418a7d872c8d58d4e1f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-1749000000-d08212ceb7e994db0f40	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0900000000-3b25595e096bedd044e0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0059-9200000000-90cd7a3b87256a3d7e40	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0009000000-0a09be49d6be31174b51	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01t9-9546000000-0c075e6e07d269d52a15	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fb9-7913000000-28a74b00aeba67eb0c5a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0009000000-06a4f7b91a99ab66773a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0019000000-c17d8fe2f9f9b3e52c16	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-1910000000-91b6cb0fac8b32075acd	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:

Gutzke, G., Fischer, B., Mendel, R. R., Schwarz, G. (2001). "Thiocarboxylation of molybdopterin synthase provides evidence for the mechanism of dithiolene formation in metal-binding pterins." J Biol Chem 276:36268-36274. Pubmed: 11459846
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
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	60210
HMDB ID	HMDB0304838
Pubchem Compound ID	25202908
Kegg ID	C18239
ChemSpider ID	17221217
Wikipedia ID	Not Available
BioCyc ID	PRECURSOR-Z
EcoCyc ID	PRECURSOR-Z

Enzymes

Protein Details

1. Molybdopterin synthase sulfur carrier subunit

General function:: Involved in Mo-molybdopterin cofactor biosynthetic process
Specific function:: Involved in sulfur transfer in the conversion of molybdopterin precursor Z to molybdopterin
Gene Name:: moaD
Uniprot ID:: P30748
Molecular weight:: 8758

Protein Details

2. Molybdopterin synthase catalytic subunit

General function:: Involved in Mo-molybdopterin cofactor biosynthetic process
Specific function:: Converts molybdopterin precursor Z to molybdopterin. This requires the incorporation of two sulfur atoms into precursor Z to generate a dithiolene group. The sulfur is provided by moaD
Gene Name:: moaE
Uniprot ID:: P30749
Molecular weight:: 16981

Reactions

Cyclic pyranopterin monophosphate + 2 [molybdopterin-synthase sulfur-carrier protein]-Gly-NH-CH(2)-C(O)SH + H(2)O = molybdopterin + 2 [molybdopterin-synthase sulfur-carrier protein].

Protein Details

3. Molybdenum cofactor biosynthesis protein A

General function:: Involved in catalytic activity
Specific function:: Together with moaC, is involved in the conversion of a guanosine derivative (5'-GTP) into molybdopterin precursor Z
Gene Name:: moaA
Uniprot ID:: P30745
Molecular weight:: 37346

Protein Details

4. Molybdenum cofactor biosynthesis protein C

General function:: Involved in Mo-molybdopterin cofactor biosynthetic process
Specific function:: Together with moaA, is involved in the conversion of a guanosine derivative (5'-GTP) into molybdopterin precursor Z
Gene Name:: moaC
Uniprot ID:: P0A738
Molecular weight:: 17467

Cyclic pyranopterin monophosphate (ECMDB20601) (M2MDB001401)

Structure for #<Compound:0xa1bcb8d4>

Enzymes

Reactions