Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:58:29 UTC
Update Date2022-08-31 17:40:42 UTC
Metabolite IDMMDBc0030209
Metabolite Identification
Common NameCyclic pyranopterin monophosphate
DescriptionCyclic 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
Synonyms
ValueSource
CPMPChEBI
Cyclic pyranopterin monophoshateChEBI
Precursor Z, hydratedChEBI
Cyclic pyranopterin phosphateKegg
Cyclic pyranopterin monophoshic acidGenerator
Cyclic pyranopterin phosphoric acidGenerator
Cyclic pyranopterin monophosphoric acidGenerator
CPMP CPDMeSH, HMDB
Molecular FormulaC10H14N5O8P
Average Mass363.2206
Monoisotopic Mass363.057998961
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 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
CAS Registry NumberNot Available
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
InChI Identifier
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
InChI KeyCZAKJJUNKNPTTO-AJFJRRQVSA-N