6-Carboxy-5,6,7,8-tetrahydropterin (PAMDB001589)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB001589
Identification
Name: 6-Carboxy-5,6,7,8-tetrahydropterin
Description:6-carboxy-5,6,7,8-tetrahydropterin is a member of the chemical class known as Alpha Amino Acids and Derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).6-carboxy-5,6,7,8-tetrahydropterin is catalyzed by QueD. Pseudomonas aeruginosa QueD is a 6-carboxy-5,6,7,8-tetrahydropterin synthase. (PMID 19231875)
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 2-Amino-4-oxo-3,4,5,6,7,8-hexahydropteridine-6-carboxylate
  • 2-Amino-4-oxo-3,4,5,6,7,8-hexahydropteridine-6-carboxylic acid
  • 5,6,7,8-Tetrahydropterin-6-carboxylate anion
  • 5,6,7,8-Tetrahydropterin-6-carboxylate(1)
  • 5,6,7,8-Tetrahydropterin-6-carboxylic acid anion
  • 5,6,7,8-Tetrahydropterin-6-carboxylic acid(1)
  • 6-Carboxy-5,6,7,8-tetrahydropterin
  • 6-Carboxylato-5,6,7,8-tetrahydropterin
  • 6-Carboxylato-5,6,7,8-tetrahydropterin anion
  • 6-Carboxylato-5,6,7,8-tetrahydropterin(1)
  • 6-Carboxytetrahydropterin
Chemical Formula: C7H9N5O3
Average Molecular Weight: 211.1781
Monoisotopic Molecular Weight: 211.070539179
InChI Key: QSIYONWVWDSRRO-UHFFFAOYSA-N
InChI:InChI=1S/C7H9N5O3/c8-7-11-4-3(5(13)12-7)10-2(1-9-4)6(14)15/h2,10H,1H2,(H,14,15)(H4,8,9,11,12,13)
CAS number: Not Available
IUPAC Name:2-amino-4-oxo-3,4,5,6,7,8-hexahydropteridine-6-carboxylic acid
Traditional IUPAC Name: 2-amino-4-oxo-5,6,7,8-tetrahydro-3H-pteridine-6-carboxylic acid
SMILES:NC1=NC2=C(NC(CN2)C(O)=O)C(=O)N1
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as pterin carboxylates. These are heterocyclic aromatic compounds containing a pterin moiety, in which one ring is substituted by one or more carboxylic acid groups. Pterin is a heterocyclic compound composed of a pteridine ring system (made up of a pyrazine fused to a pyrimidine), with a keto group and an amino group at the 2- and 4- positions, respectively.
Kingdom Organic compounds
Super ClassOrganoheterocyclic compounds
Class Pteridines and derivatives
Sub ClassPterins and derivatives
Direct Parent Pterin carboxylates
Alternative Parents
Substituents
  • Pterin-6-carboxylate
  • Alpha-amino acid or derivatives
  • Alpha-amino acid
  • Hydroxypyrimidine
  • Secondary aliphatic/aromatic amine
  • Pyrimidine
  • Heteroaromatic compound
  • Azacycle
  • Secondary amine
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • 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:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility1.21 mg/mLALOGPS
logP-1.9ALOGPS
logP-3ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)3.67ChemAxon
pKa (Strongest Basic)4.84ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area128.84 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity58.12 m3·mol-1ChemAxon
Polarizability19 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Dihydroneopterin triphosphate + Water > Acetaldehyde + 6-Carboxy-5,6,7,8-tetrahydropterin + Hydrogen ion + Triphosphate
6-Carboxy-5,6,7,8-tetrahydropterin <> 7-Carboxy-7-carbaguanine + Ammonia + 7-Deaza-7-carboxyguanine
6-Carboxy-5,6,7,8-tetrahydropterin + S-Adenosylmethionine + Hydrogen ion > 7-carboxy-7-deazaguanine + 5'-Deoxyadenosine + L-Methionine + Ammonia
Dihydroneopterin triphosphate + Water > 6-Carboxy-5,6,7,8-tetrahydropterin + Acetaldehyde + Triphosphate
6-Carboxy-5,6,7,8-tetrahydropterin > 7-Deaza-7-carboxyguanine + Ammonia
7,8-dihydroneopterin 3'-triphosphate + Water > Acetaldehyde + Triphosphate +2 Hydrogen ion + 6-Carboxy-5,6,7,8-tetrahydropterin + Triphosphate
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0980000000-77c7a65000d61e0f0097View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02tc-0920000000-51f8f3890c49ebfcaf17View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00gi-4900000000-36d0bbd2f637a9803eccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0590000000-cf2674cb4f12eea11676View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-2910000000-e531b1f110f398299483View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f6x-9200000000-89df65f3f9202446a058View in MoNA
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
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID61032
HMDB IDHMDB60410
Pubchem Compound ID44123380
Kegg IDC20239
ChemSpider ID26332086
Wikipedia IDNot Available
BioCyc IDCPD0-1699
EcoCyc IDCPD0-1699

Enzymes

Protein Details
• 6-carboxy-5,6,7,8-tetrahydropterin synthase
General function:
Coenzyme transport and metabolism
Specific function:
Catalyzes the conversion of 7,8-dihydroneopterin triphosphate (H2NTP) to 6-carboxy-5,6,7,8-tetrahydropterin (CPH4) and acetaldehyde. Can also convert 6-pyruvoyltetrahydropterin (PPH4) and sepiapterin to CPH4; these 2 compounds are probably intermediates in the reaction from H2NTP
Gene Name:
queD
Locus Tag:
PA2666
Molecular weight:
13.8 kDa
Reactions
7,8-dihydroneopterin 3'-triphosphate + H(2)O = 6-carboxy-5,6,7,8-tetrahydropterin + acetaldehyde + triphosphate.