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6-Carboxy-5,6,7,8-tetrahydropterin (M2MDB001589)

Record Information
Version2.0
Creation Date2012-07-30 14:54:47 -0600
Update Date2015-06-03 17:20:49 -0600
Secondary Accession Numbers
  • ECMDB21180
Identification
Name:6-Carboxy-5,6,7,8-tetrahydropterin
Description6-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. Escherichia coli QueD is a 6-carboxy-5,6,7,8-tetrahydropterin synthase. (PMID 19231875)
Structure
Thumb
MOLSDFPDBSMILESInChI
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
Weight:Average: 211.1781
Monoisotopic: 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
Description 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPteridines and derivatives
Sub ClassPterins and derivatives
Direct ParentPterin carboxylates
Alternative Parents
Substituents
  • Pterin-6-carboxylate
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • Aminopyrimidine
  • Pyrimidone
  • Secondary aliphatic/aromatic amine
  • Pyrimidine
  • Heteroaromatic compound
  • Vinylogous amide
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Secondary amine
  • Organonitrogen compound
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility1.21 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity58.12 m³·mol⁻¹ChemAxon
Polarizability19 ųChemAxon
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
SMPDB Pathways:
Folate biosynthesisPW000908 ThumbThumb?image type=greyscaleThumb?image type=simple
preQ0 metabolismPW001893 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-1900000000-dc3fbed489eeb7a97c42View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-014i-2900000000-adc7542017f99dcccce6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
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
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView 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
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID61032
HMDB IDHMDB0060410
Pubchem Compound ID44123380
Kegg IDC20239
ChemSpider ID26332086
Wikipedia IDNot Available
BioCyc IDCPD0-1699
EcoCyc IDCPD0-1699

Enzymes

Protein Details
1. 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
Uniprot ID:
P65870
Molecular weight:
13773
Reactions
7,8-dihydroneopterin 3'-triphosphate + H(2)O = 6-carboxy-5,6,7,8-tetrahydropterin + acetaldehyde + triphosphate.
Protein Details
2. 7-carboxy-7-deazaguanine synthase; queosine biosynthesis
General function:
Not Available
Specific function:
Not Available
Gene Name:
queE
Uniprot ID:
P64554
Molecular weight:
Not Available