MiMeDB: Showing metabocard for 6-Carboxy-5,6,7,8-tetrahydropterin (MMDBc0031589)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:40:30 UTC

Update Date

2024-04-30 19:51:08 UTC

Metabolite ID

MMDBc0031589

Metabolite Identification

Common 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. Escherichia coli QueD is a 6-carboxy-5,6,7,8-tetrahydropterin synthase. (PMID 19231875 )

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

 
  Mrv0541 07091216312D          
 
 15 16  0  0  0  0            999 V2000
    7.9747  -10.7420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9781   -9.9175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6892  -11.1611    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2635  -11.1577    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6961   -9.5088    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2635   -9.5053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4073  -10.7489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5456  -10.7420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4106   -9.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5456   -9.9175    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2635   -8.6774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8310  -11.1577    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1149   -9.5088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8295   -9.9175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1115   -8.6843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  2  0  0  0  0
  5  9  1  0  0  0  0
  6 10  1  0  0  0  0
  6 11  2  0  0  0  0
  8 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0031589

> <DATABASE_NAME>
MIME

> <SMILES>
NC1=NC2=C(NC(CN2)C(O)=O)C(=O)N1

> <INCHI_IDENTIFIER>
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)

> <INCHI_KEY>
QSIYONWVWDSRRO-UHFFFAOYSA-N

> <FORMULA>
C7H9N5O3

> <MOLECULAR_WEIGHT>
211.1781

> <EXACT_MASS>
211.070539179

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
19.00312408400456

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-4-oxo-3,4,5,6,7,8-hexahydropteridine-6-carboxylic acid

> <ALOGPS_LOGP>
-1.87

> <JCHEM_LOGP>
-2.970613747538095

> <ALOGPS_LOGS>
-2.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.121145670762168

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6692422568404885

> <JCHEM_PKA_STRONGEST_BASIC>
4.841325540574429

> <JCHEM_POLAR_SURFACE_AREA>
128.84

> <JCHEM_REFRACTIVITY>
58.1195

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.21e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-4-oxo-5,6,7,8-tetrahydro-3H-pteridine-6-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-JUL-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JUL-12         0                                  
HETATM    1  C   UNK     0      14.886 -20.052   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.893 -18.513   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      16.220 -20.834   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      13.559 -20.828   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      16.233 -17.750   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      13.559 -17.743   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.560 -20.065   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.219 -20.052   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.567 -18.519   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      12.219 -18.513   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0      13.559 -16.198   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0      10.885 -20.828   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      18.881 -17.750   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      20.215 -18.513   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      18.875 -16.211   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1    8                                                       
CONECT    5    2    9                                                       
CONECT    6    2   10   11                                                  
CONECT    7    3    9                                                       
CONECT    8    4   12   10                                                  
CONECT    9    5   13    7                                                  
CONECT   10    6    8                                                       
CONECT   11    6                                                            
CONECT   12    8                                                            
CONECT   13    9   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

Synonyms

Value	Source
6-Carboxytetrahydropterin	Kegg

Molecular Formula

C₇H₉N₅O₃

Average Mass

211.1781

Monoisotopic Mass

211.070539179

IUPAC Name

2-amino-4-oxo-3,4,5,6,7,8-hexahydropteridine-6-carboxylic acid

Traditional Name

2-amino-4-oxo-5,6,7,8-tetrahydro-3H-pteridine-6-carboxylic acid

CAS Registry Number

Not Available

SMILES

NC1=NC2=C(NC(CN2)C(O)=O)C(=O)N1

InChI Identifier

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)

InChI Key

QSIYONWVWDSRRO-UHFFFAOYSA-N

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Pterins and derivatives

Direct Parent

Pterin 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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:61126 )
tetrahydropterin (CHEBI:61126 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.21 g/L	ALOGPS
logP	-1.9	ALOGPS
logP	-3	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	3.67	ChemAxon
pKa (Strongest Basic)	4.84	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	128.84 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	58.12 m³·mol⁻¹	ChemAxon
Polarizability	19 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-1900000000-dc3fbed489eeb7a97c42	2017-09-20	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-014i-2900000000-adc7542017f99dcccce6	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dl-0980000000-77c7a65000d61e0f0097	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02tc-0920000000-51f8f3890c49ebfcaf17	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00gi-4900000000-36d0bbd2f637a9803ecc	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0590000000-cf2674cb4f12eea11676	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-2910000000-e531b1f110f398299483	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f6x-9200000000-89df65f3f9202446a058	2015-09-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192101	6-pyruvoyl tetrahydrobiopterin synthase	Unknown	Q03393	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	22	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown
Bacteria	Aquificae	1
Archaea/Archaea	Euryarchaeota	11
Bacteria	Firmicutes	3	Human feces; Human
Bacteria	nah	1
Bacteria	Bacteroidetes	2	Human ; Human feces
Bacteria	Chlorobi	1
Bacteria	Cyanobacteria	2
Archaea/Archaea	Crenarchaeota	2
Bacteria	Acidobacteria	1
Bacteria	Spirochaetes	1
Bacteria	Planctomycetes	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0060410

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C20239

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12463319

PDB ID

Not Available

ChEBI ID

61126

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Showing metabocard for 6-Carboxy-5,6,7,8-tetrahydropterin (MMDBc0031589)

MOL for #<Metabolite:0x00005634bd5c69d8>

3D MOL for #<Metabolite:0x00005634bd5c69d8>

3D SDF for #<Metabolite:0x00005634bd5c69d8>

3D-SDF for #<Metabolite:0x00005634bd5c69d8>

PDB for #<Metabolite:0x00005634bd5c69d8>

3D PDB for #<Metabolite:0x00005634bd5c69d8>

SMILES for #<Metabolite:0x00005634bd5c69d8>

INCHI for #<Metabolite:0x00005634bd5c69d8>

Structure for #<Metabolite:0x00005634bd5c69d8>

3D Structure for #<Metabolite:0x00005634bd5c69d8>