MiMeDB: Showing metabocard for Dyspropterin (MMDBc0029585)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:33:17 UTC

Update Date

2024-04-30 19:38:28 UTC

Metabolite ID

MMDBc0029585

Metabolite Identification

Common Name

Dyspropterin

Description

Dyspropterin, an intermediate formed from dihydroneopterin triphosphate in the biosynthetic pathway of tetrahydrobiopterin.

Structure

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

6459
  Mrv1652308201820142D          

 17 18  0  0  1  0            999 V2000
    9.5287   -8.2912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4162   -8.2912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1175  -10.3537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9725   -9.1162    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5287  -10.7662    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9725  -10.7662    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8275   -9.5287    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1262  -10.7662    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2712   -9.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2712  -10.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5287   -9.1162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7150   -9.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8275  -10.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4162   -9.1162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7150  -10.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1175   -9.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8187   -9.1162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  2  0  0  0  0
  2 14  2  0  0  0  0
  3 16  2  0  0  0  0
  4  9  1  0  0  0  0
  4 12  1  0  0  0  0
  5 10  1  0  0  0  0
  5 13  2  0  0  0  0
  6 10  1  0  0  0  0
  6 15  1  0  0  0  0
  7 11  1  0  0  0  0
  7 13  1  0  0  0  0
  8 13  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029585

> <DATABASE_NAME>
MIME

> <SMILES>
CC(=O)C(=O)C1CNC2=C(N1)C(=O)NC(N)=N2

> <INCHI_IDENTIFIER>
InChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h4,12H,2H2,1H3,(H4,10,11,13,14,17)

> <INCHI_KEY>
WBJZXBUVECZHCE-UHFFFAOYSA-N

> <FORMULA>
C9H11N5O3

> <MOLECULAR_WEIGHT>
237.2153

> <EXACT_MASS>
237.086189243

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
21.979402700271507

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(2-amino-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)propane-1,2-dione

> <ALOGPS_LOGP>
-1.01

> <JCHEM_LOGP>
-1.168246792333333

> <ALOGPS_LOGS>
-2.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.42365416809001

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.806759495528606

> <JCHEM_PKA_STRONGEST_BASIC>
1.8215361590403678

> <JCHEM_POLAR_SURFACE_AREA>
125.68

> <JCHEM_REFRACTIVITY>
67.0166

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.47e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(2-amino-4-oxo-5,6,7,8-tetrahydro-3H-pteridin-6-yl)propane-1,2-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-AUG-18   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 6459                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-AUG-18         0                                  
HETATM    1  O   UNK     0      17.787 -15.477   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      23.177 -15.477   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      24.486 -19.327   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      20.482 -17.017   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      17.787 -20.097   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      20.482 -20.097   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      16.478 -17.787   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      15.169 -20.097   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      19.173 -17.787   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      19.173 -19.327   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.787 -17.017   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.868 -17.787   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.478 -19.327   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      23.177 -17.017   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.868 -19.327   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      24.486 -17.787   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      25.795 -17.017   0.000  0.00  0.00           C+0
CONECT    1   11                                                            
CONECT    2   14                                                            
CONECT    3   16                                                            
CONECT    4    9   12                                                       
CONECT    5   10   13                                                       
CONECT    6   10   15                                                       
CONECT    7   11   13                                                       
CONECT    8   13                                                            
CONECT    9    4   10   11                                                  
CONECT   10    5    6    9                                                  
CONECT   11    1    7    9                                                  
CONECT   12    4   14   15                                                  
CONECT   13    5    7    8                                                  
CONECT   14    2   12   16                                                  
CONECT   15    6   12                                                       
CONECT   16    3   14   17                                                  
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0001195
HETATM    1  C1  UNL     1      -4.773   0.065  -0.070  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.472  -0.173   0.601  1.00  0.00           C  
HETATM    3  O1  UNL     1      -3.416   0.009   1.842  1.00  0.00           O  
HETATM    4  C3  UNL     1      -2.333  -0.600  -0.193  1.00  0.00           C  
HETATM    5  O2  UNL     1      -2.454  -0.764  -1.431  1.00  0.00           O  
HETATM    6  C4  UNL     1      -1.045  -0.829   0.504  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.702   0.393   1.305  1.00  0.00           C  
HETATM    8  N1  UNL     1       0.724   0.605   1.461  1.00  0.00           N  
HETATM    9  C6  UNL     1       1.602   0.366   0.369  1.00  0.00           C  
HETATM   10  N2  UNL     1       2.772   1.009   0.202  1.00  0.00           N  
HETATM   11  C7  UNL     1       3.588   0.771  -0.835  1.00  0.00           C  
HETATM   12  N3  UNL     1       4.815   1.456  -0.997  1.00  0.00           N  
HETATM   13  N4  UNL     1       3.236  -0.143  -1.748  1.00  0.00           N  
HETATM   14  C8  UNL     1       2.070  -0.833  -1.647  1.00  0.00           C  
HETATM   15  O3  UNL     1       1.723  -1.695  -2.497  1.00  0.00           O  
HETATM   16  C9  UNL     1       1.232  -0.574  -0.564  1.00  0.00           C  
HETATM   17  N5  UNL     1       0.001  -1.250  -0.385  1.00  0.00           N  
HETATM   18  H1  UNL     1      -5.632  -0.266   0.565  1.00  0.00           H  
HETATM   19  H2  UNL     1      -4.866  -0.508  -1.015  1.00  0.00           H  
HETATM   20  H3  UNL     1      -4.942   1.135  -0.312  1.00  0.00           H  
HETATM   21  H4  UNL     1      -1.226  -1.689   1.205  1.00  0.00           H  
HETATM   22  H5  UNL     1      -1.152   1.311   0.872  1.00  0.00           H  
HETATM   23  H6  UNL     1      -1.148   0.255   2.328  1.00  0.00           H  
HETATM   24  H7  UNL     1       1.162   0.936   2.363  1.00  0.00           H  
HETATM   25  H8  UNL     1       5.755   1.037  -0.851  1.00  0.00           H  
HETATM   26  H9  UNL     1       4.781   2.455  -1.285  1.00  0.00           H  
HETATM   27  H10 UNL     1       3.844  -0.363  -2.579  1.00  0.00           H  
HETATM   28  H11 UNL     1      -0.143  -2.115  -0.947  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    3    4
CONECT    4    5    5    6
CONECT    6    7   17   21
CONECT    7    8   22   23
CONECT    8    9   24
CONECT    9   10   16   16
CONECT   10   11   11
CONECT   11   12   13
CONECT   12   25   26
CONECT   13   14   27
CONECT   14   15   15   16
CONECT   16   17
CONECT   17   28
END

Synonyms

Value	Source
6-(1,2-Dioxopropyl)-5,6,7,8-tetrahydropterin	ChEBI
6-Pyruvoyl-5,6,7,8-tetrahydropterin	ChEBI
6-Pyruvoyltetrahydropterin	ChEBI
6-Pyruvoyl-tetrahydropterin	HMDB
6-Pyruvoyl tetrahydropteridine	MeSH, HMDB
Pyruvoyl-H4-pterin	MeSH, HMDB

Molecular Formula

C₉H₁₁N₅O₃

Average Mass

237.2153

Monoisotopic Mass

237.086189243

IUPAC Name

1-(2-amino-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)propane-1,2-dione

Traditional Name

1-(2-amino-4-oxo-5,6,7,8-tetrahydro-3H-pteridin-6-yl)propane-1,2-dione

CAS Registry Number

89687-39-8

SMILES

CC(=O)C(=O)C1CNC2=C(N1)C(=O)NC(N)=N2

InChI Identifier

InChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h4,12H,2H2,1H3,(H4,10,11,13,14,17)

InChI Key

WBJZXBUVECZHCE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pterins and derivatives. These are polycyclic aromatic compounds containing a pterin moiety, which consist of a pteridine ring bearing a ketone and an amine group to form 2-aminopteridin-4(3H)-one.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Pterins and derivatives

Direct Parent

Pterins and derivatives

Alternative Parents

Substituents

Pterin
Hydroxypyrimidine
Secondary aliphatic/aromatic amine
Alpha-diketone
Beta-aminoketone
Gamma-aminoketone
Pyrimidine
Alpha-aminoketone
Heteroaromatic compound
Ketone
Azacycle
Secondary amine
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Amine
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tetrahydropterin (CHEBI:17804 )
biopterins (CHEBI:17804 )
a small molecule (6-PYRUVOYL-5678-TETRAHYDROPTERIN )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.65 g/L	ALOGPS
logP	-1	ALOGPS
logP	-1.2	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	7.81	ChemAxon
pKa (Strongest Basic)	1.82	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	125.68 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	67.02 m³·mol⁻¹	ChemAxon
Polarizability	21.98 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

Not Available

Biological Properties

Cellular Locations

Nucleus

Biospecimen Locations

Feces
Fibroblasts
Placenta

Tissue Locations

Fibroblasts
Placenta

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
MMDBp0192102	Sepiapterin reductase	Enzyme	P35270	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/Eubacteria	Proteobacteria	3	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown; Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	10	Human feces; Human	Metabolic reconstruction
Bacteria/Eubacteria	Chlorobi	1

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified				HMDB
Human Fibroblasts	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0257010

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022481

KNApSAcK ID

Not Available

Chemspider ID

114280

KEGG Compound ID

C03684

BioCyc ID

6-PYRUVOYL-5678-TETRAHYDROPTERIN

BiGG ID

Not Available

Wikipedia Link

Dyspropterin

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

17804

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Niederwieser A, Curtius HC: Tetrahydrobiopterin biosynthetic pathway and deficiency. Enzyme. 1987;38(1-4):302-11. doi: 10.1159/000469220. [PubMed:3326735 ]
Bonafe L, Thony B, Leimbacher W, Kierat L, Blau N: Diagnosis of dopa-responsive dystonia and other tetrahydrobiopterin disorders by the study of biopterin metabolism in fibroblasts. Clin Chem. 2001 Mar;47(3):477-85. [PubMed:11238300 ]
Dhondt JL, Hayte JM: [Screening of tetrahydrobiopterin deficiency among hyperphenylalaninemic patients]. Ann Biol Clin (Paris). 2002 Mar-Apr;60(2):165-71. [PubMed:11937441 ]
Iwanaga N, Yamamasu S, Tachibana D, Nishio J, Nakai Y, Shintaku H, Ishiko O: Activity of synthetic enzymes of tetrahydrobiopterin in the human placenta. Int J Mol Med. 2004 Jan;13(1):117-20. [PubMed:14654981 ]

Showing metabocard for Dyspropterin (MMDBc0029585)

MOL for #<Metabolite:0x00007f91ed3588e8>

3D MOL for #<Metabolite:0x00007f91ed3588e8>

3D SDF for #<Metabolite:0x00007f91ed3588e8>

3D-SDF for #<Metabolite:0x00007f91ed3588e8>

PDB for #<Metabolite:0x00007f91ed3588e8>

3D PDB for #<Metabolite:0x00007f91ed3588e8>

SMILES for #<Metabolite:0x00007f91ed3588e8>

INCHI for #<Metabolite:0x00007f91ed3588e8>

Structure for #<Metabolite:0x00007f91ed3588e8>

3D Structure for #<Metabolite:0x00007f91ed3588e8>