MiMeDB: Showing metabocard for Dihydrobiopterin (MMDBc0032908)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:26:49 UTC

Update Date

2024-04-30 19:54:51 UTC

Metabolite ID

MMDBc0032908

Metabolite Identification

Common Name

Dihydrobiopterin

Description

Dihydrobiopterin, also known as BH2, 7,8-dihydrobiopterin, L-erythro-7,8-dihydrobiopterin, quinonoid dihydrobiopterin or q-BH2, belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. Dihydrobiopterin is also classified as a pteridine. Pteridines are aromatic compounds composed of fused pyrimidine and pyrazine rings. Dihydrobiopterin is produced during the synthesis of neurotransmitters L-DOPA, dopamine, norepinephrine and epinephrine. It is restored to the required cofactor tetrahydrobiopterin via the NADPH-dependant reduction of dihydrobiopterin reductase. Dihydrobiopterin can also be converted to tetrahydrobiopterin by nitric oxide synthase (NOS) which is catalyzed by the flavoprotein "diaphorase" activity of NOS. This activity is located on the reductase (C-terminal) domain of NOS, whereas the high affinity tetrahydrobiopterin site involved in NOS activation is located on the oxygenase (N-terminal) domain (PMID: 8626754 ). Sepiapterin reductase (SPR) is another enzyme that plays a role in the production of dihydrobiopterin. SPR catalyzes the reduction of sepiapterin to dihydrobiopterin (BH2), the precursor for tetrahydrobiopterin (BH4). BH4 is a cofactor critical for nitric oxide biosynthesis and alkylglycerol and aromatic amino acid metabolism (PMID: 25550200 ). Dihydrobiopterin is known to be synthesized in several parts of the body, including the pineal gland. Dihydrobiopterin exists in all eukaryotes, ranging from yeast to humans. In humans, dihydrobiopterin is involved in several metabolic disorders including dihydropteridine reductase (DHPR) deficiency. DHPR deficiency is a severe form of hyperphenylalaninemia (HPA) due to impaired regeneration of tetrahydrobiopterin (BH4) leading to decreased levels of neurotransmitters (dopamine, serotonin) and folate in cerebrospinal fluid, and causing neurological symptoms such as psychomotor delay, hypotonia, seizures, abnormal movements, hypersalivation, and swallowing difficulties. Dihydrobiopterin is also associated with another metabolic disorder known as sepiapterin reductase deficiency (SRD). Sepiapterin reductase catalyzes the (NADP-dependent) reduction of carbonyl derivatives, including pteridines, and plays an important role in tetrahydrobiopterin biosynthesis. Low dihydrofolate reductase activity in the brain leads to the accumulation of dihydrobiopterin, which in turn, inhibits tyrosine and tryptophan hydroxylases. This uncouples neuronal nitric oxide synthase, leading to neurotransmitter deficiencies and neuronal cell death. SRD is characterized by low cerebrospinal fluid neurotransmitter levels and the presence of elevated cerebrospinal fluid dihydrobiopterin. SRD is characterized by motor delay, axial hypotonia, language delay, diurnal fluctuation of symptoms, dystonia, weakness, oculogyric crises, dysarthria, parkinsonian signs and hyperreflexia.

Structure

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

HMDB0247294
     RDKit          3D
D-Erythro-7,8-dihydrobiopterin
 30 31  0  0  0  0  0  0  0  0999 V2000
   -4.2813   -0.2808    1.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7826   -0.0865    1.0416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4163    1.2222    1.3282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3415   -0.4100   -0.3652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9396    0.4406   -1.2665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8322   -0.3259   -0.4720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0892   -0.0244    0.5026 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3158    0.0717    0.4737 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9070   -0.1920   -0.7406 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2754   -0.1221   -0.8625 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9865    0.2067    0.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4182    0.3042    0.1975 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4173    0.4665    1.4214 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0840    0.4036    1.5612 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4958    0.6332    2.6395 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1138   -0.5310   -1.8488 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3077   -0.6242   -1.8035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7656    0.4255    1.7955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5179   -1.3424    1.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7025   -0.0963    0.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2403   -0.7922    1.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8460    1.8139    0.6738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6041   -1.4492   -0.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4349    1.2845   -1.3968 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9434    0.9478    0.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9241   -0.2958   -0.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0085    0.7240    2.2665 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6606   -0.7187   -2.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6587   -1.6766   -2.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7900    0.0237   -2.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
  9 16  1  0
 16 17  1  0
 17  6  1  0
 14  8  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
 12 25  1  0
 12 26  1  0
 13 27  1  0
 16 28  1  0
 17 29  1  0
 17 30  1  0
M  END


  Mrv1652305271900092D          

 17 18  0  0  0  0            999 V2000
    0.6257    0.6559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6257   -0.1734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0942    1.0629    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3419    1.0743    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0942   -0.5918    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3494   -0.5918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8029    0.6559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0693    0.6596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8029   -0.1734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0732   -0.1772    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3494   -1.4098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7742    1.0743    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5152   -0.5804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2239   -0.1658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5191   -1.4022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2164    0.6559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9363   -0.5692    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  2  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  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0032908

> <DATABASE_NAME>
MIME

> <SMILES>
CC(O)C(O)C1=NC2=C(NC1)N=C(N)NC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H13N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3,6,15-16H,2H2,1H3,(H4,10,11,13,14,17)

> <INCHI_KEY>
FEMXZDUTFRTWPE-UHFFFAOYSA-N

> <FORMULA>
C9H13N5O3

> <MOLECULAR_WEIGHT>
239.2312

> <EXACT_MASS>
239.101839307

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
23.041007497131407

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-6-(1,2-dihydroxypropyl)-3,4,7,8-tetrahydropteridin-4-one

> <ALOGPS_LOGP>
-1.65

> <JCHEM_LOGP>
-1.947500499333333

> <ALOGPS_LOGS>
-2.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.133901876526668

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.624833827208914

> <JCHEM_PKA_STRONGEST_BASIC>
0.5910522300598404

> <JCHEM_POLAR_SURFACE_AREA>
132.32999999999998

> <JCHEM_REFRACTIVITY>
68.31329999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.63e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7,8-dihydrobiopterin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0247294
     RDKit          3D
D-Erythro-7,8-dihydrobiopterin
 30 31  0  0  0  0  0  0  0  0999 V2000
   -4.2813   -0.2808    1.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7826   -0.0865    1.0416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4163    1.2222    1.3282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3415   -0.4100   -0.3652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9396    0.4406   -1.2665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8322   -0.3259   -0.4720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0892   -0.0244    0.5026 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3158    0.0717    0.4737 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9070   -0.1920   -0.7406 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2754   -0.1221   -0.8625 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9865    0.2067    0.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4182    0.3042    0.1975 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4173    0.4665    1.4214 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0840    0.4036    1.5612 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4958    0.6332    2.6395 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1138   -0.5310   -1.8488 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3077   -0.6242   -1.8035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7656    0.4255    1.7955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5179   -1.3424    1.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7025   -0.0963    0.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2403   -0.7922    1.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8460    1.8139    0.6738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6041   -1.4492   -0.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4349    1.2845   -1.3968 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9434    0.9478    0.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9241   -0.2958   -0.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0085    0.7240    2.2665 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6606   -0.7187   -2.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6587   -1.6766   -2.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7900    0.0237   -2.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
  9 16  1  0
 16 17  1  0
 17  6  1  0
 14  8  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
 12 25  1  0
 12 26  1  0
 13 27  1  0
 16 28  1  0
 17 29  1  0
 17 30  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       1.168   1.224   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.168  -0.324   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -0.176   1.984   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       2.505   2.005   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      -0.176  -1.105   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       2.519  -1.105   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.499   1.224   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.863   1.231   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.499  -0.324   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       3.870  -0.331   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0       2.519  -2.632   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0       5.179   2.005   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      -2.828  -1.083   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.151  -0.309   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.836  -2.617   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -4.137   1.224   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -5.481  -1.063   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   16   17                                                  
CONECT   15   13                                                            
CONECT   16   14                                                            
CONECT   17   14                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0247294
HETATM    1  C1  UNL     1      -4.281  -0.281   1.094  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.783  -0.087   1.042  1.00  0.00           C  
HETATM    3  O1  UNL     1      -2.416   1.222   1.328  1.00  0.00           O  
HETATM    4  C3  UNL     1      -2.342  -0.410  -0.365  1.00  0.00           C  
HETATM    5  O2  UNL     1      -2.940   0.441  -1.266  1.00  0.00           O  
HETATM    6  C4  UNL     1      -0.832  -0.326  -0.472  1.00  0.00           C  
HETATM    7  N1  UNL     1      -0.089  -0.024   0.503  1.00  0.00           N  
HETATM    8  C5  UNL     1       1.316   0.072   0.474  1.00  0.00           C  
HETATM    9  C6  UNL     1       1.907  -0.192  -0.741  1.00  0.00           C  
HETATM   10  N2  UNL     1       3.275  -0.122  -0.862  1.00  0.00           N  
HETATM   11  C7  UNL     1       3.986   0.207   0.229  1.00  0.00           C  
HETATM   12  N3  UNL     1       5.418   0.304   0.198  1.00  0.00           N  
HETATM   13  N4  UNL     1       3.417   0.466   1.421  1.00  0.00           N  
HETATM   14  C8  UNL     1       2.084   0.404   1.561  1.00  0.00           C  
HETATM   15  O3  UNL     1       1.496   0.633   2.640  1.00  0.00           O  
HETATM   16  N5  UNL     1       1.114  -0.531  -1.849  1.00  0.00           N  
HETATM   17  C9  UNL     1      -0.308  -0.624  -1.804  1.00  0.00           C  
HETATM   18  H1  UNL     1      -4.766   0.426   1.795  1.00  0.00           H  
HETATM   19  H2  UNL     1      -4.518  -1.342   1.337  1.00  0.00           H  
HETATM   20  H3  UNL     1      -4.703  -0.096   0.063  1.00  0.00           H  
HETATM   21  H4  UNL     1      -2.240  -0.792   1.716  1.00  0.00           H  
HETATM   22  H5  UNL     1      -2.846   1.814   0.674  1.00  0.00           H  
HETATM   23  H6  UNL     1      -2.604  -1.449  -0.648  1.00  0.00           H  
HETATM   24  H7  UNL     1      -2.435   1.285  -1.397  1.00  0.00           H  
HETATM   25  H8  UNL     1       5.943   0.948   0.821  1.00  0.00           H  
HETATM   26  H9  UNL     1       5.924  -0.296  -0.476  1.00  0.00           H  
HETATM   27  H10 UNL     1       4.008   0.724   2.267  1.00  0.00           H  
HETATM   28  H11 UNL     1       1.661  -0.719  -2.749  1.00  0.00           H  
HETATM   29  H12 UNL     1      -0.659  -1.677  -2.069  1.00  0.00           H  
HETATM   30  H13 UNL     1      -0.790   0.024  -2.587  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    4   21
CONECT    3   22
CONECT    4    5    6   23
CONECT    5   24
CONECT    6    7    7   17
CONECT    7    8
CONECT    8    9    9   14
CONECT    9   10   16
CONECT   10   11   11
CONECT   11   12   13
CONECT   12   25   26
CONECT   13   14   27
CONECT   14   15   15
CONECT   16   17   28
CONECT   17   29   30
END

HMDB0247294
     RDKit          3D
D-Erythro-7,8-dihydrobiopterin
 30 31  0  0  0  0  0  0  0  0999 V2000
   -4.2813   -0.2808    1.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7826   -0.0865    1.0416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4163    1.2222    1.3282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3415   -0.4100   -0.3652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9396    0.4406   -1.2665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8322   -0.3259   -0.4720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0892   -0.0244    0.5026 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3158    0.0717    0.4737 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9070   -0.1920   -0.7406 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2754   -0.1221   -0.8625 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9865    0.2067    0.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4182    0.3042    0.1975 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4173    0.4665    1.4214 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0840    0.4036    1.5612 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4958    0.6332    2.6395 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1138   -0.5310   -1.8488 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3077   -0.6242   -1.8035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7656    0.4255    1.7955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5179   -1.3424    1.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7025   -0.0963    0.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2403   -0.7922    1.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8460    1.8139    0.6738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6041   -1.4492   -0.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4349    1.2845   -1.3968 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9434    0.9478    0.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9241   -0.2958   -0.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0085    0.7240    2.2665 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6606   -0.7187   -2.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6587   -1.6766   -2.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7900    0.0237   -2.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
  9 16  1  0
 16 17  1  0
 17  6  1  0
 14  8  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
 12 25  1  0
 12 26  1  0
 13 27  1  0
 16 28  1  0
 17 29  1  0
 17 30  1  0
M  END

Synonyms

Value	Source
Quinonoid dihydro-(6H)-biopterin	ChEBI
(6R)-6-(L-erythro-1,2-Dihydroxypropyl)-7,8-dihydro-6H-pterin	HMDB
(S-(R,s))-2-amino-6-(1,2-dihydroxypropyl)-7,8-dihydro-4(1H)-pteridinone	HMDB
2-amino-6-((1R,2S)-1,2-Dihydroxypropyl)-7,8-dihydro-4(1H)-pteridinone	HMDB
2-amino-6-(1,2-Dihydroxypropyl)-7,8-dihydro-4(1H)-pteridinone	HMDB
6,7-Dihydrobiopterin	HMDB
7,8-dihydro-L-Biopterin	HMDB
7,8-Dihydrobiopterin	HMDB
BH2	HMDB
L-erythro-1-(2-amino-7,8-dihydro-4-Hydroxy-6-pteridinyl)-1,2-propanediol	HMDB
L-erythro-7,8-Dihydrobiopterin	HMDB
L-erythro-Dihydrobiopterin	HMDB
L-erythro-Q-Dihydrobiopterin	HMDB
Quinoid-dihydrobiopterin	HMDB
Quinonoid dihydrobiopterin	HMDB
Q-BH2	MeSH, HMDB

Molecular Formula

C₉H₁₃N₅O₃

Average Mass

239.2312

Monoisotopic Mass

239.101839307

IUPAC Name

2-amino-6-(1,2-dihydroxypropyl)-3,4,7,8-tetrahydropteridin-4-one

Traditional Name

7,8-dihydrobiopterin

CAS Registry Number

6779-87-9

SMILES

CC(O)C(O)C1=NC2=C(NC1)N=C(N)NC2=O

InChI Identifier

InChI=1S/C9H13N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3,6,15-16H,2H2,1H3,(H4,10,11,13,14,17)

InChI Key

FEMXZDUTFRTWPE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are mainly synthesized in several parts of the body, including the pineal gland.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Pterins and derivatives

Direct Parent

Biopterins and derivatives

Alternative Parents

Substituents

Biopterin
Secondary aliphatic/aromatic amine
Hydroxypyrimidine
Pyrimidine
Heteroaromatic compound
1,2-diol
Ketimine
Secondary alcohol
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Secondary amine
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Imine
Organic nitrogen compound
Amine
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dihydropterin (CHEBI:64277 )
biopterins (CHEBI:64277 )
a biopterin (BIOPTERIN )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.63 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-1.9	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	7.62	ChemAxon
pKa (Strongest Basic)	0.59	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	132.33 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	68.31 m³·mol⁻¹	ChemAxon
Polarizability	23.04 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	splash10-01ox-8930000000-836b0568b603906f549d	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0103-9108000000-2cc35139ca2f2f86d361	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 GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_5) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-0190000000-b23b7cc50e3b7bda01be	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0092-3900000000-a352eac2af4690fb47f1	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014i-9400000000-054ffe617ee964dda203	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-014i-0900000000-d07c64d8c73d1c2a5829	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-052f-2900000000-a7748084d6dd302d5fac	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006x-0190000000-d7c2e475a8d3f7b4994f	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-022c-0890000000-00cee7b9f9a6dd10e984	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03k9-1900000000-0095b515a0b62e12a2a2	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0390000000-4091667943de90fcbcad	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-1930000000-034022c1ca4ad39363fd	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9400000000-4251e4ef4f844b6962ad	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0090000000-3376871b80c100bbe6d8	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0g4l-0390000000-b87dff2ff69f44246684	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-2900000000-13aef5b83897525c0fdb	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-4f635c9ed114df17ae1f	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004l-0900000000-56e17f19175ddb356194	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9600000000-dd1e61a42da2dd5a5b93	2021-10-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-10-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-10-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-10-13	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)		2012-12-04	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Saliva

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

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0003892	4a-Hydroxytetrahydrobiopterin	Dihydrobiopterin	Not Available	VMH	10727395 1355046 1988938
MMDBr0003893	4a-Hydroxytetrahydrobiopterin	Dihydrobiopterin	pterin-4 alpha-carbinolamine dehydratase/dimerization cofactor of hepatocyte nuclear factor 1 alpha	VMH	10727395 1355046 1988938
MMDBr0004338	O2'-4a-cyclic-tetrahydrobiopterin	Dihydrobiopterin	Not Available	VMH	9647871
MMDBr0004339	O2'-4a-cyclic-tetrahydrobiopterin	Dihydrobiopterin	pterin-4 alpha-carbinolamine dehydratase/dimerization cofactor of hepatocyte nuclear factor 1 alpha	VMH	8921004

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Kidney disease	Increased	Association	Human Blood	HMDB	12032193

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown
Bacteria	Firmicutes	136	Human feces; Human ; Cattle	Metabolic reconstruction
Bacteria	Proteobacteria	149	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Bacteria	Actinobacteria	22	Human feces; Human	Metabolic reconstruction
Bacteria	Bacteroidetes	14	Human feces; Human	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	2	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	1		Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction

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
Human Feces	Detected but not Quantified									HMDB
Human Blood	Detected and Quantified	0.0635	0.0041			uM	Adult (>18 years old)	Both	Kidney disease	HMDB	12032193
Human Cerebrospinal fluid (csf)	Detected and Quantified			0.0004	0.014	uM	Adult (>18 years old)	Both	Normal	HMDB	12032193
Human Blood	Detected and Quantified	0.006	0.0003			uM	Adult (>18 years old)	Both	Normal	HMDB	12032193
Human Saliva	Detected and Quantified	1.22	3.60			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	10.8	14.7			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	23.6	28.7			uM	Adult (>18 years old)	Both	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	8.25	8.34			uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

247

KEGG Compound ID

Not Available

BioCyc ID

CPD0-2050

BiGG ID

Not Available

Wikipedia Link

Dihydrobiopterin

METLIN ID

Not Available

PubChem Compound

252

PDB ID

Not Available

ChEBI ID

64277

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Niederwieser A, Curtius HC, Bettoni O, Bieri J, Schircks B, Viscontini M, Schaub J: Atypical phenylketonuria caused by 7, 8-dihydrobiopterin synthetase deficiency. Lancet. 1979 Jan 20;1(8108):131-3. doi: 10.1016/s0140-6736(79)90521-x. [PubMed:84153 ]
Leeming RJ, Blair JA, Melikian V, O'Gorman DJ: Biopterin derivatives in human body fluids and tissues. J Clin Pathol. 1976 May;29(5):444-51. doi: 10.1136/jcp.29.5.444. [PubMed:932231 ]
Howells DW, Hyland K: Direct analysis of tetrahydrobiopterin in cerebrospinal fluid by high-performance liquid chromatography with redox electrochemistry: prevention of autoxidation during storage and analysis. Clin Chim Acta. 1987 Jul 30;167(1):23-30. doi: 10.1016/0009-8981(87)90081-7. [PubMed:3665086 ]
Witteveen CF, Giovanelli J, Kaufman S: Reduction of quinonoid dihydrobiopterin to tetrahydrobiopterin by nitric oxide synthase. J Biol Chem. 1996 Feb 23;271(8):4143-7. doi: 10.1074/jbc.271.8.4143. [PubMed:8626754 ]
Goodwill KE, Sabatier C, Stevens RC: Crystal structure of tyrosine hydroxylase with bound cofactor analogue and iron at 2.3 A resolution: self-hydroxylation of Phe300 and the pterin-binding site. Biochemistry. 1998 Sep 29;37(39):13437-45. doi: 10.1021/bi981462g. [PubMed:9753429 ]
Hagedoorn PL, Schmidt PP, Andersson KK, Hagen WR, Flatmark T, Martinez A: The effect of substrate, dihydrobiopterin, and dopamine on the EPR spectroscopic properties and the midpoint potential of the catalytic iron in recombinant human phenylalanine hydroxylase. J Biol Chem. 2001 Jun 22;276(25):22850-6. doi: 10.1074/jbc.M009458200. Epub 2001 Apr 11. [PubMed:11301319 ]
Bonafe L, Thony B, Penzien JM, Czarnecki B, Blau N: Mutations in the sepiapterin reductase gene cause a novel tetrahydrobiopterin-dependent monoamine-neurotransmitter deficiency without hyperphenylalaninemia. Am J Hum Genet. 2001 Aug;69(2):269-77. doi: 10.1086/321970. Epub 2001 Jul 6. [PubMed:11443547 ]
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Showing metabocard for Dihydrobiopterin (MMDBc0032908)

MOL for #<Metabolite:0x00007fecf532e080>

3D MOL for #<Metabolite:0x00007fecf532e080>

3D SDF for #<Metabolite:0x00007fecf532e080>

3D-SDF for #<Metabolite:0x00007fecf532e080>

PDB for #<Metabolite:0x00007fecf532e080>

3D PDB for #<Metabolite:0x00007fecf532e080>

SMILES for #<Metabolite:0x00007fecf532e080>

INCHI for #<Metabolite:0x00007fecf532e080>

Structure for #<Metabolite:0x00007fecf532e080>

3D Structure for #<Metabolite:0x00007fecf532e080>