NP-MRD: Showing NP-Card for Dihydrobiopterin (NP0000403)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-07-01 14:27:10 UTC

NP-MRD ID

NP0000403

Secondary Accession Numbers

None

Natural Product 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

HMDB0000038
     RDKit          3D
Dihydrobiopterin
 30 31  0  0  0  0  0  0  0  0999 V2000
   -3.1628    0.5544   -0.8718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1898   -0.5983    0.1175 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4621   -0.6454    0.6850 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1627   -0.4093    1.2061 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3523    0.7550    1.9177 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7630   -0.4274    0.6192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0479    0.6178    0.7798 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2711    0.7944    0.3113 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8309   -0.2579   -0.3798 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0824   -0.2078   -0.8756 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8047    0.9081   -0.6871 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1393    0.9583   -1.2171 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3027    1.9641   -0.0183 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0373    1.9233    0.4873 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5460    2.8814    1.1089 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0817   -1.4225   -0.5784 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2493   -1.5737   -0.0945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1282    0.6178   -1.2570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5073    1.4878   -0.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8008    0.2568   -1.7289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0539   -1.5140   -0.4541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5421   -1.3494    1.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2233   -1.2568    1.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4575    1.5575    1.3833 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4817   -1.0182   -1.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9433    1.0784   -0.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2493    0.8705   -2.2505 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5482   -2.2311   -1.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2695   -2.5262    0.4918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9459   -1.7877   -0.9617 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  1  0
 11 12  1  0
 11 13  2  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  6
  3 22  1  0
  4 23  1  1
  5 24  1  0
 10 25  1  0
 12 26  1  0
 12 27  1  0
 16 28  1  0
 17 29  1  0
 17 30  1  0
M  END


  Mrv1652303182019222D          

 17 18  0  0  0  0            999 V2000
10023.383810026.0447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10026.236010025.2178    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10026.951710024.8031    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10027.665210025.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10026.951710023.9791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10026.236010026.0427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10021.956710023.5613    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10023.383810025.2132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10022.669410024.8007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10022.669410023.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10023.383810023.5633    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10024.810010025.2132    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10024.095510024.8007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10024.095510023.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10024.810010023.5633    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10025.524310023.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10025.524310024.8007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  2  6  1  1  0  0  0
  3  4  1  0  0  0  0
  3  5  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  1  8  2  0  0  0  0
 10  7  1  0  0  0  0
 13 14  2  0  0  0  0
 16 17  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17  2  1  0  0  0  0
 11 14  1  0  0  0  0
  8 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000403

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](O)[C@H](O)C1=NC2=C(NC1)NC(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)/t3-,6-/m0/s1

> <INCHI_KEY>
FEMXZDUTFRTWPE-DZSWIPIPSA-N

> <FORMULA>
C9H13N5O3

> <MOLECULAR_WEIGHT>
239.2312

> <EXACT_MASS>
239.101839307

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
23.106840817612913

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1,4,7,8-tetrahydropteridin-4-one

> <ALOGPS_LOGP>
-1.43

> <JCHEM_LOGP>
-2.2885038219999996

> <ALOGPS_LOGS>
-2.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.521765739396816

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.910706687149771

> <JCHEM_PKA_STRONGEST_BASIC>
0.40083109372051184

> <JCHEM_POLAR_SURFACE_AREA>
132.32999999999998

> <JCHEM_REFRACTIVITY>
68.1133

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.63e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dihydrobiopterin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000038
     RDKit          3D
Dihydrobiopterin
 30 31  0  0  0  0  0  0  0  0999 V2000
   -3.1628    0.5544   -0.8718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1898   -0.5983    0.1175 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4621   -0.6454    0.6850 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1627   -0.4093    1.2061 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3523    0.7550    1.9177 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7630   -0.4274    0.6192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0479    0.6178    0.7798 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2711    0.7944    0.3113 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8309   -0.2579   -0.3798 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0824   -0.2078   -0.8756 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8047    0.9081   -0.6871 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1393    0.9583   -1.2171 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3027    1.9641   -0.0183 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0373    1.9233    0.4873 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5460    2.8814    1.1089 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0817   -1.4225   -0.5784 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2493   -1.5737   -0.0945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1282    0.6178   -1.2570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5073    1.4878   -0.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8008    0.2568   -1.7289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0539   -1.5140   -0.4541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5421   -1.3494    1.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2233   -1.2568    1.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4575    1.5575    1.3833 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4817   -1.0182   -1.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9433    1.0784   -0.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2493    0.8705   -2.2505 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5482   -2.2311   -1.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2695   -2.5262    0.4918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9459   -1.7877   -0.9617 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  1  0
 11 12  1  0
 11 13  2  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  6
  3 22  1  0
  4 23  1  1
  5 24  1  0
 10 25  1  0
 12 26  1  0
 12 27  1  0
 16 28  1  0
 17 29  1  0
 17 30  1  0
M  END

HEADER    PROTEIN                                 18-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-MAR-20         0                                  
HETATM    1  O   UNK     0    8710.3168715.283   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8715.6418713.740   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8716.9778712.966   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8718.3088713.740   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8716.9778711.428   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8715.6418715.280   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0    8707.6538710.648   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0    8710.3168713.731   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0    8708.9838712.961   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0    8708.9838711.421   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0    8710.3168710.651   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0    8712.9798713.731   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0    8711.6458712.961   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8711.6458711.421   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0    8712.9798710.651   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0    8714.3128711.421   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8714.3128712.961   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2    3    6   17                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    2                                                            
CONECT    7   10                                                            
CONECT    8    9    1   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11    7                                                  
CONECT   11   10   14                                                       
CONECT   12   13   17                                                       
CONECT   13   14   12    8                                                  
CONECT   14   13   15   11                                                  
CONECT   15   14   16                                                       
CONECT   16   17   15                                                       
CONECT   17   16   12    2                                                  
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0000038
HETATM    1  C1  UNL     1      -3.163   0.554  -0.872  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.190  -0.598   0.118  1.00  0.00           C  
HETATM    3  O1  UNL     1      -4.462  -0.645   0.685  1.00  0.00           O  
HETATM    4  C3  UNL     1      -2.163  -0.409   1.206  1.00  0.00           C  
HETATM    5  O2  UNL     1      -2.352   0.755   1.918  1.00  0.00           O  
HETATM    6  C4  UNL     1      -0.763  -0.427   0.619  1.00  0.00           C  
HETATM    7  N1  UNL     1      -0.048   0.618   0.780  1.00  0.00           N  
HETATM    8  C5  UNL     1       1.271   0.794   0.311  1.00  0.00           C  
HETATM    9  C6  UNL     1       1.831  -0.258  -0.380  1.00  0.00           C  
HETATM   10  N2  UNL     1       3.082  -0.208  -0.876  1.00  0.00           N  
HETATM   11  C7  UNL     1       3.805   0.908  -0.687  1.00  0.00           C  
HETATM   12  N3  UNL     1       5.139   0.958  -1.217  1.00  0.00           N  
HETATM   13  N4  UNL     1       3.303   1.964  -0.018  1.00  0.00           N  
HETATM   14  C8  UNL     1       2.037   1.923   0.487  1.00  0.00           C  
HETATM   15  O3  UNL     1       1.546   2.881   1.109  1.00  0.00           O  
HETATM   16  N5  UNL     1       1.082  -1.422  -0.578  1.00  0.00           N  
HETATM   17  C9  UNL     1      -0.249  -1.574  -0.094  1.00  0.00           C  
HETATM   18  H1  UNL     1      -2.128   0.618  -1.257  1.00  0.00           H  
HETATM   19  H2  UNL     1      -3.507   1.488  -0.386  1.00  0.00           H  
HETATM   20  H3  UNL     1      -3.801   0.257  -1.729  1.00  0.00           H  
HETATM   21  H4  UNL     1      -3.054  -1.514  -0.454  1.00  0.00           H  
HETATM   22  H5  UNL     1      -4.542  -1.349   1.347  1.00  0.00           H  
HETATM   23  H6  UNL     1      -2.223  -1.257   1.916  1.00  0.00           H  
HETATM   24  H7  UNL     1      -2.458   1.557   1.383  1.00  0.00           H  
HETATM   25  H8  UNL     1       3.482  -1.018  -1.395  1.00  0.00           H  
HETATM   26  H9  UNL     1       5.943   1.078  -0.570  1.00  0.00           H  
HETATM   27  H10 UNL     1       5.249   0.871  -2.251  1.00  0.00           H  
HETATM   28  H11 UNL     1       1.548  -2.231  -1.124  1.00  0.00           H  
HETATM   29  H12 UNL     1      -0.269  -2.526   0.492  1.00  0.00           H  
HETATM   30  H13 UNL     1      -0.946  -1.788  -0.962  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   25
CONECT   11   12   13   13
CONECT   12   26   27
CONECT   13   14
CONECT   14   15   15
CONECT   16   17   28
CONECT   17   29   30
END

HMDB0000038
     RDKit          3D
Dihydrobiopterin
 30 31  0  0  0  0  0  0  0  0999 V2000
   -3.1628    0.5544   -0.8718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1898   -0.5983    0.1175 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4621   -0.6454    0.6850 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1627   -0.4093    1.2061 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3523    0.7550    1.9177 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7630   -0.4274    0.6192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0479    0.6178    0.7798 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2711    0.7944    0.3113 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8309   -0.2579   -0.3798 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0824   -0.2078   -0.8756 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8047    0.9081   -0.6871 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1393    0.9583   -1.2171 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3027    1.9641   -0.0183 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0373    1.9233    0.4873 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5460    2.8814    1.1089 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0817   -1.4225   -0.5784 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2493   -1.5737   -0.0945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1282    0.6178   -1.2570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5073    1.4878   -0.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8008    0.2568   -1.7289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0539   -1.5140   -0.4541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5421   -1.3494    1.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2233   -1.2568    1.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4575    1.5575    1.3833 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4817   -1.0182   -1.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9433    1.0784   -0.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2493    0.8705   -2.2505 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5482   -2.2311   -1.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2695   -2.5262    0.4918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9459   -1.7877   -0.9617 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  1  0
 11 12  1  0
 11 13  2  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  6
  3 22  1  0
  4 23  1  1
  5 24  1  0
 10 25  1  0
 12 26  1  0
 12 27  1  0
 16 28  1  0
 17 29  1  0
 17 30  1  0
M  END

View in JSmol

Synonyms

Value	Source
7,8-DIHYDROBIOPTERIN	ChEBI
L-Erythro-Q-dihydrobiopterin	ChEBI
Q-BH2	ChEBI
Quinonoid dihydrobiopterin	ChEBI
L-Erythro-7,8-dihydrobiopterin	Kegg
L-Erythro-dihydrobiopterin	HMDB
7,8-Dihydro-L-biopterin	HMDB
BH2	HMDB
Dihydrobiopterin	ChEBI

Chemical Formula

C₉H₁₃N₅O₃

Average Mass

239.2312 Da

Monoisotopic Mass

239.10184 Da

IUPAC Name

2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1,4,7,8-tetrahydropteridin-4-one

Traditional Name

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO, simulated)	V.dorna83			2021-09-05	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO, experimental)	V.dorna83			2021-09-05	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO, simulated)	Varshavi.d26			2021-08-08	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Pyrrhocoris apterus	LOTUS Database	35616633
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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

7,8-dihydrobiopterin (CHEBI:43029 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.63 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-2.3	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	9.91	ChemAxon
pKa (Strongest Basic)	0.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	132.33 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	68.11 m³·mol⁻¹	ChemAxon
Polarizability	23.11 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

External Links

HMDB ID

HMDB0000038

DrugBank ID

DB04400

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021884

KNApSAcK ID

Not Available

Chemspider ID

106382

KEGG Compound ID

C02953

BioCyc ID

CPD-15159

BiGG ID

Not Available

Wikipedia Link

Dihydrobiopterin

METLIN ID

Not Available

PubChem Compound

119055

PDB ID

Not Available

ChEBI ID

43029

Good Scents ID

Not Available

References

General References

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. Epub 2001 Jul 6. [PubMed:11443547 ]
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. [PubMed:9753429 ]
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. [PubMed:932231 ]
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. [PubMed:8626754 ]
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. [PubMed:84153 ]
Topal G, Brunet A, Millanvoye E, Boucher JL, Rendu F, Devynck MA, David-Dufilho M: Homocysteine induces oxidative stress by uncoupling of NO synthase activity through reduction of tetrahydrobiopterin. Free Radic Biol Med. 2004 Jun 15;36(12):1532-41. [PubMed:15182855 ]
Yokoyama K, Tajima M, Yoshida H, Nakayama M, Tokutome G, Sakagami H, Hosoya T: Plasma pteridine concentrations in patients with chronic renal failure. Nephrol Dial Transplant. 2002 Jun;17(6):1032-6. [PubMed:12032193 ]
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. Epub 2001 Apr 11. [PubMed:11301319 ]
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. [PubMed:3665086 ]
Shinozaki K, Hirayama A, Nishio Y, Yoshida Y, Ohtani T, Okamura T, Masada M, Kikkawa R, Kodama K, Kashiwagi A: Coronary endothelial dysfunction in the insulin-resistant state is linked to abnormal pteridine metabolism and vascular oxidative stress. J Am Coll Cardiol. 2001 Dec;38(7):1821-8. [PubMed:11738280 ]
Yang S, Jan YH, Mishin V, Richardson JR, Hossain MM, Heindel ND, Heck DE, Laskin DL, Laskin JD: Sulfa drugs inhibit sepiapterin reduction and chemical redox cycling by sepiapterin reductase. J Pharmacol Exp Ther. 2015 Mar;352(3):529-40. doi: 10.1124/jpet.114.221572. Epub 2014 Dec 30. [PubMed:25550200 ]

Showing NP-Card for Dihydrobiopterin (NP0000403)

MOL for NP0000403 (Dihydrobiopterin)

3D MOL for NP0000403 (Dihydrobiopterin)

3D SDF for NP0000403 (Dihydrobiopterin)

3D-SDF for NP0000403 (Dihydrobiopterin)

PDB for NP0000403 (Dihydrobiopterin)

3D PDB for NP0000403 (Dihydrobiopterin)

SMILES for NP0000403 (Dihydrobiopterin)

INCHI for NP0000403 (Dihydrobiopterin)

Structure for NP0000403 (Dihydrobiopterin)

3D Structure for NP0000403 (Dihydrobiopterin)