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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:40:00 UTC

HMDB ID

HMDB0000468

Secondary Accession Numbers

HMDB00468

Metabolite Identification

Common Name

Biopterin

Description

Biopterin, also known as tetrahydrobiopterin or BH4, belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. Biopterin or tetrahydrobiopterin is also classified as a pterin derivative that consists of pterin group bearing an amino, an oxo and a 1,2-dihydroxypropyl substituent at positions 2, 4 and 6, respectively. Biopterin compounds found within the animals include BH4 (tetrahydrobiopterin), the free radical BH3, and BH2 (also a free radical, called Dihydrobiopterin). BH2 is produced in the synthesis of L-DOPA, dopamine, norepinephrine and epinephrine. It is restored to the required cofactor tetrahydrobiopterin by the enzyme dihydrobiopterin reductase. Tetrahydrobiopterin (BH4) is a cofactor of the three aromatic amino acid hydroxylase enzymes, used in the degradation of amino acid phenylalanine and in the biosynthesis of the neurotransmitters serotonin (5-hydroxytryptamine, 5-HT), melatonin, dopamine, norepinephrine (noradrenaline), epinephrine (adrenaline). It is also a cofactor for the production of nitric oxide (NO) by the nitric oxide syntheses. Tetrahydrobiopterin is biosynthesized from guanosine triphosphate (GTP) by three chemical reactions mediated by the enzymes GTP cyclohydrolase I (GTPCH), 6-pyruvoyltetrahydropterin synthase (PTPS), and sepiapterin reductase (SR). Biopterin synthesis disorders are a cause of hyperphenylalaninemia. There are 3 distinct forms of phenylketonuria or hyperphenylalaninemia, each caused by lack of aromatic amino acid hydroxylase enzymes. The variant forms of hyperphenylalaninemia that are caused by the lack of dihydropteridine reductase or tetrahydrobiopterin are characterized by severe neurological deterioration, impaired functioning of tyrosine and tryptophan hydroxylases, and the resultant deficiency of tyrosine- and tryptophan-derived monoamine neurotransmitters in brain. (PMID 3930837 ).

Structure

MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652305271900042D          

 17 18  0  0  0  0            999 V2000
 9997.370910000.0266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.2228 9999.1997    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.9364 9998.7851    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.6519 9999.1997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.9364 9997.9610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.222810000.0246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.9441 9997.5435    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.7953 9999.1952    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.7953 9997.5453    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5097 9997.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5097 9998.7827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.0845 9998.7828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3702 9999.1952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.6557 9998.7827    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9996.6557 9997.9578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3701 9997.5454    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.0845 9997.9578    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
 10 11  2  0  0  0  0
 11  8  1  0  0  0  0
  9 10  1  0  0  0  0
 11  2  1  0  0  0  0
 12 13  1  0  0  0  0
 17 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  1 13  2  0  0  0  0
 15  7  1  0  0  0  0
  8 12  2  0  0  0  0
 17  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000468

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@H](O)[C@H](O)C1=CNC2=NC(N)=NC(=O)C2=N1

> <INCHI_IDENTIFIER>
InChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h2-3,6,15-16H,1H3,(H3,10,11,13,14,17)/t3-,6-/m0/s1

> <INCHI_KEY>
LHQIJBMDNUYRAM-DZSWIPIPSA-N

> <FORMULA>
C9H11N5O3

> <MOLECULAR_WEIGHT>
237.2153

> <EXACT_MASS>
237.086189243

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
22.465204903692857

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.41

> <JCHEM_LOGP>
-2.202784988

> <ALOGPS_LOGS>
-2.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.202343462619009

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.182676489158556

> <JCHEM_PKA_STRONGEST_BASIC>
-1.4063089544608536

> <JCHEM_POLAR_SURFACE_AREA>
132.66

> <JCHEM_REFRACTIVITY>
57.81110000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.87e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-8H-pteridin-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

https://cactus.nci.nih.gov/chemical/structure/C%5BC@H%5D(O)%5BC@H%5D(O)C1=CNC...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:27})
 28 29  0  0  0  0  0  0  0  0999 V2000
    4.7766   -0.6125   -0.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2775   -0.3601   -0.6802 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7710   -1.3041   -0.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0682    0.5353   -1.7740 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7135    0.2586    0.6005 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2200    1.2025    0.8017 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9228   -0.6369    1.6943 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2369    0.5071    0.4303 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7624    1.8032    0.4375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5523    2.0495    0.2872 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4038    0.9961    0.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7107    1.1638   -0.0254 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5268    0.1308   -0.1791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8735    0.3818   -0.3328 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1192   -1.1294   -0.1936 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8251   -1.4376   -0.0494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4439   -2.5978   -0.0625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8768   -0.3214    0.1253 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4204   -0.5189    0.2713 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2831    0.3315   -0.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9363   -1.2955    0.3270 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1784   -1.0532   -1.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4918    1.3975   -1.6630 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4993   -1.4991    1.5833 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4508    2.6255    0.5650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8882    2.9596    0.2925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2005    1.2949   -0.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4941   -0.3549   -0.4470 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  2  3  1  6  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  4 23  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  7 24  1  0  0  0  0
  8  9  2  0  0  0  0
  8 19  1  0  0  0  0
  9 10  1  0  0  0  0
  9 25  1  0  0  0  0
 10 11  1  0  0  0  0
 10 26  1  0  0  0  0
 11 12  2  0  0  0  0
 11 18  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 14 27  1  0  0  0  0
 14 28  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  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  O   UNK     0    8661.7598666.716   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8667.0838665.173   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8668.4158664.399   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8669.7508665.173   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8668.4158662.861   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8667.0838666.713   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0    8659.0968662.081   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0    8664.4188665.164   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0    8664.4188662.085   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0    8665.7518662.854   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8665.7518664.394   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8663.0918664.395   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8661.7588665.164   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0    8660.4248664.394   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0    8660.4248662.855   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0    8661.7588662.085   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0    8663.0918662.855   0.000  0.00  0.00           C+0
CONECT    1   13                                                            
CONECT    2    3    6   11                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    2                                                            
CONECT    7   15                                                            
CONECT    8   11   12                                                       
CONECT    9   10   17                                                       
CONECT   10   11    9                                                       
CONECT   11   10    8    2                                                  
CONECT   12   13   17    8                                                  
CONECT   13   12   14    1                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16    7                                                  
CONECT   16   15   17                                                       
CONECT   17   12   16    9                                                  
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    https://cactus.nci.nih.gov/chemical/structure/C%5BC@H%5D(O)%5BC@H%5D(O)C1=CNC... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  C   UNL     1       4.777  -0.613  -0.507  1.00  0.00           C  
HETATM    2  C   UNL     1       3.277  -0.360  -0.680  1.00  0.00           C  
HETATM    3  H   UNL     1       2.771  -1.304  -0.881  1.00  0.00           H  
HETATM    4  O   UNL     1       3.068   0.535  -1.774  1.00  0.00           O  
HETATM    5  C   UNL     1       2.713   0.259   0.601  1.00  0.00           C  
HETATM    6  H   UNL     1       3.220   1.202   0.802  1.00  0.00           H  
HETATM    7  O   UNL     1       2.923  -0.637   1.694  1.00  0.00           O  
HETATM    8  C   UNL     1       1.237   0.507   0.430  1.00  0.00           C  
HETATM    9  C   UNL     1       0.762   1.803   0.438  1.00  0.00           C  
HETATM   10  N   UNL     1      -0.552   2.050   0.287  1.00  0.00           N  
HETATM   11  C   UNL     1      -1.404   0.996   0.128  1.00  0.00           C  
HETATM   12  N   UNL     1      -2.711   1.164  -0.025  1.00  0.00           N  
HETATM   13  C   UNL     1      -3.527   0.131  -0.179  1.00  0.00           C  
HETATM   14  N   UNL     1      -4.873   0.382  -0.333  1.00  0.00           N  
HETATM   15  N   UNL     1      -3.119  -1.129  -0.194  1.00  0.00           N  
HETATM   16  C   UNL     1      -1.825  -1.438  -0.049  1.00  0.00           C  
HETATM   17  O   UNL     1      -1.444  -2.598  -0.062  1.00  0.00           O  
HETATM   18  C   UNL     1      -0.877  -0.321   0.125  1.00  0.00           C  
HETATM   19  N   UNL     1       0.420  -0.519   0.271  1.00  0.00           N  
HETATM   20  H   UNL     1       5.283   0.332  -0.306  1.00  0.00           H  
HETATM   21  H   UNL     1       4.936  -1.296   0.327  1.00  0.00           H  
HETATM   22  H   UNL     1       5.178  -1.053  -1.420  1.00  0.00           H  
HETATM   23  H   UNL     1       3.492   1.397  -1.663  1.00  0.00           H  
HETATM   24  H   UNL     1       2.499  -1.499   1.583  1.00  0.00           H  
HETATM   25  H   UNL     1       1.451   2.626   0.565  1.00  0.00           H  
HETATM   26  H   UNL     1      -0.888   2.960   0.292  1.00  0.00           H  
HETATM   27  H   UNL     1      -5.200   1.295  -0.327  1.00  0.00           H  
HETATM   28  H   UNL     1      -5.494  -0.355  -0.447  1.00  0.00           H  
CONECT    1    2   20   21   22                                       
CONECT    2    1    3    4    5                                       
CONECT    3    2                                                      
CONECT    4    2   23                                                 
CONECT    5    2    6    7    8                                       
CONECT    6    5                                                      
CONECT    7    5   24                                                 
CONECT    8    5    9    9   19                                       
CONECT    9    8    8   10   25                                       
CONECT   10    9   11   26                                            
CONECT   11   10   12   12   18                                       
CONECT   12   11   11   13                                            
CONECT   13   12   14   15   15                                       
CONECT   14   13   27   28                                            
CONECT   15   13   13   16                                            
CONECT   16   15   17   17   18                                       
CONECT   17   16   16                                                 
CONECT   18   16   11   19   19                                       
CONECT   19   18   18    8                                            
CONECT   20    1                                                      
CONECT   21    1                                                      
CONECT   22    1                                                      
CONECT   23    4                                                      
CONECT   24    7                                                      
CONECT   25    9                                                      
CONECT   26   10                                                      
CONECT   27   14                                                      
CONECT   28   14                                                      
MASTER        0    0    0    0    0    0    0    0   28    0   28    0
END

https://cactus.nci.nih.gov/chemical/structure/C%5BC@H%5D(O)%5BC@H%5D(O)C1=CNC...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:27})
 28 29  0  0  0  0  0  0  0  0999 V2000
    4.7766   -0.6125   -0.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2775   -0.3601   -0.6802 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7710   -1.3041   -0.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0682    0.5353   -1.7740 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7135    0.2586    0.6005 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2200    1.2025    0.8017 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9228   -0.6369    1.6943 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2369    0.5071    0.4303 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7624    1.8032    0.4375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5523    2.0495    0.2872 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4038    0.9961    0.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7107    1.1638   -0.0254 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5268    0.1308   -0.1791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8735    0.3818   -0.3328 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1192   -1.1294   -0.1936 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8251   -1.4376   -0.0494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4439   -2.5978   -0.0625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8768   -0.3214    0.1253 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4204   -0.5189    0.2713 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2831    0.3315   -0.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9363   -1.2955    0.3270 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1784   -1.0532   -1.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4918    1.3975   -1.6630 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4993   -1.4991    1.5833 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4508    2.6255    0.5650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8882    2.9596    0.2925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2005    1.2949   -0.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4941   -0.3549   -0.4470 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  2  3  1  6  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  4 23  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  7 24  1  0  0  0  0
  8  9  2  0  0  0  0
  8 19  1  0  0  0  0
  9 10  1  0  0  0  0
  9 25  1  0  0  0  0
 10 11  1  0  0  0  0
 10 26  1  0  0  0  0
 11 12  2  0  0  0  0
 11 18  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 14 27  1  0  0  0  0
 14 28  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
$$$$

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-Biopterin	ChEBI
(1'r,1's) Biopterin	HMDB
2-amino-6-(L-erythro-1,2-Dihydroxypropyl)-4(3H)-pteridinone	HMDB
6-Biopterin	HMDB
L-Biopterin	HMDB
L-erythro-Biopterin	HMDB
Pterin H b2	HMDB
[S-(R,s)]-2-amino-6-(1,2-dihydroxypropyl)-4(1H)-pteridinone	HMDB
Orinapterin	MeSH, HMDB
Dictyopterin	MeSH, HMDB
2-amino-6-(1,2-Dihydroxypropyl)-4(1H)-pteridinone	MeSH, HMDB
Biopterin	MeSH

Chemical Formula

C₉H₁₁N₅O₃

Average Molecular Weight

237.2153

Monoisotopic Molecular Weight

237.086189243

IUPAC Name

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

Traditional Name

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

CAS Registry Number

22150-76-1

SMILES

C[C@H](O)[C@H](O)C1=CNC2=NC(N)=NC(=O)C2=N1

InChI Identifier

InChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h2-3,6,15-16H,1H3,(H3,10,11,13,14,17)/t3-,6-/m0/s1

InChI Key

LHQIJBMDNUYRAM-DZSWIPIPSA-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
Aminopyrimidine
Pyrimidone
Pyrazine
Pyrimidine
Heteroaromatic compound
Vinylogous amide
1,2-diol
Secondary alcohol
Azacycle
Organic oxygen compound
Alcohol
Aromatic alcohol
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxide
Amine
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

biopterin (CHEBI:63931 )

Ontology

Disposition

Source:

Endogenous

Biological location:

Tissue and substructures:

Epidermis

Organ and components:

Cell and elements:

Cell:

Fibroblast

Subcellular:

Cytoplasm

Biofluid and excreta:

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.7 mg/mL	Not Available
LogP	Not Available	Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.06 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-2.2	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	8.18	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	132.66 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	57.81 m³·mol⁻¹	ChemAxon
Polarizability	22.47 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

Predicted Spectral Properties

Collision Cross Sections

Name	Adduct	Type	Data Source	Value	Reference
DeepCCS	[M-H]-	Experimental	MetCCS_train_neg	148.315	30932474
DeepCCS	[M+H]+	Experimental	MetCCS_train_pos	153.479	30932474
AllCCS	[M-H]-	Experimental	Not Available	148.315	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000324
AllCCS	[M+H]+	Experimental	Not Available	153.695	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000324
DarkChem	[M+H]+	Predicted	Not Available	153.771	31661259
DarkChem	[M+H]+	Predicted	Not Available	153.771	31661259
DarkChem	[M-H]-	Predicted	Not Available	152.653	31661259
DarkChem	[M-H]-	Predicted	Not Available	152.653	31661259
AllCCS	[M+H]+	Predicted	Not Available	153.131	32859911
AllCCS	[M-H]-	Predicted	Not Available	152.117	32859911

Retention Indices

Underivatized

Not Available

Derivatized

Derivative	Value	Reference
Biopterin,1TMS,#1	2396.5205	https://arxiv.org/abs/1905.12712
Biopterin,1TMS,#2	2410.67	https://arxiv.org/abs/1905.12712
Biopterin,1TMS,#3	2434.6794	https://arxiv.org/abs/1905.12712
Biopterin,1TMS,#4	2439.1355	https://arxiv.org/abs/1905.12712
Biopterin,2TMS,#1	2362.3955	https://arxiv.org/abs/1905.12712
Biopterin,2TMS,#2	2319.9592	https://arxiv.org/abs/1905.12712
Biopterin,2TMS,#3	2394.3323	https://arxiv.org/abs/1905.12712
Biopterin,2TMS,#4	2300.3804	https://arxiv.org/abs/1905.12712
Biopterin,2TMS,#5	2387.944	https://arxiv.org/abs/1905.12712
Biopterin,2TMS,#6	2454.809	https://arxiv.org/abs/1905.12712
Biopterin,2TMS,#7	2345.0698	https://arxiv.org/abs/1905.12712
Biopterin,1TBDMS,#1	2613.242	https://arxiv.org/abs/1905.12712
Biopterin,1TBDMS,#2	2632.2427	https://arxiv.org/abs/1905.12712
Biopterin,1TBDMS,#3	2614.137	https://arxiv.org/abs/1905.12712
Biopterin,1TBDMS,#4	2678.3125	https://arxiv.org/abs/1905.12712
Biopterin,2TBDMS,#1	2758.0386	https://arxiv.org/abs/1905.12712
Biopterin,2TBDMS,#2	2682.4854	https://arxiv.org/abs/1905.12712
Biopterin,2TBDMS,#3	2823.1736	https://arxiv.org/abs/1905.12712
Biopterin,2TBDMS,#4	2686.3264	https://arxiv.org/abs/1905.12712
Biopterin,2TBDMS,#5	2812.7578	https://arxiv.org/abs/1905.12712
Biopterin,2TBDMS,#6	2852.0813	https://arxiv.org/abs/1905.12712
Biopterin,2TBDMS,#7	2721.8225	https://arxiv.org/abs/1905.12712

Spectra

GC-MS

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0aos-1922500000-07177d5a450dbf7c637a	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0aos-1922500000-07177d5a450dbf7c637a	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-3910000000-90aa51259ebfb8feb1f5	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-044i-5094000000-cf05a1ca25a8f1348f75	2017-10-06	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-3900000000-09d8331e2935931648c9	2021-09-05	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-8900000000-5b42adf83e422cffefb6	2021-09-18	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-9800000000-24fa3ff739ff064312ab	2021-09-18	View Spectrum

LC-MS/MS

Spectrum Type	Description	Splash Key	Deposition Date	View
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-0190000000-cea25aa8258af5c9e837	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004i-0900000000-32102578ef16c3df8f17	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a5c-5900000000-441b149b7ee5432cdac3	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-004l-0920000000-6ebd6d01be7b4755e765	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0290000000-b312042f86e0c7f2f21f	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-01tc-1940000000-c430f7870641b07714a1	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-01p9-0090000000-bae0fd7c5247d7cd7961	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-000i-0090000000-f4a07c087ef8fff2e2a8	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0190000000-f8f16fa810bd3969420a	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-000i-0090000000-b4b32605d4abfd33394e	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0006-8900000000-944c0957bfd73e1b3de4	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a59-4900000000-6b39c8f4e23fb16bc1bc	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-004l-1900000000-da31236bbf093051d962	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0079-0090000000-8aa892a20d8030a22d50	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dr-0190000000-55344345937d9883d783	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0h91-1920000000-a6b8c5b9d802ce02b0c5	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0290000000-f8e54aa1d030a0c8a29d	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0940000000-c3bcfa7320d53b878000	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9800000000-3ab4f0aaf7f070e3ae28	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-50efc32e534ecd957e71	2021-09-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0079-0290000000-7aaf4a05ccf0d0bdaaf1	2021-09-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00fr-2900000000-35f8aaab434d197dc7b0	2021-09-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-04539012b288ea8b093b	2021-09-07	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0900000000-4d592fa1f3ce2b33e37c	2021-09-07	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-5900000000-775111b1a2ea5bbbf8e8	2021-09-07	View Spectrum

NMR

Spectrum Type	Description	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)	2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, 100%_DMSO, predicted)	2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Cellular Cytoplasm
Cerebrospinal Fluid (CSF)
Urine

Tissue Locations

Brain
Epidermis
Fibroblasts
Liver
Prostate

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.017 +/- 0.0025 uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Cellular Cytoplasm	Detected and Quantified	0.033 +/- 0.0073 uM	Adult (>18 years old)	Not Specified	Normal	Geigy Scientific ...	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.026 - 0.052 uM	Newborn (0-30 days old)	Not Specified	Normal	15652629	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.021 - 0.038 uM	Infant (0-1 year old)	Not Specified	Normal	15652629	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0132 +/- 0.0005 uM	Not Specified	Not Specified	Normal	7669428	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0140-0.0360 uM	Adolescent (13-18 years old)	Not Specified	Normal	19304569	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.01-0.042 uM	Children (1-13 years old)	Male	Normal	18502672	details
Urine	Detected and Quantified	0.24 +/- 0.07 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	0.32 +/- 0.13 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	0.48 +/- 0.17 umol/mmol creatinine	Children (1-13 years old)	Both	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	0.13 +/- 0.084 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	3939585	details
Urine	Detected and Quantified	0.3 +/- 0.14 umol/mmol creatinine	Children (1-13 years old)	Both	Normal	3939585	details
Urine	Detected and Quantified	0.82 +/- 0.34 umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	3200274	details
Urine	Detected and Quantified	0.5-3.0 umol/mmol creatinine	Newborn (0-30 days old)	Not Specified	Normal	8178819	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0376 (0.0281-0.0471) uM	Children (1-13 years old)	Male	sepiapterin reductase deficiency	18502672	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.01 uM	Adolescent (13-18 years old)	Not Available	Urocanase deficiency	19304569	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0085 +/- 0.0003 uM	Not Specified	Not Specified	idiopathic parkinsonisam	7669428	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0142 +/- 0.0012 uM	Not Specified	Not Specified	dopa-nonresponsive dystonia	7669428	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	20.6 (19.2 - 22.0) uM	Adult (>18 years old)	Not Specified	Segawa Syndrome	16289769	details
Urine	Detected and Quantified	0.19-0.63 umol/mmol creatinine	Newborn (0-30 days old)	Both	Hyperphenylalaninemia due to 6-pyruvoyltetrahydropterin synthase deficiency (PTPS)	8178819	details
Urine	Detected and Quantified	0.62 umol/mmol creatinine	Newborn (0-30 days old)	Female	Hyperphenylalaninemia due to pterin-4a-carbinolamine dehydratase	3200274	details

Associated Disorders and Diseases

Disease References

Segawa Syndrome
Furuya H, Murai H, Takasugi K, Ohyagi Y, Urano F, Kishi T, Ichinose H, Kira J: A case of late-onset Segawa syndrome (autosomal dominant dopa-responsive dystonia) with a novel mutation of the GTP-cyclohydrase I (GCH1) gene. Clin Neurol Neurosurg. 2006 Dec;108(8):784-6. Epub 2005 Nov 14. [PubMed:16289769 ]
Sepiapterin reductase deficiency
Verbeek MM, Willemsen MA, Wevers RA, Lagerwerf AJ, Abeling NG, Blau N, Thony B, Vargiami E, Zafeiriou DI: Two Greek siblings with sepiapterin reductase deficiency. Mol Genet Metab. 2008 Aug;94(4):403-9. doi: 10.1016/j.ymgme.2008.04.003. Epub 2008 May 27. [PubMed:18502672 ]
Parkinson's disease
Furukawa Y, Nishi K, Mizuno Y, Narabayashi H: [Significance of CSF biopterin and neopterin in hereditary progressive dystonia with marked diurnal fluctuation (HPD)--a clue to pathogenesis]. No To Shinkei. 1995 Mar;47(3):261-8. [PubMed:7669428 ]
Urocanase deficiency
Espinos C, Pineda M, Martinez-Rubio D, Lupo V, Ormazabal A, Vilaseca MA, Spaapen LJ, Palau F, Artuch R: Mutations in the urocanase gene UROC1 are associated with urocanic aciduria. J Med Genet. 2009 Jun;46(6):407-11. doi: 10.1136/jmg.2008.060632. Epub 2009 Mar 19. [PubMed:19304569 ]
6-Pyruvoyltetrahydropterin synthase deficiency
Thony B, Leimbacher W, Blau N, Harvie A, Heizmann CW: Hyperphenylalaninemia due to defects in tetrahydrobiopterin metabolism: molecular characterization of mutations in 6-pyruvoyl-tetrahydropterin synthase. Am J Hum Genet. 1994 May;54(5):782-92. [PubMed:8178819 ]
Pterin-4a carbinolamine dehydratase deficiency
Blaskovics M, Giudici TA: A new variant of biopterin deficiency. N Engl J Med. 1988 Dec 15;319(24):1611-2. doi: 10.1056/NEJM198812153192420. [PubMed:3200274 ]

Associated OMIM IDs

128230 (Segawa Syndrome)
182125 (Sepiapterin reductase deficiency)
168600 (Parkinson's disease)
276880 (Urocanase deficiency)
261640 (6-Pyruvoyltetrahydropterin synthase deficiency)
264070 (Pterin-4a carbinolamine dehydratase deficiency)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Biopterin

METLIN ID

247

PubChem Compound

445040

PDB ID

Not Available

ChEBI ID

63931

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000167

References

Synthesis Reference

Mori, Kenji; Kikuchi, Haruhiko. Synthesis of (-)-biopterin. Liebigs Annalen der Chemie (1989), (10), 963-7.

Material Safety Data Sheet (MSDS)

Not Available

General References

Fiege B, Ballhausen D, Kierat L, Leimbacher W, Goriounov D, Schircks B, Thony B, Blau N: Plasma tetrahydrobiopterin and its pharmacokinetic following oral administration. Mol Genet Metab. 2004 Jan;81(1):45-51. [PubMed:14728990 ]
Friedland RP, Koss E, Haxby JV, Grady CL, Luxenberg J, Schapiro MB, Kaye J: NIH conference. Alzheimer disease: clinical and biological heterogeneity. Ann Intern Med. 1988 Aug 15;109(4):298-311. [PubMed:2969203 ]
Snyderman SE, Sansaricq C, Pulmones MT: Successful long term therapy of biopterin deficiency. J Inherit Metab Dis. 1987;10(3):260-6. [PubMed:3123784 ]
Nagatsu T, Yamaguchi T, Kato T, Sugimoto T, Matsuura S, Akino M, Nagatsu I, Iizuka R, Narabayashi H: Biopterin in human brain and urine from controls and parkinsonian patients: application of a new radioimmunoassay. Clin Chim Acta. 1981 Feb 5;109(3):305-11. [PubMed:6112078 ]
Katoh S, Sueoka T, Matsuura S, Sugimoto T: Biopterin and neopterin in human saliva. Life Sci. 1989;45(26):2561-8. [PubMed:2615555 ]
Ichinose H, Ohye T, Shinotoh H, Arai K, Yamazaki S, Mizuta E, Kuno S, Nagatsu T: Biopterin metabolism in patients with malignant syndrome. Parkinsonism Relat Disord. 2003 Apr;9 Suppl 1:S11-4. [PubMed:12735910 ]
Zurfluh MR, Giovannini M, Fiori L, Fiege B, Gokdemir Y, Baykal T, Kierat L, Gartner KH, Thony B, Blau N: Screening for tetrahydrobiopterin deficiencies using dried blood spots on filter paper. Mol Genet Metab. 2005 Dec;86 Suppl 1:S96-103. Epub 2005 Nov 7. [PubMed:16275037 ]
Ogiwara S, Kiuchi K, Nagatsu T, Teradaira R, Nagatsu I, Fujita K, Sugimoto T: Highly sensitive, specific enzyme-linked immunosorbent assay of neopterin and biopterin in biological samples. Clin Chem. 1992 Oct;38(10):1954-8. [PubMed:1394977 ]
Hirata Y, Sawada M, Minami M, Arai H, Iizuka R, Nagatsu T: Tyrosine hydroxylase, tryptophan hydroxylase, biopterin, and neopterin in the brain of anorexia nervosa. J Neural Transm Gen Sect. 1990;80(2):145-50. [PubMed:1969283 ]
Dhondt JL, Tilmont P, Ringel J, Farriaux JP: Pterins analysis in amniotic fluid for the prenatal diagnosis of GTP cyclohydrolase deficiency. J Inherit Metab Dis. 1990;13(6):879-82. [PubMed:2079836 ]
Furukawa Y, Kapatos G, Haycock JW, Worsley J, Wong H, Kish SJ, Nygaard TG: Brain biopterin and tyrosine hydroxylase in asymptomatic dopa-responsive dystonia. Ann Neurol. 2002 May;51(5):637-41. [PubMed:12112113 ]
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 ]
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 ]
Slazyk WE, Spierto FW: Liquid-chromatographic measurement of biopterin and neopterin in serum and urine. Clin Chem. 1990 Jul;36(7):1364-8. [PubMed:2372953 ]
Dhondt JL, Hayte JM, Forzy G, Delcroix M, Farriaux JP: Unconjugated pteridines in amniotic fluid during gestation. Clin Chim Acta. 1986 Dec 30;161(3):269-73. [PubMed:3802534 ]
Iizuka T, Sasaki M, Oishi K, Uemura S, Koike M, Minatogawa Y: Nitric oxide may trigger lactation in humans. J Pediatr. 1997 Dec;131(6):839-43. [PubMed:9427887 ]
Zoghbi HY, Milstien S, Butler IJ, Smith EO, Kaufman S, Glaze DG, Percy AK: Cerebrospinal fluid biogenic amines and biopterin in Rett syndrome. Ann Neurol. 1989 Jan;25(1):56-60. [PubMed:2913929 ]
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Showing metabocard for Biopterin (HMDB0000468)

MOL for HMDB0000468 (Biopterin)

3D MOL for HMDB0000468 (Biopterin)

3D SDF for HMDB0000468 (Biopterin)

3D-SDF for HMDB0000468 (Biopterin)

PDB for HMDB0000468 (Biopterin)

3D PDB for HMDB0000468 (Biopterin)

SMILES for HMDB0000468 (Biopterin)

INCHI for HMDB0000468 (Biopterin)

Structure for HMDB0000468 (Biopterin)

3D Structure for HMDB0000468 (Biopterin)

Collision Cross Sections

Retention Indices

Underivatized

Derivatized

GC-MS

LC-MS/MS

NMR