MiMeDB: Showing metabocard for L-erythro-tetrahydrobiopterin (MMDBc0032102)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 02:02:25 UTC

Update Date

2024-04-30 19:54:26 UTC

Metabolite ID

MMDBc0032102

Metabolite Identification

Common Name

L-erythro-tetrahydrobiopterin

Description

NULL

Structure

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

HMDB0000027
     RDKit          3D
Tetrahydrobiopterin
 32 33  0  0  0  0  0  0  0  0999 V2000
   -3.3834   -1.6670   -0.2413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3879   -0.2526    0.2627 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5173    0.3684   -0.3210 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2046    0.5545   -0.1578 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0205    0.6154   -1.5328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9210    0.2157    0.5433 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3745   -1.1332    0.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9875   -1.2298    0.6994 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9024   -0.2196    0.3308 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2337   -0.5047    0.2274 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0772    0.4820   -0.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4613    0.2221   -0.2424 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5979    1.7290   -0.3708 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3066    2.0493   -0.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8357    3.1908   -0.5012 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4179    1.0446    0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0214    1.2713    0.2089 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3111   -2.3541    0.6521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3743   -1.9551   -0.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6323   -1.8856   -0.9969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5007   -0.1738    1.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2832    0.4668   -1.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4379    1.6192    0.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6697    1.5100   -1.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0958    0.2493    1.6401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3115   -1.2850   -0.8977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9544   -1.9261    0.7143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3079   -2.0183    1.3211 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5611   -1.4929    0.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1527    0.9885   -0.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8207   -0.7433   -0.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3040    2.2643    0.0447 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  1  0
  7  8  1  0
  8  9  1  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
 14 16  1  0
 16 17  1  0
 17  6  1  0
 16  9  2  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  1
  3 22  1  0
  4 23  1  1
  5 24  1  0
  6 25  1  1
  7 26  1  0
  7 27  1  0
  8 28  1  0
 10 29  1  0
 12 30  1  0
 12 31  1  0
 17 32  1  0
M  END


  Mrv1652309032023502D          

 18 19  0  0  0  0            999 V2000
 9998.572710001.2338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.425110000.4068    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.1408 9999.9922    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.854510000.4068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1408 9999.1680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.425110001.2318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1454 9998.7502    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.572710000.4022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8582 9999.9897    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8582 9999.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5727 9998.7522    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.998910000.4022    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2844 9999.9897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2844 9999.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9989 9998.7522    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10000.7134 9999.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7134 9999.9897    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.710710000.8147    0.0000 H   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  1  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
 17 18  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0032102

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]1(CNC2=C(N1)C(=O)N=C(N)N2)[C@@H](O)[C@H](C)O

> <INCHI_IDENTIFIER>
InChI=1S/C9H15N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3-4,6,12,15-16H,2H2,1H3,(H4,10,11,13,14,17)/t3-,4+,6-/m0/s1

> <INCHI_KEY>
FNKQXYHWGSIFBK-RPDRRWSUSA-N

> <FORMULA>
C9H15N5O3

> <MOLECULAR_WEIGHT>
241.2471

> <EXACT_MASS>
241.117489371

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
23.669405752440387

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1,4,5,6,7,8-hexahydropteridin-4-one

> <ALOGPS_LOGP>
-1.66

> <JCHEM_LOGP>
-2.6621297606666667

> <ALOGPS_LOGS>
-2.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.060370910709416

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.518351905753281

> <JCHEM_PKA_STRONGEST_BASIC>
1.5820637408971272

> <JCHEM_POLAR_SURFACE_AREA>
132.0

> <JCHEM_REFRACTIVITY>
68.43339999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.21e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tetrahydrobiopterin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000027
     RDKit          3D
Tetrahydrobiopterin
 32 33  0  0  0  0  0  0  0  0999 V2000
   -3.3834   -1.6670   -0.2413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3879   -0.2526    0.2627 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5173    0.3684   -0.3210 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2046    0.5545   -0.1578 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0205    0.6154   -1.5328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9210    0.2157    0.5433 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3745   -1.1332    0.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9875   -1.2298    0.6994 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9024   -0.2196    0.3308 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2337   -0.5047    0.2274 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0772    0.4820   -0.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4613    0.2221   -0.2424 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5979    1.7290   -0.3708 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3066    2.0493   -0.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8357    3.1908   -0.5012 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4179    1.0446    0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0214    1.2713    0.2089 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3111   -2.3541    0.6521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3743   -1.9551   -0.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6323   -1.8856   -0.9969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5007   -0.1738    1.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2832    0.4668   -1.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4379    1.6192    0.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6697    1.5100   -1.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0958    0.2493    1.6401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3115   -1.2850   -0.8977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9544   -1.9261    0.7143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3079   -2.0183    1.3211 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5611   -1.4929    0.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1527    0.9885   -0.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8207   -0.7433   -0.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3040    2.2643    0.0447 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  1  0
  7  8  1  0
  8  9  1  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
 14 16  1  0
 16 17  1  0
 17  6  1  0
 16  9  2  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  1
  3 22  1  0
  4 23  1  1
  5 24  1  0
  6 25  1  1
  7 26  1  0
  7 27  1  0
  8 28  1  0
 10 29  1  0
 12 30  1  0
 12 31  1  0
 17 32  1  0
M  END

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  O   UNK     0    8664.0028668.970   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8669.3278667.426   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8670.6638666.652   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8671.9958667.426   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8670.6638665.114   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8669.3278668.966   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0    8661.3388664.334   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0    8664.0028667.417   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0    8662.6698666.647   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0    8662.6698665.107   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0    8664.0028664.337   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0    8666.6658667.417   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0    8665.3318666.647   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8665.3318665.107   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0    8666.6658664.337   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0    8667.9988665.107   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8667.9988666.647   0.000  0.00  0.00           C+0
HETATM   18  H   UNK     0    8667.9938668.187   0.000  0.00  0.00           H+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   18                                             
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0000027
HETATM    1  C1  UNL     1      -3.383  -1.667  -0.241  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.388  -0.253   0.263  1.00  0.00           C  
HETATM    3  O1  UNL     1      -4.517   0.368  -0.321  1.00  0.00           O  
HETATM    4  C3  UNL     1      -2.205   0.554  -0.158  1.00  0.00           C  
HETATM    5  O2  UNL     1      -2.021   0.615  -1.533  1.00  0.00           O  
HETATM    6  C4  UNL     1      -0.921   0.216   0.543  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.374  -1.133   0.196  1.00  0.00           C  
HETATM    8  N1  UNL     1       0.987  -1.230   0.699  1.00  0.00           N  
HETATM    9  C6  UNL     1       1.902  -0.220   0.331  1.00  0.00           C  
HETATM   10  N2  UNL     1       3.234  -0.505   0.227  1.00  0.00           N  
HETATM   11  C7  UNL     1       4.077   0.482  -0.126  1.00  0.00           C  
HETATM   12  N3  UNL     1       5.461   0.222  -0.242  1.00  0.00           N  
HETATM   13  N4  UNL     1       3.598   1.729  -0.371  1.00  0.00           N  
HETATM   14  C8  UNL     1       2.307   2.049  -0.281  1.00  0.00           C  
HETATM   15  O3  UNL     1       1.836   3.191  -0.501  1.00  0.00           O  
HETATM   16  C9  UNL     1       1.418   1.045   0.082  1.00  0.00           C  
HETATM   17  N5  UNL     1       0.021   1.271   0.209  1.00  0.00           N  
HETATM   18  H1  UNL     1      -3.311  -2.354   0.652  1.00  0.00           H  
HETATM   19  H2  UNL     1      -4.374  -1.955  -0.702  1.00  0.00           H  
HETATM   20  H3  UNL     1      -2.632  -1.886  -0.997  1.00  0.00           H  
HETATM   21  H4  UNL     1      -3.501  -0.174   1.345  1.00  0.00           H  
HETATM   22  H5  UNL     1      -4.283   0.467  -1.297  1.00  0.00           H  
HETATM   23  H6  UNL     1      -2.438   1.619   0.148  1.00  0.00           H  
HETATM   24  H7  UNL     1      -1.670   1.510  -1.821  1.00  0.00           H  
HETATM   25  H8  UNL     1      -1.096   0.249   1.640  1.00  0.00           H  
HETATM   26  H9  UNL     1      -0.311  -1.285  -0.898  1.00  0.00           H  
HETATM   27  H10 UNL     1      -0.954  -1.926   0.714  1.00  0.00           H  
HETATM   28  H11 UNL     1       1.308  -2.018   1.321  1.00  0.00           H  
HETATM   29  H12 UNL     1       3.561  -1.493   0.429  1.00  0.00           H  
HETATM   30  H13 UNL     1       6.153   0.988  -0.383  1.00  0.00           H  
HETATM   31  H14 UNL     1       5.821  -0.743  -0.190  1.00  0.00           H  
HETATM   32  H15 UNL     1      -0.304   2.264   0.045  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   17   25
CONECT    7    8   26   27
CONECT    8    9   28
CONECT    9   10   16   16
CONECT   10   11   29
CONECT   11   12   13   13
CONECT   12   30   31
CONECT   13   14
CONECT   14   15   15   16
CONECT   16   17
CONECT   17   32
END

HMDB0000027
     RDKit          3D
Tetrahydrobiopterin
 32 33  0  0  0  0  0  0  0  0999 V2000
   -3.3834   -1.6670   -0.2413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3879   -0.2526    0.2627 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5173    0.3684   -0.3210 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2046    0.5545   -0.1578 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0205    0.6154   -1.5328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9210    0.2157    0.5433 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3745   -1.1332    0.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9875   -1.2298    0.6994 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9024   -0.2196    0.3308 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2337   -0.5047    0.2274 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0772    0.4820   -0.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4613    0.2221   -0.2424 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5979    1.7290   -0.3708 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3066    2.0493   -0.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8357    3.1908   -0.5012 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4179    1.0446    0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0214    1.2713    0.2089 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3111   -2.3541    0.6521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3743   -1.9551   -0.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6323   -1.8856   -0.9969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5007   -0.1738    1.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2832    0.4668   -1.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4379    1.6192    0.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6697    1.5100   -1.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0958    0.2493    1.6401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3115   -1.2850   -0.8977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9544   -1.9261    0.7143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3079   -2.0183    1.3211 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5611   -1.4929    0.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1527    0.9885   -0.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8207   -0.7433   -0.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3040    2.2643    0.0447 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  1  0
  7  8  1  0
  8  9  1  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
 14 16  1  0
 16 17  1  0
 17  6  1  0
 16  9  2  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  1
  3 22  1  0
  4 23  1  1
  5 24  1  0
  6 25  1  1
  7 26  1  0
  7 27  1  0
  8 28  1  0
 10 29  1  0
 12 30  1  0
 12 31  1  0
 17 32  1  0
M  END

Synonyms

Value	Source
(-)-(6R)-2-Amino-6-((1R,2S)-1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(3H)-pteridinone	ChEBI
(6R)-L-Erythro-5,6,7,8-tetrahydrobiopterin	ChEBI
(6R)-L-Erythro-tetrahydrobiopterin	ChEBI
2-Amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydoro-4(1H)-pteridinone	ChEBI
5,6,7,8-Tetrahydrobiopterin	ChEBI
6R-5,6,7,8-Tetrahydrobiopterin	ChEBI
6R-BH4	ChEBI
6R-L-5,6,7,8-Tetrahydrobiopterin	ChEBI
R-THBP	ChEBI
Sapropterina	ChEBI
Sapropterinum	ChEBI
Tetrahydrobiopterin	ChEBI
5,6,7,8-erythro-Tetrahydrobiopterin	MeSH, HMDB
5,6,7,8-tetrahydro-L-Erythrobiopterin	MeSH, HMDB
5,6,7,8-Tetrahydrobiopterin, (S-(r,s))-isomer	MeSH, HMDB
5,6,7,8-Tetrahydrodictyopterin	MeSH, HMDB
6R-L-erythro-5,6,7,8-Tetrahydrobiopterin	MeSH, HMDB
BPH4	MeSH, HMDB
D-threo-Tetrahydrobiopterin	MeSH, HMDB
THBP	MeSH, HMDB
Kuvan	MeSH, HMDB
Phenylalanine hydroxylase cofactor	MeSH, HMDB
Sapropterin dihydrochloride	MeSH, HMDB
tetrahydro-6-Biopterin	MeSH, HMDB
2',4',5'-Trihydroxybutyrophenone	MeSH
Sapropterin	MeSH
Trihydroxybutyrophenone	MeSH
1-Butanone, 1-(2,4,5-trihydroxyphenyl)	MeSH
2,4,5-Trihydroxybutyrophenone	MeSH
(6R)-5,6,7,8-Tetrahydro-L-biopterin	HMDB
(6R)-5,6,7,8-Tetrahydrobiopterin	HMDB
(6R)-Tetrahydrobiopterin	HMDB
2-Amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(3H)-pteridinone	HMDB
6R-Tetrahydro-L-biopterin	HMDB
6beta-5,6,7,8-Tetrahydro-L-biopterin	HMDB
6β-5,6,7,8-Tetrahydro-L-biopterin	HMDB
L-erythro-Tetrahydrobiopterin	HMDB
(6R)-2-Amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydro-4(1H)-pteridinone	HMDB

Molecular Formula

C₉H₁₅N₅O₃

Average Mass

241.2471

Monoisotopic Mass

241.117489371

IUPAC Name

(6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1,4,5,6,7,8-hexahydropteridin-4-one

Traditional Name

tetrahydrobiopterin

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CNC2=C(N1)C(=O)N=C(N)N2)[C@@H](O)[C@H](C)O

InChI Identifier

InChI=1S/C9H15N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3-4,6,12,15-16H,2H2,1H3,(H4,10,11,13,14,17)/t3-,4+,6-/m0/s1

InChI Key

FNKQXYHWGSIFBK-RPDRRWSUSA-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
Secondary aliphatic/aromatic amine
Pyrimidine
1,3-aminoalcohol
Vinylogous amide
Heteroaromatic compound
Secondary alcohol
1,2-diol
1,2-aminoalcohol
Secondary amine
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

5,6,7,8-tetrahydrobiopterin (CHEBI:59560 )
Coenzymes (C00272 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	2.21 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-2.7	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	13.52	ChemAxon
pKa (Strongest Basic)	1.58	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	132 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	68.43 m³·mol⁻¹	ChemAxon
Polarizability	23.67 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (6 TMS)	splash10-0zfr-2921300000-63bf6ee58b9df85919f6	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0zfr-2921300000-63bf6ee58b9df85919f6	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0005-9810000000-1bfd11724596b460cae9	2017-09-20	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-014i-6945000000-07faa91218e86d3bfe0d	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	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 4V, positive	splash10-0006-0290000000-cd4c8c11b8279075b00a	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 5V, positive	splash10-0006-0390000000-35dddce9e2df2a9ac198	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 7V, positive	splash10-0006-0590000000-cda875209a034e44cbe1	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 10V, positive	splash10-00kf-0980000000-53721c484501c528e7a8	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 15V, positive	splash10-014l-0930000000-533fabd35a8c5ca7830e	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 17V, positive	splash10-014i-0910000000-580c038db540047891c8	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 20V, positive	splash10-014i-0910000000-8d6b754dadadb6330906	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 3V, positive	splash10-0006-0090000000-f21b677255493f1f2d1f	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 23V, positive	splash10-014i-0900000000-5c1b60d0d7ea4dd4dbff	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 25V, positive	splash10-014i-1900000000-6f22457ab99b14bb653e	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 27V, positive	splash10-014i-1900000000-cd0410f4da61716c7f9e	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 30V, positive	splash10-014i-2900000000-d4f18a979b6d07e83a63	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 16V, positive	splash10-0002-0900000000-87174b78444828c3b52d	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 16V, positive	splash10-0a4i-0900000000-dc272a476d306f26c722	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 16V, positive	splash10-014i-0900000000-ae19513d01a0046ed2e8	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 16V, positive	splash10-004i-0900000000-d4a52489d35bde573bd0	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 16V, positive	splash10-0f79-0900000000-af02b0d9eb8f6577afb8	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 16V, positive	splash10-014i-0900000000-c2259602e8f1fd522fd0	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-0006-0090000000-c88ed5ea9e11715bc275	2020-07-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006x-0090000000-e6b01d1139ccb3c6338d	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0gi3-0980000000-8963ef41f1138b05a813	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00xr-1900000000-bcfa359703563c696c0f	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0390000000-4810efa20f31adea3824	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006y-1930000000-5b32feeb643e238bb159	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9400000000-a7dbebeb1df4ea110948	2015-09-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Nucleus

Biospecimen Locations

All Tissues
Blood
Cerebrospinal Fluid (CSF)
Feces

Tissue Locations

All Tissues

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191760	Tyrosinase	Unknown	P14679	Homo sapiens
MMDBp0191943	Tyrosine 3-monooxygenase	Enzyme	P07101	Homo sapiens
MMDBp0191950	Phenylalanine-4-hydroxylase	Enzyme	P00439	Homo sapiens
MMDBp0192101	6-pyruvoyl tetrahydrobiopterin synthase	Unknown	Q03393	Homo sapiens
MMDBp0192102	Sepiapterin reductase	Enzyme	P35270	Homo sapiens
MMDBp0192127	Tryptophan 5-hydroxylase 1	Enzyme	P17752	Homo sapiens
MMDBp0192129	Tryptophan 5-hydroxylase 2	Enzyme	Q8IWU9	Homo sapiens
MMDBp0192192	Dihydropteridine reductase	Unknown	P09417	Homo sapiens
MMDBp0192544	Nitric oxide synthase, inducible	Unknown	P35228	Homo sapiens
MMDBp0192546	Nitric oxide synthase, brain	Unknown	P29475	Homo sapiens
MMDBp0192547	Nitric oxide synthase, endothelial	Unknown	P29474	Homo sapiens
MMDBp0192556	GTP cyclohydrolase 1	Unknown	P30793	Homo sapiens
MMDBp0193353	GTP cyclohydrolase 1 feedback regulatory protein	Unknown	P30047	Homo sapiens
MMDBp0193707	Pterin-4-alpha-carbinolamine dehydratase	Enzyme	P61457	Homo sapiens
MMDBp0196269	Calcium-calmodulin independent nitric oxide synthase iNOS protein	Enzyme	Q9UM94	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank
Nitric Oxide Signaling Pathway
Ion Channels and Their Functional Role in Vascular Endothelium
Succinate Signalling During Inflammation
Immunometabolism Pathway (Bacterial Activation)
Immunometabolism Pathway (Viral Activation)

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0000683	5-Methyltetrahydrofolic acid	Hydrogen Ion	Not Available	6, 7-Dihydropteridine Reduction	VMH	3735413
MMDBr0001935	Oxygen	4a-Hydroxytetrahydrobiopterin	Not Available	L-Phenylalanine, Tetrahydrobiopterin:Oxygen Oxidoreductase (4-Hydroxylating)	VMH; KEGG	30371894
MMDBr0002160	Dyspropterin	NADP	Sepiapterin reductase (7,8-dihydrobiopterin:nadp+ oxidoreductase)	Sepiapterin Reductase	VMH; KEGG	30371894
MMDBr0002162	Dyspropterin	NADP	Sepiapterin reductase (7,8-dihydrobiopterin:nadp+ oxidoreductase)	Sepiapterin Reductase, Nuclear	VMH	10727395 14729142
MMDBr0002276	Oxygen	5-Hydroxy-L-tryptophan	Tryptophan hydroxylase 1	L-Tryptophan, Tetrahydrobiopterin:Oxygen Oxidoreductase (5-Hydroxylating)	VMH	10727395 12379098
MMDBr0002295	Oxygen	L-Dopa	Tyrosine hydroxylase	Tyrosine 3-Monooxygenase	VMH	10727395 9920892
MMDBr0002538	Oxygen	4a-Carbinolamine tetrahydrobiopterin	Phenylalanine hydroxylase	L-Phenylalanine, Tetrahydrobiopterin:Oxygen Oxidoreductase (4-Hydroxylating) Phenylalanine, Tyrosine And Tryptophan Biosynthesis	VMH	3298976 4074362
MMDBr0002540	Hydrogen Ion	NADP	Sepiapterin reductase (7,8-dihydrobiopterin:nadp+ oxidoreductase)	Tetrahydrobiopterin:NADP+ Oxidoreductase	VMH; KEGG	30371894
MMDBr0002541	Oxygen	5-Hydroxy-L-tryptophan	Tryptophan hydroxylase 1	L-Tryptophan, Tetrahydrobiopterin:Oxygen Oxidoreductase (5-Hydroxylating)	VMH	30371894
MMDBr0006167	L-erythro-tetrahydrobiopterin	L-erythro-tetrahydrobiopterin	Not Available	Transport of 5,6,7,8-Tetrahydrobiopterin	VMH	30371894
MMDBr0007314	4a-Carbinolamine tetrahydrobiopterin	NAD	Not Available	6, 7-Dihydropteridine Reductase	VMH	30371894
MMDBr0007609	4a-Carbinolamine tetrahydrobiopterin	NADP	Not Available	NADPH:6, 7-Dihydropteridine Oxidoreductase Ec:1.5.1.34	VMH	30371894
MMDBr0008334	Oxygen	4a-Carbinolamine tetrahydrobiopterin	Not Available	L-Phenylalanine,tetrahydrobiopterin:oxygen oxidoreductase	VMH	30371894
MMDBr0010407	Oxygen	L-Dopa	Tyrosine hydroxylase	L-Tyrosine, Tetrahydrobiopterin:Oxygen Oxidoreductase (3-Hydroxylating)	VMH; KEGG	30371894
MMDBr0010743	L-erythro-tetrahydrobiopterin	L-erythro-tetrahydrobiopterin	Not Available	HMR_9673	VMH	30371894
MMDBr0015795	L-erythro-tetrahydrobiopterin	(6R)-6-(l-erythro-1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4a-hydroxypterin	Phenylalanine 3-hydroxylase	Hydroxylation	RHEA	34755880
MMDBr0017889	L-erythro-tetrahydrobiopterin	(6R)-6-(l-erythro-1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4a-hydroxypterin	Phenylalanine-4-hydroxylase	Hydroxylation	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Epilepsy		Association	Human Cerebrospinal Fluid (CSF)	HMDB	7869898
Myocardial infarction	Decreased	Association	Human Blood	HMDB	17726257
Septic shock		Association	Human Blood	HMDB	11573638

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	147	Human ; Human feces; Human sputum; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	136	Human feces; Human ; Cattle ; Human subgingival plaque	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Actinobacteria	7	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	16	Human feces; Human ; Human supragingival plaque; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria	Fusobacteria	3	Human feces; Human	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	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 Cerebrospinal fluid (csf)	Detected and Quantified	14400				uM	Newborn (0-30 days old)	Both	Generalized seizures	HMDB	7869898
Human Blood	Detected and Quantified	0.0044	0.0007			uM	Adult (>18 years old)	Both	Myocardial infarction	HMDB	17726257
Human Blood	Detected and Quantified	0.16		0.0	5.8	uM	Adult (>18 years old)	Both	Septic shock	HMDB	11573638
Human Blood	Detected and Quantified	1.2		0.8	14.9	uM	Adult (>18 years old)	Both	Septic shock	HMDB	11573638
Human Blood	Detected and Quantified	0.0099	0.0008			uM	Adult (>18 years old)	Both	Smoking	HMDB	10636262
Human Blood	Detected and Quantified	0.0093	0.0005			uM	Adult (>18 years old)	Both	Normal	HMDB	17726257
Human Blood	Detected and Quantified	0.0110	0.0008			uM	Adult (>18 years old)	Both	Normal	HMDB	10636262
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.026		0.014	0.038	uM	Adult (>18 years old)	Both	Normal	HMDB	16168596
Human All tissues	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0059658

DrugBank ID

DB00360

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

40270

KEGG Compound ID

C00272

BioCyc ID

CPD-14053

BiGG ID

Not Available

Wikipedia Link

Sapropterin

METLIN ID

Not Available

PubChem Compound

44257

PDB ID

Not Available

ChEBI ID

59560

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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 ]
Kaufman S: Biopterin-responsive hyperphenylalaninemia. J Nutr Sci Vitaminol (Tokyo). 1992;Spec No:601-6. doi: 10.3177/jnsv.38.special_601. [PubMed:1297822 ]
Takikawa S, Curtius HC, Redweik U, Leimbacher W, Ghisla S: Biosynthesis of tetrahydrobiopterin. Purification and characterization of 6-pyruvoyl-tetrahydropterin synthase from human liver. Eur J Biochem. 1986 Dec 1;161(2):295-302. doi: 10.1111/j.1432-1033.1986.tb10446.x. [PubMed:3536512 ]
Curtius HC, Heintel D, Ghisla S, Kuster T, Leimbacher W, Niederwieser A: Tetrahydrobiopterin biosynthesis. Studies with specifically labeled (2H)NAD(P)H and 2H2O and of the enzymes involved. Eur J Biochem. 1985 May 2;148(3):413-9. doi: 10.1111/j.1432-1033.1985.tb08855.x. [PubMed:3888618 ]
Dhondt JL, Cotton RG, Danks DM: Liver enzyme activities in hyperphenylalaninaemia due to a defective synthesis of tetrahydrobiopterin. J Inherit Metab Dis. 1985;8(2):47-8. doi: 10.1007/BF01801660. [PubMed:3939528 ]
Kaufman S, Kapatos G, Rizzo WB, Schulman JD, Tamarkin L, Van Loon GR: Tetrahydropterin therapy for hyperphenylalaninemia caused by defective synthesis of tetrahydrobiopterin. Ann Neurol. 1983 Sep;14(3):308-15. doi: 10.1002/ana.410140309. [PubMed:6139056 ]
Komori H, Matsuishi T, Yamada S, Yamashita Y, Ohtaki E, Kato H: Cerebrospinal fluid biopterin and biogenic amine metabolites during oral R-THBP therapy for infantile autism. J Autism Dev Disord. 1995 Apr;25(2):183-93. doi: 10.1007/BF02178503. [PubMed:7559284 ]
Cady EB, Lorek A, Penrice J, Reynolds EO, Iles RA, Burns SP, Coutts GA, Cowan FM: Detection of propan-1,2-diol in neonatal brain by in vivo proton magnetic resonance spectroscopy. Magn Reson Med. 1994 Dec;32(6):764-7. doi: 10.1002/mrm.1910320611. [PubMed:7869898 ]
Furukawa Y, Kish SJ, Bebin EM, Jacobson RD, Fryburg JS, Wilson WG, Shimadzu M, Hyland K, Trugman JM: Dystonia with motor delay in compound heterozygotes for GTP-cyclohydrolase I gene mutations. Ann Neurol. 1998 Jul;44(1):10-6. doi: 10.1002/ana.410440107. [PubMed:9667588 ]
Schallreuter KU, Moore J, Wood JM, Beazley WD, Peters EM, Marles LK, Behrens-Williams SC, Dummer R, Blau N, Thony B: Epidermal H(2)O(2) accumulation alters tetrahydrobiopterin (6BH4) recycling in vitiligo: identification of a general mechanism in regulation of all 6BH4-dependent processes? J Invest Dermatol. 2001 Jan;116(1):167-74. doi: 10.1046/j.1523-1747.2001.00220.x. [PubMed:11168813 ]
Walter R, Kaufmann PA, Buck A, Berthold T, Wyss C, von Schulthess GK, Schaffner A, Schoedon G: Tetrahydrobiopterin increases myocardial blood flow in healthy volunteers: a double-blind, placebo-controlled study. Swiss Med Wkly. 2001 Feb 24;131(7-8):91-4. doi: 2001/07/smw-06147. [PubMed:11416883 ]
Spaapen LJ, Bakker JA, Velter C, Loots W, Rubio-Gozalbo ME, Forget PP, Dorland L, De Koning TJ, Poll-The BT, Ploos van Amstel HK, Bekhof J, Blau N, Duran M: Tetrahydrobiopterin-responsive phenylalanine hydroxylase deficiency in Dutch neonates. J Inherit Metab Dis. 2001 Jun;24(3):352-8. doi: 10.1023/a:1010596317296. [PubMed:11486900 ]
Galley HF, Le Cras AE, Yassen K, Grant IS, Webster NR: Circulating tetrahydrobiopterin concentrations in patients with septic shock. Br J Anaesth. 2001 Apr;86(4):578-80. doi: 10.1093/bja/86.4.578. [PubMed:11573638 ]
Hyland K, Gunasekara RS, Munk-Martin TL, Arnold LA, Engle T: The hph-1 mouse: a model for dominantly inherited GTP-cyclohydrolase deficiency. Ann Neurol. 2003;54 Suppl 6:S46-8. doi: 10.1002/ana.10695. [PubMed:12891653 ]
Koch R, Moseley KD, Moats R, Yano S, Matalon R, Guttler F: Danger of high-protein dietary supplements to persons with hyperphenylalaninaemia. J Inherit Metab Dis. 2003;26(4):339-42. doi: 10.1023/a:1025103018278. [PubMed:12971421 ]
Kuhn DM, Geddes TJ: Tetrahydrobiopterin prevents nitration of tyrosine hydroxylase by peroxynitrite and nitrogen dioxide. Mol Pharmacol. 2003 Oct;64(4):946-53. doi: 10.1124/mol.64.4.946. [PubMed:14500751 ]
Matter H, Kumar HS, Fedorov R, Frey A, Kotsonis P, Hartmann E, Frohlich LG, Reif A, Pfleiderer W, Scheurer P, Ghosh DK, Schlichting I, Schmidt HH: Structural analysis of isoform-specific inhibitors targeting the tetrahydrobiopterin binding site of human nitric oxide synthases. J Med Chem. 2005 Jul 28;48(15):4783-92. doi: 10.1021/jm050007x. [PubMed:16033258 ]
Sawabe K, Suetake Y, Nakanishi N, Wakasugi KO, Hasegawa H: Cellular accumulation of tetrahydrobiopterin following its administration is mediated by two different processes; direct uptake and indirect uptake mediated by a methotrexate-sensitive process. Mol Genet Metab. 2005 Dec;86 Suppl 1:S133-8. doi: 10.1016/j.ymgme.2005.06.020. Epub 2005 Sep 13. [PubMed:16165391 ]
Toda Y, Mori K, Hashimoto T, Miyazaki M, Nozaki S, Watanabe Y, Kuroda Y, Kagami S: Administration of secretin for autism alters dopamine metabolism in the central nervous system. Brain Dev. 2006 Mar;28(2):99-103. doi: 10.1016/j.braindev.2005.05.005. Epub 2005 Sep 15. [PubMed:16168596 ]
Moens AL, Kass DA: Tetrahydrobiopterin and cardiovascular disease. Arterioscler Thromb Vasc Biol. 2006 Nov;26(11):2439-44. doi: 10.1161/01.ATV.0000243924.00970.cb. Epub 2006 Aug 31. [PubMed:16946131 ]
Sanford M, Keating GM: Spotlight on sapropterin in primary hyperphenylalaninemia. BioDrugs. 2009;23(3):201-2. doi: 10.2165/00063030-200923030-00007. [PubMed:19627172 ]
MacDonald A, Ahring K, Dokoupil K, Gokmen-Ozel H, Lammardo AM, Motzfeldt K, Robert M, Rocha JC, van Rijn M, Belanger-Quintana A: Adjusting diet with sapropterin in phenylketonuria: what factors should be considered? Br J Nutr. 2011 Jul;106(2):175-82. doi: 10.1017/S0007114511000298. [PubMed:21466737 ]
Burton BK, Nowacka M, Hennermann JB, Lipson M, Grange DK, Chakrapani A, Trefz F, Dorenbaum A, Imperiale M, Kim SS, Fernhoff PM: Safety of extended treatment with sapropterin dihydrochloride in patients with phenylketonuria: results of a phase 3b study. Mol Genet Metab. 2011 Aug;103(4):315-22. doi: 10.1016/j.ymgme.2011.03.020. Epub 2011 Mar 31. [PubMed:21646032 ]
Utz JR, Lorentz CP, Markowitz D, Rudser KD, Diethelm-Okita B, Erickson D, Whitley CB: START, a double blind, placebo-controlled pharmacogenetic test of responsiveness to sapropterin dihydrochloride in phenylketonuria patients. Mol Genet Metab. 2012 Feb;105(2):193-7. doi: 10.1016/j.ymgme.2011.10.014. Epub 2011 Oct 29. [PubMed:22112818 ]
Gordon P, Thomas JA, Suter R, Jurecki E: Evolving patient selection and clinical benefit criteria for sapropterin dihydrochloride (Kuvan(R)) treatment of PKU patients. Mol Genet Metab. 2012 Apr;105(4):672-6. doi: 10.1016/j.ymgme.2011.12.023. Epub 2012 Jan 8. [PubMed:22310224 ]
Leuret O, Barth M, Kuster A, Eyer D, de Parscau L, Odent S, Gilbert-Dussardier B, Feillet F, Labarthe F: Efficacy and safety of BH4 before the age of 4 years in patients with mild phenylketonuria. J Inherit Metab Dis. 2012 Nov;35(6):975-81. doi: 10.1007/s10545-012-9464-3. Epub 2012 Mar 3. [PubMed:22388642 ]
Ziesch B, Weigel J, Thiele A, Mutze U, Rohde C, Ceglarek U, Thiery J, Kiess W, Beblo S: Tetrahydrobiopterin (BH4) in PKU: effect on dietary treatment, metabolic control, and quality of life. J Inherit Metab Dis. 2012 Nov;35(6):983-92. doi: 10.1007/s10545-012-9458-1. Epub 2012 Mar 6. [PubMed:22391997 ]
Cunningham A, Bausell H, Brown M, Chapman M, DeFouw K, Ernst S, McClure J, McCune H, O'Steen D, Pender A, Skrabal J, Wessel A, Jurecki E, Shediac R, Prasad S, Gillis J, Cederbaum S: Recommendations for the use of sapropterin in phenylketonuria. Mol Genet Metab. 2012 Jul;106(3):269-76. doi: 10.1016/j.ymgme.2012.04.004. Epub 2012 Apr 13. [PubMed:22575621 ]
Shintaku H, Ohwada M: Long-term follow-up of tetrahydrobiopterin therapy in patients with tetrahydrobiopterin deficiency in Japan. Brain Dev. 2013 May;35(5):406-10. doi: 10.1016/j.braindev.2012.06.010. Epub 2012 Jul 24. [PubMed:22832064 ]
Somaraju UR, Merrin M: Sapropterin dihydrochloride for phenylketonuria. Cochrane Database Syst Rev. 2012 Dec 12;12:CD008005. doi: 10.1002/14651858.CD008005.pub3. [PubMed:23235653 ]
Gokmen Ozel H, Lammardo AM, Motzfeldt K, Robert M, Rocha JC, van Rijn M, Ahring K, Belanger-Quintana A, MacDonald A, Dokoupil K: Use of sapropterin in the management of phenylketonuria: seven case reports. Mol Genet Metab. 2013 Feb;108(2):109-11. doi: 10.1016/j.ymgme.2012.11.012. Epub 2012 Nov 28. [PubMed:23266371 ]
Thiele AG, Weigel JF, Ziesch B, Rohde C, Mutze U, Ceglarek U, Thiery J, Muller AS, Kiess W, Beblo S: Nutritional Changes and Micronutrient Supply in Patients with Phenylketonuria Under Therapy with Tetrahydrobiopterin (BH(4)). JIMD Rep. 2013;9:31-40. doi: 10.1007/8904_2012_176. Epub 2012 Oct 17. [PubMed:23430545 ]
Cerone R, Andria G, Giovannini M, Leuzzi V, Riva E, Burlina A: Testing for tetrahydrobiopterin responsiveness in patients with hyperphenylalaninemia due to phenylalanine hydroxylase deficiency. Adv Ther. 2013 Mar;30(3):212-28. doi: 10.1007/s12325-013-0011-x. Epub 2013 Feb 20. [PubMed:23436109 ]
Keil S, Anjema K, van Spronsen FJ, Lambruschini N, Burlina A, Belanger-Quintana A, Couce ML, Feillet F, Cerone R, Lotz-Havla AS, Muntau AC, Bosch AM, Meli CA, Billette de Villemeur T, Kern I, Riva E, Giovannini M, Damaj L, Leuzzi V, Blau N: Long-term follow-up and outcome of phenylketonuria patients on sapropterin: a retrospective study. Pediatrics. 2013 Jun;131(6):e1881-8. doi: 10.1542/peds.2012-3291. Epub 2013 May 20. [PubMed:23690520 ]
Blau N: Sapropterin dihydrochloride for the treatment of hyperphenylalaninemias. Expert Opin Drug Metab Toxicol. 2013 Sep;9(9):1207-18. doi: 10.1517/17425255.2013.804064. Epub 2013 May 27. [PubMed:23705856 ]
Douglas TD, Jinnah HA, Bernhard D, Singh RH: The effects of sapropterin on urinary monoamine metabolites in phenylketonuria. Mol Genet Metab. 2013 Jul;109(3):243-50. doi: 10.1016/j.ymgme.2013.04.017. Epub 2013 May 1. [PubMed:23712020 ]
Stanhewicz AE, Alexander LM, Kenney WL: Oral sapropterin acutely augments reflex vasodilation in aged human skin through nitric oxide-dependent mechanisms. J Appl Physiol (1985). 2013 Oct 1;115(7):972-8. doi: 10.1152/japplphysiol.00481.2013. Epub 2013 Jun 6. [PubMed:23743404 ]

Showing metabocard for L-erythro-tetrahydrobiopterin (MMDBc0032102)

MOL for #<Metabolite:0x00007fa4e81d43b0>

3D MOL for #<Metabolite:0x00007fa4e81d43b0>

3D SDF for #<Metabolite:0x00007fa4e81d43b0>

3D-SDF for #<Metabolite:0x00007fa4e81d43b0>

PDB for #<Metabolite:0x00007fa4e81d43b0>

3D PDB for #<Metabolite:0x00007fa4e81d43b0>

SMILES for #<Metabolite:0x00007fa4e81d43b0>

INCHI for #<Metabolite:0x00007fa4e81d43b0>

Structure for #<Metabolite:0x00007fa4e81d43b0>

3D Structure for #<Metabolite:0x00007fa4e81d43b0>