MiMeDB: Showing metabocard for 4a-Hydroxytetrahydrobiopterin (MMDBc0047939)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-23 23:17:02 UTC

Update Date

2022-09-01 02:02:35 UTC

Metabolite ID

MMDBc0047939

Metabolite Identification

Common Name

4a-Hydroxytetrahydrobiopterin

Description

Tetrahydrobiopterin (BH4) is essential for catalyzing the conversion of phenylalanine into tyrosine by phenylalanine hydroxylase. During this physiological reaction, the oxidation of BH4 creates 4a-hydroxytetrahydropterin (CAS: 70110-58-6) intermediates and hydrogen peroxide is formed. The hydrogen peroxide and the hydroxytetrahydropterin can both be derived from alternate breakdown routes of a common precursor, the corresponding 4a-hydroperoxytetrahydropterin (PMID: 8323303 ).

Structure

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

HMDB0002281
     RDKit          3D
4a-Hydroxytetrahydrobiopterin
 33 34  0  0  0  0  0  0  0  0999 V2000
   -3.4888    0.6039    0.5038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9049   -0.7693    0.8243 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4817   -0.8594    2.1269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9833   -1.2780   -0.2163 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7517   -2.6436    0.0432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6958   -0.5916   -0.4351 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8063    0.8020   -0.9960 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5202    1.1455   -1.5101 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5976    0.7043   -0.6395 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7893    0.7665   -1.0678 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9500    0.3706   -0.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2555    0.4756   -0.8919 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7368   -0.0848    0.8405 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4567   -0.2078    1.4262 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3497   -0.7015    2.6038 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2640    0.2268    0.6898 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7857    1.3637    1.4038 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1632   -0.7014    0.7040 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4643    0.7560   -0.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5821    0.6547    0.7863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0164    1.4061    1.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8096   -1.4555    0.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6678    0.0010    2.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6015   -1.3114   -1.1729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7923   -2.8162    0.2138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1681   -1.1777   -1.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0593    1.5698   -0.2678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4590    0.7612   -1.8876 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6784    1.6469   -2.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4688    1.2109   -1.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9876   -0.1927   -0.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9763    1.2398    2.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2466   -0.9143    1.6011 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  2  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  1
 16 18  1  0
 18  6  1  0
 16  9  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  1
  3 23  1  0
  4 24  1  6
  5 25  1  0
  6 26  1  6
  7 27  1  0
  7 28  1  0
  8 29  1  0
 12 30  1  0
 12 31  1  0
 17 32  1  0
 18 33  1  0
M  END


  Mrv1652309042000272D          

 19 20  0  0  0  0            999 V2000
 9998.0932 9999.6149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.2326 9999.2046    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.9462 9998.7900    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.6617 9999.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.9462 9997.9661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.232610000.0295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.380910000.0315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.9543 9997.5486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3809 9999.2001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.6665 9998.7876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9996.6665 9997.9626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3809 9997.5503    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8059 9999.2002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.0915 9998.7877    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.0915 9997.9627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8059 9997.5504    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5203 9997.9627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5203 9998.7877    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.5179 9999.6126    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
 14 15  1  0  0  0  0
 17 18  1  0  0  0  0
 13 14  1  0  0  0  0
 13 18  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11  8  1  0  0  0  0
  9  7  2  0  0  0  0
 18  2  1  0  0  0  0
 12 15  2  0  0  0  0
  9 14  1  0  0  0  0
 14  1  1  1  0  0  0
 18 19  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0047939

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]1(CNC2=NC(N)=NC(=O)[C@]2(O)N1)[C@@H](O)[C@H](C)O

> <INCHI_IDENTIFIER>
InChI=1S/C9H15N5O4/c1-3(15)5(16)4-2-11-6-9(18,14-4)7(17)13-8(10)12-6/h3-5,14-16,18H,2H2,1H3,(H3,10,11,12,13,17)/t3-,4+,5-,9-/m0/s1

> <INCHI_KEY>
KJKIEFUPAPPGBC-XXKOCQOQSA-N

> <FORMULA>
C9H15N5O4

> <MOLECULAR_WEIGHT>
257.25

> <EXACT_MASS>
257.112403983

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
23.974819443414184

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.29

> <JCHEM_LOGP>
-3.1342584666666666

> <ALOGPS_LOGS>
-1.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.535559580937274

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.80938680121844

> <JCHEM_PKA_STRONGEST_BASIC>
3.0972551243955766

> <JCHEM_POLAR_SURFACE_AREA>
152.56

> <JCHEM_REFRACTIVITY>
58.59530000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.81e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4aS,6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-4a-hydroxy-5,6,7,8-tetrahydropteridin-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002281
     RDKit          3D
4a-Hydroxytetrahydrobiopterin
 33 34  0  0  0  0  0  0  0  0999 V2000
   -3.4888    0.6039    0.5038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9049   -0.7693    0.8243 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4817   -0.8594    2.1269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9833   -1.2780   -0.2163 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7517   -2.6436    0.0432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6958   -0.5916   -0.4351 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8063    0.8020   -0.9960 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5202    1.1455   -1.5101 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5976    0.7043   -0.6395 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7893    0.7665   -1.0678 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9500    0.3706   -0.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2555    0.4756   -0.8919 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7368   -0.0848    0.8405 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4567   -0.2078    1.4262 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3497   -0.7015    2.6038 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2640    0.2268    0.6898 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7857    1.3637    1.4038 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1632   -0.7014    0.7040 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4643    0.7560   -0.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5821    0.6547    0.7863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0164    1.4061    1.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8096   -1.4555    0.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6678    0.0010    2.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6015   -1.3114   -1.1729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7923   -2.8162    0.2138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1681   -1.1777   -1.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0593    1.5698   -0.2678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4590    0.7612   -1.8876 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6784    1.6469   -2.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4688    1.2109   -1.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9876   -0.1927   -0.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9763    1.2398    2.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2466   -0.9143    1.6011 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  2  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  1
 16 18  1  0
 18  6  1  0
 16  9  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  1
  3 23  1  0
  4 24  1  6
  5 25  1  0
  6 26  1  6
  7 27  1  0
  7 28  1  0
  8 29  1  0
 12 30  1  0
 12 31  1  0
 17 32  1  0
 18 33  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  O   UNK     0    8663.1078665.948   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8667.1018665.182   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8668.4338664.408   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8669.7698665.182   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8668.4338662.870   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8667.1018666.722   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8661.7788666.725   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0    8659.1158662.091   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0    8661.7788665.174   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0    8660.4448664.404   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0    8660.4448662.864   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0    8661.7788662.094   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0    8664.4388665.174   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0    8663.1048664.404   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8663.1048662.864   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0    8664.4388662.094   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0    8665.7718662.864   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8665.7718664.404   0.000  0.00  0.00           C+0
HETATM   19  H   UNK     0    8665.7678665.944   0.000  0.00  0.00           H+0
CONECT    1   14                                                            
CONECT    2    3    6   18                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    2                                                            
CONECT    7    9                                                            
CONECT    8   11                                                            
CONECT    9   10    7   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12    8                                                  
CONECT   12   11   15                                                       
CONECT   13   14   18                                                       
CONECT   14   15   13    9    1                                             
CONECT   15   14   16   12                                                  
CONECT   16   15   17                                                       
CONECT   17   18   16                                                       
CONECT   18   17   13    2   19                                             
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0002281
HETATM    1  C1  UNL     1      -3.489   0.604   0.504  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.905  -0.769   0.824  1.00  0.00           C  
HETATM    3  O1  UNL     1      -2.482  -0.859   2.127  1.00  0.00           O  
HETATM    4  C3  UNL     1      -1.983  -1.278  -0.216  1.00  0.00           C  
HETATM    5  O2  UNL     1      -1.752  -2.644   0.043  1.00  0.00           O  
HETATM    6  C4  UNL     1      -0.696  -0.592  -0.435  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.806   0.802  -0.996  1.00  0.00           C  
HETATM    8  N1  UNL     1       0.520   1.145  -1.510  1.00  0.00           N  
HETATM    9  C6  UNL     1       1.598   0.704  -0.639  1.00  0.00           C  
HETATM   10  N2  UNL     1       2.789   0.766  -1.068  1.00  0.00           N  
HETATM   11  C7  UNL     1       3.950   0.371  -0.340  1.00  0.00           C  
HETATM   12  N3  UNL     1       5.256   0.476  -0.892  1.00  0.00           N  
HETATM   13  N4  UNL     1       3.737  -0.085   0.841  1.00  0.00           N  
HETATM   14  C8  UNL     1       2.457  -0.208   1.426  1.00  0.00           C  
HETATM   15  O3  UNL     1       2.350  -0.702   2.604  1.00  0.00           O  
HETATM   16  C9  UNL     1       1.264   0.227   0.690  1.00  0.00           C  
HETATM   17  O4  UNL     1       0.786   1.364   1.404  1.00  0.00           O  
HETATM   18  N5  UNL     1       0.163  -0.701   0.704  1.00  0.00           N  
HETATM   19  H1  UNL     1      -3.464   0.756  -0.580  1.00  0.00           H  
HETATM   20  H2  UNL     1      -4.582   0.655   0.786  1.00  0.00           H  
HETATM   21  H3  UNL     1      -3.016   1.406   1.101  1.00  0.00           H  
HETATM   22  H4  UNL     1      -3.810  -1.455   0.775  1.00  0.00           H  
HETATM   23  H5  UNL     1      -2.668   0.001   2.582  1.00  0.00           H  
HETATM   24  H6  UNL     1      -2.602  -1.311  -1.173  1.00  0.00           H  
HETATM   25  H7  UNL     1      -0.792  -2.816   0.214  1.00  0.00           H  
HETATM   26  H8  UNL     1      -0.168  -1.178  -1.252  1.00  0.00           H  
HETATM   27  H9  UNL     1      -1.059   1.570  -0.268  1.00  0.00           H  
HETATM   28  H10 UNL     1      -1.459   0.761  -1.888  1.00  0.00           H  
HETATM   29  H11 UNL     1       0.678   1.647  -2.395  1.00  0.00           H  
HETATM   30  H12 UNL     1       5.469   1.211  -1.572  1.00  0.00           H  
HETATM   31  H13 UNL     1       5.988  -0.193  -0.603  1.00  0.00           H  
HETATM   32  H14 UNL     1       0.976   1.240   2.354  1.00  0.00           H  
HETATM   33  H15 UNL     1      -0.247  -0.914   1.601  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    4   22
CONECT    3   23
CONECT    4    5    6   24
CONECT    5   25
CONECT    6    7   18   26
CONECT    7    8   27   28
CONECT    8    9   29
CONECT    9   10   10   16
CONECT   10   11
CONECT   11   12   13   13
CONECT   12   30   31
CONECT   13   14
CONECT   14   15   15   16
CONECT   16   17   18
CONECT   17   32
CONECT   18   33
END

HMDB0002281
     RDKit          3D
4a-Hydroxytetrahydrobiopterin
 33 34  0  0  0  0  0  0  0  0999 V2000
   -3.4888    0.6039    0.5038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9049   -0.7693    0.8243 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4817   -0.8594    2.1269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9833   -1.2780   -0.2163 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7517   -2.6436    0.0432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6958   -0.5916   -0.4351 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8063    0.8020   -0.9960 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5202    1.1455   -1.5101 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5976    0.7043   -0.6395 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7893    0.7665   -1.0678 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9500    0.3706   -0.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2555    0.4756   -0.8919 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7368   -0.0848    0.8405 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4567   -0.2078    1.4262 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3497   -0.7015    2.6038 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2640    0.2268    0.6898 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7857    1.3637    1.4038 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1632   -0.7014    0.7040 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4643    0.7560   -0.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5821    0.6547    0.7863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0164    1.4061    1.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8096   -1.4555    0.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6678    0.0010    2.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6015   -1.3114   -1.1729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7923   -2.8162    0.2138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1681   -1.1777   -1.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0593    1.5698   -0.2678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4590    0.7612   -1.8876 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6784    1.6469   -2.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4688    1.2109   -1.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9876   -0.1927   -0.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9763    1.2398    2.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2466   -0.9143    1.6011 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  2  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  1
 16 18  1  0
 18  6  1  0
 16  9  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  1
  3 23  1  0
  4 24  1  6
  5 25  1  0
  6 26  1  6
  7 27  1  0
  7 28  1  0
  8 29  1  0
 12 30  1  0
 12 31  1  0
 17 32  1  0
 18 33  1  0
M  END

Synonyms

Value	Source
(4AS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin	ChEBI
(6R)-6-(L-Erythro-1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4a-hydroxypterin	ChEBI
4a-Hydroxy-5,6,4,8-tetrahydrobiopterin	Kegg
6-[(1R,2S)-1,2-Dihydroxypropyl]-5,6,7,8-tetrahydro-4a-hydroxypterin	Kegg
4a-HTHB	HMDB
4a-Hydroxy-5,6,7,8-tetrahydrobiopterin	HMDB
4a-Hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin	HMDB
4a-Hydroxytetrahydrobiopterin	HMDB

Molecular Formula

C₉H₁₅N₅O₄

Average Mass

257.25

Monoisotopic Mass

257.112403983

IUPAC Name

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

Traditional Name

(4aS,6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-4a-hydroxy-5,6,7,8-tetrahydropteridin-4-one

CAS Registry Number

1379003-93-6

SMILES

[H][C@@]1(CNC2=NC(N)=NC(=O)[C@]2(O)N1)[C@@H](O)[C@H](C)O

InChI Identifier

InChI=1S/C9H15N5O4/c1-3(15)5(16)4-2-11-6-9(18,14-4)7(17)13-8(10)12-6/h3-5,14-16,18H,2H2,1H3,(H3,10,11,12,13,17)/t3-,4+,5-,9-/m0/s1

InChI Key

KJKIEFUPAPPGBC-XXKOCQOQSA-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
Alpha-amino acid or derivatives
Pyrimidone
Imidolactam
Hydropyrimidine
1,4,5,6-tetrahydropyrimidine
Pyrimidine
1,2-diol
Amino acid or derivatives
Guanidine
N-acylimine
Secondary alcohol
Alkanolamine
Amidine
Carboxylic acid amidine
Carboxylic acid derivative
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Secondary amine
Carbonyl group
Organic nitrogen compound
Organic oxygen compound
Alcohol
Amine
Organonitrogen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	4.81 g/L	ALOGPS
logP	-2.3	ALOGPS
logP	-3.1	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	9.81	ChemAxon
pKa (Strongest Basic)	3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	152.56 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	58.6 m³·mol⁻¹	ChemAxon
Polarizability	23.97 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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4l-0090000000-364ec2c50acd77d83ef0	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00gl-0690000000-f15f00b5ba6b8f2959b9	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0005-9720000000-9884aa4c6eb7899b87e9	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0bt9-2290000000-43723819afb4c98b5ceb	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9210000000-fa8eb33fdfed731f1c82	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-c550affb7745a16d59b4	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0090000000-2e38d752208e421512bf	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052f-0390000000-b6be9ce0bc335a474657	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-1900000000-d33dcfe8d8e5a4b0dbc4	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0190000000-41b062345c98026b7320	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bti-1390000000-91a5c824226e2ce65d2b	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001l-4900000000-3857d5c10638c2febd7c	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191943	Tyrosine 3-monooxygenase	Enzyme	P07101	Homo sapiens
MMDBp0191950	Phenylalanine-4-hydroxylase	Enzyme	P00439	Homo sapiens
MMDBp0192127	Tryptophan 5-hydroxylase 1	Enzyme	P17752	Homo sapiens
MMDBp0192129	Tryptophan 5-hydroxylase 2	Enzyme	Q8IWU9	Homo sapiens
MMDBp0193707	Pterin-4-alpha-carbinolamine dehydratase	Enzyme	P61457	Homo sapiens
MMDBp0196204	Pterin-4-alpha-carbinolamine dehydratase 2	Enzyme	Q9H0N5	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0001935	Oxygen	4a-Hydroxytetrahydrobiopterin	Not Available	L-Phenylalanine, Tetrahydrobiopterin:Oxygen Oxidoreductase (4-Hydroxylating)	VMH	30371894
MMDBr0002225	4a-Hydroxytetrahydrobiopterin	4a-Carbinolamine tetrahydrobiopterin	Not Available	Tetrahydrobiopterin-4A-Carbinolamine Dehydratase	VMH	10727395
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
MMDBr0003892	4a-Hydroxytetrahydrobiopterin	Dihydrobiopterin	Not Available	4A-Hydroxytetrahydrobiopterin Dehydratase	VMH	10727395 1355046 1988938
MMDBr0003893	4a-Hydroxytetrahydrobiopterin	Dihydrobiopterin	Pterin-4 alpha-carbinolamine dehydratase/dimerization cofactor of hepatocyte nuclear factor 1 alpha	4A-Hydroxytetrahydrobiopterin Dehydratase	VMH	10727395 1355046 1988938
MMDBr0004046	4a-Hydroxytetrahydrobiopterin	O2'-4a-cyclic-tetrahydrobiopterin	Not Available	4A-Hydroxytetrahydrobiopterin Dehydratase	VMH	10727395 8921004
MMDBr0004047	4a-Hydroxytetrahydrobiopterin	O2'-4a-cyclic-tetrahydrobiopterin	Pterin-4 alpha-carbinolamine dehydratase/dimerization cofactor of hepatocyte nuclear factor 1 alpha	4A-Hydroxytetrahydrobiopterin Dehydratase	VMH	10727395 8921004
MMDBr0010288	4a-Hydroxytetrahydrobiopterin	4a-Hydroxytetrahydrobiopterin	Not Available	HMR_4538	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	51	Human feces; Human sputum; Human ; Human pleural fluid plaque	Metabolic reconstruction
Bacteria	Synergistetes	2	Human feces	Metabolic reconstruction
Bacteria	Firmicutes	22	Human feces; Human	Metabolic reconstruction
Bacteria	Actinobacteria	16	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Bacteroidetes	4	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	1		Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0002281

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022944

KNApSAcK ID

Not Available

Chemspider ID

30792101

KEGG Compound ID

C15522

BioCyc ID

CPD-5881

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6591

PubChem Compound

135476770

PDB ID

Not Available

ChEBI ID

15642

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Rebrin I, Bailey SW, Boerth SR, Ardell MD, Ayling JE: Catalytic characterization of 4a-hydroxytetrahydropterin dehydratase. Biochemistry. 1995 May 2;34(17):5801-10. doi: 10.1021/bi00017a011. [PubMed:7727440 ]
Davis MD, Kaufman S: Products of the tyrosine-dependent oxidation of tetrahydrobiopterin by rat liver phenylalanine hydroxylase. Arch Biochem Biophys. 1993 Jul;304(1):9-16. doi: 10.1006/abbi.1993.1315. [PubMed:8323303 ]
Almas B, Haavik J, Flatmark T: Characterization of a novel pterin intermediate formed in the catalytic cycle of tyrosine hydroxylase. Biochem J. 1996 Nov 1;319 ( Pt 3):947-51. doi: 10.1042/bj3190947. [PubMed:8921004 ]
Rebrin I, Thony B, Bailey SW, Ayling JE: Stereospecificity and catalytic function of histidine residues in 4a-hydroxy-tetrahydropterin dehydratase/DCoH. Biochemistry. 1998 Aug 11;37(32):11246-54. doi: 10.1021/bi980663h. [PubMed:9698371 ]

Showing metabocard for 4a-Hydroxytetrahydrobiopterin (MMDBc0047939)

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