MiMeDB: Showing metabocard for 4a-Carbinolamine tetrahydrobiopterin (MMDBc0032005)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:58:20 UTC

Update Date

2024-10-13 14:10:22 UTC

Metabolite ID

MMDBc0032005

Metabolite Identification

Common Name

4a-Carbinolamine tetrahydrobiopterin

Description

NULL

Structure

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

HMDB0002215
     RDKit          3D
4a-Carbinolamine tetrahydrobiopterin
 30 31  0  0  0  0  0  0  0  0999 V2000
   -3.6864    0.8308    0.5723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2350    0.5263    0.3068 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6836    1.5944   -0.3522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1565   -0.7579   -0.4845 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7574   -1.7538    0.3104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7490   -1.1576   -0.8448 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1858   -0.2968   -1.9155 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1211    0.2401   -1.5971 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7620    0.0186   -0.5211 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9781    0.6065   -0.3953 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6599    0.3749    0.7395 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9479    0.9894    0.8880 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1792   -0.3998    1.7185 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9797   -1.0003    1.6346 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4940   -1.7309    2.5250 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2387   -0.7855    0.4721 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0856   -1.3248    0.3199 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2501    0.9960   -0.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7321    1.7886    1.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1856    0.0254    1.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7612    0.3459    1.2978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1075    2.0960    0.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7666   -0.6527   -1.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7306   -1.6951    0.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8519   -2.2063   -1.2685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0349   -0.8767   -2.8775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8314    0.5458   -2.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3904    1.2185   -1.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4377    1.4251    0.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4312    1.0159    1.8118 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  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17  6  1  0
 16  9  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  1
  3 22  1  0
  4 23  1  6
  5 24  1  0
  6 25  1  6
  7 26  1  0
  7 27  1  0
 10 28  1  0
 12 29  1  0
 12 30  1  0
M  END


  Mrv0541 02231219262D          

 18 19  0  0  1  0            999 V2000
   29.0166   -5.6375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5845   -6.4570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.6753   -6.4371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2463   -3.9621    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.6753   -3.9621    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.1273   -3.9334    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.1273   -5.6407    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.9608   -5.1996    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.3037   -5.2223    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   27.5876   -5.6320    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   28.3069   -4.3972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8747   -5.2167    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.8747   -4.3574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9608   -4.3746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3897   -4.3746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6753   -5.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3897   -5.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8709   -5.8767    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  1  6  0  0  0
 10  2  1  6  0  0  0
  3 16  2  0  0  0  0
  4 14  1  0  0  0  0
  5 14  1  0  0  0  0
  5 15  1  0  0  0  0
  6 13  1  0  0  0  0
  6 15  2  0  0  0  0
  7 12  1  0  0  0  0
  7 17  2  0  0  0  0
  8 14  2  0  0  0  0
  8 16  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 18  1  1  0  0  0
 15 17  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0032005

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]1(CN=C2NC(N)=NC(=O)C2=N1)[C@@H](O)[C@H](C)O

> <INCHI_IDENTIFIER>
InChI=1S/C9H13N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3-4,6,15-16H,2H2,1H3,(H3,10,11,13,14,17)/t3-,4+,6-/m0/s1

> <INCHI_KEY>
ZHQJVZLJDXWFFX-RPDRRWSUSA-N

> <FORMULA>
C9H13N5O3

> <MOLECULAR_WEIGHT>
239.2312

> <EXACT_MASS>
239.101839307

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
22.767269838087163

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.41

> <JCHEM_LOGP>
-1.9607441773333334

> <ALOGPS_LOGS>
-2.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.306047403596985

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.687962413210548

> <JCHEM_PKA_STRONGEST_BASIC>
1.8206611525535423

> <JCHEM_POLAR_SURFACE_AREA>
132.66

> <JCHEM_REFRACTIVITY>
57.03320000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.45e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-6,7-dihydro-1H-pteridin-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002215
     RDKit          3D
4a-Carbinolamine tetrahydrobiopterin
 30 31  0  0  0  0  0  0  0  0999 V2000
   -3.6864    0.8308    0.5723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2350    0.5263    0.3068 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6836    1.5944   -0.3522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1565   -0.7579   -0.4845 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7574   -1.7538    0.3104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7490   -1.1576   -0.8448 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1858   -0.2968   -1.9155 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1211    0.2401   -1.5971 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7620    0.0186   -0.5211 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9781    0.6065   -0.3953 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6599    0.3749    0.7395 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9479    0.9894    0.8880 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1792   -0.3998    1.7185 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9797   -1.0003    1.6346 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4940   -1.7309    2.5250 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2387   -0.7855    0.4721 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0856   -1.3248    0.3199 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2501    0.9960   -0.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7321    1.7886    1.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1856    0.0254    1.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7612    0.3459    1.2978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1075    2.0960    0.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7666   -0.6527   -1.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7306   -1.6951    0.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8519   -2.2063   -1.2685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0349   -0.8767   -2.8775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8314    0.5458   -2.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3904    1.2185   -1.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4377    1.4251    0.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4312    1.0159    1.8118 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  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17  6  1  0
 16  9  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  1
  3 22  1  0
  4 23  1  6
  5 24  1  0
  6 25  1  6
  7 26  1  0
  7 27  1  0
 10 28  1  0
 12 29  1  0
 12 30  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      54.164 -10.523   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      51.491 -12.053   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      46.061 -12.016   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      43.393  -7.396   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      46.061  -7.396   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      48.771  -7.342   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      48.771 -10.529   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      44.727  -9.706   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      52.834  -9.748   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      51.497 -10.513   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      52.840  -8.208   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      50.166  -9.738   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      50.166  -8.134   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      44.727  -8.166   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      47.394  -8.166   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      46.061 -10.476   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      47.394  -9.706   0.000  0.00  0.00           C+0
HETATM   18  H   UNK     0      50.159 -10.970   0.000  0.00  0.00           H+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   16                                                            
CONECT    4   14                                                            
CONECT    5   14   15                                                       
CONECT    6   13   15                                                       
CONECT    7   12   17                                                       
CONECT    8   14   16                                                       
CONECT    9    1   10   11                                                  
CONECT   10    2    9   12                                                  
CONECT   11    9                                                            
CONECT   12    7   10   13   18                                             
CONECT   13    6   12                                                       
CONECT   14    4    5    8                                                  
CONECT   15    5    6   17                                                  
CONECT   16    3    8   17                                                  
CONECT   17    7   15   16                                                  
CONECT   18   12                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0002215
HETATM    1  C1  UNL     1      -3.686   0.831   0.572  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.235   0.526   0.307  1.00  0.00           C  
HETATM    3  O1  UNL     1      -1.684   1.594  -0.352  1.00  0.00           O  
HETATM    4  C3  UNL     1      -2.156  -0.758  -0.484  1.00  0.00           C  
HETATM    5  O2  UNL     1      -2.757  -1.754   0.310  1.00  0.00           O  
HETATM    6  C4  UNL     1      -0.749  -1.158  -0.845  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.186  -0.297  -1.915  1.00  0.00           C  
HETATM    8  N1  UNL     1       1.121   0.240  -1.597  1.00  0.00           N  
HETATM    9  C6  UNL     1       1.762   0.019  -0.521  1.00  0.00           C  
HETATM   10  N2  UNL     1       2.978   0.606  -0.395  1.00  0.00           N  
HETATM   11  C7  UNL     1       3.660   0.375   0.740  1.00  0.00           C  
HETATM   12  N3  UNL     1       4.948   0.989   0.888  1.00  0.00           N  
HETATM   13  N4  UNL     1       3.179  -0.400   1.719  1.00  0.00           N  
HETATM   14  C8  UNL     1       1.980  -1.000   1.635  1.00  0.00           C  
HETATM   15  O3  UNL     1       1.494  -1.731   2.525  1.00  0.00           O  
HETATM   16  C9  UNL     1       1.239  -0.785   0.472  1.00  0.00           C  
HETATM   17  N5  UNL     1       0.086  -1.325   0.320  1.00  0.00           N  
HETATM   18  H1  UNL     1      -4.250   0.996  -0.385  1.00  0.00           H  
HETATM   19  H2  UNL     1      -3.732   1.789   1.161  1.00  0.00           H  
HETATM   20  H3  UNL     1      -4.186   0.025   1.145  1.00  0.00           H  
HETATM   21  H4  UNL     1      -1.761   0.346   1.298  1.00  0.00           H  
HETATM   22  H5  UNL     1      -1.108   2.096   0.250  1.00  0.00           H  
HETATM   23  H6  UNL     1      -2.767  -0.653  -1.396  1.00  0.00           H  
HETATM   24  H7  UNL     1      -3.731  -1.695   0.148  1.00  0.00           H  
HETATM   25  H8  UNL     1      -0.852  -2.206  -1.269  1.00  0.00           H  
HETATM   26  H9  UNL     1      -0.035  -0.877  -2.878  1.00  0.00           H  
HETATM   27  H10 UNL     1      -0.831   0.546  -2.212  1.00  0.00           H  
HETATM   28  H11 UNL     1       3.390   1.219  -1.136  1.00  0.00           H  
HETATM   29  H12 UNL     1       5.438   1.425   0.085  1.00  0.00           H  
HETATM   30  H13 UNL     1       5.431   1.016   1.812  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    9
CONECT    9   10   16
CONECT   10   11   28
CONECT   11   12   13   13
CONECT   12   29   30
CONECT   13   14
CONECT   14   15   15   16
CONECT   16   17   17
END

HMDB0002215
     RDKit          3D
4a-Carbinolamine tetrahydrobiopterin
 30 31  0  0  0  0  0  0  0  0999 V2000
   -3.6864    0.8308    0.5723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2350    0.5263    0.3068 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6836    1.5944   -0.3522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1565   -0.7579   -0.4845 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7574   -1.7538    0.3104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7490   -1.1576   -0.8448 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1858   -0.2968   -1.9155 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1211    0.2401   -1.5971 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7620    0.0186   -0.5211 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9781    0.6065   -0.3953 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6599    0.3749    0.7395 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9479    0.9894    0.8880 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1792   -0.3998    1.7185 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9797   -1.0003    1.6346 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4940   -1.7309    2.5250 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2387   -0.7855    0.4721 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0856   -1.3248    0.3199 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2501    0.9960   -0.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7321    1.7886    1.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1856    0.0254    1.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7612    0.3459    1.2978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1075    2.0960    0.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7666   -0.6527   -1.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7306   -1.6951    0.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8519   -2.2063   -1.2685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0349   -0.8767   -2.8775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8314    0.5458   -2.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3904    1.2185   -1.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4377    1.4251    0.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4312    1.0159    1.8118 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  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17  6  1  0
 16  9  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  1
  3 22  1  0
  4 23  1  6
  5 24  1  0
  6 25  1  6
  7 26  1  0
  7 27  1  0
 10 28  1  0
 12 29  1  0
 12 30  1  0
M  END

Synonyms

Value	Source
(6R)-2-Amino-6-[(1R,2S)-1,2-dihydroxypropyl]-7,8-dihydro-6H-pteridin-4-one	ChEBI
(6R)-6-[(1R,2S)-1,2-Dihydroxypropyl]-7,8-dihydro-6H-pterin	ChEBI
6,7-Dihydrobiopterin	ChEBI
Q-H2BPT	ChEBI
Quinoid-dihydrobiopterin	ChEBI
Quinonoid 6,7-dihydrobiopterin	ChEBI
6-[(1R,2S)-1,2-Dihydroxypropyl]-6,7-dihydropterin	Kegg
(6R)-6-(L-erythro-1,2-Dihydroxypropyl)-7,8-dihydro-6H-pterin	KEGG
1,3,5-Benzenetriol	HMDB
1,3,5-Trihydroxybenzene	HMDB
1,3,5-Trihydroxybenzene anhydrate	HMDB
1,3,5-Trihydroxybenzene anhydrous	HMDB
1,3,5-Trihydroxybenzene dihydrate	HMDB
1.3.5-Trihydroxybenzene	HMDB
4a-Hydroxy-BH4	HMDB
Phloroglucin	HMDB
Phloroglucinol	HMDB
Phloroglucinol 2-hydrate	HMDB
Phloroglucinol anhydrous	HMDB
Phloroglucinol dihydrate	HMDB
4a-Carbinolamine tetrahydrobiopterin	ChEBI

Molecular Formula

C₉H₁₃N₅O₃

Average Mass

239.2312

Monoisotopic Mass

239.101839307

IUPAC Name

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

Traditional Name

(6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-6,7-dihydro-1H-pteridin-4-one

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CN=C2NC(N)=NC(=O)C2=N1)[C@@H](O)[C@H](C)O

InChI Identifier

InChI=1S/C9H13N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3-4,6,15-16H,2H2,1H3,(H3,10,11,13,14,17)/t3-,4+,6-/m0/s1

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.45 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-2	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	7.69	ChemAxon
pKa (Strongest Basic)	1.82	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	57.03 m³·mol⁻¹	ChemAxon
Polarizability	22.77 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-006y-9720000000-50fd5953817583278634	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-000i-8195000000-9404a6359e671c74945f	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 (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006x-0090000000-b31c78b3d2240e4d4d45	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0h93-0970000000-508a25d7544d515036cb	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03ka-1900000000-1e9eed496ea8538f6b17	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0390000000-2d9ea64f3bb5145f0a23	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0930000000-8ebd581c355cfdf37d59	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f6x-9600000000-17f4849b21b55c8bd6b3	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0090000000-4a6c2eb22faca2bd9c6b	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dl-0290000000-bd0c7392c3c2b36c22d8	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0005-3900000000-5b4e107d96010101e0f1	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0920000000-a8316dedaf2ff7f68dc9	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03fu-0910000000-d37051ed31fd26c17d8a	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0uxu-8900000000-28d0495ab110064f993b	2021-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Epidermis
Feces

Tissue Locations

Epidermis

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
MMDBp0192192	Dihydropteridine reductase	Unknown	P09417	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

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0000683	5-Methyltetrahydrofolic acid	5,10-Methylene-THF	Not Available	VMH	3735413
MMDBr0002225	4a-Hydroxytetrahydrobiopterin	4a-Carbinolamine tetrahydrobiopterin	Not Available	VMH	10727395
MMDBr0002538	L-Phenylalanine	4a-Carbinolamine tetrahydrobiopterin	phenylalanine hydroxylase	VMH	3298976 4074362
MMDBr0002541	L-erythro-tetrahydrobiopterin	5-Hydroxy-L-tryptophan	tryptophan hydroxylase 1	VMH	30371894
MMDBr0007314	4a-Carbinolamine tetrahydrobiopterin	L-erythro-tetrahydrobiopterin	Not Available	VMH	30371894
MMDBr0007609	4a-Carbinolamine tetrahydrobiopterin	L-erythro-tetrahydrobiopterin	Not Available	VMH	30371894
MMDBr0008334	L-Phenylalanine	4a-Carbinolamine tetrahydrobiopterin	Not Available	VMH	30371894
MMDBr0010407	L-erythro-tetrahydrobiopterin	L-Dopa	tyrosine hydroxylase	VMH; KEGG	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	305	Human feces; Human sputum; Human ; Human pleural fluid plaque; Human unknown; Pig ; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal; River trout ; Turkey ; Sheep ; American dog tick	Unknown; Metabolic reconstruction
Bacteria	Synergistetes	1		Metabolic reconstruction
Bacteria	Firmicutes	135	Human feces; Human ; Human subgingival plaque; Cattle	Metabolic reconstruction
Bacteria	Actinobacteria	42	Human feces; Human ; Cattle	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Bacteroidetes	16	Human feces; Human ; Human supragingival plaque; Human subgingival plaque; Human saliva	Metabolic reconstruction
Archaea	Euryarchaeota	1		Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Bacteria	Verrucomicrobia	2	Human ; Human feces	Metabolic reconstruction
Bacteria	Fusobacteria	2	Human feces; Human	Metabolic reconstruction
Bacteria	Acidobacteria	3
Bacteria	Aquificae	1
Bacteria	Chloroflexi	7
Bacteria	Chlorobi	5
Bacteria	Cyanobacteria	22	Human
Archaea/Archaea	Euryarchaeota	5		Metabolic reconstruction
Archaea/Archaea	Crenarchaeota	6		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	2
Bacteria	nah	1

Exposure Sources

Source Type	Activity	Data Source	Reference
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified							HMDB
Human Blood	Detected and Quantified	4.18	0.04	uM	Adult (>18 years old)	Male	Normal	HMDB	8376528
Human Epidermis	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0002215

DrugBank ID

DB02562

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022911

KNApSAcK ID

Not Available

Chemspider ID

117564

KEGG Compound ID

C00268

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6552

PubChem Compound

133246

PDB ID

Not Available

ChEBI ID

43120

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Fiset C, LeBel M: Influence of the menstrual cycle on the absorption and elimination of D-xylose. Clin Pharmacol Ther. 1990 Nov;48(5):529-36. doi: 10.1038/clpt.1990.189. [PubMed:2225712 ]
Davis MD, Kaufman S: Evidence for the formation of the 4a-carbinolamine during the tyrosine-dependent oxidation of tetrahydrobiopterin by rat liver phenylalanine hydroxylase. J Biol Chem. 1989 May 25;264(15):8585-96. [PubMed:2722790 ]
Armarego WL, Randles D, Taguchi H: Peroxidase catalysed aerobic degradation of 5,6,7,8-tetrahydrobiopterin at physiological pH. Eur J Biochem. 1983 Oct 3;135(3):393-403. doi: 10.1111/j.1432-1033.1983.tb07666.x. [PubMed:6617639 ]
Schallreuter KU, Wood JM, Pittelkow MR, Gutlich M, Lemke KR, Rodl W, Swanson NN, Hitzemann K, Ziegler I: Regulation of melanin biosynthesis in the human epidermis by tetrahydrobiopterin. Science. 1994 Mar 11;263(5152):1444-6. doi: 10.1126/science.8128228. [PubMed:8128228 ]
Kim H, Roh H, Lee HJ, Chung SY, Choi SO, Lee KR, Han SB: Determination of phloroglucinol in human plasma by high-performance liquid chromatography-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 25;792(2):307-12. doi: 10.1016/s1570-0232(03)00316-7. [PubMed:12860038 ]
Ismaili L, Refouvelet B, Xicluna A, Robert JF, Guillaume YC: Phloroglucinol: novel synthesis and role of the magnesium cation on its binding with human serum albumin (HSA) using a biochromatographic approach based on Langmuir isotherms. J Pharm Biomed Anal. 2003 Jul 14;32(3):549-53. doi: 10.1016/s0731-7085(03)00220-6. [PubMed:14565560 ]
Jafri W, Yakoob J, Hussain S, Jafri N, Islam M: Phloroglucinol in irritable bowel syndrome. J Pak Med Assoc. 2006 Jan;56(1):5-8. [PubMed:16454126 ]

Showing metabocard for 4a-Carbinolamine tetrahydrobiopterin (MMDBc0032005)

MOL for #<Metabolite:0x00007fdb2f6cc5e8>

3D MOL for #<Metabolite:0x00007fdb2f6cc5e8>

3D SDF for #<Metabolite:0x00007fdb2f6cc5e8>

3D-SDF for #<Metabolite:0x00007fdb2f6cc5e8>

PDB for #<Metabolite:0x00007fdb2f6cc5e8>

3D PDB for #<Metabolite:0x00007fdb2f6cc5e8>

SMILES for #<Metabolite:0x00007fdb2f6cc5e8>

INCHI for #<Metabolite:0x00007fdb2f6cc5e8>

Structure for #<Metabolite:0x00007fdb2f6cc5e8>

3D Structure for #<Metabolite:0x00007fdb2f6cc5e8>