MiMeDB: Showing metabocard for Dihydroneopterin (MMDBc0049934)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-29 22:46:35 UTC

Update Date

2023-12-14 16:53:09 UTC

Metabolite ID

MMDBc0049934

Metabolite Identification

Common Name

Dihydroneopterin

Description

7,8-Dihydroneopterin, also known as dihydroneopterin, 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 synthesized in several parts of the body, including the pineal gland. 7,8-Dihydroneopterin is a strong basic compound (based on its pKa). Within humans, 7,8-dihydroneopterin participates in a number of enzymatic reactions. In particular, 7,8-dihydroneopterin can be biosynthesized from sepiapterin; which is catalyzed by the enzyme sepiapterin reductase or carbonyl reductase [NADPH] 1. In humans, 7,8-dihydroneopterin is involved in the metabolic disorder called hyperphenylalaninemia due to 6-pyruvoyltetrahydropterin synthase (PTPS) deficiency. 7,8-Dihydroneopterin is produced by human monocyte-derived macrophages upon stimulation with interferon-gamma. Increased amounts of 7,8-dihydroneopterin in human body fluids are found in many disorders, including viral infections and autoimmune diseases (PMID: 12804528 ).

Structure

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

HMDB0002275
     RDKit          3D
7,8-Dihydroneopterin
 31 32  0  0  0  0  0  0  0  0999 V2000
    5.6831   -0.2607   -0.4323 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2666   -0.1463   -0.6064 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7152   -0.2645   -1.8286 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3825   -0.1564   -1.9869 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8360   -0.2648   -3.1360 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5269    0.0766   -0.9274 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1158    0.1949    0.3181 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4565    0.0805    0.4391 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2608    0.4463    1.4114 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1582    0.5189    1.2784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6273    0.3792   -0.0836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1050    0.4858   -0.3443 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5505    1.7505    0.0211 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7617   -0.6184    0.4470 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2152   -1.8176   -0.0102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2686   -0.6154    0.2663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8423    0.5508    0.7059 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1211    0.1796   -1.0790 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2103   -1.1114   -0.6466 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2287    0.5644   -0.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8798    0.1753    1.4066 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7303    0.5822    2.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5579    1.4424    1.7865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5426   -0.3815    1.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3176    0.3941   -1.4353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4314    1.9135    0.9816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5093   -0.4743    1.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4948   -2.5551    0.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4802   -0.8577   -0.7813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6520   -1.4398    0.9318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8994    1.2290   -0.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 11 18  2  0
  8  2  1  0
 18  6  1  0
  1 19  1  0
  1 20  1  0
  8 21  1  0
  9 22  1  0
 10 23  1  0
 10 24  1  0
 12 25  1  6
 13 26  1  0
 14 27  1  1
 15 28  1  0
 16 29  1  0
 16 30  1  0
 17 31  1  0
M  END


  Mrv1652304222019492D          

 18 19  0  0  0  0            999 V2000
 9996.990410000.0315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.5617 9997.5486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.8415 9999.2046    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.5571 9998.7900    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.841510000.0295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.2706 9999.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.5571 9997.9661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.9842 9998.7900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.9904 9999.2001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.2760 9998.7876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9996.2760 9997.9626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.9904 9997.5503    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4160 9999.2002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.7016 9998.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.7016 9997.9627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4160 9997.5504    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1304 9997.9627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1304 9998.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  6  0  0  0
  4  6  1  0  0  0  0
  4  7  1  1  0  0  0
  6  8  1  0  0  0  0
 14 15  2  0  0  0  0
 17 18  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
 13 14  1  0  0  0  0
 13 18  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  1  9  2  0  0  0  0
 11  2  1  0  0  0  0
 18  3  1  0  0  0  0
 12 15  1  0  0  0  0
  9 14  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0049934

> <DATABASE_NAME>
MIME

> <SMILES>
NC1=NC(=O)C2=C(NCC(=N2)[C@H](O)[C@H](O)CO)N1

> <INCHI_IDENTIFIER>
InChI=1S/C9H13N5O4/c10-9-13-7-5(8(18)14-9)12-3(1-11-7)6(17)4(16)2-15/h4,6,15-17H,1-2H2,(H4,10,11,13,14,18)/t4-,6+/m1/s1

> <INCHI_KEY>
YQIFAMYNGGOTFB-XINAWCOVSA-N

> <FORMULA>
C9H13N5O4

> <MOLECULAR_WEIGHT>
255.2306

> <EXACT_MASS>
255.096753929

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
24.004282973536625

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-6-[(1S,2R)-1,2,3-trihydroxypropyl]-1,4,7,8-tetrahydropteridin-4-one

> <ALOGPS_LOGP>
-2.10

> <JCHEM_LOGP>
-3.3354137886666666

> <ALOGPS_LOGS>
-2.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.244737730644115

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.371218174035606

> <JCHEM_PKA_STRONGEST_BASIC>
0.2826065573151887

> <JCHEM_POLAR_SURFACE_AREA>
152.56000000000003

> <JCHEM_REFRACTIVITY>
69.657

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.86e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-6-[(1S,2R)-1,2,3-trihydroxypropyl]-7,8-dihydro-1H-pteridin-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002275
     RDKit          3D
7,8-Dihydroneopterin
 31 32  0  0  0  0  0  0  0  0999 V2000
    5.6831   -0.2607   -0.4323 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2666   -0.1463   -0.6064 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7152   -0.2645   -1.8286 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3825   -0.1564   -1.9869 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8360   -0.2648   -3.1360 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5269    0.0766   -0.9274 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1158    0.1949    0.3181 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4565    0.0805    0.4391 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2608    0.4463    1.4114 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1582    0.5189    1.2784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6273    0.3792   -0.0836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1050    0.4858   -0.3443 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5505    1.7505    0.0211 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7617   -0.6184    0.4470 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2152   -1.8176   -0.0102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2686   -0.6154    0.2663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8423    0.5508    0.7059 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1211    0.1796   -1.0790 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2103   -1.1114   -0.6466 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2287    0.5644   -0.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8798    0.1753    1.4066 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7303    0.5822    2.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5579    1.4424    1.7865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5426   -0.3815    1.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3176    0.3941   -1.4353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4314    1.9135    0.9816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5093   -0.4743    1.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4948   -2.5551    0.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4802   -0.8577   -0.7813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6520   -1.4398    0.9318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8994    1.2290   -0.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 11 18  2  0
  8  2  1  0
 18  6  1  0
  1 19  1  0
  1 20  1  0
  8 21  1  0
  9 22  1  0
 10 23  1  0
 10 24  1  0
 12 25  1  6
 13 26  1  0
 14 27  1  1
 15 28  1  0
 16 29  1  0
 16 30  1  0
 17 31  1  0
M  END

HEADER    PROTEIN                                 22-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-20         0                                  
HETATM    1  O   UNK     0    8661.0498666.725   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0    8658.3828662.091   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    8666.3718665.182   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8667.7078664.408   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8666.3718666.722   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8669.0388665.182   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8667.7078662.870   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8670.3718664.408   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    8661.0498665.173   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0    8659.7158664.404   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0    8659.7158662.864   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0    8661.0498662.094   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0    8663.7108665.174   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0    8662.3768664.404   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8662.3768662.864   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0    8663.7108662.094   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0    8665.0438662.864   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8665.0438664.404   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2   11                                                            
CONECT    3    4    5   18                                                  
CONECT    4    3    6    7                                                  
CONECT    5    3                                                            
CONECT    6    4    8                                                       
CONECT    7    4                                                            
CONECT    8    6                                                            
CONECT    9   10    1   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12    2                                                  
CONECT   12   11   15                                                       
CONECT   13   14   18                                                       
CONECT   14   15   13    9                                                  
CONECT   15   14   16   12                                                  
CONECT   16   15   17                                                       
CONECT   17   18   16                                                       
CONECT   18   17   13    3                                                  
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0002275
HETATM    1  N1  UNL     1       5.683  -0.261  -0.432  1.00  0.00           N  
HETATM    2  C1  UNL     1       4.267  -0.146  -0.606  1.00  0.00           C  
HETATM    3  N2  UNL     1       3.715  -0.265  -1.829  1.00  0.00           N  
HETATM    4  C2  UNL     1       2.383  -0.156  -1.987  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.836  -0.265  -3.136  1.00  0.00           O  
HETATM    6  C3  UNL     1       1.527   0.077  -0.927  1.00  0.00           C  
HETATM    7  C4  UNL     1       2.116   0.195   0.318  1.00  0.00           C  
HETATM    8  N3  UNL     1       3.456   0.080   0.439  1.00  0.00           N  
HETATM    9  N4  UNL     1       1.261   0.446   1.411  1.00  0.00           N  
HETATM   10  C5  UNL     1      -0.158   0.519   1.278  1.00  0.00           C  
HETATM   11  C6  UNL     1      -0.627   0.379  -0.084  1.00  0.00           C  
HETATM   12  C7  UNL     1      -2.105   0.486  -0.344  1.00  0.00           C  
HETATM   13  O2  UNL     1      -2.550   1.750   0.021  1.00  0.00           O  
HETATM   14  C8  UNL     1      -2.762  -0.618   0.447  1.00  0.00           C  
HETATM   15  O3  UNL     1      -2.215  -1.818  -0.010  1.00  0.00           O  
HETATM   16  C9  UNL     1      -4.269  -0.615   0.266  1.00  0.00           C  
HETATM   17  O4  UNL     1      -4.842   0.551   0.706  1.00  0.00           O  
HETATM   18  N5  UNL     1       0.121   0.180  -1.079  1.00  0.00           N  
HETATM   19  H1  UNL     1       6.210  -1.111  -0.647  1.00  0.00           H  
HETATM   20  H2  UNL     1       6.229   0.564  -0.065  1.00  0.00           H  
HETATM   21  H3  UNL     1       3.880   0.175   1.407  1.00  0.00           H  
HETATM   22  H4  UNL     1       1.730   0.582   2.358  1.00  0.00           H  
HETATM   23  H5  UNL     1      -0.558   1.442   1.787  1.00  0.00           H  
HETATM   24  H6  UNL     1      -0.543  -0.381   1.878  1.00  0.00           H  
HETATM   25  H7  UNL     1      -2.318   0.394  -1.435  1.00  0.00           H  
HETATM   26  H8  UNL     1      -2.431   1.913   0.982  1.00  0.00           H  
HETATM   27  H9  UNL     1      -2.509  -0.474   1.509  1.00  0.00           H  
HETATM   28  H10 UNL     1      -2.495  -2.555   0.591  1.00  0.00           H  
HETATM   29  H11 UNL     1      -4.480  -0.858  -0.781  1.00  0.00           H  
HETATM   30  H12 UNL     1      -4.652  -1.440   0.932  1.00  0.00           H  
HETATM   31  H13 UNL     1      -4.899   1.229  -0.023  1.00  0.00           H  
CONECT    1    2   19   20
CONECT    2    3    3    8
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7    7   18
CONECT    7    8    9
CONECT    8   21
CONECT    9   10   22
CONECT   10   11   23   24
CONECT   11   12   18   18
CONECT   12   13   14   25
CONECT   13   26
CONECT   14   15   16   27
CONECT   15   28
CONECT   16   17   29   30
CONECT   17   31
END

HMDB0002275
     RDKit          3D
7,8-Dihydroneopterin
 31 32  0  0  0  0  0  0  0  0999 V2000
    5.6831   -0.2607   -0.4323 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2666   -0.1463   -0.6064 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7152   -0.2645   -1.8286 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3825   -0.1564   -1.9869 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8360   -0.2648   -3.1360 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5269    0.0766   -0.9274 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1158    0.1949    0.3181 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4565    0.0805    0.4391 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2608    0.4463    1.4114 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1582    0.5189    1.2784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6273    0.3792   -0.0836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1050    0.4858   -0.3443 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5505    1.7505    0.0211 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7617   -0.6184    0.4470 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2152   -1.8176   -0.0102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2686   -0.6154    0.2663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8423    0.5508    0.7059 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1211    0.1796   -1.0790 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2103   -1.1114   -0.6466 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2287    0.5644   -0.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8798    0.1753    1.4066 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7303    0.5822    2.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5579    1.4424    1.7865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5426   -0.3815    1.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3176    0.3941   -1.4353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4314    1.9135    0.9816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5093   -0.4743    1.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4948   -2.5551    0.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4802   -0.8577   -0.7813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6520   -1.4398    0.9318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8994    1.2290   -0.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 11 18  2  0
  8  2  1  0
 18  6  1  0
  1 19  1  0
  1 20  1  0
  8 21  1  0
  9 22  1  0
 10 23  1  0
 10 24  1  0
 12 25  1  6
 13 26  1  0
 14 27  1  1
 15 28  1  0
 16 29  1  0
 16 30  1  0
 17 31  1  0
M  END

Synonyms

Value	Source
2-Amino-4-hydroxy-6-(D-erythro-1,2,3-trihydroxypropyl)-7,8-dihydropteridine	ChEBI
2-AMINO-7,8-dihydro-6-(1,2,3-trihydroxypropyl)-4(1H)-pteridinone	ChEBI
Dihydroneopterin	ChEBI
7,8-Dihydro-neopterin	HMDB
2-Amino-4-hydroxy-6-(D-erythro-1',2',3'-trihydroxypropyl)-7,8-dihydropteridine	HMDB
2-Amino-4-hydroxy-6-(D-erythro-1’,2’,3’-trihydroxypropyl)-7,8-dihydropteridine	HMDB
2-Amino-7,8-dihydro-6-[(1S,2R)-1,2,3-trihydroxypropyl]-4(3H)-pteridinone	HMDB
7,8-Dihydro-D-erythro-neopterin	HMDB
7,8-Dihydro-D-neopterin	HMDB
D-Erythro-7,8-dihydroneopterin	HMDB
7,8-Dihydroneopterin	HMDB

Molecular Formula

C₉H₁₃N₅O₄

Average Mass

255.2306

Monoisotopic Mass

255.096753929

IUPAC Name

2-amino-6-[(1S,2R)-1,2,3-trihydroxypropyl]-1,4,7,8-tetrahydropteridin-4-one

Traditional Name

2-amino-6-[(1S,2R)-1,2,3-trihydroxypropyl]-7,8-dihydro-1H-pteridin-4-one

CAS Registry Number

Not Available

SMILES

NC1=NC(=O)C2=C(NCC(=N2)[C@H](O)[C@H](O)CO)N1

InChI Identifier

InChI=1S/C9H13N5O4/c10-9-13-7-5(8(18)14-9)12-3(1-11-7)6(17)4(16)2-15/h4,6,15-17H,1-2H2,(H4,10,11,13,14,18)/t4-,6+/m1/s1

InChI Key

YQIFAMYNGGOTFB-XINAWCOVSA-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
Vinylogous amide
Heteroaromatic compound
Ketimine
Secondary alcohol
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Secondary amine
Polyol
Amine
Organopnictogen compound
Primary amine
Primary alcohol
Organic oxide
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Imine
Organic oxygen compound
Organic nitrogen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dihydropterin (CHEBI:17001 )
neopterins (CHEBI:17001 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.86 g/L	ALOGPS
logP	-2.1	ALOGPS
logP	-3.3	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	9.37	ChemAxon
pKa (Strongest Basic)	0.28	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	3	ChemAxon
Refractivity	69.66 m³·mol⁻¹	ChemAxon
Polarizability	24 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

Not Available

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
MMDBp0191763	Alkaline phosphatase, placental type	Unknown	P05187	Homo sapiens
MMDBp0191766	Intestinal-type alkaline phosphatase	Unknown	P09923	Homo sapiens
MMDBp0191769	Alkaline phosphatase, tissue-nonspecific isozyme	Unknown	P05186	Homo sapiens
MMDBp0191772	Alkaline phosphatase, placental-like	Unknown	P10696	Homo sapiens
MMDBp0192101	6-pyruvoyl tetrahydrobiopterin synthase	Unknown	Q03393	Homo sapiens
MMDBp0194160	RuvB-like 2	Enzyme	Q9Y230	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0007615	Dihydroneopterin	6-Hydroxymethyl dihydropterin	Not Available	Dihydroneopterin aldolase	VMH	30371894
MMDBr0007674	Dihydroneopterin triphosphate	Dihydroneopterin	Not Available	Alkaline phosphatase (Dihydroneopterin)	VMH	30371894
MMDBr0008476	Dihydroneopterin monophosphate	Dihydroneopterin	Not Available	Dihydroneopterin monophosphate dephosphorylase	VMH	30371894
MMDBr0012920	Dihydroneopterin	6-Hydroxymethyl dihydropterin	Folic acid synthesis protein fol1	Aldol addition (or reverse)	RHEA	34755880
MMDBr0016128	Dihydroneopterin	7,8-dihydromonapterin	Dihydroneopterin aldolase	Aldol addition (or reverse)	RHEA	34755880
MMDBr0016129	Dihydroneopterin	7,8-dihydroxanthopterin	Dihydroneopterin aldolase	Aldol addition (or reverse)	RHEA	34755880

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	166	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal; Human stool	Metabolic reconstruction
Bacteria	Firmicutes	282	Pig ; Human feces; Human ; Cattle ; Human pleural fluid plaque; Human supragingival plaque; Human saliva; Human subgingival plaque	Metabolic reconstruction
Bacteria	Actinobacteria	98	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human ; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva; Cattle	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	127	Human feces; Human appendix biopsy; Human ; Human stool; Human urine; Human gastric fluid; Human saliva; Human supragingival plaque; Human subgingival plaque	Metabolic reconstruction
Bacteria	Fusobacteria	18	Human feces; Human	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	4		Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Bacteria	Synergistetes	2	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Archaea	Euryarchaeota	1		Metabolic reconstruction
Bacteria	Chlamydiae	3	Human
Bacteria	nah	1
Archaea/Archaea	Euryarchaeota	3		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

HMDB0002275

DrugBank ID

DB04425

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

65074

PDB ID

Not Available

ChEBI ID

17001

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Fuchs D, Reibnegger G, Werner ER, Wachter H: Increased 7,8-dihydroneopterin and reduced methyl-group metabolism in HIV-1 infection. Lancet. 1990 May 12;335(8698):1167. doi: 10.1016/0140-6736(90)91176-b. [PubMed:1971904 ]
Gieseg SP, Reibnegger G, Wachter H, Esterbauer H: 7,8 Dihydroneopterin inhibits low density lipoprotein oxidation in vitro. Evidence that this macrophage secreted pteridine is an anti-oxidant. Free Radic Res. 1995 Aug;23(2):123-36. doi: 10.3109/10715769509064027. [PubMed:7581810 ]
Baier-Bitterlich G, Baier G, Fuchs D, Bock G, Hausen A, Utermann G, Pavelka M, Wachter H: Role of 7,8-dihydroneopterin in T-cell apoptosis and HTLV-1 transcription in vitro. Oncogene. 1996 Nov 21;13(10):2281-5. [PubMed:8950996 ]
Baier-Bitterlich G, Fuchs D, Zangerle R, Baeuerle PA, Werner ER, Fresser F, Uberall F, Baier G, Wachter H: trans-Activation of the HIV type 1 promoter by 7,8-dihydroneopterin in vitro. AIDS Res Hum Retroviruses. 1997 Jan 20;13(2):173-8. doi: 10.1089/aid.1997.13.173. [PubMed:9007202 ]
Baier-Bitterlich G, Fuchs D, Wachter H: 7,8-Dihydroneopterin upregulates interferon-gamma promoter in T cells. Immunobiology. 1996;196(4):350-5. doi: 10.1016/s0171-2985(96)80057-x. [PubMed:9061375 ]
Wirleitner B, Baier-Bitterlich G, Bock G, Widner B, Fuchs D: 7,8-Dihydroneopterin-induced apoptosis in Jurkat T lymphocytes: a comparison with anti-Fas- and hydrogen peroxide-mediated cell death. Biochem Pharmacol. 1998 Nov 1;56(9):1181-7. doi: 10.1016/s0006-2952(98)00168-3. [PubMed:9802329 ]
Pagel H, Fandrey J, Schobersberger W, Fuchs D, Jelkmann W: Effects of neopterin and 7,8-dihydroneopterin on hypoxia-induced renal erythropoietin production. Eur J Haematol. 1999 May;62(5):341-5. doi: 10.1111/j.1600-0609.1999.tb01913.x. [PubMed:10359064 ]
Speth C, Stockl G, Fuchs D, Wirleitner B, Widner B, Wurzner R, Mohsenipour I, Lass-Florl C, Dierich MP: Inflammation marker 7,8-dihydroneopterin induces apoptosis of neurons and glial cells: a potential contribution to neurodegenerative processes. Immunobiology. 2000 Nov;202(5):460-76. doi: 10.1016/S0171-2985(00)80104-7. [PubMed:11205375 ]
Gieseg SP, Maghzal G, Glubb D: Protection of erythrocytes by the macrophage synthesized antioxidant 7,8 dihydroneopterin. Free Radic Res. 2001 Feb;34(2):123-36. doi: 10.1080/10715760100300121. [PubMed:11264890 ]
Wirleitner B, Czaputa R, Oettl K, Bock G, Widner B, Reibnegger G, Baier G, Fuchs D, Baier-Bitterlich G: Induction of apoptosis by 7,8-dihydroneopterin: involvement of radical formation. Immunobiology. 2001 May;203(4):629-41. doi: 10.1016/s0171-2985(01)80012-7. [PubMed:11402497 ]
Gieseg SP, Whybrow J, Glubb D, Rait C: Protection of U937 cells from free radical damage by the macrophage synthesized antioxidant 7,8-dihydroneopterin. Free Radic Res. 2001 Sep;35(3):311-8. doi: 10.1080/10715760100300841. [PubMed:11697129 ]
Enzinger C, Wirleitner B, Lutz C, Bock G, Tomaselli B, Baier G, Fuchs D, Baier-Bitterlich G: 7,8-Dihydroneopterin induces apoptosis of Jurkat T-lymphocytes via a Bcl-2-sensitive pathway. Eur J Cell Biol. 2002 Apr;81(4):197-202. doi: 10.1078/0171-9335-00236. [PubMed:12018387 ]
Horejsi R, Jung C, Moller R, Tafeit E, Reibnegger G: Generation of carbon monoxide and iron from hemeproteins in the presence of 7,8-dihydroneopterin. Biochim Biophys Acta. 2002 Jun 6;1571(2):124-30. doi: 10.1016/s0304-4165(02)00206-4. [PubMed:12049792 ]
Herpfer I, Greilberger J, Ledinski G, Widner B, Fuchs D, Jurgens G: Neopterin and 7,8-dihydroneopterin interfere with low density lipoprotein oxidation mediated by peroxynitrite and/or copper. Free Radic Res. 2002 May;36(5):509-20. doi: 10.1080/10715760290025898. [PubMed:12150539 ]
Duggan S, Rait C, Platt A, Gieseg S: Protein and thiol oxidation in cells exposed to peroxyl radicals is inhibited by the macrophage synthesised pterin 7,8-dihydroneopterin. Biochim Biophys Acta. 2002 Aug 19;1591(1-3):139-145. doi: 10.1016/s0167-4889(02)00272-0. [PubMed:12183064 ]
Gieseg SP, Cato S: Inhibition of THP-1 cell-mediated low-density lipoprotein oxidation by the macrophage-synthesised pterin, 7,8-dihydroneopterin. Redox Rep. 2003;8(2):113-5. doi: 10.1179/135100003125001396. [PubMed:12804014 ]
Wirleitner B, Obermoser G, Bock G, Neurauter G, Schennach H, Sepp N, Fuchs D: Induction of apoptosis in human blood T cells by 7,8-dihydroneopterin: the difference between healthy controls and patients with systemic lupus erythematosus. Clin Immunol. 2003 Jun;107(3):152-9. doi: 10.1016/s1521-6616(03)00040-8. [PubMed:12804528 ]
Greilberger J, Oettl K, Cvirn G, Reibnegger G, Jurgens G: Modulation of LDL oxidation by 7,8-dihydroneopterin. Free Radic Res. 2004 Jan;38(1):9-17. doi: 10.1080/10715760310001623322. [PubMed:15061649 ]
Baird SK, Reid L, Hampton MB, Gieseg SP: OxLDL induced cell death is inhibited by the macrophage synthesised pterin, 7,8-dihydroneopterin, in U937 cells but not THP-1 cells. Biochim Biophys Acta. 2005 Sep 30;1745(3):361-9. doi: 10.1016/j.bbamcr.2005.07.001. [PubMed:16084608 ]

Showing metabocard for Dihydroneopterin (MMDBc0049934)

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