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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 14:57:15 UTC

HMDB ID

HMDB0000845

Secondary Accession Numbers

HMDB0000838
HMDB00838
HMDB00845

Metabolite Identification

Common Name

Neopterin

Description

Neopterin, also known as monapterin, belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative and are mainly synthesized in several parts of the body, including the pineal gland. Neopterin is a solid that is soluble in water. Neopterin is a catabolic product of guanosine triphosphate (GTP). In humans, it is involved in pterine biosynthesis and it also serves as a precursor in the biosynthesis of biopterin, which is an essential cofactor in neurotransmitter synthesis. Neopterin has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ). Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces. Uremic toxins can cause kidney, liver and heart damage. They can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Uremic toxins such as neopterin are actively transported into the kidneys via organic ion transporters (especially OAT3). Elevated levels of neopterin result from immune system activation, including from malignant cancer, allograft rejection, viral infection, and autoimmune disorders (PMID: 19500901 ). Measurement of neopterin concentration allows estimation of the extent of oxidative stress elicited by the immune system. Neopterin concentrations usually correlate with the extent and activity of a given disease, and are also used to monitor the course of the disease. Elevated neopterin concentrations are among the best predictors of adverse outcome in patients with HIV infection, in cardiovascular disease, and in various types of cancer.

Structure

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

HMDB0259432
     RDKit          3D
L-Erythro-neopterin
 29 30  0  0  0  0  0  0  0  0999 V2000
    5.8096   -0.1134   -0.2899 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4228    0.0214   -0.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4835   -0.3957   -0.9210 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1701   -0.2595   -0.6684 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2165   -0.6750   -1.5444 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1053   -0.5237   -1.2606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5341    0.0440   -0.1009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9244    0.2570    0.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0824   -0.1918    1.6159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9666   -0.3991   -0.5259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9240   -0.0036   -1.8384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3222    0.0143    0.0386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3621   -0.5894   -0.6663 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4479    0.4520    0.7604 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7394    0.3157    0.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6888    0.7424    1.4066 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3959    1.2786    2.5050 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9877    0.5811    1.1018 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2933   -0.9834   -0.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3486    0.6413   -0.7485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8253   -0.8712   -1.9825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1266    1.3482    0.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2128   -0.2468    2.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9377   -1.5087   -0.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4594   -0.6186   -2.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3807   -0.2677    1.0927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4551    1.1160   -0.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1010   -0.7212   -0.0193 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7158    0.8993    1.7729 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
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
  7 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18  2  1  0
 15  4  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  0
  8 22  1  0
  9 23  1  0
 10 24  1  0
 11 25  1  0
 12 26  1  0
 12 27  1  0
 13 28  1  0
 18 29  1  0
M  END

Neopterin.mol
  Mrv1652304202019232D          

 18 19  0  0  0  0            999 V2000
   -1.6500   -0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -1.4289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
  5 10  2  0  0  0  0
  4 11  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 12 17  1  0  0  0  0
  7 12  1  0  0  0  0
  2 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000845

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=NC2=C(N=C(C=N2)C(O)C(O)CO)C(=O)N1

> <INCHI_IDENTIFIER>
InChI=1S/C9H11N5O4/c10-9-13-7-5(8(18)14-9)12-3(1-11-7)6(17)4(16)2-15/h1,4,6,15-17H,2H2,(H3,10,11,13,14,18)

> <INCHI_KEY>
BMQYVXCPAOLZOK-UHFFFAOYSA-N

> <FORMULA>
C9H11N5O4

> <MOLECULAR_WEIGHT>
253.2147

> <EXACT_MASS>
253.081103865

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
23.36441654476471

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-6-(1,2,3-trihydroxypropyl)-3,4-dihydropteridin-4-one

> <ALOGPS_LOGP>
-1.75

> <JCHEM_LOGP>
-2.752333907333333

> <ALOGPS_LOGS>
-1.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.461214090260292

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.985898622053663

> <JCHEM_PKA_STRONGEST_BASIC>
-2.1965078567606993

> <JCHEM_POLAR_SURFACE_AREA>
153.95000000000002

> <JCHEM_REFRACTIVITY>
60.1102

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.26e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-6-(1,2,3-trihydroxypropyl)-3H-pteridin-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0259432
     RDKit          3D
L-Erythro-neopterin
 29 30  0  0  0  0  0  0  0  0999 V2000
    5.8096   -0.1134   -0.2899 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4228    0.0214   -0.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4835   -0.3957   -0.9210 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1701   -0.2595   -0.6684 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2165   -0.6750   -1.5444 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1053   -0.5237   -1.2606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5341    0.0440   -0.1009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9244    0.2570    0.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0824   -0.1918    1.6159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9666   -0.3991   -0.5259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9240   -0.0036   -1.8384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3222    0.0143    0.0386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3621   -0.5894   -0.6663 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4479    0.4520    0.7604 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7394    0.3157    0.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6888    0.7424    1.4066 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3959    1.2786    2.5050 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9877    0.5811    1.1018 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2933   -0.9834   -0.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3486    0.6413   -0.7485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8253   -0.8712   -1.9825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1266    1.3482    0.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2128   -0.2468    2.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9377   -1.5087   -0.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4594   -0.6186   -2.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3807   -0.2677    1.0927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4551    1.1160   -0.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1010   -0.7212   -0.0193 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7158    0.8993    1.7729 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
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
  7 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18  2  1  0
 15  4  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  0
  8 22  1  0
  9 23  1  0
 10 24  1  0
 11 25  1  0
 12 26  1  0
 12 27  1  0
 13 28  1  0
 18 29  1  0
M  END

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Neopterin.mol                                     
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  N   UNK     0      -3.080  -1.334   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -3.850   0.000   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -3.080   1.334   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -1.540   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.770   0.000   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       0.770   0.000   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       1.540  -1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.770  -2.667   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -0.770  -2.667   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -1.540  -1.334   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.770   2.667   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.080  -1.334   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.850   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.080   1.334   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.540   1.334   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       5.390   0.000   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       3.850  -2.667   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0      -5.390   0.000   0.000  0.00  0.00           N+0
CONECT    1    2   10                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    1    5                                                  
CONECT   11    4                                                            
CONECT   12   13   17    7                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13                                                            
CONECT   17   12                                                            
CONECT   18    2                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0259432
HETATM    1  N1  UNL     1       5.810  -0.113  -0.290  1.00  0.00           N  
HETATM    2  C1  UNL     1       4.423   0.021  -0.042  1.00  0.00           C  
HETATM    3  N2  UNL     1       3.483  -0.396  -0.921  1.00  0.00           N  
HETATM    4  C2  UNL     1       2.170  -0.260  -0.668  1.00  0.00           C  
HETATM    5  N3  UNL     1       1.216  -0.675  -1.544  1.00  0.00           N  
HETATM    6  C3  UNL     1      -0.105  -0.524  -1.261  1.00  0.00           C  
HETATM    7  C4  UNL     1      -0.534   0.044  -0.101  1.00  0.00           C  
HETATM    8  C5  UNL     1      -1.924   0.257   0.299  1.00  0.00           C  
HETATM    9  O1  UNL     1      -2.082  -0.192   1.616  1.00  0.00           O  
HETATM   10  C6  UNL     1      -2.967  -0.399  -0.526  1.00  0.00           C  
HETATM   11  O2  UNL     1      -2.924  -0.004  -1.838  1.00  0.00           O  
HETATM   12  C7  UNL     1      -4.322   0.014   0.039  1.00  0.00           C  
HETATM   13  O3  UNL     1      -5.362  -0.589  -0.666  1.00  0.00           O  
HETATM   14  N4  UNL     1       0.448   0.452   0.760  1.00  0.00           N  
HETATM   15  C8  UNL     1       1.739   0.316   0.507  1.00  0.00           C  
HETATM   16  C9  UNL     1       2.689   0.742   1.407  1.00  0.00           C  
HETATM   17  O4  UNL     1       2.396   1.279   2.505  1.00  0.00           O  
HETATM   18  N5  UNL     1       3.988   0.581   1.102  1.00  0.00           N  
HETATM   19  H1  UNL     1       6.293  -0.983  -0.007  1.00  0.00           H  
HETATM   20  H2  UNL     1       6.349   0.641  -0.748  1.00  0.00           H  
HETATM   21  H3  UNL     1      -0.825  -0.871  -1.982  1.00  0.00           H  
HETATM   22  H4  UNL     1      -2.127   1.348   0.315  1.00  0.00           H  
HETATM   23  H5  UNL     1      -1.213  -0.247   2.092  1.00  0.00           H  
HETATM   24  H6  UNL     1      -2.938  -1.509  -0.492  1.00  0.00           H  
HETATM   25  H7  UNL     1      -3.459  -0.619  -2.380  1.00  0.00           H  
HETATM   26  H8  UNL     1      -4.381  -0.268   1.093  1.00  0.00           H  
HETATM   27  H9  UNL     1      -4.455   1.116  -0.021  1.00  0.00           H  
HETATM   28  H10 UNL     1      -6.101  -0.721  -0.019  1.00  0.00           H  
HETATM   29  H11 UNL     1       4.716   0.899   1.773  1.00  0.00           H  
CONECT    1    2   19   20
CONECT    2    3    3   18
CONECT    3    4
CONECT    4    5    5   15
CONECT    5    6
CONECT    6    7    7   21
CONECT    7    8   14
CONECT    8    9   10   22
CONECT    9   23
CONECT   10   11   12   24
CONECT   11   25
CONECT   12   13   26   27
CONECT   13   28
CONECT   14   15   15
CONECT   15   16
CONECT   16   17   17   18
CONECT   18   29
END

HMDB0259432
     RDKit          3D
L-Erythro-neopterin
 29 30  0  0  0  0  0  0  0  0999 V2000
    5.8096   -0.1134   -0.2899 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4228    0.0214   -0.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4835   -0.3957   -0.9210 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1701   -0.2595   -0.6684 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2165   -0.6750   -1.5444 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1053   -0.5237   -1.2606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5341    0.0440   -0.1009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9244    0.2570    0.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0824   -0.1918    1.6159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9666   -0.3991   -0.5259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9240   -0.0036   -1.8384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3222    0.0143    0.0386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3621   -0.5894   -0.6663 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4479    0.4520    0.7604 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7394    0.3157    0.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6888    0.7424    1.4066 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3959    1.2786    2.5050 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9877    0.5811    1.1018 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2933   -0.9834   -0.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3486    0.6413   -0.7485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8253   -0.8712   -1.9825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1266    1.3482    0.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2128   -0.2468    2.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9377   -1.5087   -0.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4594   -0.6186   -2.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3807   -0.2677    1.0927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4551    1.1160   -0.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1010   -0.7212   -0.0193 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7158    0.8993    1.7729 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
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
  7 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18  2  1  0
 15  4  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  0
  8 22  1  0
  9 23  1  0
 10 24  1  0
 11 25  1  0
 12 26  1  0
 12 27  1  0
 13 28  1  0
 18 29  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
6-(D-erythro-1,2,3-Trihydroxypropyl)pterin	HMDB
6-D-erythro-Neopterin	HMDB
D-erythro-Neopterin	HMDB
D-Neopterin	HMDB
Neopterine	HMDB
[S-(R,s)]-2-amino-6-(1,2,3-trihydroxypropyl)-1H-pteridin-4-ON	HMDB
[S-(R,s)]-2-amino-6-(1,2,3-trihydroxypropyl)-1H-pteridin-4-one	HMDB
[S-(R,s)]-2-amino-6-(1,2,3-trihydroxypropyl)-1H-pteridine-4-one	HMDB
Monapterin	MeSH, HMDB
Neopterin, (r, r)-isomer	MeSH, HMDB
Umanopterin	MeSH, HMDB
Neopterin, (erythro-D)-isomer	MeSH, HMDB
2-amino-6-(1,2,3-Trihydroxypropyl)-4(3H)-pteridinone	MeSH, HMDB
Neopterin, (erythro-L)-isomer	MeSH, HMDB
Neopterin, (threo-D)-isomer	MeSH, HMDB
Neopterin, (threo-L)-isomer	MeSH, HMDB

Chemical Formula

C₉H₁₁N₅O₄

Average Molecular Weight

253.2147

Monoisotopic Molecular Weight

253.081103865

IUPAC Name

2-amino-6-(1,2,3-trihydroxypropyl)-3,4-dihydropteridin-4-one

Traditional Name

2-amino-6-(1,2,3-trihydroxypropyl)-3H-pteridin-4-one

CAS Registry Number

2009-64-5

SMILES

NC1=NC2=C(N=C(C=N2)C(O)C(O)CO)C(=O)N1

InChI Identifier

InChI=1S/C9H11N5O4/c10-9-13-7-5(8(18)14-9)12-3(1-11-7)6(17)4(16)2-15/h1,4,6,15-17H,2H2,(H3,10,11,13,14,18)

InChI Key

BMQYVXCPAOLZOK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are mainly synthesized in several parts of the body, including the pineal gland.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Pterins and derivatives

Direct Parent

Biopterins and derivatives

Alternative Parents

Substituents

Biopterin
Aminopyrimidine
Pyrimidone
Pyrazine
Pyrimidine
Heteroaromatic compound
Vinylogous amide
Secondary alcohol
Polyol
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Primary amine
Primary alcohol
Alcohol
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Aromatic alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 7707089)
Cerebrospinal Fluid (CSF) (PMID: 7707089)
Lymph (HMDB: HMDB0000845)

Tissue

Connective tissue

Bone marrow (HMDB: HMDB0000845)

Epithelium

Epidermis (HMDB: HMDB0000845)

Urine (PMID: 3939585)
Feces (PMID: 27609529)

Cellular substructure

Cytoplasm (HMDB: HMDB0000845)
Membrane (HMDB: HMDB0000845)

Central Nervous System (HMDB: HMDB0000845)
Activated T-Lymphocytes (HMDB: HMDB0000845)
T-Lymphocyte (HMDB: HMDB0000845)

Source

Exogenous

Exogenous (HMDB: HMDB0000845)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0000845)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Pterine Biosynthesis (HMDB: HMDB0000845)

Disease pathway

Hyperphenylalaninemia Due to DHPR-Deficiency (HMDB: HMDB0000845)
DOPA-Responsive Dystonia (PathBank: SMP0120771)
Segawa Syndrome (PathBank: SMP0120775)
Hyperphenylalaninemia Due to 6-Pyruvoyltetrahydropterin Synthase Deficiency (ptps) (PathBank: SMP0120553)
Hyperphenylalaninemia Due to Guanosine Triphosphate Cyclohydrolase Deficiency (PathBank: SMP0120772)
Sepiapterin Reductase Deficiency (PathBank: SMP0120776)

Role

Industrial application

Pharmaceutical industry

Biomarker

Multiple sclerosis (MarkerDB: MDB00000264)
Sepiapterin reductase deficiency (MarkerDB: MDB00000264)
Parkinson's disease (MarkerDB: MDB00000264)
Urocanase Deficiency (MarkerDB: MDB00000264)
Hydrocephalus (MarkerDB: MDB00000264)
CNS Infections (MarkerDB: MDB00000264)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	150.307	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000332
[M+H]+	Not Available	157.304	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000332

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.26 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-2.8	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	9.99	ChemAxon
pKa (Strongest Basic)	-2.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	153.95 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	60.11 m³·mol⁻¹	ChemAxon
Polarizability	23.36 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	159.394	31661259
DarkChem	[M-H]-	156.176	31661259
AllCCS	[M+H]+	156.196	32859911
AllCCS	[M-H]-	154.802	32859911
DeepCCS	[M+H]+	154.131	30932474
DeepCCS	[M-H]-	151.773	30932474
DeepCCS	[M-2H]-	184.715	30932474
DeepCCS	[M+Na]+	160.224	30932474
AllCCS	[M+H]+	156.2	32859911
AllCCS	[M+H-H2O]+	152.5	32859911
AllCCS	[M+NH4]+	159.6	32859911
AllCCS	[M+Na]+	160.6	32859911
AllCCS	[M-H]-	154.8	32859911
AllCCS	[M+Na-2H]-	154.6	32859911
AllCCS	[M+HCOO]-	154.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Neopterin	NC1=NC2=C(N=C(C=N2)C(O)C(O)CO)C(=O)N1	3502.9	Standard polar	33892256
Neopterin	NC1=NC2=C(N=C(C=N2)C(O)C(O)CO)C(=O)N1	2337.6	Standard non polar	33892256
Neopterin	NC1=NC2=C(N=C(C=N2)C(O)C(O)CO)C(=O)N1	2989.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Neopterin,1TMS,isomer #1	C[Si](C)(C)OC(C1=CN=C2N=C(N)[NH]C(=O)C2=N1)C(O)CO	2689.3	Semi standard non polar	33892256
Neopterin,1TMS,isomer #2	C[Si](C)(C)OC(CO)C(O)C1=CN=C2N=C(N)[NH]C(=O)C2=N1	2699.0	Semi standard non polar	33892256
Neopterin,1TMS,isomer #3	C[Si](C)(C)OCC(O)C(O)C1=CN=C2N=C(N)[NH]C(=O)C2=N1	2684.1	Semi standard non polar	33892256
Neopterin,1TMS,isomer #4	C[Si](C)(C)NC1=NC2=NC=C(C(O)C(O)CO)N=C2C(=O)[NH]1	2773.8	Semi standard non polar	33892256
Neopterin,1TMS,isomer #5	C[Si](C)(C)N1C(N)=NC2=NC=C(C(O)C(O)CO)N=C2C1=O	2728.9	Semi standard non polar	33892256
Neopterin,2TMS,isomer #1	C[Si](C)(C)OC(CO)C(O[Si](C)(C)C)C1=CN=C2N=C(N)[NH]C(=O)C2=N1	2538.4	Semi standard non polar	33892256
Neopterin,2TMS,isomer #10	C[Si](C)(C)N(C1=NC2=NC=C(C(O)C(O)CO)N=C2C(=O)[NH]1)[Si](C)(C)C	2657.6	Semi standard non polar	33892256
Neopterin,2TMS,isomer #11	C[Si](C)(C)NC1=NC2=NC=C(C(O)C(O)CO)N=C2C(=O)N1[Si](C)(C)C	2705.1	Semi standard non polar	33892256
Neopterin,2TMS,isomer #2	C[Si](C)(C)OCC(O)C(O[Si](C)(C)C)C1=CN=C2N=C(N)[NH]C(=O)C2=N1	2594.7	Semi standard non polar	33892256
Neopterin,2TMS,isomer #3	C[Si](C)(C)NC1=NC2=NC=C(C(O[Si](C)(C)C)C(O)CO)N=C2C(=O)[NH]1	2561.2	Semi standard non polar	33892256
Neopterin,2TMS,isomer #4	C[Si](C)(C)OC(C1=CN=C2N=C(N)N([Si](C)(C)C)C(=O)C2=N1)C(O)CO	2579.3	Semi standard non polar	33892256
Neopterin,2TMS,isomer #5	C[Si](C)(C)OCC(O[Si](C)(C)C)C(O)C1=CN=C2N=C(N)[NH]C(=O)C2=N1	2565.1	Semi standard non polar	33892256
Neopterin,2TMS,isomer #6	C[Si](C)(C)NC1=NC2=NC=C(C(O)C(CO)O[Si](C)(C)C)N=C2C(=O)[NH]1	2562.9	Semi standard non polar	33892256
Neopterin,2TMS,isomer #7	C[Si](C)(C)OC(CO)C(O)C1=CN=C2N=C(N)N([Si](C)(C)C)C(=O)C2=N1	2592.4	Semi standard non polar	33892256
Neopterin,2TMS,isomer #8	C[Si](C)(C)NC1=NC2=NC=C(C(O)C(O)CO[Si](C)(C)C)N=C2C(=O)[NH]1	2601.3	Semi standard non polar	33892256
Neopterin,2TMS,isomer #9	C[Si](C)(C)OCC(O)C(O)C1=CN=C2N=C(N)N([Si](C)(C)C)C(=O)C2=N1	2613.0	Semi standard non polar	33892256
Neopterin,3TMS,isomer #1	C[Si](C)(C)OCC(O[Si](C)(C)C)C(O[Si](C)(C)C)C1=CN=C2N=C(N)[NH]C(=O)C2=N1	2503.4	Semi standard non polar	33892256
Neopterin,3TMS,isomer #10	C[Si](C)(C)OC(CO)C(O)C1=CN=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C(=O)C2=N1	2505.6	Semi standard non polar	33892256
Neopterin,3TMS,isomer #11	C[Si](C)(C)NC1=NC2=NC=C(C(O)C(CO)O[Si](C)(C)C)N=C2C(=O)N1[Si](C)(C)C	2540.1	Semi standard non polar	33892256
Neopterin,3TMS,isomer #12	C[Si](C)(C)OCC(O)C(O)C1=CN=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C(=O)C2=N1	2533.3	Semi standard non polar	33892256
Neopterin,3TMS,isomer #13	C[Si](C)(C)NC1=NC2=NC=C(C(O)C(O)CO[Si](C)(C)C)N=C2C(=O)N1[Si](C)(C)C	2547.2	Semi standard non polar	33892256
Neopterin,3TMS,isomer #14	C[Si](C)(C)N(C1=NC2=NC=C(C(O)C(O)CO)N=C2C(=O)N1[Si](C)(C)C)[Si](C)(C)C	2658.0	Semi standard non polar	33892256
Neopterin,3TMS,isomer #2	C[Si](C)(C)NC1=NC2=NC=C(C(O[Si](C)(C)C)C(CO)O[Si](C)(C)C)N=C2C(=O)[NH]1	2459.0	Semi standard non polar	33892256
Neopterin,3TMS,isomer #3	C[Si](C)(C)OC(CO)C(O[Si](C)(C)C)C1=CN=C2N=C(N)N([Si](C)(C)C)C(=O)C2=N1	2524.3	Semi standard non polar	33892256
Neopterin,3TMS,isomer #4	C[Si](C)(C)NC1=NC2=NC=C(C(O[Si](C)(C)C)C(O)CO[Si](C)(C)C)N=C2C(=O)[NH]1	2485.1	Semi standard non polar	33892256
Neopterin,3TMS,isomer #5	C[Si](C)(C)OCC(O)C(O[Si](C)(C)C)C1=CN=C2N=C(N)N([Si](C)(C)C)C(=O)C2=N1	2548.0	Semi standard non polar	33892256
Neopterin,3TMS,isomer #6	C[Si](C)(C)OC(C1=CN=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C(=O)C2=N1)C(O)CO	2463.3	Semi standard non polar	33892256
Neopterin,3TMS,isomer #7	C[Si](C)(C)NC1=NC2=NC=C(C(O[Si](C)(C)C)C(O)CO)N=C2C(=O)N1[Si](C)(C)C	2529.9	Semi standard non polar	33892256
Neopterin,3TMS,isomer #8	C[Si](C)(C)NC1=NC2=NC=C(C(O)C(CO[Si](C)(C)C)O[Si](C)(C)C)N=C2C(=O)[NH]1	2471.7	Semi standard non polar	33892256
Neopterin,3TMS,isomer #9	C[Si](C)(C)OCC(O[Si](C)(C)C)C(O)C1=CN=C2N=C(N)N([Si](C)(C)C)C(=O)C2=N1	2501.2	Semi standard non polar	33892256
Neopterin,4TMS,isomer #1	C[Si](C)(C)NC1=NC2=NC=C(C(O[Si](C)(C)C)C(CO[Si](C)(C)C)O[Si](C)(C)C)N=C2C(=O)[NH]1	2472.3	Semi standard non polar	33892256
Neopterin,4TMS,isomer #1	C[Si](C)(C)NC1=NC2=NC=C(C(O[Si](C)(C)C)C(CO[Si](C)(C)C)O[Si](C)(C)C)N=C2C(=O)[NH]1	2577.6	Standard non polar	33892256
Neopterin,4TMS,isomer #1	C[Si](C)(C)NC1=NC2=NC=C(C(O[Si](C)(C)C)C(CO[Si](C)(C)C)O[Si](C)(C)C)N=C2C(=O)[NH]1	3666.9	Standard polar	33892256
Neopterin,4TMS,isomer #10	C[Si](C)(C)OC(CO)C(O)C1=CN=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C(=O)C2=N1	2573.8	Semi standard non polar	33892256
Neopterin,4TMS,isomer #10	C[Si](C)(C)OC(CO)C(O)C1=CN=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C(=O)C2=N1	2781.2	Standard non polar	33892256
Neopterin,4TMS,isomer #10	C[Si](C)(C)OC(CO)C(O)C1=CN=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C(=O)C2=N1	3575.4	Standard polar	33892256
Neopterin,4TMS,isomer #11	C[Si](C)(C)OCC(O)C(O)C1=CN=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C(=O)C2=N1	2579.1	Semi standard non polar	33892256
Neopterin,4TMS,isomer #11	C[Si](C)(C)OCC(O)C(O)C1=CN=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C(=O)C2=N1	2828.7	Standard non polar	33892256
Neopterin,4TMS,isomer #11	C[Si](C)(C)OCC(O)C(O)C1=CN=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C(=O)C2=N1	3584.5	Standard polar	33892256
Neopterin,4TMS,isomer #2	C[Si](C)(C)OCC(O[Si](C)(C)C)C(O[Si](C)(C)C)C1=CN=C2N=C(N)N([Si](C)(C)C)C(=O)C2=N1	2517.0	Semi standard non polar	33892256
Neopterin,4TMS,isomer #2	C[Si](C)(C)OCC(O[Si](C)(C)C)C(O[Si](C)(C)C)C1=CN=C2N=C(N)N([Si](C)(C)C)C(=O)C2=N1	2542.7	Standard non polar	33892256
Neopterin,4TMS,isomer #2	C[Si](C)(C)OCC(O[Si](C)(C)C)C(O[Si](C)(C)C)C1=CN=C2N=C(N)N([Si](C)(C)C)C(=O)C2=N1	3824.7	Standard polar	33892256
Neopterin,4TMS,isomer #3	C[Si](C)(C)OC(CO)C(O[Si](C)(C)C)C1=CN=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C(=O)C2=N1	2492.7	Semi standard non polar	33892256
Neopterin,4TMS,isomer #3	C[Si](C)(C)OC(CO)C(O[Si](C)(C)C)C1=CN=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C(=O)C2=N1	2730.6	Standard non polar	33892256
Neopterin,4TMS,isomer #3	C[Si](C)(C)OC(CO)C(O[Si](C)(C)C)C1=CN=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C(=O)C2=N1	3551.6	Standard polar	33892256
Neopterin,4TMS,isomer #4	C[Si](C)(C)NC1=NC2=NC=C(C(O[Si](C)(C)C)C(CO)O[Si](C)(C)C)N=C2C(=O)N1[Si](C)(C)C	2541.5	Semi standard non polar	33892256
Neopterin,4TMS,isomer #4	C[Si](C)(C)NC1=NC2=NC=C(C(O[Si](C)(C)C)C(CO)O[Si](C)(C)C)N=C2C(=O)N1[Si](C)(C)C	2626.5	Standard non polar	33892256
Neopterin,4TMS,isomer #4	C[Si](C)(C)NC1=NC2=NC=C(C(O[Si](C)(C)C)C(CO)O[Si](C)(C)C)N=C2C(=O)N1[Si](C)(C)C	3635.5	Standard polar	33892256
Neopterin,4TMS,isomer #5	C[Si](C)(C)OCC(O)C(O[Si](C)(C)C)C1=CN=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C(=O)C2=N1	2498.0	Semi standard non polar	33892256
Neopterin,4TMS,isomer #5	C[Si](C)(C)OCC(O)C(O[Si](C)(C)C)C1=CN=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C(=O)C2=N1	2742.3	Standard non polar	33892256
Neopterin,4TMS,isomer #5	C[Si](C)(C)OCC(O)C(O[Si](C)(C)C)C1=CN=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C(=O)C2=N1	3539.5	Standard polar	33892256
Neopterin,4TMS,isomer #6	C[Si](C)(C)NC1=NC2=NC=C(C(O[Si](C)(C)C)C(O)CO[Si](C)(C)C)N=C2C(=O)N1[Si](C)(C)C	2539.7	Semi standard non polar	33892256
Neopterin,4TMS,isomer #6	C[Si](C)(C)NC1=NC2=NC=C(C(O[Si](C)(C)C)C(O)CO[Si](C)(C)C)N=C2C(=O)N1[Si](C)(C)C	2621.8	Standard non polar	33892256
Neopterin,4TMS,isomer #6	C[Si](C)(C)NC1=NC2=NC=C(C(O[Si](C)(C)C)C(O)CO[Si](C)(C)C)N=C2C(=O)N1[Si](C)(C)C	3625.6	Standard polar	33892256
Neopterin,4TMS,isomer #7	C[Si](C)(C)OC(C1=CN=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C(=O)C2=N1)C(O)CO	2572.6	Semi standard non polar	33892256
Neopterin,4TMS,isomer #7	C[Si](C)(C)OC(C1=CN=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C(=O)C2=N1)C(O)CO	2782.3	Standard non polar	33892256
Neopterin,4TMS,isomer #7	C[Si](C)(C)OC(C1=CN=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C(=O)C2=N1)C(O)CO	3578.3	Standard polar	33892256
Neopterin,4TMS,isomer #8	C[Si](C)(C)OCC(O[Si](C)(C)C)C(O)C1=CN=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C(=O)C2=N1	2481.2	Semi standard non polar	33892256
Neopterin,4TMS,isomer #8	C[Si](C)(C)OCC(O[Si](C)(C)C)C(O)C1=CN=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C(=O)C2=N1	2752.3	Standard non polar	33892256
Neopterin,4TMS,isomer #8	C[Si](C)(C)OCC(O[Si](C)(C)C)C(O)C1=CN=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C(=O)C2=N1	3555.3	Standard polar	33892256
Neopterin,4TMS,isomer #9	C[Si](C)(C)NC1=NC2=NC=C(C(O)C(CO[Si](C)(C)C)O[Si](C)(C)C)N=C2C(=O)N1[Si](C)(C)C	2515.5	Semi standard non polar	33892256
Neopterin,4TMS,isomer #9	C[Si](C)(C)NC1=NC2=NC=C(C(O)C(CO[Si](C)(C)C)O[Si](C)(C)C)N=C2C(=O)N1[Si](C)(C)C	2641.4	Standard non polar	33892256
Neopterin,4TMS,isomer #9	C[Si](C)(C)NC1=NC2=NC=C(C(O)C(CO[Si](C)(C)C)O[Si](C)(C)C)N=C2C(=O)N1[Si](C)(C)C	3646.7	Standard polar	33892256
Neopterin,5TMS,isomer #1	C[Si](C)(C)OCC(O[Si](C)(C)C)C(O[Si](C)(C)C)C1=CN=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C(=O)C2=N1	2534.3	Semi standard non polar	33892256
Neopterin,5TMS,isomer #1	C[Si](C)(C)OCC(O[Si](C)(C)C)C(O[Si](C)(C)C)C1=CN=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C(=O)C2=N1	2709.4	Standard non polar	33892256
Neopterin,5TMS,isomer #1	C[Si](C)(C)OCC(O[Si](C)(C)C)C(O[Si](C)(C)C)C1=CN=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C(=O)C2=N1	3336.3	Standard polar	33892256
Neopterin,5TMS,isomer #2	C[Si](C)(C)NC1=NC2=NC=C(C(O[Si](C)(C)C)C(CO[Si](C)(C)C)O[Si](C)(C)C)N=C2C(=O)N1[Si](C)(C)C	2561.4	Semi standard non polar	33892256
Neopterin,5TMS,isomer #2	C[Si](C)(C)NC1=NC2=NC=C(C(O[Si](C)(C)C)C(CO[Si](C)(C)C)O[Si](C)(C)C)N=C2C(=O)N1[Si](C)(C)C	2624.6	Standard non polar	33892256
Neopterin,5TMS,isomer #2	C[Si](C)(C)NC1=NC2=NC=C(C(O[Si](C)(C)C)C(CO[Si](C)(C)C)O[Si](C)(C)C)N=C2C(=O)N1[Si](C)(C)C	3405.9	Standard polar	33892256
Neopterin,5TMS,isomer #3	C[Si](C)(C)OC(CO)C(O[Si](C)(C)C)C1=CN=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C(=O)C2=N1	2609.2	Semi standard non polar	33892256
Neopterin,5TMS,isomer #3	C[Si](C)(C)OC(CO)C(O[Si](C)(C)C)C1=CN=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C(=O)C2=N1	2782.4	Standard non polar	33892256
Neopterin,5TMS,isomer #3	C[Si](C)(C)OC(CO)C(O[Si](C)(C)C)C1=CN=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C(=O)C2=N1	3321.9	Standard polar	33892256
Neopterin,5TMS,isomer #4	C[Si](C)(C)OCC(O)C(O[Si](C)(C)C)C1=CN=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C(=O)C2=N1	2606.7	Semi standard non polar	33892256
Neopterin,5TMS,isomer #4	C[Si](C)(C)OCC(O)C(O[Si](C)(C)C)C1=CN=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C(=O)C2=N1	2780.0	Standard non polar	33892256
Neopterin,5TMS,isomer #4	C[Si](C)(C)OCC(O)C(O[Si](C)(C)C)C1=CN=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C(=O)C2=N1	3305.5	Standard polar	33892256
Neopterin,5TMS,isomer #5	C[Si](C)(C)OCC(O[Si](C)(C)C)C(O)C1=CN=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C(=O)C2=N1	2575.5	Semi standard non polar	33892256
Neopterin,5TMS,isomer #5	C[Si](C)(C)OCC(O[Si](C)(C)C)C(O)C1=CN=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C(=O)C2=N1	2802.2	Standard non polar	33892256
Neopterin,5TMS,isomer #5	C[Si](C)(C)OCC(O[Si](C)(C)C)C(O)C1=CN=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C(=O)C2=N1	3324.4	Standard polar	33892256
Neopterin,6TMS,isomer #1	C[Si](C)(C)OCC(O[Si](C)(C)C)C(O[Si](C)(C)C)C1=CN=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C(=O)C2=N1	2634.2	Semi standard non polar	33892256
Neopterin,6TMS,isomer #1	C[Si](C)(C)OCC(O[Si](C)(C)C)C(O[Si](C)(C)C)C1=CN=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C(=O)C2=N1	2773.3	Standard non polar	33892256
Neopterin,6TMS,isomer #1	C[Si](C)(C)OCC(O[Si](C)(C)C)C(O[Si](C)(C)C)C1=CN=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C(=O)C2=N1	3130.0	Standard polar	33892256
Neopterin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(C1=CN=C2N=C(N)[NH]C(=O)C2=N1)C(O)CO	2920.4	Semi standard non polar	33892256
Neopterin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(CO)C(O)C1=CN=C2N=C(N)[NH]C(=O)C2=N1	2893.8	Semi standard non polar	33892256
Neopterin,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OCC(O)C(O)C1=CN=C2N=C(N)[NH]C(=O)C2=N1	2904.8	Semi standard non polar	33892256
Neopterin,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC2=NC=C(C(O)C(O)CO)N=C2C(=O)[NH]1	2940.8	Semi standard non polar	33892256
Neopterin,1TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N1C(N)=NC2=NC=C(C(O)C(O)CO)N=C2C1=O	2933.7	Semi standard non polar	33892256
Neopterin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(CO)C(O[Si](C)(C)C(C)(C)C)C1=CN=C2N=C(N)[NH]C(=O)C2=N1	2951.6	Semi standard non polar	33892256
Neopterin,2TBDMS,isomer #10	CC(C)(C)[Si](C)(C)N(C1=NC2=NC=C(C(O)C(O)CO)N=C2C(=O)[NH]1)[Si](C)(C)C(C)(C)C	2991.3	Semi standard non polar	33892256
Neopterin,2TBDMS,isomer #11	CC(C)(C)[Si](C)(C)NC1=NC2=NC=C(C(O)C(O)CO)N=C2C(=O)N1[Si](C)(C)C(C)(C)C	3071.5	Semi standard non polar	33892256
Neopterin,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC(O)C(O[Si](C)(C)C(C)(C)C)C1=CN=C2N=C(N)[NH]C(=O)C2=N1	3011.0	Semi standard non polar	33892256
Neopterin,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=NC2=NC=C(C(O[Si](C)(C)C(C)(C)C)C(O)CO)N=C2C(=O)[NH]1	2932.3	Semi standard non polar	33892256
Neopterin,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(C1=CN=C2N=C(N)N([Si](C)(C)C(C)(C)C)C(=O)C2=N1)C(O)CO	3027.1	Semi standard non polar	33892256
Neopterin,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)C(O)C1=CN=C2N=C(N)[NH]C(=O)C2=N1	2990.0	Semi standard non polar	33892256
Neopterin,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)NC1=NC2=NC=C(C(O)C(CO)O[Si](C)(C)C(C)(C)C)N=C2C(=O)[NH]1	2914.5	Semi standard non polar	33892256
Neopterin,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC(CO)C(O)C1=CN=C2N=C(N)N([Si](C)(C)C(C)(C)C)C(=O)C2=N1	2996.0	Semi standard non polar	33892256
Neopterin,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)NC1=NC2=NC=C(C(O)C(O)CO[Si](C)(C)C(C)(C)C)N=C2C(=O)[NH]1	2947.2	Semi standard non polar	33892256
Neopterin,2TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OCC(O)C(O)C1=CN=C2N=C(N)N([Si](C)(C)C(C)(C)C)C(=O)C2=N1	3043.9	Semi standard non polar	33892256
Neopterin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1=CN=C2N=C(N)[NH]C(=O)C2=N1	3084.3	Semi standard non polar	33892256
Neopterin,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC(CO)C(O)C1=CN=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C(=O)C2=N1	3042.1	Semi standard non polar	33892256
Neopterin,3TBDMS,isomer #11	CC(C)(C)[Si](C)(C)NC1=NC2=NC=C(C(O)C(CO)O[Si](C)(C)C(C)(C)C)N=C2C(=O)N1[Si](C)(C)C(C)(C)C	3133.0	Semi standard non polar	33892256
Neopterin,3TBDMS,isomer #12	CC(C)(C)[Si](C)(C)OCC(O)C(O)C1=CN=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C(=O)C2=N1	3059.4	Semi standard non polar	33892256
Neopterin,3TBDMS,isomer #13	CC(C)(C)[Si](C)(C)NC1=NC2=NC=C(C(O)C(O)CO[Si](C)(C)C(C)(C)C)N=C2C(=O)N1[Si](C)(C)C(C)(C)C	3168.0	Semi standard non polar	33892256
Neopterin,3TBDMS,isomer #14	CC(C)(C)[Si](C)(C)N(C1=NC2=NC=C(C(O)C(O)CO)N=C2C(=O)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3224.1	Semi standard non polar	33892256
Neopterin,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC2=NC=C(C(O[Si](C)(C)C(C)(C)C)C(CO)O[Si](C)(C)C(C)(C)C)N=C2C(=O)[NH]1	3019.3	Semi standard non polar	33892256
Neopterin,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(CO)C(O[Si](C)(C)C(C)(C)C)C1=CN=C2N=C(N)N([Si](C)(C)C(C)(C)C)C(=O)C2=N1	3135.1	Semi standard non polar	33892256
Neopterin,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC2=NC=C(C(O[Si](C)(C)C(C)(C)C)C(O)CO[Si](C)(C)C(C)(C)C)N=C2C(=O)[NH]1	3057.8	Semi standard non polar	33892256
Neopterin,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OCC(O)C(O[Si](C)(C)C(C)(C)C)C1=CN=C2N=C(N)N([Si](C)(C)C(C)(C)C)C(=O)C2=N1	3183.4	Semi standard non polar	33892256
Neopterin,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(C1=CN=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C(=O)C2=N1)C(O)CO	3050.1	Semi standard non polar	33892256
Neopterin,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)NC1=NC2=NC=C(C(O[Si](C)(C)C(C)(C)C)C(O)CO)N=C2C(=O)N1[Si](C)(C)C(C)(C)C	3142.9	Semi standard non polar	33892256
Neopterin,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)NC1=NC2=NC=C(C(O)C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)N=C2C(=O)[NH]1	3044.3	Semi standard non polar	33892256
Neopterin,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)C(O)C1=CN=C2N=C(N)N([Si](C)(C)C(C)(C)C)C(=O)C2=N1	3156.2	Semi standard non polar	33892256
Neopterin,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC2=NC=C(C(O[Si](C)(C)C(C)(C)C)C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)N=C2C(=O)[NH]1	3216.9	Semi standard non polar	33892256
Neopterin,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC2=NC=C(C(O[Si](C)(C)C(C)(C)C)C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)N=C2C(=O)[NH]1	3390.3	Standard non polar	33892256
Neopterin,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC2=NC=C(C(O[Si](C)(C)C(C)(C)C)C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)N=C2C(=O)[NH]1	3841.0	Standard polar	33892256
Neopterin,4TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC(CO)C(O)C1=CN=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)C2=N1	3308.3	Semi standard non polar	33892256
Neopterin,4TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC(CO)C(O)C1=CN=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)C2=N1	3486.8	Standard non polar	33892256
Neopterin,4TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC(CO)C(O)C1=CN=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)C2=N1	3703.6	Standard polar	33892256
Neopterin,4TBDMS,isomer #11	CC(C)(C)[Si](C)(C)OCC(O)C(O)C1=CN=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)C2=N1	3323.8	Semi standard non polar	33892256
Neopterin,4TBDMS,isomer #11	CC(C)(C)[Si](C)(C)OCC(O)C(O)C1=CN=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)C2=N1	3494.3	Standard non polar	33892256
Neopterin,4TBDMS,isomer #11	CC(C)(C)[Si](C)(C)OCC(O)C(O)C1=CN=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)C2=N1	3714.6	Standard polar	33892256
Neopterin,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1=CN=C2N=C(N)N([Si](C)(C)C(C)(C)C)C(=O)C2=N1	3324.5	Semi standard non polar	33892256
Neopterin,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1=CN=C2N=C(N)N([Si](C)(C)C(C)(C)C)C(=O)C2=N1	3338.0	Standard non polar	33892256
Neopterin,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1=CN=C2N=C(N)N([Si](C)(C)C(C)(C)C)C(=O)C2=N1	3937.5	Standard polar	33892256
Neopterin,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(CO)C(O[Si](C)(C)C(C)(C)C)C1=CN=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C(=O)C2=N1	3193.2	Semi standard non polar	33892256
Neopterin,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(CO)C(O[Si](C)(C)C(C)(C)C)C1=CN=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C(=O)C2=N1	3468.9	Standard non polar	33892256
Neopterin,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(CO)C(O[Si](C)(C)C(C)(C)C)C1=CN=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C(=O)C2=N1	3710.3	Standard polar	33892256
Neopterin,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC2=NC=C(C(O[Si](C)(C)C(C)(C)C)C(CO)O[Si](C)(C)C(C)(C)C)N=C2C(=O)N1[Si](C)(C)C(C)(C)C	3305.3	Semi standard non polar	33892256
Neopterin,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC2=NC=C(C(O[Si](C)(C)C(C)(C)C)C(CO)O[Si](C)(C)C(C)(C)C)N=C2C(=O)N1[Si](C)(C)C(C)(C)C	3403.6	Standard non polar	33892256
Neopterin,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC2=NC=C(C(O[Si](C)(C)C(C)(C)C)C(CO)O[Si](C)(C)C(C)(C)C)N=C2C(=O)N1[Si](C)(C)C(C)(C)C	3759.9	Standard polar	33892256
Neopterin,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OCC(O)C(O[Si](C)(C)C(C)(C)C)C1=CN=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C(=O)C2=N1	3212.2	Semi standard non polar	33892256
Neopterin,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OCC(O)C(O[Si](C)(C)C(C)(C)C)C1=CN=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C(=O)C2=N1	3470.8	Standard non polar	33892256
Neopterin,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OCC(O)C(O[Si](C)(C)C(C)(C)C)C1=CN=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C(=O)C2=N1	3708.4	Standard polar	33892256
Neopterin,4TBDMS,isomer #6	CC(C)(C)[Si](C)(C)NC1=NC2=NC=C(C(O[Si](C)(C)C(C)(C)C)C(O)CO[Si](C)(C)C(C)(C)C)N=C2C(=O)N1[Si](C)(C)C(C)(C)C	3337.0	Semi standard non polar	33892256
Neopterin,4TBDMS,isomer #6	CC(C)(C)[Si](C)(C)NC1=NC2=NC=C(C(O[Si](C)(C)C(C)(C)C)C(O)CO[Si](C)(C)C(C)(C)C)N=C2C(=O)N1[Si](C)(C)C(C)(C)C	3401.3	Standard non polar	33892256
Neopterin,4TBDMS,isomer #6	CC(C)(C)[Si](C)(C)NC1=NC2=NC=C(C(O[Si](C)(C)C(C)(C)C)C(O)CO[Si](C)(C)C(C)(C)C)N=C2C(=O)N1[Si](C)(C)C(C)(C)C	3758.0	Standard polar	33892256
Neopterin,4TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC(C1=CN=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)C2=N1)C(O)CO	3337.7	Semi standard non polar	33892256
Neopterin,4TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC(C1=CN=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)C2=N1)C(O)CO	3470.6	Standard non polar	33892256
Neopterin,4TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC(C1=CN=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)C2=N1)C(O)CO	3704.4	Standard polar	33892256
Neopterin,4TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)C(O)C1=CN=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C(=O)C2=N1	3193.8	Semi standard non polar	33892256
Neopterin,4TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)C(O)C1=CN=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C(=O)C2=N1	3468.0	Standard non polar	33892256
Neopterin,4TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)C(O)C1=CN=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C(=O)C2=N1	3713.5	Standard polar	33892256
Neopterin,4TBDMS,isomer #9	CC(C)(C)[Si](C)(C)NC1=NC2=NC=C(C(O)C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)N=C2C(=O)N1[Si](C)(C)C(C)(C)C	3304.0	Semi standard non polar	33892256
Neopterin,4TBDMS,isomer #9	CC(C)(C)[Si](C)(C)NC1=NC2=NC=C(C(O)C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)N=C2C(=O)N1[Si](C)(C)C(C)(C)C	3401.0	Standard non polar	33892256
Neopterin,4TBDMS,isomer #9	CC(C)(C)[Si](C)(C)NC1=NC2=NC=C(C(O)C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)N=C2C(=O)N1[Si](C)(C)C(C)(C)C	3768.6	Standard polar	33892256
Neopterin,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1=CN=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C(=O)C2=N1	3380.0	Semi standard non polar	33892256
Neopterin,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1=CN=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C(=O)C2=N1	3618.2	Standard non polar	33892256
Neopterin,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1=CN=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C(=O)C2=N1	3634.3	Standard polar	33892256
Neopterin,5TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC2=NC=C(C(O[Si](C)(C)C(C)(C)C)C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)N=C2C(=O)N1[Si](C)(C)C(C)(C)C	3477.9	Semi standard non polar	33892256
Neopterin,5TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC2=NC=C(C(O[Si](C)(C)C(C)(C)C)C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)N=C2C(=O)N1[Si](C)(C)C(C)(C)C	3568.0	Standard non polar	33892256
Neopterin,5TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC2=NC=C(C(O[Si](C)(C)C(C)(C)C)C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)N=C2C(=O)N1[Si](C)(C)C(C)(C)C	3702.9	Standard polar	33892256
Neopterin,5TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(CO)C(O[Si](C)(C)C(C)(C)C)C1=CN=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)C2=N1	3495.5	Semi standard non polar	33892256
Neopterin,5TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(CO)C(O[Si](C)(C)C(C)(C)C)C1=CN=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)C2=N1	3652.1	Standard non polar	33892256
Neopterin,5TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(CO)C(O[Si](C)(C)C(C)(C)C)C1=CN=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)C2=N1	3595.9	Standard polar	33892256
Neopterin,5TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OCC(O)C(O[Si](C)(C)C(C)(C)C)C1=CN=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)C2=N1	3519.0	Semi standard non polar	33892256
Neopterin,5TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OCC(O)C(O[Si](C)(C)C(C)(C)C)C1=CN=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)C2=N1	3655.6	Standard non polar	33892256
Neopterin,5TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OCC(O)C(O[Si](C)(C)C(C)(C)C)C1=CN=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)C2=N1	3591.8	Standard polar	33892256
Neopterin,5TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)C(O)C1=CN=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)C2=N1	3474.1	Semi standard non polar	33892256
Neopterin,5TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)C(O)C1=CN=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)C2=N1	3659.0	Standard non polar	33892256
Neopterin,5TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)C(O)C1=CN=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)C2=N1	3608.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Neopterin GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ox-9720000000-287de905bc263a1d3fef	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Neopterin GC-MS (3 TMS) - 70eV, Positive	splash10-0pb9-3393300000-91821528c6f566d17174	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Neopterin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Neopterin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Neopterin GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Neopterin GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Neopterin GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Neopterin GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Neopterin GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Neopterin GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Neopterin GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Neopterin GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Neopterin GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Neopterin GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Neopterin GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Neopterin GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Neopterin GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Neopterin GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Neopterin GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Neopterin GC-MS (TMS_2_11) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Neopterin GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Neopterin GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Neopterin GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Neopterin GC-MS (TMS_3_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Neopterin GC-MS (TMS_3_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Neopterin Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0udi-0090000000-3a09212908092a492f4d	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Neopterin Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-054y-0920000000-6241d1b694e32019a927	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Neopterin Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-05mp-4900000000-877883fea7e0d415c840	2012-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neopterin 10V, Positive-QTOF	splash10-0udi-0090000000-bd6cd1a1bfbd14b712cf	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neopterin 20V, Positive-QTOF	splash10-0f79-1190000000-2cfad581ae89edd75d7a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neopterin 40V, Positive-QTOF	splash10-03dm-9610000000-935c14541b2551e1a2ae	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neopterin 10V, Negative-QTOF	splash10-0udl-1490000000-873c74c47753e32ed9f4	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neopterin 20V, Negative-QTOF	splash10-01ox-4950000000-0c17274f2f41e583bbd6	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neopterin 40V, Negative-QTOF	splash10-052f-9400000000-8ae2879ae5357154c5d1	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neopterin 10V, Positive-QTOF	splash10-0udr-0190000000-5eeae3db4e4f85b1ce39	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neopterin 20V, Positive-QTOF	splash10-0o70-0390000000-a441f62b61df43ffd7a6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neopterin 40V, Positive-QTOF	splash10-00b9-0910000000-a539711a0c44dc33cde8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neopterin 10V, Negative-QTOF	splash10-0006-0910000000-0a62087f9b31592e385c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neopterin 20V, Negative-QTOF	splash10-01ox-0900000000-6854f20331ecc6eb7d8d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neopterin 40V, Negative-QTOF	splash10-0006-6910000000-b1ce97d80b5467300fd9	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Urine

Tissue Locations

Bone Marrow
Brain
Epidermis
Erythrocyte
Fibroblasts
Kidney
Leukocyte
Liver
Pancreas
Spleen

Pathways

Name	SMPDB/PathBank	KEGG
Pterine Biosynthesis
Dopa-responsive dystonia		Not Available
Hyperphenylalaniemia due to guanosine triphosphate cyclohydrolase deficiency		Not Available
Hyperphenylalaninemia due to 6-pyruvoyltetrahydropterin synthase deficiency (ptps)		Not Available
Hyperphenylalaninemia due to dhpr-deficiency		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.0060 +/- 0.0016 uM	Adult (>18 years old)	Both	Normal	1565552	details
Blood	Detected and Quantified	0.0150 +/- 0.0041 uM	Adult (>18 years old)	Not Specified	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	0.005 +/- 0.002 uM	Adult (>18 years old)	Both	Normal	22626821	details
Blood	Detected and Quantified	0.0038 +/- 0.0022 uM	Adult (>18 years old)	Both	Normal	7707089	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.018 +/- 0.002 uM	Adult (>18 years old)	Not Specified	Normal	8583213	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.01 uM	Adult (>18 years old)	Not Specified	Normal	7855550	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0252 +/- 0.002 uM	Not Specified	Not Specified	Normal	7669428	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0110-0.0240 uM	Adolescent (13-18 years old)	Not Specified	Normal	19304569	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.002-0.014 uM	Children (1-13 years old)	Male	Normal	18502672	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Normal	27609529	details
Urine	Detected and Quantified	2.0+/-0.8 umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	3200274	details
Urine	Detected and Quantified	0.21 +/- 0.08 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	0.23 +/- 0.08 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	0.36 +/- 0.07 umol/mmol creatinine	Children (1-13 years old)	Both	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	1.4 +/- 0.71 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	3939585	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.0347 +/- 0.0250 uM	Children (1-13 years old)	Both	AIDS	1565552	details
Blood	Detected and Quantified	0.33 +/- 0.04 uM	Adult (>18 years old)	Both	uremia	22626821	details
Blood	Detected and Quantified	0.0050 +/- 0.0028 uM	Adult (>18 years old)	Both	Multiple sclerosis	7707089	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.01175 (0.008-0.0155) uM	Children (1-13 years old)	Male	sepiapterin reductase deficiency	18502672	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0091 +/- 0.0074 uM	Adult (>18 years old)	Not Specified	Multiple Sclerosis	7707089	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.01 +/- 0.001 uM	Adult (>18 years old)	Not Specified	Hydrocephalus	8583213	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.023 +/- 0.01 uM	Adult (>18 years old)	Not Specified	CNS Tumors	8583213	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.12 +/- 0.083 uM	Adult (>18 years old)	Not Specified	CNS Infections	8583213	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.009 uM	Adolescent (13-18 years old)	Not Available	Urocanase deficiency	19304569	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0226 +/- 0.001 uM	Not Specified	Not Specified	idiopathic parkinsonisam	7669428	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0252 +/- 0.0022 uM	Not Specified	Not Specified	dopa-nonresponsive dystonia	7669428	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Crohns disease	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Ulcerative colitis	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Unclassified IBD	27609529	details
Urine	Detected and Quantified	22.6 umol/mmol creatinine	Newborn (0-30 days old)	Female	Hyperphenylalaninemia due to pterin-4a-carbinolamine dehydratase	3200274	details

Associated Disorders and Diseases

Disease References

AIDS
Ellaurie M, Calvelli T, Rubinstein A: Neopterin concentrations in pediatric human immunodeficiency virus infection as predictor of disease activity. Pediatr Infect Dis J. 1992 Apr;11(4):286-9. [PubMed:1565552 ]
Uremia
Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
Multiple sclerosis
Shaw CE, Dunbar PR, Macaulay HA, Neale TJ: Measurement of immune markers in the serum and cerebrospinal fluid of multiple sclerosis patients during clinical remission. J Neurol. 1995 Jan;242(2):53-8. [PubMed:7707089 ]
Hydrocephalus
Heyes MP, Saito K, Milstien S, Schiff SJ: Quinolinic acid in tumors, hemorrhage and bacterial infections of the central nervous system in children. J Neurol Sci. 1995 Nov;133(1-2):112-8. [PubMed:8583213 ]
CNS tumors
Heyes MP, Saito K, Milstien S, Schiff SJ: Quinolinic acid in tumors, hemorrhage and bacterial infections of the central nervous system in children. J Neurol Sci. 1995 Nov;133(1-2):112-8. [PubMed:8583213 ]
CNS infections
Heyes MP, Saito K, Milstien S, Schiff SJ: Quinolinic acid in tumors, hemorrhage and bacterial infections of the central nervous system in children. J Neurol Sci. 1995 Nov;133(1-2):112-8. [PubMed:8583213 ]
Sepiapterin reductase deficiency
Verbeek MM, Willemsen MA, Wevers RA, Lagerwerf AJ, Abeling NG, Blau N, Thony B, Vargiami E, Zafeiriou DI: Two Greek siblings with sepiapterin reductase deficiency. Mol Genet Metab. 2008 Aug;94(4):403-9. doi: 10.1016/j.ymgme.2008.04.003. Epub 2008 May 27. [PubMed:18502672 ]
Parkinson's disease
Furukawa Y, Nishi K, Mizuno Y, Narabayashi H: [Significance of CSF biopterin and neopterin in hereditary progressive dystonia with marked diurnal fluctuation (HPD)--a clue to pathogenesis]. No To Shinkei. 1995 Mar;47(3):261-8. [PubMed:7669428 ]
Urocanase deficiency
Espinos C, Pineda M, Martinez-Rubio D, Lupo V, Ormazabal A, Vilaseca MA, Spaapen LJ, Palau F, Artuch R: Mutations in the urocanase gene UROC1 are associated with urocanic aciduria. J Med Genet. 2009 Jun;46(6):407-11. doi: 10.1136/jmg.2008.060632. Epub 2009 Mar 19. [PubMed:19304569 ]
Crohn's disease
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Ulcerative colitis
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Pterin-4a carbinolamine dehydratase deficiency
Blaskovics M, Giudici TA: A new variant of biopterin deficiency. N Engl J Med. 1988 Dec 15;319(24):1611-2. doi: 10.1056/NEJM198812153192420. [PubMed:3200274 ]

Associated OMIM IDs

126200 (Multiple sclerosis)
182125 (Sepiapterin reductase deficiency)
168600 (Parkinson's disease)
276880 (Urocanase deficiency)
266600 (Crohn's disease)
264070 (Pterin-4a carbinolamine dehydratase deficiency)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB112166

KNApSAcK ID

C00007312

Chemspider ID

4300

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Neopterin

METLIN ID

Not Available

PubChem Compound

135408877

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000264

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Heyes MP, Saito K, Milstien S, Schiff SJ: Quinolinic acid in tumors, hemorrhage and bacterial infections of the central nervous system in children. J Neurol Sci. 1995 Nov;133(1-2):112-8. [PubMed:8583213 ]
Azumagawa K, Suzuki S, Tanabe T, Wakamiya E, Kawamura N, Tamai H: Neopterin, biopterin, and nitric oxide concentrations in the cerebrospinal fluid of children with central nervous system infections. Brain Dev. 2003 Apr;25(3):200-2. [PubMed:12689700 ]
Shaw CE, Dunbar PR, Macaulay HA, Neale TJ: Measurement of immune markers in the serum and cerebrospinal fluid of multiple sclerosis patients during clinical remission. J Neurol. 1995 Jan;242(2):53-8. [PubMed:7707089 ]
Gisslen M, Chiodi F, Fuchs D, Norkrans G, Svennerholm B, Wachter H, Hagberg L: Markers of immune stimulation in the cerebrospinal fluid during HIV infection: a longitudinal study. Scand J Infect Dis. 1994;26(5):523-33. [PubMed:7855550 ]
Reibnegger GJ, Bichler AH, Dapunt O, Fuchs DN, Fuith LC, Hausen A, Hetzel HM, Lutz H, Werner ER, Wachter H: Neopterin as a prognostic indicator in patients with carcinoma of the uterine cervix. Cancer Res. 1986 Feb;46(2):950-5. [PubMed:3940654 ]
Niederwieser D, Huber C, Wachter H: [Neopterin, a new biochemical marker for the detection of activated T lymphocytes]. Wien Klin Wochenschr. 1983 Mar 4;95(5):161-4. [PubMed:6602425 ]
Abdulle S, Hagberg L, Svennerholm B, Fuchs D, Gisslen M: Continuing intrathecal immunoactivation despite two years of effective antiretroviral therapy against HIV-1 infection. AIDS. 2002 Nov 8;16(16):2145-9. [PubMed:12409735 ]
Niederwieser A, Curtius HC: Tetrahydrobiopterin biosynthetic pathway and deficiency. Enzyme. 1987;38(1-4):302-11. [PubMed:3326735 ]
Kokcam I, Naziroglu M: Effects of vitamin E supplementation on blood antioxidants levels in patients with Behcet's disease. Clin Biochem. 2002 Nov;35(8):633-9. [PubMed:12498998 ]
Margreiter R, Aichberger C, Konigsrainer A, Reibnegger G, Weiss G, Wachter H: Biliary neopterin for differentiation between liver allograft rejection and viral graft infection. Transpl Int. 1992;5 Suppl 1:S199-200. [PubMed:14621776 ]
Steiner G, Zlabinger G, Karamehic J, Pohanka E, Kovarik J, Woloszczuk W: Interferon-gamma, neopterin, and interleukin-2 receptor levels in the serum of kidney transplant recipients. Transplant Proc. 1990 Aug;22(4):1857-8. [PubMed:2117813 ]
Inci Fisenk B, Us D, Ozcebe OI, Hascelik G: The value of increased neopterin levels in reducing transfusion-transmitted virus infections: detection of a donation from a HBsAg positive chronic carrier by screening of neopterin in Turkish blood donors. Scand J Infect Dis. 2005;37(8):599-604. [PubMed:16099770 ]
Antoniello S, Auletta M, Magri P, Russo N: Serum neopterin levels in patients with hepatocellular carcinoma. Biol Chem Hoppe Seyler. 1992 Nov;373(11):1165-8. [PubMed:1282321 ]
Barani J, Nilsson JA, Mattiasson I, Lindblad B, Gottsater A: Inflammatory mediators are associated with 1-year mortality in critical limb ischemia. J Vasc Surg. 2005 Jul;42(1):75-80. [PubMed:16012455 ]
Millner MM, Franthal W, Thalhammer GH, Berghold A, Aigner RM, Fuger GF, Reibnegger G: Neopterin concentrations in cerebrospinal fluid and serum as an aid in differentiating central nervous system and peripheral infections in children. Clin Chem. 1998 Jan;44(1):161-7. [PubMed:9550574 ]
Muller TF, Trosch F, Ebel H, Grussner RW, Feiber H, Goke B, Greger B, Lange H: Pancreas-specific protein (PASP), serum amyloid A (SAA), and neopterin (NEOP) in the diagnosis of rejection after simultaneous pancreas and kidney transplantation. Transpl Int. 1997;10(3):185-91. [PubMed:9163857 ]
Beckham JC, Caldwell DS, Peterson BL, Pippen AM, Currie MS, Keefe FJ, Weinberg JB: Disease severity in rheumatoid arthritis: relationships of plasma tumor necrosis factor-alpha, soluble interleukin 2-receptor, soluble CD4/CD8 ratio, neopterin, and fibrin D-dimer to traditional severity and functional measures. J Clin Immunol. 1992 Sep;12(5):353-61. [PubMed:1430106 ]
Prior C, Bollbach R, Fuchs D, Hausen A, Judmaier G, Niederwieser D, Reibnegger G, Rotthauwe HW, Werner ER, Wachter H: Urinary neopterin, a marker of clinical activity in patients with Crohn's disease. Clin Chim Acta. 1986 Feb 28;155(1):11-21. [PubMed:3698305 ]
Hagberg L, Dotevall L, Norkrans G, Larsson M, Wachter H, Fuchs D: Cerebrospinal fluid neopterin concentrations in central nervous system infection. J Infect Dis. 1993 Nov;168(5):1285-8. [PubMed:8228365 ]
Toncheva D, Galabov AS, Laich A, Atanassova S, Kamarinchev B, Dimitrov T, Fuchs D: Urinary neopterin concentrations in patients with Balkan endemic nephropathy (BEN). Kidney Int. 2003 Nov;64(5):1817-21. [PubMed:14531816 ]
Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
Sucher R, Schroecksnadel K, Weiss G, Margreiter R, Fuchs D, Brandacher G: Neopterin, a prognostic marker in human malignancies. Cancer Lett. 2010 Jan 1;287(1):13-22. doi: 10.1016/j.canlet.2009.05.008. Epub 2009 Jun 4. [PubMed:19500901 ]

Showing metabocard for Neopterin (HMDB0000845)

MOL for HMDB0000845 (Neopterin)

3D MOL for HMDB0000845 (Neopterin)

3D SDF for HMDB0000845 (Neopterin)

3D-SDF for HMDB0000845 (Neopterin)

PDB for HMDB0000845 (Neopterin)

3D PDB for HMDB0000845 (Neopterin)

SMILES for HMDB0000845 (Neopterin)

INCHI for HMDB0000845 (Neopterin)

Structure for HMDB0000845 (Neopterin)

3D Structure for HMDB0000845 (Neopterin)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra