NP-MRD: Showing NP-Card for Neopterin (NP0000404)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-08-19 23:58:05 UTC

NP-MRD ID

NP0000404

Secondary Accession Numbers

None

Natural Product 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

HMDB0000845
     RDKit          3D
Neopterin
 29 30  0  0  0  0  0  0  0  0999 V2000
    5.5729   -0.2706    1.0124 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2263   -0.1054    0.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3533   -1.1216    0.5186 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0789   -0.8861    0.1548 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1726   -1.8818    0.0249 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1012   -1.6383   -0.3396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5321   -0.3585   -0.5954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9287   -0.0565   -0.9988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3912   -0.9202   -1.9601 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8110   -0.0659    0.2411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3318    0.8125    1.2060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2001    0.3807   -0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0322    0.3657    0.9449 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3654    0.6352   -0.4675 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6431    0.3984   -0.1028 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5561    1.4252    0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1535    2.5960   -0.2107 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8263    1.1758    0.3896 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3085   -0.2500    0.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8140   -0.4111    2.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8040   -2.4799   -0.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9842    0.9702   -1.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6565   -1.4096   -2.4296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8766   -1.1111    0.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8142    1.6828    1.0755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1029    1.4060   -0.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6388   -0.3259   -0.9261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3553   -0.5305    1.1326 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4899    1.9747    0.4770 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>
NP0000404

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

HMDB0000845
     RDKit          3D
Neopterin
 29 30  0  0  0  0  0  0  0  0999 V2000
    5.5729   -0.2706    1.0124 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2263   -0.1054    0.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3533   -1.1216    0.5186 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0789   -0.8861    0.1548 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1726   -1.8818    0.0249 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1012   -1.6383   -0.3396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5321   -0.3585   -0.5954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9287   -0.0565   -0.9988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3912   -0.9202   -1.9601 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8110   -0.0659    0.2411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3318    0.8125    1.2060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2001    0.3807   -0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0322    0.3657    0.9449 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3654    0.6352   -0.4675 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6431    0.3984   -0.1028 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5561    1.4252    0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1535    2.5960   -0.2107 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8263    1.1758    0.3896 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3085   -0.2500    0.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8140   -0.4111    2.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8040   -2.4799   -0.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9842    0.9702   -1.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6565   -1.4096   -2.4296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8766   -1.1111    0.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8142    1.6828    1.0755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1029    1.4060   -0.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6388   -0.3259   -0.9261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3553   -0.5305    1.1326 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4899    1.9747    0.4770 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    HMDB0000845
HETATM    1  N1  UNL     1       5.573  -0.271   1.012  1.00  0.00           N  
HETATM    2  C1  UNL     1       4.226  -0.105   0.637  1.00  0.00           C  
HETATM    3  N2  UNL     1       3.353  -1.122   0.519  1.00  0.00           N  
HETATM    4  C2  UNL     1       2.079  -0.886   0.155  1.00  0.00           C  
HETATM    5  N3  UNL     1       1.173  -1.882   0.025  1.00  0.00           N  
HETATM    6  C3  UNL     1      -0.101  -1.638  -0.340  1.00  0.00           C  
HETATM    7  C4  UNL     1      -0.532  -0.359  -0.595  1.00  0.00           C  
HETATM    8  C5  UNL     1      -1.929  -0.057  -0.999  1.00  0.00           C  
HETATM    9  O1  UNL     1      -2.391  -0.920  -1.960  1.00  0.00           O  
HETATM   10  C6  UNL     1      -2.811  -0.066   0.241  1.00  0.00           C  
HETATM   11  O2  UNL     1      -2.332   0.812   1.206  1.00  0.00           O  
HETATM   12  C7  UNL     1      -4.200   0.381  -0.192  1.00  0.00           C  
HETATM   13  O3  UNL     1      -5.032   0.366   0.945  1.00  0.00           O  
HETATM   14  N4  UNL     1       0.365   0.635  -0.468  1.00  0.00           N  
HETATM   15  C8  UNL     1       1.643   0.398  -0.103  1.00  0.00           C  
HETATM   16  C9  UNL     1       2.556   1.425   0.026  1.00  0.00           C  
HETATM   17  O4  UNL     1       2.153   2.596  -0.211  1.00  0.00           O  
HETATM   18  N5  UNL     1       3.826   1.176   0.390  1.00  0.00           N  
HETATM   19  H1  UNL     1       6.309  -0.250   0.296  1.00  0.00           H  
HETATM   20  H2  UNL     1       5.814  -0.411   2.001  1.00  0.00           H  
HETATM   21  H3  UNL     1      -0.804  -2.480  -0.433  1.00  0.00           H  
HETATM   22  H4  UNL     1      -1.984   0.970  -1.407  1.00  0.00           H  
HETATM   23  H5  UNL     1      -1.656  -1.410  -2.430  1.00  0.00           H  
HETATM   24  H6  UNL     1      -2.877  -1.111   0.614  1.00  0.00           H  
HETATM   25  H7  UNL     1      -2.814   1.683   1.076  1.00  0.00           H  
HETATM   26  H8  UNL     1      -4.103   1.406  -0.596  1.00  0.00           H  
HETATM   27  H9  UNL     1      -4.639  -0.326  -0.926  1.00  0.00           H  
HETATM   28  H10 UNL     1      -5.355  -0.530   1.133  1.00  0.00           H  
HETATM   29  H11 UNL     1       4.490   1.975   0.477  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

HMDB0000845
     RDKit          3D
Neopterin
 29 30  0  0  0  0  0  0  0  0999 V2000
    5.5729   -0.2706    1.0124 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2263   -0.1054    0.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3533   -1.1216    0.5186 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0789   -0.8861    0.1548 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1726   -1.8818    0.0249 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1012   -1.6383   -0.3396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5321   -0.3585   -0.5954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9287   -0.0565   -0.9988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3912   -0.9202   -1.9601 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8110   -0.0659    0.2411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3318    0.8125    1.2060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2001    0.3807   -0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0322    0.3657    0.9449 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3654    0.6352   -0.4675 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6431    0.3984   -0.1028 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5561    1.4252    0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1535    2.5960   -0.2107 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8263    1.1758    0.3896 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3085   -0.2500    0.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8140   -0.4111    2.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8040   -2.4799   -0.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9842    0.9702   -1.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6565   -1.4096   -2.4296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8766   -1.1111    0.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8142    1.6828    1.0755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1029    1.4060   -0.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6388   -0.3259   -0.9261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3553   -0.5305    1.1326 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4899    1.9747    0.4770 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

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	HMDB
Neopterin, (r, r)-isomer	HMDB
Umanopterin	HMDB
Neopterin, (erythro-D)-isomer	HMDB
2-Amino-6-(1,2,3-trihydroxypropyl)-4(3H)-pteridinone	HMDB
Neopterin, (erythro-L)-isomer	HMDB
Neopterin, (threo-D)-isomer	HMDB
Neopterin, (threo-L)-isomer	HMDB

Chemical Formula

C₉H₁₁N₅O₄

Average Mass

253.2147 Da

Monoisotopic Mass

253.08110 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Arabidopsis thaliana	KNApSAcK Database	22123792
Tetrahymena pyriformis	LOTUS Database	35616633

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

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1000000 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Predicted 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

External Links

HMDB ID

HMDB0000845

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Neopterin

METLIN ID

248

PubChem Compound

4455

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

rw1233561

References

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 NP-Card for Neopterin (NP0000404)

MOL for NP0000404 (Neopterin)

3D MOL for NP0000404 (Neopterin)

3D SDF for NP0000404 (Neopterin)

3D-SDF for NP0000404 (Neopterin)

PDB for NP0000404 (Neopterin)

3D PDB for NP0000404 (Neopterin)

SMILES for NP0000404 (Neopterin)

INCHI for NP0000404 (Neopterin)

Structure for NP0000404 (Neopterin)

3D Structure for NP0000404 (Neopterin)