MiMeDB: Showing metabocard for Dihydropteroate (MMDBc0049935)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-29 22:46:36 UTC

Update Date

2023-12-14 16:53:09 UTC

Metabolite ID

MMDBc0049935

Metabolite Identification

Common Name

Dihydropteroate

Description

In the mammalian host, dihydrofolate biosynthesis occurs via the reduction of folic acid, whereas in plasmodia (e.g. Plasmodium berghei, a malaria parasite) the biosynthesis of 7,8-dihydropteroate, an intermediate product in dihydrofolate synthesis, occurs via the enzymic catalysis of the reaction of 2-amino-4-hydroxy-6-hydroxymethyl-7,8-dihydropteridine pyrophosphate with p-aminobenzoate. Malaria parasites synthesize their folate cofactors de novo and the antimalarial action of sulfonamides is due to their inhibiting the plasmodial dihydropteroate synthesis. The enzymes 6-hydroxymethylpterin pyrophosphokinase (EC 2.7.6.3, HPPK) and dihydropteroate synthase (EC 2.5.1.15, DHPS) catalyze sequential steps in folate biosynthesis. They are present in microorganisms but absent in mammals and therefore are especially suitable targets for antimicrobials. Sulfa drugs (sulfonamides and sulfones) currently are used as antimicrobials targeting DHPS, although resistance to these drugs is increasing. An NADPH-coupled microplate photometric assay could be used for rapid screening of chemical libraries for novel inhibitors of folate biosynthesis as the first step in developing new antimicrobial drugs targeting the folate biosynthetic pathway; in the microplate, the product of the DHPS reaction, 7,8-dihydropteroic acid, is reduced to tetrahydropteroate by excess dihydrofolate reductase (DHFR) using the cofactor NADPH (PMID: 17134675 , 4354403 , 3546688 ).

Structure

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

HMDB0001412
     RDKit          3D
7,8-Dihydropteroic acid
 37 39  0  0  0  0  0  0  0  0999 V2000
    7.3258    0.5676    0.0205 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9474    0.3920   -0.2164 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0800   -0.0648    0.7050 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7702   -0.2346    0.4890 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2543    0.0790   -0.7723 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1324    0.5477   -1.7247 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7323    0.8476   -2.8783 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4344    0.6886   -1.4237 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8744   -0.0895   -1.0288 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0599   -0.5160   -0.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4163   -0.6751   -0.5084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1918    0.1804    0.3685 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5967    0.2314    0.2792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3485    1.0359    1.1016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7450    1.0712    0.9956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3783    0.2831    0.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8313    0.3072   -0.0771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4894    1.0443    0.6796 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4435   -0.4927   -1.0364 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6279   -0.5193   -0.7729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2418   -0.5433   -0.6552 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4680   -0.8807    1.1954 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8576   -0.7106    1.4414 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8602   -0.1288    0.5602 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8067    1.4008   -0.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0838    1.0526   -2.1819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7162   -1.7312   -0.3189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5571   -0.4443   -1.5728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7177    0.7757    1.0832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8778    1.6680    1.8582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3568    1.6950    1.6302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6760   -1.4407   -0.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1153   -1.1401   -1.5186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6588   -1.1772   -1.3042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8906   -0.1812    1.8773 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1746   -1.9400    1.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2340   -0.9583    2.4065 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
  6  8  1  0
  5  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 16 20  1  0
 20 21  2  0
 10 22  1  0
 22 23  1  0
  8  2  1  0
 21 13  1  0
 23  4  1  0
  1 24  1  0
  1 25  1  0
  8 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 14 30  1  0
 15 31  1  0
 19 32  1  0
 20 33  1  0
 21 34  1  0
 22 35  1  0
 22 36  1  0
 23 37  1  0
M  END


  Mrv1652309042000222D          

 23 25  0  0  0  0            999 V2000
   -2.1993    0.0074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1993   -0.8175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4830    0.4274    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9155    0.4162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4793   -1.2299    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9155   -1.2337    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7631    0.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6204    0.0074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9155    1.2337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7556   -0.8175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6204   -0.8175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0581    0.4237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3292   -1.2187    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6571    0.0127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7997    1.2516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0853    1.6641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3707    1.2515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3707    0.4266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0852    0.0141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7997    0.4266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5142    1.6642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5142    2.4892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2287    1.2517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  2  0  0  0  0
  4  8  1  0  0  0  0
  4  9  2  0  0  0  0
  5 10  1  0  0  0  0
  6 11  2  0  0  0  0
  7 12  1  0  0  0  0
 11 13  1  0  0  0  0
  7 10  1  0  0  0  0
  8 11  1  0  0  0  0
 12 14  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 15  1  0  0  0  0
 14 18  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0049935

> <DATABASE_NAME>
MIME

> <SMILES>
NC1=NC2=C(N=C(CNC3=CC=C(C=C3)C(O)=O)CN2)C(=O)N1

> <INCHI_IDENTIFIER>
InChI=1S/C14H14N6O3/c15-14-19-11-10(12(21)20-14)18-9(6-17-11)5-16-8-3-1-7(2-4-8)13(22)23/h1-4,16H,5-6H2,(H,22,23)(H4,15,17,19,20,21)

> <INCHI_KEY>
WBFYVDCHGVNRBH-UHFFFAOYSA-N

> <FORMULA>
C14H14N6O3

> <MOLECULAR_WEIGHT>
314.2994

> <EXACT_MASS>
314.112738344

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
31.60301914773058

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{[(2-amino-4-oxo-3,4,7,8-tetrahydropteridin-6-yl)methyl]amino}benzoic acid

> <ALOGPS_LOGP>
-0.21

> <JCHEM_LOGP>
-0.26374587966666674

> <ALOGPS_LOGS>
-3.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.625756651743142

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.722559013545812

> <JCHEM_PKA_STRONGEST_BASIC>
1.7618126836811636

> <JCHEM_POLAR_SURFACE_AREA>
141.2

> <JCHEM_REFRACTIVITY>
93.10359999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.37e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7,8-dihydropteroic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001412
     RDKit          3D
7,8-Dihydropteroic acid
 37 39  0  0  0  0  0  0  0  0999 V2000
    7.3258    0.5676    0.0205 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9474    0.3920   -0.2164 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0800   -0.0648    0.7050 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7702   -0.2346    0.4890 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2543    0.0790   -0.7723 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1324    0.5477   -1.7247 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7323    0.8476   -2.8783 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4344    0.6886   -1.4237 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8744   -0.0895   -1.0288 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0599   -0.5160   -0.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4163   -0.6751   -0.5084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1918    0.1804    0.3685 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5967    0.2314    0.2792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3485    1.0359    1.1016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7450    1.0712    0.9956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3783    0.2831    0.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8313    0.3072   -0.0771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4894    1.0443    0.6796 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4435   -0.4927   -1.0364 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6279   -0.5193   -0.7729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2418   -0.5433   -0.6552 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4680   -0.8807    1.1954 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8576   -0.7106    1.4414 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8602   -0.1288    0.5602 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8067    1.4008   -0.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0838    1.0526   -2.1819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7162   -1.7312   -0.3189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5571   -0.4443   -1.5728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7177    0.7757    1.0832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8778    1.6680    1.8582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3568    1.6950    1.6302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6760   -1.4407   -0.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1153   -1.1401   -1.5186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6588   -1.1772   -1.3042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8906   -0.1812    1.8773 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1746   -1.9400    1.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2340   -0.9583    2.4065 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
  6  8  1  0
  5  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 16 20  1  0
 20 21  2  0
 10 22  1  0
 22 23  1  0
  8  2  1  0
 21 13  1  0
 23  4  1  0
  1 24  1  0
  1 25  1  0
  8 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 14 30  1  0
 15 31  1  0
 19 32  1  0
 20 33  1  0
 21 34  1  0
 22 35  1  0
 22 36  1  0
 23 37  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      -4.105   0.014   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.105  -1.526   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -2.768   0.798   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -5.442   0.777   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -2.761  -2.296   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      -5.442  -2.303   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -1.424   0.028   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -6.758   0.014   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0      -5.442   2.303   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.410  -1.526   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.758  -1.526   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.108   0.791   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -8.081  -2.275   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       1.227   0.024   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       5.226   2.336   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.893   3.106   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.559   2.336   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.559   0.796   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.892   0.026   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.226   0.796   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.560   3.107   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.560   4.647   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       7.894   2.337   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1    8    9                                                  
CONECT    5    2   10                                                       
CONECT    6    2   11                                                       
CONECT    7    3   12   10                                                  
CONECT    8    4   11                                                       
CONECT    9    4                                                            
CONECT   10    5    7                                                       
CONECT   11    6   13    8                                                  
CONECT   12    7   14                                                       
CONECT   13   11                                                            
CONECT   14   12   18                                                       
CONECT   15   16   20   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   14                                                  
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
CONECT   21   15   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0001412
HETATM    1  N1  UNL     1       7.326   0.568   0.020  1.00  0.00           N  
HETATM    2  C1  UNL     1       5.947   0.392  -0.216  1.00  0.00           C  
HETATM    3  N2  UNL     1       5.080  -0.065   0.705  1.00  0.00           N  
HETATM    4  C2  UNL     1       3.770  -0.235   0.489  1.00  0.00           C  
HETATM    5  C3  UNL     1       3.254   0.079  -0.772  1.00  0.00           C  
HETATM    6  C4  UNL     1       4.132   0.548  -1.725  1.00  0.00           C  
HETATM    7  O1  UNL     1       3.732   0.848  -2.878  1.00  0.00           O  
HETATM    8  N3  UNL     1       5.434   0.689  -1.424  1.00  0.00           N  
HETATM    9  N4  UNL     1       1.874  -0.090  -1.029  1.00  0.00           N  
HETATM   10  C5  UNL     1       1.060  -0.516  -0.168  1.00  0.00           C  
HETATM   11  C6  UNL     1      -0.416  -0.675  -0.508  1.00  0.00           C  
HETATM   12  N5  UNL     1      -1.192   0.180   0.369  1.00  0.00           N  
HETATM   13  C7  UNL     1      -2.597   0.231   0.279  1.00  0.00           C  
HETATM   14  C8  UNL     1      -3.349   1.036   1.102  1.00  0.00           C  
HETATM   15  C9  UNL     1      -4.745   1.071   0.996  1.00  0.00           C  
HETATM   16  C10 UNL     1      -5.378   0.283   0.047  1.00  0.00           C  
HETATM   17  C11 UNL     1      -6.831   0.307  -0.077  1.00  0.00           C  
HETATM   18  O2  UNL     1      -7.489   1.044   0.680  1.00  0.00           O  
HETATM   19  O3  UNL     1      -7.444  -0.493  -1.036  1.00  0.00           O  
HETATM   20  C12 UNL     1      -4.628  -0.519  -0.773  1.00  0.00           C  
HETATM   21  C13 UNL     1      -3.242  -0.543  -0.655  1.00  0.00           C  
HETATM   22  C14 UNL     1       1.468  -0.881   1.195  1.00  0.00           C  
HETATM   23  N6  UNL     1       2.858  -0.711   1.441  1.00  0.00           N  
HETATM   24  H1  UNL     1       7.860  -0.129   0.560  1.00  0.00           H  
HETATM   25  H2  UNL     1       7.807   1.401  -0.349  1.00  0.00           H  
HETATM   26  H3  UNL     1       6.084   1.053  -2.182  1.00  0.00           H  
HETATM   27  H4  UNL     1      -0.716  -1.731  -0.319  1.00  0.00           H  
HETATM   28  H5  UNL     1      -0.557  -0.444  -1.573  1.00  0.00           H  
HETATM   29  H6  UNL     1      -0.718   0.776   1.083  1.00  0.00           H  
HETATM   30  H7  UNL     1      -2.878   1.668   1.858  1.00  0.00           H  
HETATM   31  H8  UNL     1      -5.357   1.695   1.630  1.00  0.00           H  
HETATM   32  H9  UNL     1      -7.676  -1.441  -0.770  1.00  0.00           H  
HETATM   33  H10 UNL     1      -5.115  -1.140  -1.519  1.00  0.00           H  
HETATM   34  H11 UNL     1      -2.659  -1.177  -1.304  1.00  0.00           H  
HETATM   35  H12 UNL     1       0.891  -0.181   1.877  1.00  0.00           H  
HETATM   36  H13 UNL     1       1.175  -1.940   1.434  1.00  0.00           H  
HETATM   37  H14 UNL     1       3.234  -0.958   2.406  1.00  0.00           H  
CONECT    1    2   24   25
CONECT    2    3    3    8
CONECT    3    4
CONECT    4    5    5   23
CONECT    5    6    9
CONECT    6    7    7    8
CONECT    8   26
CONECT    9   10   10
CONECT   10   11   22
CONECT   11   12   27   28
CONECT   12   13   29
CONECT   13   14   14   21
CONECT   14   15   30
CONECT   15   16   16   31
CONECT   16   17   20
CONECT   17   18   18   19
CONECT   19   32
CONECT   20   21   21   33
CONECT   21   34
CONECT   22   23   35   36
CONECT   23   37
END

HMDB0001412
     RDKit          3D
7,8-Dihydropteroic acid
 37 39  0  0  0  0  0  0  0  0999 V2000
    7.3258    0.5676    0.0205 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9474    0.3920   -0.2164 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0800   -0.0648    0.7050 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7702   -0.2346    0.4890 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2543    0.0790   -0.7723 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1324    0.5477   -1.7247 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7323    0.8476   -2.8783 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4344    0.6886   -1.4237 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8744   -0.0895   -1.0288 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0599   -0.5160   -0.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4163   -0.6751   -0.5084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1918    0.1804    0.3685 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5967    0.2314    0.2792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3485    1.0359    1.1016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7450    1.0712    0.9956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3783    0.2831    0.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8313    0.3072   -0.0771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4894    1.0443    0.6796 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4435   -0.4927   -1.0364 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6279   -0.5193   -0.7729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2418   -0.5433   -0.6552 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4680   -0.8807    1.1954 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8576   -0.7106    1.4414 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8602   -0.1288    0.5602 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8067    1.4008   -0.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0838    1.0526   -2.1819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7162   -1.7312   -0.3189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5571   -0.4443   -1.5728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7177    0.7757    1.0832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8778    1.6680    1.8582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3568    1.6950    1.6302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6760   -1.4407   -0.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1153   -1.1401   -1.5186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6588   -1.1772   -1.3042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8906   -0.1812    1.8773 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1746   -1.9400    1.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2340   -0.9583    2.4065 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
  6  8  1  0
  5  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 16 20  1  0
 20 21  2  0
 10 22  1  0
 22 23  1  0
  8  2  1  0
 21 13  1  0
 23  4  1  0
  1 24  1  0
  1 25  1  0
  8 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 14 30  1  0
 15 31  1  0
 19 32  1  0
 20 33  1  0
 21 34  1  0
 22 35  1  0
 22 36  1  0
 23 37  1  0
M  END

Synonyms

Value	Source
4-(((2-Amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl)amino)benzoic acid	ChEBI
7,8-Dihydropteroate	ChEBI
Dihydropteroate	ChEBI
Dihydropteroinsaeure	ChEBI
4-(((2-Amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl)amino)benzoate	Generator
Dihydropteroic acid	Generator
4-[[(2-Amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]-benzoate	HMDB
4-[[(2-Amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]-benzoic acid	HMDB
4-[[(2-Amino-3,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]-benzoate	HMDB
4-[[(2-Amino-3,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]-benzoic acid	HMDB
Dihydropterate	HMDB
H2Pte	HMDB
p-[[(2-Amino-7,8-dihydro-4-hydroxy-6-pteridinyl)methyl]amino]-benzoate	HMDB
p-[[(2-Amino-7,8-dihydro-4-hydroxy-6-pteridinyl)methyl]amino]-benzoic acid	HMDB

Molecular Formula

C₁₄H₁₄N₆O₃

Average Mass

314.2994

Monoisotopic Mass

314.112738344

IUPAC Name

4-{[(2-amino-4-oxo-3,4,7,8-tetrahydropteridin-6-yl)methyl]amino}benzoic acid

Traditional Name

7,8-dihydropteroic acid

CAS Registry Number

Not Available

SMILES

NC1=NC2=C(N=C(CNC3=CC=C(C=C3)C(O)=O)CN2)C(=O)N1

InChI Identifier

InChI=1S/C14H14N6O3/c15-14-19-11-10(12(21)20-14)18-9(6-17-11)5-16-8-3-1-7(2-4-8)13(22)23/h1-4,16H,5-6H2,(H,22,23)(H4,15,17,19,20,21)

InChI Key

WBFYVDCHGVNRBH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pterins and derivatives. These are polycyclic aromatic compounds containing a pterin moiety, which consist of a pteridine ring bearing a ketone and an amine group to form 2-aminopteridin-4(3H)-one.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Pterins and derivatives

Direct Parent

Pterins and derivatives

Alternative Parents

Substituents

Pterin
Aminobenzoic acid
Aminobenzoic acid or derivatives
Benzoic acid or derivatives
Benzoic acid
Benzoyl
Aniline or substituted anilines
Phenylalkylamine
Hydroxypyrimidine
Secondary aliphatic/aromatic amine
Monocyclic benzene moiety
Pyrimidine
Benzenoid
Heteroaromatic compound
Amino acid or derivatives
Amino acid
Ketimine
Azacycle
Secondary amine
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Organic nitrogen compound
Imine
Organonitrogen compound
Organic oxide
Organopnictogen compound
Amine
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

pteroic acids (CHEBI:4581 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	-0.21	ALOGPS
logP	-0.26	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	4.72	ChemAxon
pKa (Strongest Basic)	1.76	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	141.2 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	93.1 m³·mol⁻¹	ChemAxon
Polarizability	31.6 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fe0-0790000000-51d5d3b08e34c7becd27	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0v4l-2409000000-f79f449589d2247daeca	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-016s-0595000000-4ed77e34023ff886c2a5	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0940000000-de25deb5daf6b50a16a3	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ti-0900000000-958eaaf4ee915da489c4	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0169000000-2f49a3d279aabb04affa	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-02tl-2392000000-9a4efdf541287a8562e5	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9420000000-e5fb759142be19739bd5	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0019000000-0ca8b4ed5ec637c71d37	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9231000000-4adcc7bed47beb3f3fb9	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9460000000-8c4fef4ee51806b3dc9e	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0209000000-907bcfac745eb62d4d42	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-016r-0958000000-1babfb4ccb2f4798f7d1	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-06vr-0920000000-ccfcce4cf4171ef887fa	2021-09-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192469	Folylpolyglutamate synthase, mitochondrial	Enzyme	Q05932	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0007310	Adenosine triphosphate	ADP	Not Available	Dihydrofolate synthase	VMH	30371894
MMDBr0007617	4-Aminobenzoate	Dihydropteroate	Not Available	Dihydropteroate synthase	VMH	30371894

Health Effects and Bioactivity

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

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	177	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Metabolic reconstruction
Bacteria	Firmicutes	381	Pig ; Human feces; Human ; Human supragingival plaque; Human saliva; Cattle ; Human stool; Human subgingival plaque	Metabolic reconstruction
Bacteria	Actinobacteria	127	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	129	Human feces; Human appendix biopsy; Human ; Human stool; Human urine; Human gastric fluid; Human saliva; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Bacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Bacteria	Synergistetes	2	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	2		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1		Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

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

External Links

HMDB ID

HMDB0001412

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6228

PubChem Compound

170

PDB ID

Not Available

ChEBI ID

4581

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

De Benedetti PG, Iarossi D, Menziani C, Caiolfa V, Frassineti C, Cennamo C: Quantitative structure-activity analysis in dihydropteroate synthase inhibition by sulfones. Comparison with sulfanilamides. J Med Chem. 1987 Mar;30(3):459-64. doi: 10.1021/jm00386a004. [PubMed:3546688 ]
Ferone R: The enzymic synthesis of dihydropteroate and dihydrofolate by Plasmodium berghei. J Protozool. 1973 Aug;20(3):459-64. doi: 10.1111/j.1550-7408.1973.tb00926.x. [PubMed:4354403 ]
Fernley RT, Iliades P, Macreadie I: A rapid assay for dihydropteroate synthase activity suitable for identification of inhibitors. Anal Biochem. 2007 Jan 15;360(2):227-34. doi: 10.1016/j.ab.2006.10.036. Epub 2006 Nov 13. [PubMed:17134675 ]

Showing metabocard for Dihydropteroate (MMDBc0049935)

MOL for #<Metabolite:0x00007fe2b401e2a0>

3D MOL for #<Metabolite:0x00007fe2b401e2a0>

3D SDF for #<Metabolite:0x00007fe2b401e2a0>

3D-SDF for #<Metabolite:0x00007fe2b401e2a0>

PDB for #<Metabolite:0x00007fe2b401e2a0>

3D PDB for #<Metabolite:0x00007fe2b401e2a0>

SMILES for #<Metabolite:0x00007fe2b401e2a0>

INCHI for #<Metabolite:0x00007fe2b401e2a0>

Structure for #<Metabolite:0x00007fe2b401e2a0>

3D Structure for #<Metabolite:0x00007fe2b401e2a0>