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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 17:08:00 UTC

Update Date

2021-09-26 23:12:24 UTC

HMDB ID

HMDB0256609

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Piromidic acid

Description

Piromidic acid, also known as panacid or acide piromidique, belongs to the class of organic compounds known as pyrido[2,3-d]pyrimidines. Pyrido[2,3-d]pyrimidines are compounds containing the pyrido[2,3-d]pyrimidine ring system, which is a pyridopyrimidine isomer with three ring nitrogen atoms at the 1-, 3-, and 8- position. Based on a literature review a significant number of articles have been published on Piromidic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Piromidic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Piromidic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0256609
     RDKit          3D
Piromidic acid
 37 39  0  0  0  0  0  0  0  0999 V2000
    1.4380   -2.9293   -0.8053 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4975   -2.2834    0.5640 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9522   -0.9105    0.4320 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2492   -0.5718    0.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7064    0.7094    0.3610 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1119    1.0725    0.4156 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9959    0.1983    0.5813 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5254    2.3893    0.2874 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.7126    0.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1146    2.9018    0.0584 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4578    1.3713    0.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4937    2.3698   -0.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7946    1.9941   -0.1055 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2151    0.7220    0.0169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6157    0.3971   -0.0419 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6689    1.3627   -0.2305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9406    0.6785    0.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6077   -0.7738    0.3221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1421   -0.9341    0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2853   -0.2302    0.1951 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0282    0.0680    0.2510 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3446   -3.5573   -0.9914 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4116   -2.1394   -1.5775 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4940   -3.5196   -0.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2407   -2.8887    1.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5261   -2.3206    1.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9723   -1.3654    0.6269 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9592    2.7573   -0.5491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8303    3.3938   -0.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4912    2.2526    0.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6378    1.6872   -1.2981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4242    1.1017    1.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6913    0.8064   -0.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8749   -1.1413    1.3403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1822   -1.4219   -0.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9082   -1.5531   -0.8077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6468   -1.4060    0.9528 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  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
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 14 20  1  0
 20 21  2  0
 21  3  1  0
 21 11  1  0
 19 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  4 27  1  0
  8 28  1  0
 12 29  1  0
 16 30  1  0
 16 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  0
 18 35  1  0
 19 36  1  0
 19 37  1  0
M  END

  Mrv1533004261519022D          

 21 23  0  0  0  0            999 V2000
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0405   -1.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5925   -1.9275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1800   -2.6420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3731   -2.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
  3 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
  5 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0256609

> <DATABASE_NAME>
hmdb

> <SMILES>
CCN1C=C(C(O)=O)C(=O)C2=CN=C(N=C12)N1CCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C14H16N4O3/c1-2-17-8-10(13(20)21)11(19)9-7-15-14(16-12(9)17)18-5-3-4-6-18/h7-8H,2-6H2,1H3,(H,20,21)

> <INCHI_KEY>
RCIMBBZXSXFZBV-UHFFFAOYSA-N

> <FORMULA>
C14H16N4O3

> <MOLECULAR_WEIGHT>
288.307

> <EXACT_MASS>
288.122240391

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
29.78331159593219

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-ethyl-5-oxo-2-(pyrrolidin-1-yl)-5H,8H-pyrido[2,3-d]pyrimidine-6-carboxylic acid

> <ALOGPS_LOGP>
0.42

> <JCHEM_LOGP>
1.5934879106666664

> <ALOGPS_LOGS>
-2.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.612598220200083

> <JCHEM_PKA_STRONGEST_BASIC>
3.029259218784226

> <JCHEM_POLAR_SURFACE_AREA>
86.63000000000001

> <JCHEM_REFRACTIVITY>
78.96979999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.21e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
enterol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0256609
     RDKit          3D
Piromidic acid
 37 39  0  0  0  0  0  0  0  0999 V2000
    1.4380   -2.9293   -0.8053 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4975   -2.2834    0.5640 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9522   -0.9105    0.4320 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2492   -0.5718    0.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7064    0.7094    0.3610 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1119    1.0725    0.4156 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9959    0.1983    0.5813 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5254    2.3893    0.2874 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.7126    0.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1146    2.9018    0.0584 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4578    1.3713    0.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4937    2.3698   -0.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7946    1.9941   -0.1055 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2151    0.7220    0.0169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6157    0.3971   -0.0419 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6689    1.3627   -0.2305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9406    0.6785    0.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6077   -0.7738    0.3221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1421   -0.9341    0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2853   -0.2302    0.1951 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0282    0.0680    0.2510 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3446   -3.5573   -0.9914 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4116   -2.1394   -1.5775 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4940   -3.5196   -0.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2407   -2.8887    1.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5261   -2.3206    1.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9723   -1.3654    0.6269 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9592    2.7573   -0.5491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8303    3.3938   -0.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4912    2.2526    0.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6378    1.6872   -1.2981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4242    1.1017    1.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6913    0.8064   -0.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8749   -1.1413    1.3403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1822   -1.4219   -0.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9082   -1.5531   -0.8077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6468   -1.4060    0.9528 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  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
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 14 20  1  0
 20 21  2  0
 21  3  1  0
 21 11  1  0
 19 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  4 27  1  0
  8 28  1  0
 12 29  1  0
 16 30  1  0
 16 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  0
 18 35  1  0
 19 36  1  0
 19 37  1  0
M  END

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       6.668  -0.770   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       5.335  -3.080   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       8.002  -3.080   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       9.409  -2.454   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.439  -3.598   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.669  -4.932   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.163  -4.612   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   19                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12    8    3                                                  
CONECT   14   11   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   14                                                       
CONECT   19    5   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0256609
HETATM    1  C1  UNL     1       1.438  -2.929  -0.805  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.498  -2.283   0.564  1.00  0.00           C  
HETATM    3  N1  UNL     1       1.952  -0.910   0.432  1.00  0.00           N  
HETATM    4  C3  UNL     1       3.249  -0.572   0.482  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.706   0.709   0.361  1.00  0.00           C  
HETATM    6  C5  UNL     1       5.112   1.073   0.416  1.00  0.00           C  
HETATM    7  O1  UNL     1       5.996   0.198   0.581  1.00  0.00           O  
HETATM    8  O2  UNL     1       5.525   2.389   0.287  1.00  0.00           O  
HETATM    9  C6  UNL     1       2.777   1.713   0.177  1.00  0.00           C  
HETATM   10  O3  UNL     1       3.115   2.902   0.058  1.00  0.00           O  
HETATM   11  C7  UNL     1       1.458   1.371   0.126  1.00  0.00           C  
HETATM   12  C8  UNL     1       0.494   2.370  -0.061  1.00  0.00           C  
HETATM   13  N2  UNL     1      -0.795   1.994  -0.105  1.00  0.00           N  
HETATM   14  C9  UNL     1      -1.215   0.722   0.017  1.00  0.00           C  
HETATM   15  N3  UNL     1      -2.616   0.397  -0.042  1.00  0.00           N  
HETATM   16  C10 UNL     1      -3.669   1.363  -0.230  1.00  0.00           C  
HETATM   17  C11 UNL     1      -4.941   0.678   0.150  1.00  0.00           C  
HETATM   18  C12 UNL     1      -4.608  -0.774   0.322  1.00  0.00           C  
HETATM   19  C13 UNL     1      -3.142  -0.934   0.080  1.00  0.00           C  
HETATM   20  N4  UNL     1      -0.285  -0.230   0.195  1.00  0.00           N  
HETATM   21  C14 UNL     1       1.028   0.068   0.251  1.00  0.00           C  
HETATM   22  H1  UNL     1       2.345  -3.557  -0.991  1.00  0.00           H  
HETATM   23  H2  UNL     1       1.412  -2.139  -1.578  1.00  0.00           H  
HETATM   24  H3  UNL     1       0.494  -3.520  -0.943  1.00  0.00           H  
HETATM   25  H4  UNL     1       2.241  -2.889   1.159  1.00  0.00           H  
HETATM   26  H5  UNL     1       0.526  -2.321   1.057  1.00  0.00           H  
HETATM   27  H6  UNL     1       3.972  -1.365   0.627  1.00  0.00           H  
HETATM   28  H7  UNL     1       5.959   2.757  -0.549  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.830   3.394  -0.159  1.00  0.00           H  
HETATM   30  H9  UNL     1      -3.491   2.253   0.440  1.00  0.00           H  
HETATM   31  H10 UNL     1      -3.638   1.687  -1.298  1.00  0.00           H  
HETATM   32  H11 UNL     1      -5.424   1.102   1.053  1.00  0.00           H  
HETATM   33  H12 UNL     1      -5.691   0.806  -0.673  1.00  0.00           H  
HETATM   34  H13 UNL     1      -4.875  -1.141   1.340  1.00  0.00           H  
HETATM   35  H14 UNL     1      -5.182  -1.422  -0.383  1.00  0.00           H  
HETATM   36  H15 UNL     1      -2.908  -1.553  -0.808  1.00  0.00           H  
HETATM   37  H16 UNL     1      -2.647  -1.406   0.953  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   25   26
CONECT    3    4   21
CONECT    4    5    5   27
CONECT    5    6    9
CONECT    6    7    7    8
CONECT    8   28
CONECT    9   10   10   11
CONECT   11   12   12   21
CONECT   12   13   29
CONECT   13   14   14
CONECT   14   15   20
CONECT   15   16   19
CONECT   16   17   30   31
CONECT   17   18   32   33
CONECT   18   19   34   35
CONECT   19   36   37
CONECT   20   21   21
END

HMDB0256609
     RDKit          3D
Piromidic acid
 37 39  0  0  0  0  0  0  0  0999 V2000
    1.4380   -2.9293   -0.8053 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4975   -2.2834    0.5640 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9522   -0.9105    0.4320 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2492   -0.5718    0.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7064    0.7094    0.3610 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1119    1.0725    0.4156 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9959    0.1983    0.5813 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5254    2.3893    0.2874 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.7126    0.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1146    2.9018    0.0584 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4578    1.3713    0.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4937    2.3698   -0.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7946    1.9941   -0.1055 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2151    0.7220    0.0169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6157    0.3971   -0.0419 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6689    1.3627   -0.2305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9406    0.6785    0.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6077   -0.7738    0.3221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1421   -0.9341    0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2853   -0.2302    0.1951 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0282    0.0680    0.2510 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3446   -3.5573   -0.9914 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4116   -2.1394   -1.5775 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4940   -3.5196   -0.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2407   -2.8887    1.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5261   -2.3206    1.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9723   -1.3654    0.6269 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9592    2.7573   -0.5491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8303    3.3938   -0.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4912    2.2526    0.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6378    1.6872   -1.2981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4242    1.1017    1.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6913    0.8064   -0.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8749   -1.1413    1.3403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1822   -1.4219   -0.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9082   -1.5531   -0.8077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6468   -1.4060    0.9528 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  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
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 14 20  1  0
 20 21  2  0
 21  3  1  0
 21 11  1  0
 19 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  4 27  1  0
  8 28  1  0
 12 29  1  0
 16 30  1  0
 16 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  0
 18 35  1  0
 19 36  1  0
 19 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
8-Ethyl-5,8-dihydro-5-oxo-2-(1-pyrrolidinyl)pyrido(2,3-D)pyrimidine-6-carboxylic acid	ChEBI
Acide piromidique	ChEBI
Acido piromidico	ChEBI
Acidum piromidicum	ChEBI
Actrun C	ChEBI
Bactramyl	ChEBI
Enterol	ChEBI
Gastrurol	ChEBI
Panacid	ChEBI
Pyromidic acid	ChEBI
Reelon	ChEBI
Septural	ChEBI
Uropir	ChEBI
8-Ethyl-5,8-dihydro-5-oxo-2-(1-pyrrolidinyl)pyrido(2,3-D)pyrimidine-6-carboxylate	Generator
Pyromidate	Generator
Piromidate	Generator
PA	KEGG
Acid, piromidic	MeSH

Chemical Formula

C₁₄H₁₆N₄O₃

Average Molecular Weight

288.307

Monoisotopic Molecular Weight

288.122240391

IUPAC Name

8-ethyl-5-oxo-2-(pyrrolidin-1-yl)-5H,8H-pyrido[2,3-d]pyrimidine-6-carboxylic acid

Traditional Name

enterol

CAS Registry Number

Not Available

SMILES

CCN1C=C(C(O)=O)C(=O)C2=CN=C(N=C12)N1CCCC1

InChI Identifier

InChI=1S/C14H16N4O3/c1-2-17-8-10(13(20)21)11(19)9-7-15-14(16-12(9)17)18-5-3-4-6-18/h7-8H,2-6H2,1H3,(H,20,21)

InChI Key

RCIMBBZXSXFZBV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrido[2,3-d]pyrimidines. Pyrido[2,3-d]pyrimidines are compounds containing the pyrido[2,3-d]pyrimidine ring system, which is a pyridopyrimidine isomer with three ring nitrogen atoms at the 1-, 3-, and 8- position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridopyrimidines

Sub Class

Pyrido[2,3-d]pyrimidines

Direct Parent

Pyrido[2,3-d]pyrimidines

Alternative Parents

Substituents

Pyrido[2,3-d]pyrimidine
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Dialkylarylamine
Aminopyrimidine
Pyrimidine
Pyridine
Heteroaromatic compound
Vinylogous amide
Pyrrolidine
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
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: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0256609)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.42	ALOGPS
logP	1.59	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	5.61	ChemAxon
pKa (Strongest Basic)	3.03	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	86.63 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	78.97 m³·mol⁻¹	ChemAxon
Polarizability	29.78 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	196.945	30932474
DeepCCS	[M+Na]+	172.173	30932474
AllCCS	[M+H]+	165.0	32859911
AllCCS	[M+H-H2O]+	161.6	32859911
AllCCS	[M+NH4]+	168.1	32859911
AllCCS	[M+Na]+	169.0	32859911
AllCCS	[M-H]-	168.3	32859911
AllCCS	[M+Na-2H]-	168.0	32859911
AllCCS	[M+HCOO]-	167.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Piromidic acid	CCN1C=C(C(O)=O)C(=O)C2=CN=C(N=C12)N1CCCC1	3332.0	Standard polar	33892256
Piromidic acid	CCN1C=C(C(O)=O)C(=O)C2=CN=C(N=C12)N1CCCC1	2537.1	Standard non polar	33892256
Piromidic acid	CCN1C=C(C(O)=O)C(=O)C2=CN=C(N=C12)N1CCCC1	3061.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Piromidic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-0980000000-e0572e12c19b3c4fdc72	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Piromidic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Piromidic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Piromidic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piromidic acid 10V, Positive-QTOF	splash10-000i-0090000000-6dac86f0218e62a678da	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piromidic acid 20V, Positive-QTOF	splash10-00dv-0090000000-1c0f05e8b35af7223253	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piromidic acid 40V, Positive-QTOF	splash10-006x-6790000000-78a7c8439d721f499128	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piromidic acid 10V, Negative-QTOF	splash10-000f-0090000000-dc4762fae5c89796d99a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piromidic acid 20V, Negative-QTOF	splash10-014l-0090000000-69c6b20abe5c1bb4e3e8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piromidic acid 40V, Negative-QTOF	splash10-02ta-4490000000-8348d7b2352fe3679cbf	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB13744

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4689

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Piromidic_acid

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

32019

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Piromidic acid (HMDB0256609)

MOL for HMDB0256609 (Piromidic acid)

3D MOL for HMDB0256609 (Piromidic acid)

3D SDF for HMDB0256609 (Piromidic acid)

3D-SDF for HMDB0256609 (Piromidic acid)

PDB for HMDB0256609 (Piromidic acid)

3D PDB for HMDB0256609 (Piromidic acid)

SMILES for HMDB0256609 (Piromidic acid)

INCHI for HMDB0256609 (Piromidic acid)

Structure for HMDB0256609 (Piromidic acid)

3D Structure for HMDB0256609 (Piromidic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra