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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 15:30:30 UTC

Update Date

2021-09-26 23:10:45 UTC

HMDB ID

HMDB0255698

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Nolatrexed

Description

Nolatrexed belongs to the class of organic compounds known as quinazolinamines. These are heterocyclic aromatic compounds containing a quianazoline moiety substituted by one or more amine groups. Based on a literature review a significant number of articles have been published on Nolatrexed. This compound has been identified in human blood as reported by (PMID: 31557052 ). Nolatrexed is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Nolatrexed 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

HMDB0255698
     RDKit          3D
Nolatrexed
 32 34  0  0  0  0  0  0  0  0999 V2000
    1.0605   -2.4546   -1.9106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1021   -1.8151   -1.2325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1405   -2.6526   -0.8145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2457   -2.1347   -0.1820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3130   -0.7830    0.0324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3878   -0.2982    0.6449 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5090    1.0025    0.8799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6866    1.4908    1.5451 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5323    1.8425    0.4938 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4332    1.3945   -0.1263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5202    2.2090   -0.4833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2791    0.0456   -0.3844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1743   -0.4606   -1.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1204    0.6010   -1.5343 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3800    0.8175   -0.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3111    0.1997    0.9454 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3207    0.4079    1.8713 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3768    1.1988    1.6099 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4706    1.8098    0.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4784    1.6182   -0.5113 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0922   -3.5250   -1.6782 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0787   -2.2678   -2.9980 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9846   -1.9881   -1.4938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0895   -3.7350   -0.9847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0735   -2.7776    0.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6923    1.6739    2.5711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5172    1.6485    0.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6693    2.8599    0.6990 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4828   -0.4417    1.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2909   -0.0638    2.8427 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3395    2.4566    0.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5784    2.1211   -1.4545 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
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 13  2  1  0
 20 15  1  0
 12  5  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
 16 29  1  0
 17 30  1  0
 19 31  1  0
 20 32  1  0
M  END


  Mrv1652310211603142D          

 20 22  0  0  0  0            999 V2000
   -1.4289    0.0000    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
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   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
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 S   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
   -1.4289    0.8250    0.0000 C   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
   -2.1434    2.0625    0.0000 N   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
   -0.7145    2.0625    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 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
    1.4289   -1.6500    0.0000 N   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
  1  2  1  0  0  0  0
  2  3  2  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
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
  5 19  1  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0255698

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC=C2N=C(N)NC(=O)C2=C1SC1=CC=NC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H12N4OS/c1-8-2-3-10-11(13(19)18-14(15)17-10)12(8)20-9-4-6-16-7-5-9/h2-7H,1H3,(H3,15,17,18,19)

> <INCHI_KEY>
XHWRWCSCBDLOLM-UHFFFAOYSA-N

> <FORMULA>
C14H12N4OS

> <MOLECULAR_WEIGHT>
284.34

> <EXACT_MASS>
284.073182196

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
28.753790404406505

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-amino-6-methyl-5-(pyridin-4-ylsulfanyl)-3,4-dihydroquinazolin-4-one

> <ALOGPS_LOGP>
1.90

> <JCHEM_LOGP>
1.981560060333333

> <ALOGPS_LOGS>
-3.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.233814050857148

> <JCHEM_PKA_STRONGEST_BASIC>
4.656540616498878

> <JCHEM_POLAR_SURFACE_AREA>
80.37

> <JCHEM_REFRACTIVITY>
81.75710000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.86e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-6-methyl-5-(pyridin-4-ylsulfanyl)-3H-quinazolin-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0255698
     RDKit          3D
Nolatrexed
 32 34  0  0  0  0  0  0  0  0999 V2000
    1.0605   -2.4546   -1.9106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1021   -1.8151   -1.2325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1405   -2.6526   -0.8145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2457   -2.1347   -0.1820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3130   -0.7830    0.0324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3878   -0.2982    0.6449 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5090    1.0025    0.8799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6866    1.4908    1.5451 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5323    1.8425    0.4938 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4332    1.3945   -0.1263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5202    2.2090   -0.4833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2791    0.0456   -0.3844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1743   -0.4606   -1.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1204    0.6010   -1.5343 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3800    0.8175   -0.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3111    0.1997    0.9454 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3207    0.4079    1.8713 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3768    1.1988    1.6099 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4706    1.8098    0.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4784    1.6182   -0.5113 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0922   -3.5250   -1.6782 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0787   -2.2678   -2.9980 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9846   -1.9881   -1.4938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0895   -3.7350   -0.9847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0735   -2.7776    0.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6923    1.6739    2.5711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5172    1.6485    0.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6693    2.8599    0.6990 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4828   -0.4417    1.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2909   -0.0638    2.8427 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3395    2.4566    0.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5784    2.1211   -1.4545 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
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 13  2  1  0
 20 15  1  0
 12  5  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
 16 29  1  0
 17 30  1  0
 19 31  1  0
 20 32  1  0
M  END

HEADER    PROTEIN                                 21-OCT-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-OCT-16         0                                  
HETATM    1  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    8  S   UNK     0       0.000   1.540   0.000  0.00  0.00           S+0
HETATM    9  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      -4.001   3.850   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0       5.335  -3.080   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   19                                                  
CONECT    6    5    7   15                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
CONECT   15    6   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18    5                                                       
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0255698
HETATM    1  C1  UNL     1       1.060  -2.455  -1.911  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.102  -1.815  -1.232  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.141  -2.653  -0.815  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.246  -2.135  -0.182  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.313  -0.783   0.032  1.00  0.00           C  
HETATM    6  N1  UNL     1      -3.388  -0.298   0.645  1.00  0.00           N  
HETATM    7  C6  UNL     1      -3.509   1.002   0.880  1.00  0.00           C  
HETATM    8  N2  UNL     1      -4.687   1.491   1.545  1.00  0.00           N  
HETATM    9  N3  UNL     1      -2.532   1.843   0.494  1.00  0.00           N  
HETATM   10  C7  UNL     1      -1.433   1.395  -0.126  1.00  0.00           C  
HETATM   11  O1  UNL     1      -0.520   2.209  -0.483  1.00  0.00           O  
HETATM   12  C8  UNL     1      -1.279   0.046  -0.384  1.00  0.00           C  
HETATM   13  C9  UNL     1      -0.174  -0.461  -1.015  1.00  0.00           C  
HETATM   14  S1  UNL     1       1.120   0.601  -1.534  1.00  0.00           S  
HETATM   15  C10 UNL     1       2.380   0.817  -0.286  1.00  0.00           C  
HETATM   16  C11 UNL     1       2.311   0.200   0.945  1.00  0.00           C  
HETATM   17  C12 UNL     1       3.321   0.408   1.871  1.00  0.00           C  
HETATM   18  N4  UNL     1       4.377   1.199   1.610  1.00  0.00           N  
HETATM   19  C13 UNL     1       4.471   1.810   0.427  1.00  0.00           C  
HETATM   20  C14 UNL     1       3.478   1.618  -0.511  1.00  0.00           C  
HETATM   21  H1  UNL     1       1.092  -3.525  -1.678  1.00  0.00           H  
HETATM   22  H2  UNL     1       1.079  -2.268  -2.998  1.00  0.00           H  
HETATM   23  H3  UNL     1       1.985  -1.988  -1.494  1.00  0.00           H  
HETATM   24  H4  UNL     1      -1.090  -3.735  -0.985  1.00  0.00           H  
HETATM   25  H5  UNL     1      -3.074  -2.778   0.155  1.00  0.00           H  
HETATM   26  H6  UNL     1      -4.692   1.674   2.571  1.00  0.00           H  
HETATM   27  H7  UNL     1      -5.517   1.648   0.958  1.00  0.00           H  
HETATM   28  H8  UNL     1      -2.669   2.860   0.699  1.00  0.00           H  
HETATM   29  H9  UNL     1       1.483  -0.442   1.195  1.00  0.00           H  
HETATM   30  H10 UNL     1       3.291  -0.064   2.843  1.00  0.00           H  
HETATM   31  H11 UNL     1       5.339   2.457   0.220  1.00  0.00           H  
HETATM   32  H12 UNL     1       3.578   2.121  -1.454  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    3   13
CONECT    3    4   24
CONECT    4    5    5   25
CONECT    5    6   12
CONECT    6    7    7
CONECT    7    8    9
CONECT    8   26   27
CONECT    9   10   28
CONECT   10   11   11   12
CONECT   12   13   13
CONECT   13   14
CONECT   14   15
CONECT   15   16   16   20
CONECT   16   17   29
CONECT   17   18   18   30
CONECT   18   19
CONECT   19   20   20   31
CONECT   20   32
END

HMDB0255698
     RDKit          3D
Nolatrexed
 32 34  0  0  0  0  0  0  0  0999 V2000
    1.0605   -2.4546   -1.9106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1021   -1.8151   -1.2325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1405   -2.6526   -0.8145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2457   -2.1347   -0.1820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3130   -0.7830    0.0324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3878   -0.2982    0.6449 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5090    1.0025    0.8799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6866    1.4908    1.5451 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5323    1.8425    0.4938 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4332    1.3945   -0.1263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5202    2.2090   -0.4833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2791    0.0456   -0.3844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1743   -0.4606   -1.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1204    0.6010   -1.5343 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3800    0.8175   -0.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3111    0.1997    0.9454 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3207    0.4079    1.8713 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3768    1.1988    1.6099 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4706    1.8098    0.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4784    1.6182   -0.5113 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0922   -3.5250   -1.6782 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0787   -2.2678   -2.9980 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9846   -1.9881   -1.4938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0895   -3.7350   -0.9847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0735   -2.7776    0.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6923    1.6739    2.5711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5172    1.6485    0.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6693    2.8599    0.6990 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4828   -0.4417    1.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2909   -0.0638    2.8427 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3395    2.4566    0.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5784    2.1211   -1.4545 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
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 13  2  1  0
 20 15  1  0
 12  5  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
 16 29  1  0
 17 30  1  0
 19 31  1  0
 20 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Nolatrexed dihydrochloride	MeSH
3,4-dihydro-2-amino-6-Methyl-4-oxo-5-(4-pyridylthio)quinazoline dihydrochloride	MeSH
Thymitaq	MeSH
2-Imino-6-methyl-5-(pyridin-4-ylsulphanyl)-1,2-dihydroquinazolin-4-ol	Generator

Chemical Formula

C₁₄H₁₂N₄OS

Average Molecular Weight

284.34

Monoisotopic Molecular Weight

284.073182196

IUPAC Name

2-amino-6-methyl-5-(pyridin-4-ylsulfanyl)-3,4-dihydroquinazolin-4-one

Traditional Name

2-amino-6-methyl-5-(pyridin-4-ylsulfanyl)-3H-quinazolin-4-one

CAS Registry Number

Not Available

SMILES

CC1=CC=C2N=C(N)NC(=O)C2=C1SC1=CC=NC=C1

InChI Identifier

InChI=1S/C14H12N4OS/c1-8-2-3-10-11(13(19)18-14(15)17-10)12(8)20-9-4-6-16-7-5-9/h2-7H,1H3,(H3,15,17,18,19)

InChI Key

XHWRWCSCBDLOLM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinazolinamines. These are heterocyclic aromatic compounds containing a quianazoline moiety substituted by one or more amine groups.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Benzodiazines

Direct Parent

Quinazolinamines

Alternative Parents

Substituents

Quinazolinamine
Diarylthioether
Aryl thioether
Thiophenol ether
Aminopyrimidine
Pyrimidone
Pyridine
Pyrimidine
Vinylogous thioester
Benzenoid
Heteroaromatic compound
Vinylogous amide
Thioether
Azacycle
Sulfenyl compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Amine
Organic nitrogen 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: HMDB0255698)

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	1.9	ALOGPS
logP	1.98	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	11.23	ChemAxon
pKa (Strongest Basic)	4.66	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	80.37 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	81.76 m³·mol⁻¹	ChemAxon
Polarizability	28.75 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+H]+	164.233	30932474
DeepCCS	[M-H]-	161.875	30932474
DeepCCS	[M-2H]-	194.761	30932474
DeepCCS	[M+Na]+	170.327	30932474
AllCCS	[M+H]+	163.9	32859911
AllCCS	[M+H-H2O]+	160.3	32859911
AllCCS	[M+NH4]+	167.2	32859911
AllCCS	[M+Na]+	168.1	32859911
AllCCS	[M-H]-	165.4	32859911
AllCCS	[M+Na-2H]-	164.8	32859911
AllCCS	[M+HCOO]-	164.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	9.8919 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.79 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	950.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	236.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	130.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	163.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	75.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	320.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	397.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	194.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	727.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	51.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	914.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	196.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	279.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	387.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	250.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	137.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nolatrexed	CC1=CC=C2N=C(N)NC(=O)C2=C1SC1=CC=NC=C1	4015.9	Standard polar	33892256
Nolatrexed	CC1=CC=C2N=C(N)NC(=O)C2=C1SC1=CC=NC=C1	2715.5	Standard non polar	33892256
Nolatrexed	CC1=CC=C2N=C(N)NC(=O)C2=C1SC1=CC=NC=C1	3156.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nolatrexed,1TMS,isomer #1	CC1=CC=C2N=C(N[Si](C)(C)C)[NH]C(=O)C2=C1SC1=CC=NC=C1	2797.8	Semi standard non polar	33892256
Nolatrexed,1TMS,isomer #1	CC1=CC=C2N=C(N[Si](C)(C)C)[NH]C(=O)C2=C1SC1=CC=NC=C1	2591.6	Standard non polar	33892256
Nolatrexed,1TMS,isomer #1	CC1=CC=C2N=C(N[Si](C)(C)C)[NH]C(=O)C2=C1SC1=CC=NC=C1	3811.2	Standard polar	33892256
Nolatrexed,1TMS,isomer #2	CC1=CC=C2N=C(N)N([Si](C)(C)C)C(=O)C2=C1SC1=CC=NC=C1	2825.8	Semi standard non polar	33892256
Nolatrexed,1TMS,isomer #2	CC1=CC=C2N=C(N)N([Si](C)(C)C)C(=O)C2=C1SC1=CC=NC=C1	2652.6	Standard non polar	33892256
Nolatrexed,1TMS,isomer #2	CC1=CC=C2N=C(N)N([Si](C)(C)C)C(=O)C2=C1SC1=CC=NC=C1	4000.3	Standard polar	33892256
Nolatrexed,2TMS,isomer #1	CC1=CC=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C(=O)C2=C1SC1=CC=NC=C1	2741.1	Semi standard non polar	33892256
Nolatrexed,2TMS,isomer #1	CC1=CC=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C(=O)C2=C1SC1=CC=NC=C1	2734.4	Standard non polar	33892256
Nolatrexed,2TMS,isomer #1	CC1=CC=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C(=O)C2=C1SC1=CC=NC=C1	3544.4	Standard polar	33892256
Nolatrexed,2TMS,isomer #2	CC1=CC=C2N=C(N[Si](C)(C)C)N([Si](C)(C)C)C(=O)C2=C1SC1=CC=NC=C1	2798.0	Semi standard non polar	33892256
Nolatrexed,2TMS,isomer #2	CC1=CC=C2N=C(N[Si](C)(C)C)N([Si](C)(C)C)C(=O)C2=C1SC1=CC=NC=C1	2682.1	Standard non polar	33892256
Nolatrexed,2TMS,isomer #2	CC1=CC=C2N=C(N[Si](C)(C)C)N([Si](C)(C)C)C(=O)C2=C1SC1=CC=NC=C1	3567.3	Standard polar	33892256
Nolatrexed,3TMS,isomer #1	CC1=CC=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C(=O)C2=C1SC1=CC=NC=C1	2829.3	Semi standard non polar	33892256
Nolatrexed,3TMS,isomer #1	CC1=CC=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C(=O)C2=C1SC1=CC=NC=C1	2825.8	Standard non polar	33892256
Nolatrexed,3TMS,isomer #1	CC1=CC=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C(=O)C2=C1SC1=CC=NC=C1	3296.1	Standard polar	33892256
Nolatrexed,1TBDMS,isomer #1	CC1=CC=C2N=C(N[Si](C)(C)C(C)(C)C)[NH]C(=O)C2=C1SC1=CC=NC=C1	2967.0	Semi standard non polar	33892256
Nolatrexed,1TBDMS,isomer #1	CC1=CC=C2N=C(N[Si](C)(C)C(C)(C)C)[NH]C(=O)C2=C1SC1=CC=NC=C1	2807.2	Standard non polar	33892256
Nolatrexed,1TBDMS,isomer #1	CC1=CC=C2N=C(N[Si](C)(C)C(C)(C)C)[NH]C(=O)C2=C1SC1=CC=NC=C1	3848.1	Standard polar	33892256
Nolatrexed,1TBDMS,isomer #2	CC1=CC=C2N=C(N)N([Si](C)(C)C(C)(C)C)C(=O)C2=C1SC1=CC=NC=C1	3034.0	Semi standard non polar	33892256
Nolatrexed,1TBDMS,isomer #2	CC1=CC=C2N=C(N)N([Si](C)(C)C(C)(C)C)C(=O)C2=C1SC1=CC=NC=C1	2860.3	Standard non polar	33892256
Nolatrexed,1TBDMS,isomer #2	CC1=CC=C2N=C(N)N([Si](C)(C)C(C)(C)C)C(=O)C2=C1SC1=CC=NC=C1	3971.6	Standard polar	33892256
Nolatrexed,2TBDMS,isomer #1	CC1=CC=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C(=O)C2=C1SC1=CC=NC=C1	3093.1	Semi standard non polar	33892256
Nolatrexed,2TBDMS,isomer #1	CC1=CC=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C(=O)C2=C1SC1=CC=NC=C1	3078.5	Standard non polar	33892256
Nolatrexed,2TBDMS,isomer #1	CC1=CC=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C(=O)C2=C1SC1=CC=NC=C1	3604.5	Standard polar	33892256
Nolatrexed,2TBDMS,isomer #2	CC1=CC=C2N=C(N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)C2=C1SC1=CC=NC=C1	3184.7	Semi standard non polar	33892256
Nolatrexed,2TBDMS,isomer #2	CC1=CC=C2N=C(N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)C2=C1SC1=CC=NC=C1	3067.0	Standard non polar	33892256
Nolatrexed,2TBDMS,isomer #2	CC1=CC=C2N=C(N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)C2=C1SC1=CC=NC=C1	3638.3	Standard polar	33892256
Nolatrexed,3TBDMS,isomer #1	CC1=CC=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)C2=C1SC1=CC=NC=C1	3374.4	Semi standard non polar	33892256
Nolatrexed,3TBDMS,isomer #1	CC1=CC=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)C2=C1SC1=CC=NC=C1	3306.1	Standard non polar	33892256
Nolatrexed,3TBDMS,isomer #1	CC1=CC=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)C2=C1SC1=CC=NC=C1	3510.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Nolatrexed GC-MS (Non-derivatized) - 70eV, Positive	splash10-03dl-0290000000-e49bc306dd65c67391d5	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nolatrexed GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - Nolatrexed 10V, Positive-QTOF	splash10-000i-0090000000-d0c9165364ab4971b07b	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nolatrexed 20V, Positive-QTOF	splash10-000i-0190000000-9c643b0fb98b9168c60e	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nolatrexed 40V, Positive-QTOF	splash10-0a4r-5960000000-fcd9131e30aee7a4ac42	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nolatrexed 10V, Negative-QTOF	splash10-001i-0090000000-434ca7982730a8b192d0	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nolatrexed 20V, Negative-QTOF	splash10-001i-1290000000-519d784d082b3d91a56c	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nolatrexed 40V, Negative-QTOF	splash10-01tc-8940000000-66610699d26ef0219c82	2017-07-26	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

DB12912

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

97268

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nolatrexed

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

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 Nolatrexed (HMDB0255698)

MOL for HMDB0255698 (Nolatrexed)

3D MOL for HMDB0255698 (Nolatrexed)

3D SDF for HMDB0255698 (Nolatrexed)

3D-SDF for HMDB0255698 (Nolatrexed)

PDB for HMDB0255698 (Nolatrexed)

3D PDB for HMDB0255698 (Nolatrexed)

SMILES for HMDB0255698 (Nolatrexed)

INCHI for HMDB0255698 (Nolatrexed)

Structure for HMDB0255698 (Nolatrexed)

3D Structure for HMDB0255698 (Nolatrexed)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra