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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 20:36:48 UTC

Update Date

2021-09-26 23:16:01 UTC

HMDB ID

HMDB0258834

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Terizidone

Description

4-{[(4-{[(3-hydroxy-4,5-dihydro-1,2-oxazol-4-yl)imino]methyl}phenyl)methylidene]amino}-4,5-dihydro-1,2-oxazol-3-ol belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Based on a literature review very few articles have been published on 4-{[(4-{[(3-hydroxy-4,5-dihydro-1,2-oxazol-4-yl)imino]methyl}phenyl)methylidene]amino}-4,5-dihydro-1,2-oxazol-3-ol. This compound has been identified in human blood as reported by (PMID: 31557052 ). Terizidone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Terizidone 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

HMDB0258834
     RDKit          3D
Terizidone
 36 38  0  0  0  0  0  0  0  0999 V2000
   -5.3551   -1.7088   -1.2949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7547   -0.6525   -0.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8387    0.0366   -0.5083 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8415    1.0018    0.4869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4551    1.2665    0.7676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9155   -0.1400    0.6291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5104   -0.1741    0.3273 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6766   -0.2045    1.3079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2553   -0.2390    1.0029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7746   -0.2402   -0.2847 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5907   -0.2737   -0.5363 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5133   -0.3069    0.4869 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9532   -0.3427    0.2845 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3594   -0.3425   -0.9469 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7748   -0.3774   -1.1928 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0646    0.1121   -2.6141 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0286    1.5292   -2.3967 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5175    1.7588   -1.1316 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4022    0.7094   -0.3938 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7817    0.5567    0.9328 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0347   -0.3057    1.7774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3216   -0.2724    2.0207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8830   -1.5032   -2.1894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1119    1.9021   -0.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3092    1.7037    1.7506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1612   -0.6846    1.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9822   -0.2056    2.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4719   -0.2148   -1.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9855   -0.2751   -1.5493 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6415   -0.3680    1.1160 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2305   -1.3599   -1.0103 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0968   -0.1545   -2.8852 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3037   -0.2113   -3.3299 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3153    1.2763    1.4276 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7003   -0.3308    2.6478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6759   -0.2722    3.0504 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  3
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  3
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 12 21  1  0
 21 22  2  0
  6  2  1  0
 22  9  1  0
 19 15  1  0
  1 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 16 33  1  0
 20 34  1  0
 21 35  1  0
 22 36  1  0
M  END


  Mrv1652306031607542D          

 22 24  0  0  0  0            999 V2000
   -0.6078    6.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078    6.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0367    6.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0367    6.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    4.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    8.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3693    3.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2752    9.7876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    5.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    7.2402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0367    3.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078    9.3027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7041    3.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0597    9.7876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0367    4.3527    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078    8.4777    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4492    2.2581    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1953   10.5722    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4888    3.2977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8443    9.5327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6242    2.2581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0203   10.5722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  2  0  0  0  0
  9  1  2  0  0  0  0
  9  3  1  0  0  0  0
  9  5  1  0  0  0  0
 10  2  2  0  0  0  0
 10  4  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15  5  2  0  0  0  0
 15 11  1  4  0  0  0
 16  6  2  0  0  0  0
 16 12  1  4  0  0  0
 17 13  2  0  0  0  0
 18 14  2  0  0  0  0
 19 13  1  0  0  0  0
 20 14  1  0  0  0  0
 21  7  1  0  0  0  0
 21 17  1  0  0  0  0
 22  8  1  0  0  0  0
 22 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0258834

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=NOCC1N=CC1=CC=C(C=NC2CON=C2O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H14N4O4/c19-13-11(7-21-17-13)15-5-9-1-2-10(4-3-9)6-16-12-8-22-18-14(12)20/h1-6,11-12H,7-8H2,(H,17,19)(H,18,20)

> <INCHI_KEY>
ODKYYBOHSVLGNU-UHFFFAOYSA-N

> <FORMULA>
C14H14N4O4

> <MOLECULAR_WEIGHT>
302.29

> <EXACT_MASS>
302.101504947

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
29.868027783832275

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-{[(4-{[(3-hydroxy-4,5-dihydro-1,2-oxazol-4-yl)imino]methyl}phenyl)methylidene]amino}-4,5-dihydro-1,2-oxazol-3-ol

> <ALOGPS_LOGP>
0.97

> <JCHEM_LOGP>
-1.0209485482428207

> <ALOGPS_LOGS>
-3.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
-0.27549706017427944

> <JCHEM_PKA_STRONGEST_ACIDIC>
-0.9009888705842029

> <JCHEM_PKA_STRONGEST_BASIC>
4.488664487360008

> <JCHEM_POLAR_SURFACE_AREA>
108.36000000000001

> <JCHEM_REFRACTIVITY>
78.03700000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.61e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-{[(4-{[(3-hydroxy-4,5-dihydro-1,2-oxazol-4-yl)imino]methyl}phenyl)methylidene]amino}-4,5-dihydro-1,2-oxazol-3-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0258834
     RDKit          3D
Terizidone
 36 38  0  0  0  0  0  0  0  0999 V2000
   -5.3551   -1.7088   -1.2949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7547   -0.6525   -0.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8387    0.0366   -0.5083 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8415    1.0018    0.4869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4551    1.2665    0.7676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9155   -0.1400    0.6291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5104   -0.1741    0.3273 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6766   -0.2045    1.3079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2553   -0.2390    1.0029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7746   -0.2402   -0.2847 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5907   -0.2737   -0.5363 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5133   -0.3069    0.4869 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9532   -0.3427    0.2845 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3594   -0.3425   -0.9469 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7748   -0.3774   -1.1928 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0646    0.1121   -2.6141 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0286    1.5292   -2.3967 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5175    1.7588   -1.1316 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4022    0.7094   -0.3938 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7817    0.5567    0.9328 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0347   -0.3057    1.7774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3216   -0.2724    2.0207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8830   -1.5032   -2.1894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1119    1.9021   -0.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3092    1.7037    1.7506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1612   -0.6846    1.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9822   -0.2056    2.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4719   -0.2148   -1.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9855   -0.2751   -1.5493 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6415   -0.3680    1.1160 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2305   -1.3599   -1.0103 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0968   -0.1545   -2.8852 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3037   -0.2113   -3.3299 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3153    1.2763    1.4276 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7003   -0.3308    2.6478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6759   -0.2722    3.0504 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  3
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  3
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 12 21  1  0
 21 22  2  0
  6  2  1  0
 22  9  1  0
 19 15  1  0
  1 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 16 33  1  0
 20 34  1  0
 21 35  1  0
 22 36  1  0
M  END

HEADER    PROTEIN                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0      -1.134  11.205   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.134  12.745   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.802  11.205   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.802  12.745   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.468   8.895   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.468  15.055   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.556   5.680   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.380  18.270   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.468  10.435   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.468  13.515   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.802   6.585   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.134  17.365   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.048   5.680   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.111  18.270   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      -3.802   8.125   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0      -1.134  15.825   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0      -4.572   4.215   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0      -0.364  19.735   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0      -6.512   6.156   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.576  17.794   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -3.032   4.215   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.904  19.735   0.000  0.00  0.00           O+0
CONECT    1    2    9                                                       
CONECT    2    1   10                                                       
CONECT    3    4    9                                                       
CONECT    4    3   10                                                       
CONECT    5    9   15                                                       
CONECT    6   10   16                                                       
CONECT    7   11   21                                                       
CONECT    8   12   22                                                       
CONECT    9    1    3    5                                                  
CONECT   10    2    4    6                                                  
CONECT   11    7   13   15                                                  
CONECT   12    8   14   16                                                  
CONECT   13   11   17   19                                                  
CONECT   14   12   18   20                                                  
CONECT   15    5   11                                                       
CONECT   16    6   12                                                       
CONECT   17   13   21                                                       
CONECT   18   14   22                                                       
CONECT   19   13                                                            
CONECT   20   14                                                            
CONECT   21    7   17                                                       
CONECT   22    8   18                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0258834
HETATM    1  O1  UNL     1      -5.355  -1.709  -1.295  1.00  0.00           O  
HETATM    2  C1  UNL     1      -5.755  -0.653  -0.477  1.00  0.00           C  
HETATM    3  N1  UNL     1      -6.839   0.037  -0.508  1.00  0.00           N  
HETATM    4  O2  UNL     1      -6.841   1.002   0.487  1.00  0.00           O  
HETATM    5  C2  UNL     1      -5.455   1.266   0.768  1.00  0.00           C  
HETATM    6  C3  UNL     1      -4.915  -0.140   0.629  1.00  0.00           C  
HETATM    7  N2  UNL     1      -3.510  -0.174   0.327  1.00  0.00           N  
HETATM    8  C4  UNL     1      -2.677  -0.205   1.308  1.00  0.00           C  
HETATM    9  C5  UNL     1      -1.255  -0.239   1.003  1.00  0.00           C  
HETATM   10  C6  UNL     1      -0.775  -0.240  -0.285  1.00  0.00           C  
HETATM   11  C7  UNL     1       0.591  -0.274  -0.536  1.00  0.00           C  
HETATM   12  C8  UNL     1       1.513  -0.307   0.487  1.00  0.00           C  
HETATM   13  C9  UNL     1       2.953  -0.343   0.284  1.00  0.00           C  
HETATM   14  N3  UNL     1       3.359  -0.343  -0.947  1.00  0.00           N  
HETATM   15  C10 UNL     1       4.775  -0.377  -1.193  1.00  0.00           C  
HETATM   16  C11 UNL     1       5.065   0.112  -2.614  1.00  0.00           C  
HETATM   17  O3  UNL     1       5.029   1.529  -2.397  1.00  0.00           O  
HETATM   18  N4  UNL     1       5.517   1.759  -1.132  1.00  0.00           N  
HETATM   19  C12 UNL     1       5.402   0.709  -0.394  1.00  0.00           C  
HETATM   20  O4  UNL     1       5.782   0.557   0.933  1.00  0.00           O  
HETATM   21  C13 UNL     1       1.035  -0.306   1.777  1.00  0.00           C  
HETATM   22  C14 UNL     1      -0.322  -0.272   2.021  1.00  0.00           C  
HETATM   23  H1  UNL     1      -4.883  -1.503  -2.189  1.00  0.00           H  
HETATM   24  H2  UNL     1      -5.112   1.902  -0.077  1.00  0.00           H  
HETATM   25  H3  UNL     1      -5.309   1.704   1.751  1.00  0.00           H  
HETATM   26  H4  UNL     1      -5.161  -0.685   1.566  1.00  0.00           H  
HETATM   27  H5  UNL     1      -2.982  -0.206   2.344  1.00  0.00           H  
HETATM   28  H6  UNL     1      -1.472  -0.215  -1.107  1.00  0.00           H  
HETATM   29  H7  UNL     1       0.985  -0.275  -1.549  1.00  0.00           H  
HETATM   30  H8  UNL     1       3.641  -0.368   1.116  1.00  0.00           H  
HETATM   31  H9  UNL     1       5.230  -1.360  -1.010  1.00  0.00           H  
HETATM   32  H10 UNL     1       6.097  -0.154  -2.885  1.00  0.00           H  
HETATM   33  H11 UNL     1       4.304  -0.211  -3.330  1.00  0.00           H  
HETATM   34  H12 UNL     1       6.315   1.276   1.428  1.00  0.00           H  
HETATM   35  H13 UNL     1       1.700  -0.331   2.648  1.00  0.00           H  
HETATM   36  H14 UNL     1      -0.676  -0.272   3.050  1.00  0.00           H  
CONECT    1    2   23
CONECT    2    3    3    6
CONECT    3    4
CONECT    4    5
CONECT    5    6   24   25
CONECT    6    7   26
CONECT    7    8    8
CONECT    8    9   27
CONECT    9   10   10   22
CONECT   10   11   28
CONECT   11   12   12   29
CONECT   12   13   21
CONECT   13   14   14   30
CONECT   14   15
CONECT   15   16   19   31
CONECT   16   17   32   33
CONECT   17   18
CONECT   18   19   19
CONECT   19   20
CONECT   20   34
CONECT   21   22   22   35
CONECT   22   36
END

HMDB0258834
     RDKit          3D
Terizidone
 36 38  0  0  0  0  0  0  0  0999 V2000
   -5.3551   -1.7088   -1.2949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7547   -0.6525   -0.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8387    0.0366   -0.5083 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8415    1.0018    0.4869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4551    1.2665    0.7676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9155   -0.1400    0.6291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5104   -0.1741    0.3273 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6766   -0.2045    1.3079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2553   -0.2390    1.0029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7746   -0.2402   -0.2847 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5907   -0.2737   -0.5363 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5133   -0.3069    0.4869 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9532   -0.3427    0.2845 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3594   -0.3425   -0.9469 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7748   -0.3774   -1.1928 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0646    0.1121   -2.6141 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0286    1.5292   -2.3967 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5175    1.7588   -1.1316 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4022    0.7094   -0.3938 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7817    0.5567    0.9328 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0347   -0.3057    1.7774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3216   -0.2724    2.0207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8830   -1.5032   -2.1894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1119    1.9021   -0.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3092    1.7037    1.7506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1612   -0.6846    1.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9822   -0.2056    2.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4719   -0.2148   -1.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9855   -0.2751   -1.5493 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6415   -0.3680    1.1160 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2305   -1.3599   -1.0103 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0968   -0.1545   -2.8852 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3037   -0.2113   -3.3299 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3153    1.2763    1.4276 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7003   -0.3308    2.6478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6759   -0.2722    3.0504 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  3
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  3
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 12 21  1  0
 21 22  2  0
  6  2  1  0
 22  9  1  0
 19 15  1  0
  1 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 16 33  1  0
 20 34  1  0
 21 35  1  0
 22 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Terizidon	MeSH
Terazolidone	MeSH
Terizidone, calcium salt, (R-(r,r))-isomer	MeSH
Terivalidin	MeSH
4,4'-(p-Phenylenebis(methyleneimino))bis-3-isoxazolidone	MeSH
Terivalidine	MeSH

Chemical Formula

C₁₄H₁₄N₄O₄

Average Molecular Weight

302.29

Monoisotopic Molecular Weight

302.101504947

IUPAC Name

4-{[(4-{[(3-hydroxy-4,5-dihydro-1,2-oxazol-4-yl)imino]methyl}phenyl)methylidene]amino}-4,5-dihydro-1,2-oxazol-3-ol

Traditional Name

4-{[(4-{[(3-hydroxy-4,5-dihydro-1,2-oxazol-4-yl)imino]methyl}phenyl)methylidene]amino}-4,5-dihydro-1,2-oxazol-3-ol

CAS Registry Number

Not Available

SMILES

OC1=NOCC1N=CC1=CC=C(C=NC2CON=C2O)C=C1

InChI Identifier

InChI=1S/C14H14N4O4/c19-13-11(7-21-17-13)15-5-9-1-2-10(4-3-9)6-16-12-8-22-18-14(12)20/h1-6,11-12H,7-8H2,(H,17,19)(H,18,20)

InChI Key

ODKYYBOHSVLGNU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Not Available

Direct Parent

Benzene and substituted derivatives

Alternative Parents

Substituents

Monocyclic benzene moiety
Isoxazoline
Shiff base
Aldimine
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organoheterocyclic compound
Azacycle
Oxacycle
Organopnictogen compound
Organooxygen compound
Organic nitrogen compound
Imine
Organic oxygen compound
Organonitrogen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

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	0.97	ALOGPS
logP	-1	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	-0.9	ChemAxon
pKa (Strongest Basic)	4.49	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	108.36 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	78.04 m³·mol⁻¹	ChemAxon
Polarizability	29.87 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	169.293	30932474
DeepCCS	[M-H]-	166.935	30932474
DeepCCS	[M-2H]-	199.822	30932474
DeepCCS	[M+Na]+	175.387	30932474
AllCCS	[M+H]+	170.8	32859911
AllCCS	[M+H-H2O]+	167.4	32859911
AllCCS	[M+NH4]+	174.0	32859911
AllCCS	[M+Na]+	174.9	32859911
AllCCS	[M-H]-	170.5	32859911
AllCCS	[M+Na-2H]-	170.2	32859911
AllCCS	[M+HCOO]-	169.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Terizidone	OC1=NOCC1N=CC1=CC=C(C=NC2CON=C2O)C=C1	3747.4	Standard polar	33892256
Terizidone	OC1=NOCC1N=CC1=CC=C(C=NC2CON=C2O)C=C1	2825.5	Standard non polar	33892256
Terizidone	OC1=NOCC1N=CC1=CC=C(C=NC2CON=C2O)C=C1	3297.1	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 - Terizidone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-2090000000-060f80f73cdc3014aac9	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Terizidone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Terizidone GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Terizidone GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Terizidone GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Terizidone GC-MS (TBDMS_2_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 - Terizidone 10V, Positive-QTOF	splash10-0udi-1059000000-73136041c906706233f3	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Terizidone 20V, Positive-QTOF	splash10-0udi-1290000000-962013c1c4b308295295	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Terizidone 40V, Positive-QTOF	splash10-0f7a-9820000000-5f1af0cc8aff66388db6	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Terizidone 10V, Negative-QTOF	splash10-0udl-0395000000-c0f5e522d7934436781d	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Terizidone 20V, Negative-QTOF	splash10-0fbc-4294000000-4e219c17cbb4c76f5fcb	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Terizidone 40V, Negative-QTOF	splash10-0006-9000000000-de30aec4dfff17188062	2019-02-23	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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

21173035

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

65720

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 Terizidone (HMDB0258834)

MOL for HMDB0258834 (Terizidone)

3D MOL for HMDB0258834 (Terizidone)

3D SDF for HMDB0258834 (Terizidone)

3D-SDF for HMDB0258834 (Terizidone)

PDB for HMDB0258834 (Terizidone)

3D PDB for HMDB0258834 (Terizidone)

SMILES for HMDB0258834 (Terizidone)

INCHI for HMDB0258834 (Terizidone)

Structure for HMDB0258834 (Terizidone)

3D Structure for HMDB0258834 (Terizidone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra