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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:18:30 UTC

Update Date

2019-07-23 07:15:46 UTC

HMDB ID

HMDB0061101

Secondary Accession Numbers

HMDB61101

Metabolite Identification

Common Name

2-oxobrimonidine

Description

2-oxobrimonidine belongs to the class of organic compounds known as quinoxalines. Quinoxalines are compounds containing a quinoxaline moiety, a bicyclic heterocycle made up of a benzene ring fused to a pyrazine ring. 2-oxobrimonidine is a very strong basic compound (based on its pKa). 2-oxobrimonidine is a metabolite of brimonidine. Brimonidine (bri-MOE-ni-deen, brand names Alphagan and Alphagan-P) is a drug used to treat open-angle glaucoma or ocular hypertension. As a treatment for glaucoma, it is usually given in eyedrop form. It acts via decreasing synthesis of aqueous humor, and increasing the amount that drains from the eye through uveoscleral outflow.

Structure

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

HMDB0061101
     RDKit          3D
2-oxobrimonidine
 28 30  0  0  0  0  0  0  0  0999 V2000
    5.9342    0.5047    0.0981 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7514    0.0828   -0.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5862   -1.0523   -0.8928 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3567   -1.5254   -1.1525 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2794   -0.8578   -0.6441 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0209   -1.3496   -0.9151 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8221   -2.9210   -1.9738 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0794   -0.6927   -0.4128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4040   -1.1696   -0.6703 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5212   -0.4591   -0.1307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9888   -0.6384    1.0675 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1232    0.2309    1.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9293    1.2923    0.2521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2838    0.5360   -0.8017 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1014    0.4408    0.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3779    0.9253    0.6140 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4826    0.2711    0.1134 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7077    0.7567    0.3818 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4873   -1.5545   -1.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5043   -2.0223   -1.2451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0934   -0.2759    1.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1047    0.6583    2.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2298    2.0912    0.5806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9177    1.6818   -0.0456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3196    0.6361   -1.8388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7379    0.9841    0.7608 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5387    1.8107    1.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7906    1.6158    0.9619 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  8 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18  2  1  0
 17  5  1  0
 14 10  1  0
  3 19  1  0
  9 20  1  0
 12 21  1  0
 12 22  1  0
 13 23  1  0
 13 24  1  0
 14 25  1  0
 15 26  1  0
 16 27  1  0
 18 28  1  0
M  END


  Mrv0541 07091309182D          

 18 20  0  0  0  0            999 V2000
    0.7145    2.0625    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
   -1.6077    2.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0202    1.5150    0.0000 C   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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    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
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.8007    2.0580    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4681    0.9019    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  4  3  1  0  0  0  0
  6  1  1  0  0  0  0
  7  2  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  7  2  0  0  0  0
 10  9  1  0  0  0  0
 12  9  1  0  0  0  0
 13  3  1  0  0  0  0
 13 11  2  0  0  0  0
 14  4  1  0  0  0  0
 14 11  1  0  0  0  0
 15  5  2  0  0  0  0
 15 10  1  0  0  0  0
 16  7  1  0  0  0  0
 16  8  1  0  0  0  0
 17  6  1  0  0  0  0
 17 11  1  0  0  0  0
 18  8  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061101

> <DATABASE_NAME>
hmdb

> <SMILES>
BrC1=C(NC2=NCCN2)C=CC2=C1N=CC(=O)N2

> <INCHI_IDENTIFIER>
InChI=1S/C11H10BrN5O/c12-9-6(17-11-13-3-4-14-11)1-2-7-10(9)15-5-8(18)16-7/h1-2,5H,3-4H2,(H,16,18)(H2,13,14,17)

> <INCHI_KEY>
BUVCZMAMYHMOPB-UHFFFAOYSA-N

> <FORMULA>
C11H10BrN5O

> <MOLECULAR_WEIGHT>
308.134

> <EXACT_MASS>
307.006872614

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
26.717060552740577

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-bromo-6-[(4,5-dihydro-1H-imidazol-2-yl)amino]-1,2-dihydroquinoxalin-2-one

> <ALOGPS_LOGP>
1.37

> <JCHEM_LOGP>
1.3340791049999998

> <ALOGPS_LOGS>
-3.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.051989091846508

> <JCHEM_PKA_STRONGEST_BASIC>
8.089446967151027

> <JCHEM_POLAR_SURFACE_AREA>
77.88

> <JCHEM_REFRACTIVITY>
75.5089

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.06e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-bromo-6-(4,5-dihydro-1H-imidazol-2-ylamino)-1H-quinoxalin-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0061101
     RDKit          3D
2-oxobrimonidine
 28 30  0  0  0  0  0  0  0  0999 V2000
    5.9342    0.5047    0.0981 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7514    0.0828   -0.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5862   -1.0523   -0.8928 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3567   -1.5254   -1.1525 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2794   -0.8578   -0.6441 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0209   -1.3496   -0.9151 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8221   -2.9210   -1.9738 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0794   -0.6927   -0.4128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4040   -1.1696   -0.6703 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5212   -0.4591   -0.1307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9888   -0.6384    1.0675 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1232    0.2309    1.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9293    1.2923    0.2521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2838    0.5360   -0.8017 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1014    0.4408    0.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3779    0.9253    0.6140 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4826    0.2711    0.1134 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7077    0.7567    0.3818 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4873   -1.5545   -1.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5043   -2.0223   -1.2451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0934   -0.2759    1.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1047    0.6583    2.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2298    2.0912    0.5806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9177    1.6818   -0.0456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3196    0.6361   -1.8388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7379    0.9841    0.7608 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5387    1.8107    1.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7906    1.6158    0.9619 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  8 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18  2  1  0
 17  5  1  0
 14 10  1  0
  3 19  1  0
  9 20  1  0
 12 21  1  0
 12 22  1  0
 13 23  1  0
 13 24  1  0
 14 25  1  0
 15 26  1  0
 16 27  1  0
 18 28  1  0
M  END

HEADER    PROTEIN                                 09-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JUL-13         0                                  
HETATM    1  C   UNK     0       1.334   3.850   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  C   UNK     0      -3.001   4.162   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.771   2.828   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12 Br   UNK     0       2.667   0.000   0.000  0.00  0.00          Br+0
HETATM   13  N   UNK     0      -1.495   3.842   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0      -2.740   1.684   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       5.335   1.540   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0       5.335   4.620   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0       0.000   1.540   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    7                                                       
CONECT    3    4   13                                                       
CONECT    4    3   14                                                       
CONECT    5    8   15                                                       
CONECT    6    1    9   17                                                  
CONECT    7    2   10   16                                                  
CONECT    8    5   16   18                                                  
CONECT    9    6   10   12                                                  
CONECT   10    7    9   15                                                  
CONECT   11   13   14   17                                                  
CONECT   12    9                                                            
CONECT   13    3   11                                                       
CONECT   14    4   11                                                       
CONECT   15    5   10                                                       
CONECT   16    7    8                                                       
CONECT   17    6   11                                                       
CONECT   18    8                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0061101
HETATM    1  O1  UNL     1       5.934   0.505   0.098  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.751   0.083  -0.129  1.00  0.00           C  
HETATM    3  C2  UNL     1       4.586  -1.052  -0.893  1.00  0.00           C  
HETATM    4  N1  UNL     1       3.357  -1.525  -1.152  1.00  0.00           N  
HETATM    5  C3  UNL     1       2.279  -0.858  -0.644  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.021  -1.350  -0.915  1.00  0.00           C  
HETATM    7 BR1  UNL     1       0.822  -2.921  -1.974  1.00  0.00          BR  
HETATM    8  C5  UNL     1      -0.079  -0.693  -0.413  1.00  0.00           C  
HETATM    9  N2  UNL     1      -1.404  -1.170  -0.670  1.00  0.00           N  
HETATM   10  C6  UNL     1      -2.521  -0.459  -0.131  1.00  0.00           C  
HETATM   11  N3  UNL     1      -2.989  -0.638   1.067  1.00  0.00           N  
HETATM   12  C7  UNL     1      -4.123   0.231   1.314  1.00  0.00           C  
HETATM   13  C8  UNL     1      -3.929   1.292   0.252  1.00  0.00           C  
HETATM   14  N4  UNL     1      -3.284   0.536  -0.802  1.00  0.00           N  
HETATM   15  C9  UNL     1       0.101   0.441   0.349  1.00  0.00           C  
HETATM   16  C10 UNL     1       1.378   0.925   0.614  1.00  0.00           C  
HETATM   17  C11 UNL     1       2.483   0.271   0.113  1.00  0.00           C  
HETATM   18  N5  UNL     1       3.708   0.757   0.382  1.00  0.00           N  
HETATM   19  H1  UNL     1       5.487  -1.555  -1.280  1.00  0.00           H  
HETATM   20  H2  UNL     1      -1.504  -2.022  -1.245  1.00  0.00           H  
HETATM   21  H3  UNL     1      -5.093  -0.276   1.125  1.00  0.00           H  
HETATM   22  H4  UNL     1      -4.105   0.658   2.337  1.00  0.00           H  
HETATM   23  H5  UNL     1      -3.230   2.091   0.581  1.00  0.00           H  
HETATM   24  H6  UNL     1      -4.918   1.682  -0.046  1.00  0.00           H  
HETATM   25  H7  UNL     1      -3.320   0.636  -1.839  1.00  0.00           H  
HETATM   26  H8  UNL     1      -0.738   0.984   0.761  1.00  0.00           H  
HETATM   27  H9  UNL     1       1.539   1.811   1.208  1.00  0.00           H  
HETATM   28  H10 UNL     1       3.791   1.616   0.962  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   18
CONECT    3    4    4   19
CONECT    4    5
CONECT    5    6    6   17
CONECT    6    7    8
CONECT    8    9   15   15
CONECT    9   10   20
CONECT   10   11   11   14
CONECT   11   12
CONECT   12   13   21   22
CONECT   13   14   23   24
CONECT   14   25
CONECT   15   16   26
CONECT   16   17   17   27
CONECT   17   18
CONECT   18   28
END

HMDB0061101
     RDKit          3D
2-oxobrimonidine
 28 30  0  0  0  0  0  0  0  0999 V2000
    5.9342    0.5047    0.0981 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7514    0.0828   -0.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5862   -1.0523   -0.8928 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3567   -1.5254   -1.1525 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2794   -0.8578   -0.6441 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0209   -1.3496   -0.9151 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8221   -2.9210   -1.9738 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0794   -0.6927   -0.4128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4040   -1.1696   -0.6703 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5212   -0.4591   -0.1307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9888   -0.6384    1.0675 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1232    0.2309    1.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9293    1.2923    0.2521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2838    0.5360   -0.8017 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1014    0.4408    0.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3779    0.9253    0.6140 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4826    0.2711    0.1134 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7077    0.7567    0.3818 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4873   -1.5545   -1.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5043   -2.0223   -1.2451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0934   -0.2759    1.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1047    0.6583    2.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2298    2.0912    0.5806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9177    1.6818   -0.0456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3196    0.6361   -1.8388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7379    0.9841    0.7608 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5387    1.8107    1.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7906    1.6158    0.9619 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  8 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18  2  1  0
 17  5  1  0
 14 10  1  0
  3 19  1  0
  9 20  1  0
 12 21  1  0
 12 22  1  0
 13 23  1  0
 13 24  1  0
 14 25  1  0
 15 26  1  0
 16 27  1  0
 18 28  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₁H₁₀BrN₅O

Average Molecular Weight

308.134

Monoisotopic Molecular Weight

307.006872614

IUPAC Name

5-bromo-6-[(4,5-dihydro-1H-imidazol-2-yl)amino]-1,2-dihydroquinoxalin-2-one

Traditional Name

5-bromo-6-(4,5-dihydro-1H-imidazol-2-ylamino)-1H-quinoxalin-2-one

CAS Registry Number

Not Available

SMILES

BrC1=C(NC2=NCCN2)C=CC2=C1N=CC(=O)N2

InChI Identifier

InChI=1S/C11H10BrN5O/c12-9-6(17-11-13-3-4-14-11)1-2-7-10(9)15-5-8(18)16-7/h1-2,5H,3-4H2,(H,16,18)(H2,13,14,17)

InChI Key

BUVCZMAMYHMOPB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinoxalines. Quinoxalines are compounds containing a quinoxaline moiety, a bicyclic heterocycle made up of a benzene ring fused to a pyrazine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Benzodiazines

Direct Parent

Quinoxalines

Alternative Parents

Substituents

Quinoxaline
Aryl bromide
Aryl halide
Pyrazine
Benzenoid
2-imidazoline
Heteroaromatic compound
Guanidine
Lactam
Azacycle
Carboximidamide
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organobromide
Organohalogen compound
Organic nitrogen compound
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 (HMDB: HMDB0061101)

Organ

Kidney (HMDB: HMDB0061101)
Liver (HMDB: HMDB0061101)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0061101)

Cellular substructure

Cytoplasm (HMDB: HMDB0061101)

Source

Endogenous

Endogenous (HMDB: HMDB0061101)

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
Water Solubility	0.11 g/L	ALOGPS
logP	1.37	ALOGPS
logP	1.33	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	12.05	ChemAxon
pKa (Strongest Basic)	8.09	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.88 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	75.51 m³·mol⁻¹	ChemAxon
Polarizability	26.72 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]+	150.871	30932474
DeepCCS	[M-H]-	148.514	30932474
DeepCCS	[M-2H]-	181.889	30932474
DeepCCS	[M+Na]+	156.965	30932474
AllCCS	[M+H]+	164.9	32859911
AllCCS	[M+H-H2O]+	161.3	32859911
AllCCS	[M+NH4]+	168.1	32859911
AllCCS	[M+Na]+	169.1	32859911
AllCCS	[M-H]-	159.6	32859911
AllCCS	[M+Na-2H]-	159.5	32859911
AllCCS	[M+HCOO]-	159.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.64 minutes	32390414
Predicted by Siyang on May 30, 2022	9.8265 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.39 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	778.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	266.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	88.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	171.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	80.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	304.8 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	325.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	325.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	648.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	236.1 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	887.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	217.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	202.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	545.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	329.2 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	112.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-oxobrimonidine	BrC1=C(NC2=NCCN2)C=CC2=C1N=CC(=O)N2	3664.2	Standard polar	33892256
2-oxobrimonidine	BrC1=C(NC2=NCCN2)C=CC2=C1N=CC(=O)N2	3089.2	Standard non polar	33892256
2-oxobrimonidine	BrC1=C(NC2=NCCN2)C=CC2=C1N=CC(=O)N2	3102.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-oxobrimonidine,1TMS,isomer #1	C[Si](C)(C)N(C1=NCCN1)C1=CC=C2[NH]C(=O)C=NC2=C1Br	2838.5	Semi standard non polar	33892256
2-oxobrimonidine,1TMS,isomer #1	C[Si](C)(C)N(C1=NCCN1)C1=CC=C2[NH]C(=O)C=NC2=C1Br	2635.0	Standard non polar	33892256
2-oxobrimonidine,1TMS,isomer #1	C[Si](C)(C)N(C1=NCCN1)C1=CC=C2[NH]C(=O)C=NC2=C1Br	5206.5	Standard polar	33892256
2-oxobrimonidine,1TMS,isomer #2	C[Si](C)(C)N1CCN=C1NC1=CC=C2[NH]C(=O)C=NC2=C1Br	2900.7	Semi standard non polar	33892256
2-oxobrimonidine,1TMS,isomer #2	C[Si](C)(C)N1CCN=C1NC1=CC=C2[NH]C(=O)C=NC2=C1Br	2687.8	Standard non polar	33892256
2-oxobrimonidine,1TMS,isomer #2	C[Si](C)(C)N1CCN=C1NC1=CC=C2[NH]C(=O)C=NC2=C1Br	4607.0	Standard polar	33892256
2-oxobrimonidine,1TMS,isomer #3	C[Si](C)(C)N1C(=O)C=NC2=C(Br)C(NC3=NCCN3)=CC=C21	2918.7	Semi standard non polar	33892256
2-oxobrimonidine,1TMS,isomer #3	C[Si](C)(C)N1C(=O)C=NC2=C(Br)C(NC3=NCCN3)=CC=C21	2679.3	Standard non polar	33892256
2-oxobrimonidine,1TMS,isomer #3	C[Si](C)(C)N1C(=O)C=NC2=C(Br)C(NC3=NCCN3)=CC=C21	5494.4	Standard polar	33892256
2-oxobrimonidine,2TMS,isomer #1	C[Si](C)(C)N1CCN=C1N(C1=CC=C2[NH]C(=O)C=NC2=C1Br)[Si](C)(C)C	2716.3	Semi standard non polar	33892256
2-oxobrimonidine,2TMS,isomer #1	C[Si](C)(C)N1CCN=C1N(C1=CC=C2[NH]C(=O)C=NC2=C1Br)[Si](C)(C)C	2712.1	Standard non polar	33892256
2-oxobrimonidine,2TMS,isomer #1	C[Si](C)(C)N1CCN=C1N(C1=CC=C2[NH]C(=O)C=NC2=C1Br)[Si](C)(C)C	4193.9	Standard polar	33892256
2-oxobrimonidine,2TMS,isomer #2	C[Si](C)(C)N(C1=NCCN1)C1=CC=C2C(=C1Br)N=CC(=O)N2[Si](C)(C)C	2805.6	Semi standard non polar	33892256
2-oxobrimonidine,2TMS,isomer #2	C[Si](C)(C)N(C1=NCCN1)C1=CC=C2C(=C1Br)N=CC(=O)N2[Si](C)(C)C	2652.6	Standard non polar	33892256
2-oxobrimonidine,2TMS,isomer #2	C[Si](C)(C)N(C1=NCCN1)C1=CC=C2C(=C1Br)N=CC(=O)N2[Si](C)(C)C	5142.7	Standard polar	33892256
2-oxobrimonidine,2TMS,isomer #3	C[Si](C)(C)N1CCN=C1NC1=CC=C2C(=C1Br)N=CC(=O)N2[Si](C)(C)C	2866.2	Semi standard non polar	33892256
2-oxobrimonidine,2TMS,isomer #3	C[Si](C)(C)N1CCN=C1NC1=CC=C2C(=C1Br)N=CC(=O)N2[Si](C)(C)C	2736.3	Standard non polar	33892256
2-oxobrimonidine,2TMS,isomer #3	C[Si](C)(C)N1CCN=C1NC1=CC=C2C(=C1Br)N=CC(=O)N2[Si](C)(C)C	4533.5	Standard polar	33892256
2-oxobrimonidine,3TMS,isomer #1	C[Si](C)(C)N1CCN=C1N(C1=CC=C2C(=C1Br)N=CC(=O)N2[Si](C)(C)C)[Si](C)(C)C	2715.3	Semi standard non polar	33892256
2-oxobrimonidine,3TMS,isomer #1	C[Si](C)(C)N1CCN=C1N(C1=CC=C2C(=C1Br)N=CC(=O)N2[Si](C)(C)C)[Si](C)(C)C	2760.0	Standard non polar	33892256
2-oxobrimonidine,3TMS,isomer #1	C[Si](C)(C)N1CCN=C1N(C1=CC=C2C(=C1Br)N=CC(=O)N2[Si](C)(C)C)[Si](C)(C)C	3912.4	Standard polar	33892256
2-oxobrimonidine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=NCCN1)C1=CC=C2[NH]C(=O)C=NC2=C1Br	3068.1	Semi standard non polar	33892256
2-oxobrimonidine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=NCCN1)C1=CC=C2[NH]C(=O)C=NC2=C1Br	2832.0	Standard non polar	33892256
2-oxobrimonidine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=NCCN1)C1=CC=C2[NH]C(=O)C=NC2=C1Br	5179.9	Standard polar	33892256
2-oxobrimonidine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1CCN=C1NC1=CC=C2[NH]C(=O)C=NC2=C1Br	3144.6	Semi standard non polar	33892256
2-oxobrimonidine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1CCN=C1NC1=CC=C2[NH]C(=O)C=NC2=C1Br	2882.6	Standard non polar	33892256
2-oxobrimonidine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1CCN=C1NC1=CC=C2[NH]C(=O)C=NC2=C1Br	4721.7	Standard polar	33892256
2-oxobrimonidine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)C=NC2=C(Br)C(NC3=NCCN3)=CC=C21	3121.7	Semi standard non polar	33892256
2-oxobrimonidine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)C=NC2=C(Br)C(NC3=NCCN3)=CC=C21	2888.9	Standard non polar	33892256
2-oxobrimonidine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)C=NC2=C(Br)C(NC3=NCCN3)=CC=C21	5579.3	Standard polar	33892256
2-oxobrimonidine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN=C1N(C1=CC=C2[NH]C(=O)C=NC2=C1Br)[Si](C)(C)C(C)(C)C	3124.9	Semi standard non polar	33892256
2-oxobrimonidine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN=C1N(C1=CC=C2[NH]C(=O)C=NC2=C1Br)[Si](C)(C)C(C)(C)C	3082.4	Standard non polar	33892256
2-oxobrimonidine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN=C1N(C1=CC=C2[NH]C(=O)C=NC2=C1Br)[Si](C)(C)C(C)(C)C	4180.2	Standard polar	33892256
2-oxobrimonidine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=NCCN1)C1=CC=C2C(=C1Br)N=CC(=O)N2[Si](C)(C)C(C)(C)C	3212.2	Semi standard non polar	33892256
2-oxobrimonidine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=NCCN1)C1=CC=C2C(=C1Br)N=CC(=O)N2[Si](C)(C)C(C)(C)C	3048.3	Standard non polar	33892256
2-oxobrimonidine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=NCCN1)C1=CC=C2C(=C1Br)N=CC(=O)N2[Si](C)(C)C(C)(C)C	5089.0	Standard polar	33892256
2-oxobrimonidine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1CCN=C1NC1=CC=C2C(=C1Br)N=CC(=O)N2[Si](C)(C)C(C)(C)C	3293.0	Semi standard non polar	33892256
2-oxobrimonidine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1CCN=C1NC1=CC=C2C(=C1Br)N=CC(=O)N2[Si](C)(C)C(C)(C)C	3117.9	Standard non polar	33892256
2-oxobrimonidine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1CCN=C1NC1=CC=C2C(=C1Br)N=CC(=O)N2[Si](C)(C)C(C)(C)C	4550.3	Standard polar	33892256
2-oxobrimonidine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN=C1N(C1=CC=C2C(=C1Br)N=CC(=O)N2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3293.9	Semi standard non polar	33892256
2-oxobrimonidine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN=C1N(C1=CC=C2C(=C1Br)N=CC(=O)N2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3301.8	Standard non polar	33892256
2-oxobrimonidine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN=C1N(C1=CC=C2C(=C1Br)N=CC(=O)N2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3932.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-oxobrimonidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fw9-1190000000-3c118cb8c426c950f319	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-oxobrimonidine 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 - 2-oxobrimonidine 10V, Positive-QTOF	splash10-0a4i-0009000000-9efa281c07fe28d33dd2	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-oxobrimonidine 20V, Positive-QTOF	splash10-0a4i-2029000000-0e6325c25c18251c7ca6	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-oxobrimonidine 40V, Positive-QTOF	splash10-015c-9030000000-cb539342741b0ee1fbd0	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-oxobrimonidine 10V, Negative-QTOF	splash10-0a4i-0019000000-0a8ec29a29d617c47734	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-oxobrimonidine 20V, Negative-QTOF	splash10-0a4i-1069000000-83a107a7ffd6d788d895	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-oxobrimonidine 40V, Negative-QTOF	splash10-01s6-5090000000-6c567ee33e8d03c8b296	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-oxobrimonidine 10V, Negative-QTOF	splash10-0a4i-0019000000-157e38d3f1da01f259ca	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-oxobrimonidine 20V, Negative-QTOF	splash10-0a4i-0139000000-85073c3578035b847b7c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-oxobrimonidine 40V, Negative-QTOF	splash10-0a6r-8973000000-a9b7291750c4dce22e73	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-oxobrimonidine 10V, Positive-QTOF	splash10-0a4i-0009000000-88d92cd61d8241107230	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-oxobrimonidine 20V, Positive-QTOF	splash10-0a4i-0029000000-a83d3078f40ae0e993d9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-oxobrimonidine 40V, Positive-QTOF	splash10-03dr-0291000000-e221fc3b49183e992181	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131770028

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

Not Available

Showing metabocard for 2-oxobrimonidine (HMDB0061101)

MOL for HMDB0061101 (2-oxobrimonidine)

3D MOL for HMDB0061101 (2-oxobrimonidine)

3D SDF for HMDB0061101 (2-oxobrimonidine)

3D-SDF for HMDB0061101 (2-oxobrimonidine)

PDB for HMDB0061101 (2-oxobrimonidine)

3D PDB for HMDB0061101 (2-oxobrimonidine)

SMILES for HMDB0061101 (2-oxobrimonidine)

INCHI for HMDB0061101 (2-oxobrimonidine)

Structure for HMDB0061101 (2-oxobrimonidine)

3D Structure for HMDB0061101 (2-oxobrimonidine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra