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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:35:49 UTC

Update Date

2022-03-07 02:52:29 UTC

HMDB ID

HMDB0030269

Secondary Accession Numbers

HMDB30269

Metabolite Identification

Common Name

Nigellicine

Description

Nigellicine belongs to the class of organic compounds known as pyridazinoindazoles. Pyridazinoindazoles are compounds containing a pyridazinoindazole moiety, which consists of a pyridazine ring fused to an indazole. Based on a literature review a significant number of articles have been published on Nigellicine.

Structure

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

HMDB0030269
     RDKit          3D
Nigellicine
 32 34  0  0  0  0  0  0  0  0999 V2000
    4.1129   -1.4913   -0.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9231   -0.6367   -0.1908 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1004    0.7314   -0.1429 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0187    1.6007   -0.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2530    2.9853    0.0094 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7629    1.0483    0.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5134    1.6009    0.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8145    3.0024    0.2104 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0013    3.9213    0.1992 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1691    3.4033    0.3168 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.4198    0.5646    0.1405 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.7828   -0.5628    0.0508 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5477   -0.3182   -0.0243 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6458   -1.1534   -0.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4121   -1.8872    0.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8683   -1.7770    0.4284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4730   -0.5843   -0.2872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8552    0.6694    0.2357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8230   -2.5554   -0.1480 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8973   -1.2008    0.3991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5063   -1.4262   -1.3534 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0785    1.1843   -0.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1628    3.3677   -0.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5445   -2.2168   -0.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9053   -2.5846    0.7350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3773   -2.3491   -0.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4232   -2.6712    0.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0290   -1.6942    1.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5702   -0.5424   -0.0744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2796   -0.7374   -1.3706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2017    0.8030    1.2865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2838    1.5063   -0.3532 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
  4  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 14  2  1  0
 13  6  1  0
 18 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  5 23  1  0
 14 24  1  0
 15 25  1  0
 15 26  1  0
 16 27  1  0
 16 28  1  0
 17 29  1  0
 17 30  1  0
 18 31  1  0
 18 32  1  0
M  CHG  2  10  -1  11   1
M  END


  Mrv0541 02241214592D          

 18 20  0  0  0  0            999 V2000
   -1.3197    0.8655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8247    0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0004    0.2880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3296   -0.4530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0721   -0.7005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3197   -1.4430    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.7321   -0.1238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1546    1.1955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3296    1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1654    1.6905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9896    1.6080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4846    2.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3296   -1.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3296   -1.0305    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -0.9896   -0.6180    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7321   -1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7321   -1.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9896   -2.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1 11  1  0  0  0  0
  2  3  1  0  0  0  0
  2 15  1  0  0  0  0
  3  4  1  0  0  0  0
  3  9  2  0  0  0  0
  4  5  1  0  0  0  0
  4 14  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 13 18  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
M  CHG  2   6  -1  14   1
M  END
> <DATABASE_ID>
HMDB0030269

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC(O)=C2C(=C1)N1CCCC[N+]1=C2C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H14N2O3/c1-8-6-9-11(10(16)7-8)12(13(17)18)15-5-3-2-4-14(9)15/h6-7H,2-5H2,1H3,(H,17,18)

> <INCHI_KEY>
FEJTUHSIRAJLOJ-UHFFFAOYSA-N

> <FORMULA>
C13H14N2O3

> <MOLECULAR_WEIGHT>
246.2619

> <EXACT_MASS>
246.100442324

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
25.670294325032607

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-hydroxy-3-methyl-6H,7H,8H,9H-10λ⁵-pyridazino[1,2-a]indazol-10-ylium-11-carboxylate

> <ALOGPS_LOGP>
-0.70

> <JCHEM_LOGP>
-1.757974191471746

> <ALOGPS_LOGS>
-3.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.246741426694694

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.033693310390402

> <JCHEM_PKA_STRONGEST_BASIC>
-5.798307922424319

> <JCHEM_POLAR_SURFACE_AREA>
69.16999999999999

> <JCHEM_REFRACTIVITY>
99.363

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.31e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-hydroxy-3-methyl-6H,7H,8H,9H-10λ⁵-pyridazino[1,2-a]indazol-10-ylium-11-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030269
     RDKit          3D
Nigellicine
 32 34  0  0  0  0  0  0  0  0999 V2000
    4.1129   -1.4913   -0.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9231   -0.6367   -0.1908 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1004    0.7314   -0.1429 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0187    1.6007   -0.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2530    2.9853    0.0094 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7629    1.0483    0.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5134    1.6009    0.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8145    3.0024    0.2104 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0013    3.9213    0.1992 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1691    3.4033    0.3168 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.4198    0.5646    0.1405 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.7828   -0.5628    0.0508 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5477   -0.3182   -0.0243 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6458   -1.1534   -0.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4121   -1.8872    0.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8683   -1.7770    0.4284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4730   -0.5843   -0.2872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8552    0.6694    0.2357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8230   -2.5554   -0.1480 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8973   -1.2008    0.3991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5063   -1.4262   -1.3534 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0785    1.1843   -0.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1628    3.3677   -0.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5445   -2.2168   -0.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9053   -2.5846    0.7350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3773   -2.3491   -0.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4232   -2.6712    0.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0290   -1.6942    1.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5702   -0.5424   -0.0744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2796   -0.7374   -1.3706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2017    0.8030    1.2865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2838    1.5063   -0.3532 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
  4  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 14  2  1  0
 13  6  1  0
 18 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  5 23  1  0
 14 24  1  0
 15 25  1  0
 15 26  1  0
 16 27  1  0
 16 28  1  0
 17 29  1  0
 17 30  1  0
 18 31  1  0
 18 32  1  0
M  CHG  2  10  -1  11   1
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.463   1.616   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.539   0.384   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.001   0.538   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.615  -0.846   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.001  -1.308   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.463  -2.694   0.000  0.00  0.00           O-1
HETATM    7  O   UNK     0       3.233  -0.231   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       2.155   2.232   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.615   1.924   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.309   3.156   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.847   3.002   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.771   4.234   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.615  -3.464   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      -0.615  -1.924   0.000  0.00  0.00           N+1
HETATM   15  N   UNK     0      -1.847  -1.154   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      -3.233  -1.924   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.233  -3.464   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.847  -4.234   0.000  0.00  0.00           C+0
CONECT    1    2   11                                                       
CONECT    2    1    3   15                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5   14                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    9                                                            
CONECT    9    3    8   10                                                  
CONECT   10    9   11                                                       
CONECT   11    1   10   12                                                  
CONECT   12   11                                                            
CONECT   13   14   18                                                       
CONECT   14    4   13   15                                                  
CONECT   15    2   14   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   13   17                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0030269
HETATM    1  C1  UNL     1       4.113  -1.491  -0.304  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.923  -0.637  -0.191  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.100   0.731  -0.143  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.019   1.601  -0.036  1.00  0.00           C  
HETATM    5  O1  UNL     1       2.253   2.985   0.009  1.00  0.00           O  
HETATM    6  C5  UNL     1       0.763   1.048   0.021  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.513   1.601   0.127  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.815   3.002   0.210  1.00  0.00           C  
HETATM    9  O2  UNL     1       0.001   3.921   0.199  1.00  0.00           O  
HETATM   10  O3  UNL     1      -2.169   3.403   0.317  1.00  0.00           O1-
HETATM   11  N1  UNL     1      -1.420   0.565   0.141  1.00  0.00           N1+
HETATM   12  N2  UNL     1      -0.783  -0.563   0.051  1.00  0.00           N  
HETATM   13  C8  UNL     1       0.548  -0.318  -0.024  1.00  0.00           C  
HETATM   14  C9  UNL     1       1.646  -1.153  -0.131  1.00  0.00           C  
HETATM   15  C10 UNL     1      -1.412  -1.887   0.040  1.00  0.00           C  
HETATM   16  C11 UNL     1      -2.868  -1.777   0.428  1.00  0.00           C  
HETATM   17  C12 UNL     1      -3.473  -0.584  -0.287  1.00  0.00           C  
HETATM   18  C13 UNL     1      -2.855   0.669   0.236  1.00  0.00           C  
HETATM   19  H1  UNL     1       3.823  -2.555  -0.148  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.897  -1.201   0.399  1.00  0.00           H  
HETATM   21  H3  UNL     1       4.506  -1.426  -1.353  1.00  0.00           H  
HETATM   22  H4  UNL     1       4.079   1.184  -0.186  1.00  0.00           H  
HETATM   23  H5  UNL     1       3.163   3.368  -0.032  1.00  0.00           H  
HETATM   24  H6  UNL     1       1.544  -2.217  -0.171  1.00  0.00           H  
HETATM   25  H7  UNL     1      -0.905  -2.585   0.735  1.00  0.00           H  
HETATM   26  H8  UNL     1      -1.377  -2.349  -0.962  1.00  0.00           H  
HETATM   27  H9  UNL     1      -3.423  -2.671   0.058  1.00  0.00           H  
HETATM   28  H10 UNL     1      -3.029  -1.694   1.509  1.00  0.00           H  
HETATM   29  H11 UNL     1      -4.570  -0.542  -0.074  1.00  0.00           H  
HETATM   30  H12 UNL     1      -3.280  -0.737  -1.371  1.00  0.00           H  
HETATM   31  H13 UNL     1      -3.202   0.803   1.286  1.00  0.00           H  
HETATM   32  H14 UNL     1      -3.284   1.506  -0.353  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3   14
CONECT    3    4   22
CONECT    4    5    6    6
CONECT    5   23
CONECT    6    7   13
CONECT    7    8   11   11
CONECT    8    9    9   10
CONECT   11   12   18
CONECT   12   13   15
CONECT   13   14   14
CONECT   14   24
CONECT   15   16   25   26
CONECT   16   17   27   28
CONECT   17   18   29   30
CONECT   18   31   32
END

HMDB0030269
     RDKit          3D
Nigellicine
 32 34  0  0  0  0  0  0  0  0999 V2000
    4.1129   -1.4913   -0.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9231   -0.6367   -0.1908 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1004    0.7314   -0.1429 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0187    1.6007   -0.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2530    2.9853    0.0094 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7629    1.0483    0.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5134    1.6009    0.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8145    3.0024    0.2104 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0013    3.9213    0.1992 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1691    3.4033    0.3168 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.4198    0.5646    0.1405 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.7828   -0.5628    0.0508 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5477   -0.3182   -0.0243 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6458   -1.1534   -0.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4121   -1.8872    0.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8683   -1.7770    0.4284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4730   -0.5843   -0.2872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8552    0.6694    0.2357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8230   -2.5554   -0.1480 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8973   -1.2008    0.3991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5063   -1.4262   -1.3534 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0785    1.1843   -0.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1628    3.3677   -0.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5445   -2.2168   -0.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9053   -2.5846    0.7350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3773   -2.3491   -0.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4232   -2.6712    0.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0290   -1.6942    1.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5702   -0.5424   -0.0744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2796   -0.7374   -1.3706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2017    0.8030    1.2865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2838    1.5063   -0.3532 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
  4  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 14  2  1  0
 13  6  1  0
 18 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  5 23  1  0
 14 24  1  0
 15 25  1  0
 15 26  1  0
 16 27  1  0
 16 28  1  0
 17 29  1  0
 17 30  1  0
 18 31  1  0
 18 32  1  0
M  CHG  2  10  -1  11   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-Methyl-1-oxo-1H,6H,7H,8H,9H-pyridazino[1,2-a]indazole-11-carboxylate	HMDB
Nigellicine	MeSH

Chemical Formula

C₁₃H₁₄N₂O₃

Average Molecular Weight

246.2619

Monoisotopic Molecular Weight

246.100442324

IUPAC Name

1-hydroxy-3-methyl-6H,7H,8H,9H-10λ⁵-pyridazino[1,2-a]indazol-10-ylium-11-carboxylate

Traditional Name

1-hydroxy-3-methyl-6H,7H,8H,9H-10λ⁵-pyridazino[1,2-a]indazol-10-ylium-11-carboxylate

CAS Registry Number

98063-20-8

SMILES

CC1=CC(O)=C2C(=C1)N1CCCC[N+]1=C2C([O-])=O

InChI Identifier

InChI=1S/C13H14N2O3/c1-8-6-9-11(10(16)7-8)12(13(17)18)15-5-3-2-4-14(9)15/h6-7H,2-5H2,1H3,(H,17,18)

InChI Key

FEJTUHSIRAJLOJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyridazinoindazoles. Pyridazinoindazoles are compounds containing a pyridazinoindazole moiety, which consists of a pyridazine ring fused to an indazole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrazoles

Sub Class

Indazoles

Direct Parent

Pyridazinoindazoles

Alternative Parents

Substituents

Pyridazinoindazole
Pyrazole-5-carboxylic acid or derivatives
Pyrazole-3-carboxylic acid or derivatives
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Pyridazine
Azole
Heteroaromatic compound
Pyrazole
Carboxylic acid salt
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organic nitrogen compound
Organic zwitterion
Organic salt
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030269)
Cytoplasm (HMDB: HMDB0030269)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030269)

Source

Endogenous

Endogenous (HMDB: HMDB0030269)

Plant

Plant (HMDB: HMDB0030269)

Exogenous

Food

Food (HMDB: HMDB0030269)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

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	0.23 g/L	ALOGPS
logP	-0.7	ALOGPS
logP	-1.8	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	2.03	ChemAxon
pKa (Strongest Basic)	-5.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	69.17 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	99.36 m³·mol⁻¹	ChemAxon
Polarizability	25.67 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
DarkChem	[M+H]+	157.4	31661259
DarkChem	[M-H]-	156.105	31661259
DeepCCS	[M+H]+	152.911	30932474
DeepCCS	[M-H]-	150.553	30932474
DeepCCS	[M-2H]-	183.677	30932474
DeepCCS	[M+Na]+	159.323	30932474
AllCCS	[M+H]+	153.5	32859911
AllCCS	[M+H-H2O]+	149.7	32859911
AllCCS	[M+NH4]+	157.0	32859911
AllCCS	[M+Na]+	158.1	32859911
AllCCS	[M-H]-	158.7	32859911
AllCCS	[M+Na-2H]-	158.3	32859911
AllCCS	[M+HCOO]-	158.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nigellicine	CC1=CC(O)=C2C(=C1)N1CCCC[N+]1=C2C([O-])=O	3286.3	Standard polar	33892256
Nigellicine	CC1=CC(O)=C2C(=C1)N1CCCC[N+]1=C2C([O-])=O	2324.9	Standard non polar	33892256
Nigellicine	CC1=CC(O)=C2C(=C1)N1CCCC[N+]1=C2C([O-])=O	2662.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nigellicine,1TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=C2C(C(=O)[O-])=[N+]3CCCCN3C2=C1	2435.2	Semi standard non polar	33892256
Nigellicine,1TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(C(=O)[O-])=[N+]3CCCCN3C2=C1	2645.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Nigellicine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0il0-0590000000-6921f5972e7773a50da9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nigellicine GC-MS (1 TMS) - 70eV, Positive	splash10-0fk9-3394000000-9e8975148d1e663333ce	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nigellicine 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 - Nigellicine 10V, Positive-QTOF	splash10-002b-0090000000-978fa98900985f1e5ce2	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nigellicine 20V, Positive-QTOF	splash10-0fba-0090000000-e0709a3844b163789814	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nigellicine 40V, Positive-QTOF	splash10-0f9f-4980000000-4f325fe25660252482d4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nigellicine 10V, Negative-QTOF	splash10-0f6t-0090000000-74ba8bd2b056292c5754	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nigellicine 20V, Negative-QTOF	splash10-0udi-0290000000-c48d0a6b94b8e48afdfc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nigellicine 40V, Negative-QTOF	splash10-000i-1940000000-63a5e0edd4fbb43be935	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nigellicine 10V, Negative-QTOF	splash10-0udj-0090000000-ba92633025182ce5ec98	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nigellicine 20V, Negative-QTOF	splash10-0f6t-0290000000-10f4eee6f4dc25824cab	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nigellicine 40V, Negative-QTOF	splash10-015a-0910000000-c38f54b8d3a193a04433	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nigellicine 10V, Positive-QTOF	splash10-0002-0090000000-4b96f2fb9c6435e34917	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nigellicine 20V, Positive-QTOF	splash10-0002-0090000000-360167aec658ca76c222	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nigellicine 40V, Positive-QTOF	splash10-0cki-0910000000-e9c09a512e2e3d46c03e	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB002099

KNApSAcK ID

C00028686

Chemspider ID

9577233

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11402337

PDB ID

Not Available

ChEBI ID

168947

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1818551

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Nigellicine (HMDB0030269)

MOL for HMDB0030269 (Nigellicine)

3D MOL for HMDB0030269 (Nigellicine)

3D SDF for HMDB0030269 (Nigellicine)

3D-SDF for HMDB0030269 (Nigellicine)

PDB for HMDB0030269 (Nigellicine)

3D PDB for HMDB0030269 (Nigellicine)

SMILES for HMDB0030269 (Nigellicine)

INCHI for HMDB0030269 (Nigellicine)

Structure for HMDB0030269 (Nigellicine)

3D Structure for HMDB0030269 (Nigellicine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra