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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:35:28 UTC

Update Date

2022-03-07 02:52:28 UTC

HMDB ID

HMDB0030210

Secondary Accession Numbers

HMDB30210

Metabolite Identification

Common Name

Koenimbine

Description

Koenimbine belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring. Based on a literature review a significant number of articles have been published on Koenimbine.

Structure

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

HMDB0030210
     RDKit          3D
Koenimbine
 41 44  0  0  0  0  0  0  0  0999 V2000
    7.0224    0.3439   -0.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7961    0.5707    0.4488 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5986    0.2177   -0.1460 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5902   -0.3565   -1.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3801   -0.7032   -1.9732 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1912   -0.4610   -1.2748 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8887   -0.6864   -1.5770 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0986   -0.2728   -0.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2670   -0.2683   -0.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8190    0.2330    0.8139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0226    0.7461    1.8150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6462    1.2799    3.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3322    0.7459    1.6189 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8904    0.2428    0.4439 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1843    0.1146   -0.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4209    0.4508    0.5311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1795    0.2050    0.9495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0975   -0.2836    0.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9231   -1.3596    0.6973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0597    0.7997   -0.4149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4368   -0.8036   -1.2072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1321   -0.8015   -1.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1629   -0.7564   -0.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8817    0.7667    0.3245 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9483    0.8054   -1.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5371   -0.5197   -1.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3481   -1.1567   -2.9550 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5904   -1.1190   -2.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0348    1.0000    3.9478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6546    0.8669    3.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7550    2.3868    3.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9910    1.1350    2.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3770    0.8999    1.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9793   -1.0531    0.8459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9501   -2.2916    0.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5095   -1.6287    1.6876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7120    1.0041    0.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5564    1.7267   -0.7156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6884    0.3787   -1.2225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0898   -1.2027   -1.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7168   -1.1958   -2.3088 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 10 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 21 22  2  0
 16  3  1  0
 15  6  1  0
 14  8  1  0
 22  9  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  7 28  1  0
 12 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 16 33  1  0
 19 34  1  0
 19 35  1  0
 19 36  1  0
 20 37  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
 22 41  1  0
M  END


  Mrv0541 05061305052D          

 22 25  0  0  0  0            999 V2000
    2.6777    2.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6585   -0.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7191    1.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1214    2.1285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5058    0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8117   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5144   -0.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6908   -0.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8724    1.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7333    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0487    1.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4665    0.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9671    0.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0392    0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2434    1.0079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0784   -0.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7907    0.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5961    1.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3198    0.4596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3068   -0.3254    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1606    1.3045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7724    1.1494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  8  7  2  0  0  0  0
 11  1  1  0  0  0  0
 11  9  1  0  0  0  0
 12  5  1  0  0  0  0
 12 10  2  0  0  0  0
 13  7  1  0  0  0  0
 14 10  1  0  0  0  0
 15  9  2  0  0  0  0
 15 14  1  0  0  0  0
 16  6  1  0  0  0  0
 16 14  2  0  0  0  0
 17 13  2  0  0  0  0
 17 15  1  0  0  0  0
 18 11  2  0  0  0  0
 18 13  1  0  0  0  0
 19  2  1  0  0  0  0
 19  3  1  0  0  0  0
 19  8  1  0  0  0  0
 20 16  1  0  0  0  0
 20 17  1  0  0  0  0
 21  4  1  0  0  0  0
 21 12  1  0  0  0  0
 22 18  1  0  0  0  0
 22 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030210

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(NC3=C4C=CC(C)(C)OC4=C(C)C=C23)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H19NO2/c1-11-9-15-14-10-12(21-4)5-6-16(14)20-17(15)13-7-8-19(2,3)22-18(11)13/h5-10,20H,1-4H3

> <INCHI_KEY>
OSERHKINMDLESD-UHFFFAOYSA-N

> <FORMULA>
C19H19NO2

> <MOLECULAR_WEIGHT>
293.3597

> <EXACT_MASS>
293.141578857

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
33.9959417312772

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
13-methoxy-5,5,8-trimethyl-6-oxa-17-azatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1,3,7,9,11(16),12,14-heptaene

> <ALOGPS_LOGP>
5.33

> <JCHEM_LOGP>
4.347259215

> <ALOGPS_LOGS>
-5.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.008159854884209

> <JCHEM_PKA_STRONGEST_BASIC>
-4.566757075870211

> <JCHEM_POLAR_SURFACE_AREA>
34.25

> <JCHEM_REFRACTIVITY>
89.37000000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.87e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13-methoxy-5,5,8-trimethyl-6-oxa-17-azatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1,3,7,9,11(16),12,14-heptaene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0030210
     RDKit          3D
Koenimbine
 41 44  0  0  0  0  0  0  0  0999 V2000
    7.0224    0.3439   -0.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7961    0.5707    0.4488 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5986    0.2177   -0.1460 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5902   -0.3565   -1.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3801   -0.7032   -1.9732 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1912   -0.4610   -1.2748 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8887   -0.6864   -1.5770 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0986   -0.2728   -0.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2670   -0.2683   -0.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8190    0.2330    0.8139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0226    0.7461    1.8150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6462    1.2799    3.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3322    0.7459    1.6189 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8904    0.2428    0.4439 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1843    0.1146   -0.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4209    0.4508    0.5311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1795    0.2050    0.9495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0975   -0.2836    0.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9231   -1.3596    0.6973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0597    0.7997   -0.4149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4368   -0.8036   -1.2072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1321   -0.8015   -1.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1629   -0.7564   -0.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8817    0.7667    0.3245 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9483    0.8054   -1.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5371   -0.5197   -1.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3481   -1.1567   -2.9550 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5904   -1.1190   -2.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0348    1.0000    3.9478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6546    0.8669    3.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7550    2.3868    3.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9910    1.1350    2.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3770    0.8999    1.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9793   -1.0531    0.8459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9501   -2.2916    0.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5095   -1.6287    1.6876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7120    1.0041    0.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5564    1.7267   -0.7156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6884    0.3787   -1.2225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0898   -1.2027   -1.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7168   -1.1958   -2.3088 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 10 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 21 22  2  0
 16  3  1  0
 15  6  1  0
 14  8  1  0
 22  9  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  7 28  1  0
 12 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 16 33  1  0
 19 34  1  0
 19 35  1  0
 19 36  1  0
 20 37  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
 22 41  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       4.998   4.720   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.229  -0.063   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.342   1.914   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.293   3.973   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.144   0.064   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.849  -0.768   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.694  -0.606   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.156  -0.517   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.228   3.257   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.702   2.308   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.691   3.345   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.071   1.603   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.539   0.682   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.407   1.476   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.921   1.881   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.480  -0.063   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.076   0.594   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.846   2.057   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.464   0.858   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       8.039  -0.607   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0      13.366   2.435   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.308   2.146   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   19                                                            
CONECT    3   19                                                            
CONECT    4   21                                                            
CONECT    5    6   12                                                       
CONECT    6    5   16                                                       
CONECT    7    8   13                                                       
CONECT    8    7   19                                                       
CONECT    9   11   15                                                       
CONECT   10   12   14                                                       
CONECT   11    1    9   18                                                  
CONECT   12    5   10   21                                                  
CONECT   13    7   17   18                                                  
CONECT   14   10   15   16                                                  
CONECT   15    9   14   17                                                  
CONECT   16    6   14   20                                                  
CONECT   17   13   15   20                                                  
CONECT   18   11   13   22                                                  
CONECT   19    2    3    8   22                                             
CONECT   20   16   17                                                       
CONECT   21    4   12                                                       
CONECT   22   18   19                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0030210
HETATM    1  C1  UNL     1       7.022   0.344  -0.222  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.796   0.571   0.449  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.599   0.218  -0.146  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.590  -0.357  -1.394  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.380  -0.703  -1.973  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.191  -0.461  -1.275  1.00  0.00           C  
HETATM    7  N1  UNL     1       0.889  -0.686  -1.577  1.00  0.00           N  
HETATM    8  C6  UNL     1       0.099  -0.273  -0.563  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.267  -0.268  -0.356  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.819   0.233   0.814  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.023   0.746   1.815  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.646   1.280   3.066  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.332   0.746   1.619  1.00  0.00           C  
HETATM   14  C12 UNL     1       0.890   0.243   0.444  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.184   0.115  -0.022  1.00  0.00           C  
HETATM   16  C14 UNL     1       3.421   0.451   0.531  1.00  0.00           C  
HETATM   17  O2  UNL     1      -3.180   0.205   0.949  1.00  0.00           O  
HETATM   18  C15 UNL     1      -4.097  -0.284   0.019  1.00  0.00           C  
HETATM   19  C16 UNL     1      -4.923  -1.360   0.697  1.00  0.00           C  
HETATM   20  C17 UNL     1      -5.060   0.800  -0.415  1.00  0.00           C  
HETATM   21  C18 UNL     1      -3.437  -0.804  -1.207  1.00  0.00           C  
HETATM   22  C19 UNL     1      -2.132  -0.801  -1.391  1.00  0.00           C  
HETATM   23  H1  UNL     1       7.163  -0.756  -0.295  1.00  0.00           H  
HETATM   24  H2  UNL     1       7.882   0.767   0.325  1.00  0.00           H  
HETATM   25  H3  UNL     1       6.948   0.805  -1.243  1.00  0.00           H  
HETATM   26  H4  UNL     1       5.537  -0.520  -1.886  1.00  0.00           H  
HETATM   27  H5  UNL     1       3.348  -1.157  -2.955  1.00  0.00           H  
HETATM   28  H6  UNL     1       0.590  -1.119  -2.475  1.00  0.00           H  
HETATM   29  H7  UNL     1      -1.035   1.000   3.948  1.00  0.00           H  
HETATM   30  H8  UNL     1      -2.655   0.867   3.215  1.00  0.00           H  
HETATM   31  H9  UNL     1      -1.755   2.387   3.007  1.00  0.00           H  
HETATM   32  H10 UNL     1       0.991   1.135   2.370  1.00  0.00           H  
HETATM   33  H11 UNL     1       3.377   0.900   1.514  1.00  0.00           H  
HETATM   34  H12 UNL     1      -5.979  -1.053   0.846  1.00  0.00           H  
HETATM   35  H13 UNL     1      -4.950  -2.292   0.101  1.00  0.00           H  
HETATM   36  H14 UNL     1      -4.510  -1.629   1.688  1.00  0.00           H  
HETATM   37  H15 UNL     1      -5.712   1.004   0.477  1.00  0.00           H  
HETATM   38  H16 UNL     1      -4.556   1.727  -0.716  1.00  0.00           H  
HETATM   39  H17 UNL     1      -5.688   0.379  -1.222  1.00  0.00           H  
HETATM   40  H18 UNL     1      -4.090  -1.203  -1.981  1.00  0.00           H  
HETATM   41  H19 UNL     1      -1.717  -1.196  -2.309  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4   16
CONECT    4    5   26
CONECT    5    6    6   27
CONECT    6    7   15
CONECT    7    8   28
CONECT    8    9    9   14
CONECT    9   10   22
CONECT   10   11   11   17
CONECT   11   12   13
CONECT   12   29   30   31
CONECT   13   14   14   32
CONECT   14   15
CONECT   15   16   16
CONECT   16   33
CONECT   17   18
CONECT   18   19   20   21
CONECT   19   34   35   36
CONECT   20   37   38   39
CONECT   21   22   22   40
CONECT   22   41
END

HMDB0030210
     RDKit          3D
Koenimbine
 41 44  0  0  0  0  0  0  0  0999 V2000
    7.0224    0.3439   -0.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7961    0.5707    0.4488 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5986    0.2177   -0.1460 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5902   -0.3565   -1.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3801   -0.7032   -1.9732 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1912   -0.4610   -1.2748 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8887   -0.6864   -1.5770 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0986   -0.2728   -0.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2670   -0.2683   -0.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8190    0.2330    0.8139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0226    0.7461    1.8150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6462    1.2799    3.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3322    0.7459    1.6189 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8904    0.2428    0.4439 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1843    0.1146   -0.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4209    0.4508    0.5311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1795    0.2050    0.9495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0975   -0.2836    0.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9231   -1.3596    0.6973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0597    0.7997   -0.4149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4368   -0.8036   -1.2072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1321   -0.8015   -1.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1629   -0.7564   -0.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8817    0.7667    0.3245 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9483    0.8054   -1.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5371   -0.5197   -1.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3481   -1.1567   -2.9550 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5904   -1.1190   -2.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0348    1.0000    3.9478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6546    0.8669    3.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7550    2.3868    3.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9910    1.1350    2.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3770    0.8999    1.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9793   -1.0531    0.8459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9501   -2.2916    0.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5095   -1.6287    1.6876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7120    1.0041    0.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5564    1.7267   -0.7156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6884    0.3787   -1.2225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0898   -1.2027   -1.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7168   -1.1958   -2.3088 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 10 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 21 22  2  0
 16  3  1  0
 15  6  1  0
 14  8  1  0
 22  9  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  7 28  1  0
 12 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 16 33  1  0
 19 34  1  0
 19 35  1  0
 19 36  1  0
 20 37  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
 22 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,11-Dihydro-8-methoxy-3,3,5-trimethylpyrano[3,2-a]carbazole, 9ci	HMDB
Kenimbine	HMDB
Koenimbin	HMDB
8-Methoxy-3,3,5-trimethyl-11H-pyrano(3,2-a)carbazole	MeSH

Chemical Formula

C₁₉H₁₉NO₂

Average Molecular Weight

293.3597

Monoisotopic Molecular Weight

293.141578857

IUPAC Name

13-methoxy-5,5,8-trimethyl-6-oxa-17-azatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1,3,7,9,11(16),12,14-heptaene

Traditional Name

13-methoxy-5,5,8-trimethyl-6-oxa-17-azatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1,3,7,9,11(16),12,14-heptaene

CAS Registry Number

21087-98-9

SMILES

COC1=CC2=C(NC3=C4C=CC(C)(C)OC4=C(C)C=C23)C=C1

InChI Identifier

InChI=1S/C19H19NO2/c1-11-9-15-14-10-12(21-4)5-6-16(14)20-17(15)13-7-8-19(2,3)22-18(11)13/h5-10,20H,1-4H3

InChI Key

OSERHKINMDLESD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Carbazoles

Direct Parent

Carbazoles

Alternative Parents

Substituents

Carbazole
2,2-dimethyl-1-benzopyran
Benzopyran
1-benzopyran
Indole
Anisole
Alkyl aryl ether
Benzenoid
Heteroaromatic compound
Pyrrole
Ether
Oxacycle
Azacycle
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030210)
Cell membrane (HMDB: HMDB0030210)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030210)

Source

Endogenous

Endogenous (HMDB: HMDB0030210)

Plant

Plant (HMDB: HMDB0030210)

Exogenous

Food

Food (HMDB: HMDB0030210)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0030210)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	194 - 195 °C	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	0.00079 g/L	ALOGPS
logP	5.33	ALOGPS
logP	4.35	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	15.01	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	34.25 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	89.37 m³·mol⁻¹	ChemAxon
Polarizability	34 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	171.679	31661259
DarkChem	[M-H]-	174.335	31661259
DeepCCS	[M-2H]-	213.757	30932474
DeepCCS	[M+Na]+	189.277	30932474
AllCCS	[M+H]+	169.7	32859911
AllCCS	[M+H-H2O]+	166.0	32859911
AllCCS	[M+NH4]+	173.0	32859911
AllCCS	[M+Na]+	174.0	32859911
AllCCS	[M-H]-	176.9	32859911
AllCCS	[M+Na-2H]-	176.0	32859911
AllCCS	[M+HCOO]-	175.2	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.	6.72 minutes	32390414
Predicted by Siyang on May 30, 2022	15.6677 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.66 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	27.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2435.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	423.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	202.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	217.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	231.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	780.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	656.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	101.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1375.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	589.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1413.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	548.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	413.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	378.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	423.1 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	8.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Koenimbine	COC1=CC2=C(NC3=C4C=CC(C)(C)OC4=C(C)C=C23)C=C1	3673.9	Standard polar	33892256
Koenimbine	COC1=CC2=C(NC3=C4C=CC(C)(C)OC4=C(C)C=C23)C=C1	2789.4	Standard non polar	33892256
Koenimbine	COC1=CC2=C(NC3=C4C=CC(C)(C)OC4=C(C)C=C23)C=C1	2824.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Koenimbine,1TMS,isomer #1	COC1=CC=C2C(=C1)C1=CC(C)=C3OC(C)(C)C=CC3=C1N2[Si](C)(C)C	2977.3	Semi standard non polar	33892256
Koenimbine,1TMS,isomer #1	COC1=CC=C2C(=C1)C1=CC(C)=C3OC(C)(C)C=CC3=C1N2[Si](C)(C)C	2481.3	Standard non polar	33892256
Koenimbine,1TBDMS,isomer #1	COC1=CC=C2C(=C1)C1=CC(C)=C3OC(C)(C)C=CC3=C1N2[Si](C)(C)C(C)(C)C	3094.3	Semi standard non polar	33892256
Koenimbine,1TBDMS,isomer #1	COC1=CC=C2C(=C1)C1=CC(C)=C3OC(C)(C)C=CC3=C1N2[Si](C)(C)C(C)(C)C	2694.6	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Koenimbine GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-0290000000-dfd9f19a83c8266db33e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Koenimbine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Koenimbine 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 - Koenimbine 10V, Positive-QTOF	splash10-0006-0090000000-4270e2965a99d1c5e3da	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenimbine 20V, Positive-QTOF	splash10-0006-0090000000-20b4f72c40f10fa290cd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenimbine 40V, Positive-QTOF	splash10-05nr-2190000000-8bcf2a6a33863e5eb320	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenimbine 10V, Negative-QTOF	splash10-0006-0090000000-91c46a3905540c41e5e4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenimbine 20V, Negative-QTOF	splash10-0006-0090000000-c3c87733ef889c4e7fa0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenimbine 40V, Negative-QTOF	splash10-0pk9-0290000000-16d0f35388ab0bf60a2b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenimbine 10V, Positive-QTOF	splash10-0006-0090000000-c0ae6c1ee6eacc17ae1d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenimbine 20V, Positive-QTOF	splash10-0006-0090000000-1a0b237e4e93652f5fb9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenimbine 40V, Positive-QTOF	splash10-002r-1190000000-db3b177d0f4f971c7b9b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenimbine 10V, Negative-QTOF	splash10-0006-0090000000-80f6742b4f6b5e8352cf	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenimbine 20V, Negative-QTOF	splash10-002f-0090000000-907aa049544222e8b63b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenimbine 40V, Negative-QTOF	splash10-001i-0090000000-2550143bbf44789f8f06	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

FDB002028

KNApSAcK ID

Not Available

Chemspider ID

87989

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

97487

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1817961

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 Koenimbine (HMDB0030210)

MOL for HMDB0030210 (Koenimbine)

3D MOL for HMDB0030210 (Koenimbine)

3D SDF for HMDB0030210 (Koenimbine)

3D-SDF for HMDB0030210 (Koenimbine)

PDB for HMDB0030210 (Koenimbine)

3D PDB for HMDB0030210 (Koenimbine)

SMILES for HMDB0030210 (Koenimbine)

INCHI for HMDB0030210 (Koenimbine)

Structure for HMDB0030210 (Koenimbine)

3D Structure for HMDB0030210 (Koenimbine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra