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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

HMDB0030209

Secondary Accession Numbers

HMDB30209

Metabolite Identification

Common Name

Koenine

Description

Koenine 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 very few articles have been published on Koenine.

Structure

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

HMDB0030209
     RDKit          3D
Koenine
 38 41  0  0  0  0  0  0  0  0999 V2000
   -1.3058    2.7464    1.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5892    1.6088    0.8032 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7885    1.5414    0.7603 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4456    0.4749    0.1543 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7344   -0.5547   -0.4263 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6047   -1.4556   -0.9394 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8681   -1.0586   -0.7189 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0710   -1.6269   -1.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2207   -0.9631   -0.6727 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1703    0.2344    0.0055 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3060    0.9355    0.3986 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9370    0.7796    0.3183 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7764    0.1507   -0.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6479   -0.4925   -0.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2755    0.5652    0.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6524    0.5829    0.2293 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4793   -0.3993   -0.3241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2996    0.2507   -1.4209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3586   -1.0101    0.7416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7109   -1.5118   -0.9566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4026   -1.5668   -0.9922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2519    2.9843    0.9272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6840    3.6656    1.4358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5058    2.5359    2.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3624    2.3452    1.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3468   -2.3447   -1.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1856   -2.5626   -1.5749 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1762   -1.3726   -0.9079 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6666    0.7023    1.3245 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8937    1.7140    0.8475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6874    1.2028   -1.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1218   -0.3757   -1.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5827    0.5196   -2.2267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3901   -1.1260    0.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0366   -2.0261    1.0353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3963   -0.3931    1.6604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2983   -2.3020   -1.4021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8772   -2.3978   -1.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  5 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
 20 21  2  0
 15  2  1  0
 13  4  1  0
 21 14  1  0
 13  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  6 26  1  0
  8 27  1  0
  9 28  1  0
 11 29  1  0
 12 30  1  0
 18 31  1  0
 18 32  1  0
 18 33  1  0
 19 34  1  0
 19 35  1  0
 19 36  1  0
 20 37  1  0
 21 38  1  0
M  END


  Mrv0541 05061305052D          

 21 24  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
    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
  5  4  2  0  0  0  0
  7  6  2  0  0  0  0
 10  1  1  0  0  0  0
 10  8  1  0  0  0  0
 11  4  1  0  0  0  0
 11  9  2  0  0  0  0
 12  6  1  0  0  0  0
 13  9  1  0  0  0  0
 14  8  2  0  0  0  0
 14 13  1  0  0  0  0
 15  5  1  0  0  0  0
 15 13  2  0  0  0  0
 16 12  2  0  0  0  0
 16 14  1  0  0  0  0
 17 10  2  0  0  0  0
 17 12  1  0  0  0  0
 18  2  1  0  0  0  0
 18  3  1  0  0  0  0
 18  7  1  0  0  0  0
 19 15  1  0  0  0  0
 19 16  1  0  0  0  0
 20 11  1  0  0  0  0
 21 17  1  0  0  0  0
 21 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030209

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C2OC(C)(C)C=CC2=C2NC3=C(C=C(O)C=C3)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H17NO2/c1-10-8-14-13-9-11(20)4-5-15(13)19-16(14)12-6-7-18(2,3)21-17(10)12/h4-9,19-20H,1-3H3

> <INCHI_KEY>
VISKLVOLGCYFCW-UHFFFAOYSA-N

> <FORMULA>
C18H17NO2

> <MOLECULAR_WEIGHT>
279.3331

> <EXACT_MASS>
279.125928793

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
31.876751793334485

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,3,5-trimethyl-3H,11H-pyrano[3,2-a]carbazol-8-ol

> <ALOGPS_LOGP>
4.32

> <JCHEM_LOGP>
4.201365159

> <ALOGPS_LOGS>
-4.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.670938360018322

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.9656556178051

> <JCHEM_PKA_STRONGEST_BASIC>
-4.918789527674288

> <JCHEM_POLAR_SURFACE_AREA>
45.25

> <JCHEM_REFRACTIVITY>
84.88770000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.66e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,3,5-trimethyl-11H-pyrano[3,2-a]carbazol-8-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030209
     RDKit          3D
Koenine
 38 41  0  0  0  0  0  0  0  0999 V2000
   -1.3058    2.7464    1.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5892    1.6088    0.8032 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7885    1.5414    0.7603 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4456    0.4749    0.1543 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7344   -0.5547   -0.4263 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6047   -1.4556   -0.9394 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8681   -1.0586   -0.7189 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0710   -1.6269   -1.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2207   -0.9631   -0.6727 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1703    0.2344    0.0055 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3060    0.9355    0.3986 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9370    0.7796    0.3183 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7764    0.1507   -0.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6479   -0.4925   -0.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2755    0.5652    0.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6524    0.5829    0.2293 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4793   -0.3993   -0.3241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2996    0.2507   -1.4209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3586   -1.0101    0.7416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7109   -1.5118   -0.9566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4026   -1.5668   -0.9922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2519    2.9843    0.9272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6840    3.6656    1.4358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5058    2.5359    2.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3624    2.3452    1.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3468   -2.3447   -1.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1856   -2.5626   -1.5749 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1762   -1.3726   -0.9079 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6666    0.7023    1.3245 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8937    1.7140    0.8475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6874    1.2028   -1.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1218   -0.3757   -1.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5827    0.5196   -2.2267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3901   -1.1260    0.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0366   -2.0261    1.0353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3963   -0.3931    1.6604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2983   -2.3020   -1.4021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8772   -2.3978   -1.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  5 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
 20 21  2  0
 15  2  1  0
 13  4  1  0
 21 14  1  0
 13  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  6 26  1  0
  8 27  1  0
  9 28  1  0
 11 29  1  0
 12 30  1  0
 18 31  1  0
 18 32  1  0
 18 33  1  0
 19 34  1  0
 19 35  1  0
 19 36  1  0
 20 37  1  0
 21 38  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      12.144   0.064   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.849  -0.768   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.694  -0.606   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.156  -0.517   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.228   3.257   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.702   2.308   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.691   3.345   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.071   1.603   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.539   0.682   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.407   1.476   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.921   1.881   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.480  -0.063   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.076   0.594   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.846   2.057   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.464   0.858   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       8.039  -0.607   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0      13.366   2.435   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       3.308   2.146   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   18                                                            
CONECT    3   18                                                            
CONECT    4    5   11                                                       
CONECT    5    4   15                                                       
CONECT    6    7   12                                                       
CONECT    7    6   18                                                       
CONECT    8   10   14                                                       
CONECT    9   11   13                                                       
CONECT   10    1    8   17                                                  
CONECT   11    4    9   20                                                  
CONECT   12    6   16   17                                                  
CONECT   13    9   14   15                                                  
CONECT   14    8   13   16                                                  
CONECT   15    5   13   19                                                  
CONECT   16   12   14   19                                                  
CONECT   17   10   12   21                                                  
CONECT   18    2    3    7   21                                             
CONECT   19   15   16                                                       
CONECT   20   11                                                            
CONECT   21   17   18                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0030209
HETATM    1  C1  UNL     1      -1.306   2.746   1.450  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.589   1.609   0.803  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.789   1.541   0.760  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.446   0.475   0.154  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.734  -0.555  -0.426  1.00  0.00           C  
HETATM    6  N1  UNL     1       1.605  -1.456  -0.939  1.00  0.00           N  
HETATM    7  C6  UNL     1       2.868  -1.059  -0.719  1.00  0.00           C  
HETATM    8  C7  UNL     1       4.071  -1.627  -1.045  1.00  0.00           C  
HETATM    9  C8  UNL     1       5.221  -0.963  -0.673  1.00  0.00           C  
HETATM   10  C9  UNL     1       5.170   0.234   0.005  1.00  0.00           C  
HETATM   11  O1  UNL     1       6.306   0.936   0.399  1.00  0.00           O  
HETATM   12  C10 UNL     1       3.937   0.780   0.318  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.776   0.151  -0.034  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.648  -0.492  -0.386  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.275   0.565   0.215  1.00  0.00           C  
HETATM   16  O2  UNL     1      -2.652   0.583   0.229  1.00  0.00           O  
HETATM   17  C14 UNL     1      -3.479  -0.399  -0.324  1.00  0.00           C  
HETATM   18  C15 UNL     1      -4.300   0.251  -1.421  1.00  0.00           C  
HETATM   19  C16 UNL     1      -4.359  -1.010   0.742  1.00  0.00           C  
HETATM   20  C17 UNL     1      -2.711  -1.512  -0.957  1.00  0.00           C  
HETATM   21  C18 UNL     1      -1.403  -1.567  -0.992  1.00  0.00           C  
HETATM   22  H1  UNL     1      -2.252   2.984   0.927  1.00  0.00           H  
HETATM   23  H2  UNL     1      -0.684   3.666   1.436  1.00  0.00           H  
HETATM   24  H3  UNL     1      -1.506   2.536   2.527  1.00  0.00           H  
HETATM   25  H4  UNL     1       1.362   2.345   1.213  1.00  0.00           H  
HETATM   26  H5  UNL     1       1.347  -2.345  -1.442  1.00  0.00           H  
HETATM   27  H6  UNL     1       4.186  -2.563  -1.575  1.00  0.00           H  
HETATM   28  H7  UNL     1       6.176  -1.373  -0.908  1.00  0.00           H  
HETATM   29  H8  UNL     1       6.667   0.702   1.324  1.00  0.00           H  
HETATM   30  H9  UNL     1       3.894   1.714   0.848  1.00  0.00           H  
HETATM   31  H10 UNL     1      -4.687   1.203  -1.014  1.00  0.00           H  
HETATM   32  H11 UNL     1      -5.122  -0.376  -1.777  1.00  0.00           H  
HETATM   33  H12 UNL     1      -3.583   0.520  -2.227  1.00  0.00           H  
HETATM   34  H13 UNL     1      -5.390  -1.126   0.307  1.00  0.00           H  
HETATM   35  H14 UNL     1      -4.037  -2.026   1.035  1.00  0.00           H  
HETATM   36  H15 UNL     1      -4.396  -0.393   1.660  1.00  0.00           H  
HETATM   37  H16 UNL     1      -3.298  -2.302  -1.402  1.00  0.00           H  
HETATM   38  H17 UNL     1      -0.877  -2.398  -1.464  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    3   15
CONECT    3    4   25
CONECT    4    5    5   13
CONECT    5    6   14
CONECT    6    7   26
CONECT    7    8    8   13
CONECT    8    9   27
CONECT    9   10   10   28
CONECT   10   11   12
CONECT   11   29
CONECT   12   13   13   30
CONECT   14   15   15   21
CONECT   15   16
CONECT   16   17
CONECT   17   18   19   20
CONECT   18   31   32   33
CONECT   19   34   35   36
CONECT   20   21   21   37
CONECT   21   38
END

HMDB0030209
     RDKit          3D
Koenine
 38 41  0  0  0  0  0  0  0  0999 V2000
   -1.3058    2.7464    1.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5892    1.6088    0.8032 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7885    1.5414    0.7603 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4456    0.4749    0.1543 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7344   -0.5547   -0.4263 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6047   -1.4556   -0.9394 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8681   -1.0586   -0.7189 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0710   -1.6269   -1.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2207   -0.9631   -0.6727 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1703    0.2344    0.0055 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3060    0.9355    0.3986 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9370    0.7796    0.3183 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7764    0.1507   -0.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6479   -0.4925   -0.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2755    0.5652    0.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6524    0.5829    0.2293 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4793   -0.3993   -0.3241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2996    0.2507   -1.4209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3586   -1.0101    0.7416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7109   -1.5118   -0.9566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4026   -1.5668   -0.9922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2519    2.9843    0.9272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6840    3.6656    1.4358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5058    2.5359    2.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3624    2.3452    1.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3468   -2.3447   -1.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1856   -2.5626   -1.5749 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1762   -1.3726   -0.9079 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6666    0.7023    1.3245 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8937    1.7140    0.8475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6874    1.2028   -1.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1218   -0.3757   -1.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5827    0.5196   -2.2267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3901   -1.1260    0.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0366   -2.0261    1.0353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3963   -0.3931    1.6604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2983   -2.3020   -1.4021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8772   -2.3978   -1.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  5 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
 20 21  2  0
 15  2  1  0
 13  4  1  0
 21 14  1  0
 13  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  6 26  1  0
  8 27  1  0
  9 28  1  0
 11 29  1  0
 12 30  1  0
 18 31  1  0
 18 32  1  0
 18 33  1  0
 19 34  1  0
 19 35  1  0
 19 36  1  0
 20 37  1  0
 21 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,11-Dihydro-3,3,5-trimethylpyrano[3,2-a]carbazol-8-ol, 9ci	HMDB
Kenine	HMDB

Chemical Formula

C₁₈H₁₇NO₂

Average Molecular Weight

279.3331

Monoisotopic Molecular Weight

279.125928793

IUPAC Name

3,3,5-trimethyl-3H,11H-pyrano[3,2-a]carbazol-8-ol

Traditional Name

3,3,5-trimethyl-11H-pyrano[3,2-a]carbazol-8-ol

CAS Registry Number

28200-63-7

SMILES

CC1=C2OC(C)(C)C=CC2=C2NC3=C(C=C(O)C=C3)C2=C1

InChI Identifier

InChI=1S/C18H17NO2/c1-10-8-14-13-9-11(20)4-5-15(13)19-16(14)12-6-7-18(2,3)21-17(10)12/h4-9,19-20H,1-3H3

InChI Key

VISKLVOLGCYFCW-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
Hydroxyindole
Indole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Heteroaromatic compound
Pyrrole
Oxacycle
Azacycle
Ether
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030209)
Cell membrane (HMDB: HMDB0030209)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030209)

Source

Endogenous

Endogenous (HMDB: HMDB0030209)

Plant

Plant (HMDB: HMDB0030209)

Exogenous

Food

Food (HMDB: HMDB0030209)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0030209)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	250 - 252 °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	0.0057 g/L	ALOGPS
logP	4.32	ALOGPS
logP	4.2	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	9.97	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	45.25 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	84.89 m³·mol⁻¹	ChemAxon
Polarizability	31.88 Å³	ChemAxon
Number of Rings	4	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
DarkChem	[M+H]+	165.844	31661259
DarkChem	[M-H]-	167.036	31661259
DeepCCS	[M+H]+	171.177	30932474
DeepCCS	[M-H]-	168.819	30932474
DeepCCS	[M-2H]-	202.441	30932474
DeepCCS	[M+Na]+	177.668	30932474
AllCCS	[M+H]+	165.3	32859911
AllCCS	[M+H-H2O]+	161.5	32859911
AllCCS	[M+NH4]+	168.8	32859911
AllCCS	[M+Na]+	169.8	32859911
AllCCS	[M-H]-	171.7	32859911
AllCCS	[M+Na-2H]-	170.8	32859911
AllCCS	[M+HCOO]-	169.8	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.	6.15 minutes	32390414
Predicted by Siyang on May 30, 2022	12.8675 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.84 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	26.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2227.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	325.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	169.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	188.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	295.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	730.0 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	522.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	120.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1061.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	480.7 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	1325.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	477.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	363.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	342.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	217.0 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	9.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Koenine	CC1=C2OC(C)(C)C=CC2=C2NC3=C(C=C(O)C=C3)C2=C1	3790.7	Standard polar	33892256
Koenine	CC1=C2OC(C)(C)C=CC2=C2NC3=C(C=C(O)C=C3)C2=C1	2899.0	Standard non polar	33892256
Koenine	CC1=C2OC(C)(C)C=CC2=C2NC3=C(C=C(O)C=C3)C2=C1	2878.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Koenine,1TMS,isomer #1	CC1=CC2=C([NH]C3=CC=C(O[Si](C)(C)C)C=C32)C2=C1OC(C)(C)C=C2	3039.6	Semi standard non polar	33892256
Koenine,1TMS,isomer #2	CC1=CC2=C(C3=C1OC(C)(C)C=C3)N([Si](C)(C)C)C1=CC=C(O)C=C21	2892.3	Semi standard non polar	33892256
Koenine,2TMS,isomer #1	CC1=CC2=C(C3=C1OC(C)(C)C=C3)N([Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C=C21	2974.4	Semi standard non polar	33892256
Koenine,2TMS,isomer #1	CC1=CC2=C(C3=C1OC(C)(C)C=C3)N([Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C=C21	2543.8	Standard non polar	33892256
Koenine,1TBDMS,isomer #1	CC1=CC2=C([NH]C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C32)C2=C1OC(C)(C)C=C2	3200.0	Semi standard non polar	33892256
Koenine,1TBDMS,isomer #2	CC1=CC2=C(C3=C1OC(C)(C)C=C3)N([Si](C)(C)C(C)(C)C)C1=CC=C(O)C=C21	3051.6	Semi standard non polar	33892256
Koenine,2TBDMS,isomer #1	CC1=CC2=C(C3=C1OC(C)(C)C=C3)N([Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C21	3275.3	Semi standard non polar	33892256
Koenine,2TBDMS,isomer #1	CC1=CC2=C(C3=C1OC(C)(C)C=C3)N([Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C21	2961.7	Standard non polar	33892256

Spectra

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

FDB002027

KNApSAcK ID

C00051148

Chemspider ID

4477291

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5318827

PDB ID

Not Available

ChEBI ID

173980

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

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

Showing metabocard for Koenine (HMDB0030209)

MOL for HMDB0030209 (Koenine)

3D MOL for HMDB0030209 (Koenine)

3D SDF for HMDB0030209 (Koenine)

3D-SDF for HMDB0030209 (Koenine)

PDB for HMDB0030209 (Koenine)

3D PDB for HMDB0030209 (Koenine)

SMILES for HMDB0030209 (Koenine)

INCHI for HMDB0030209 (Koenine)

Structure for HMDB0030209 (Koenine)

3D Structure for HMDB0030209 (Koenine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized