Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:11:12 UTC

Update Date

2022-03-07 02:53:42 UTC

HMDB ID

HMDB0033452

Secondary Accession Numbers

HMDB33452

Metabolite Identification

Common Name

Koenoline

Description

Koenoline 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. Koenoline has been detected, but not quantified in, herbs and spices. This could make koenoline a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Koenoline.

Structure

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

HMDB0033452
     RDKit          3D
Koenoline
 30 32  0  0  0  0  0  0  0  0999 V2000
    2.9380    2.8777   -0.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5849    2.4854   -0.3402 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2472    1.2083    0.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1721    0.3368    0.6484 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8016   -0.9234    1.0694 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7968   -1.8678    1.6676 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3859   -2.6548    0.6523 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4749   -1.2700    0.9132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4652   -0.4198    0.3648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0853    0.8426   -0.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1681    1.4896   -0.5540 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2548    0.6950   -0.4780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5673    0.8967   -0.8501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4666   -0.1253   -0.6417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0411   -1.3268   -0.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7224   -1.4851    0.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8203   -0.4877    0.0909 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5884    2.1867   -0.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1107    3.9062   -0.5466 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2368    2.7595    0.8837 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1976    0.6732    0.7418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2853   -2.5992    2.3417 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5738   -1.3390    2.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7410   -3.3044    0.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1800   -2.2508    1.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1473    2.4622   -0.9378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9338    1.8098   -1.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5080   -0.0325   -0.9101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7517   -2.1273    0.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3832   -2.4157    0.7359 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  1  0
  6  7  1  0
  5  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 10  3  1  0
 17 12  1  0
 17  9  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
 11 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
M  END


  Mrv0541 05061307082D          

 17 19  0  0  0  0            999 V2000
    0.7566   -1.7698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896    1.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339   -0.6855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1966    1.4672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2046   -1.1567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  9  6  2  0  0  0  0
  9  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  4  2  0  0  0  0
 11  6  1  0  0  0  0
 11 10  1  0  0  0  0
 12  5  2  0  0  0  0
 12 10  1  0  0  0  0
 13  7  2  0  0  0  0
 14 11  2  0  0  0  0
 14 13  1  0  0  0  0
 15 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16  8  1  0  0  0  0
 17  1  1  0  0  0  0
 17 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033452

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(CO)=CC2=C1NC1=CC=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C14H13NO2/c1-17-13-7-9(8-16)6-11-10-4-2-3-5-12(10)15-14(11)13/h2-7,15-16H,8H2,1H3

> <INCHI_KEY>
KNKVHLASDDREQS-UHFFFAOYSA-N

> <FORMULA>
C14H13NO2

> <MOLECULAR_WEIGHT>
227.2585

> <EXACT_MASS>
227.094628665

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
25.060931657633706

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1-methoxy-9H-carbazol-3-yl)methanol

> <ALOGPS_LOGP>
2.91

> <JCHEM_LOGP>
2.1658646563333335

> <ALOGPS_LOGS>
-3.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.874813052849237

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.798431776394668

> <JCHEM_PKA_STRONGEST_BASIC>
-2.894362688899725

> <JCHEM_POLAR_SURFACE_AREA>
45.25

> <JCHEM_REFRACTIVITY>
66.7513

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.19e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1-methoxy-9H-carbazol-3-yl)methanol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033452
     RDKit          3D
Koenoline
 30 32  0  0  0  0  0  0  0  0999 V2000
    2.9380    2.8777   -0.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5849    2.4854   -0.3402 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2472    1.2083    0.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1721    0.3368    0.6484 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8016   -0.9234    1.0694 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7968   -1.8678    1.6676 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3859   -2.6548    0.6523 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4749   -1.2700    0.9132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4652   -0.4198    0.3648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0853    0.8426   -0.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1681    1.4896   -0.5540 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2548    0.6950   -0.4780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5673    0.8967   -0.8501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4666   -0.1253   -0.6417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0411   -1.3268   -0.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7224   -1.4851    0.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8203   -0.4877    0.0909 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5884    2.1867   -0.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1107    3.9062   -0.5466 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2368    2.7595    0.8837 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1976    0.6732    0.7418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2853   -2.5992    2.3417 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5738   -1.3390    2.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7410   -3.3044    0.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1800   -2.2508    1.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1473    2.4622   -0.9378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9338    1.8098   -1.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5080   -0.0325   -0.9101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7517   -2.1273    0.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3832   -2.4157    0.7359 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  1  0
  6  7  1  0
  5  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 10  3  1  0
 17 12  1  0
 17  9  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
 11 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  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       1.412  -3.304   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.917   1.914   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.393   0.450   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.411   2.235   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.362  -0.695   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.810   2.235   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.173   0.450   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.727   3.059   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.303   1.914   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.380   1.090   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.840   1.090   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.856  -0.374   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.858  -0.695   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.364  -0.374   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       3.610  -1.280   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0      -2.234   2.739   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.382  -2.159   0.000  0.00  0.00           O+0
CONECT    1   17                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2   10                                                       
CONECT    5    3   12                                                       
CONECT    6    9   11                                                       
CONECT    7    9   13                                                       
CONECT    8    9   16                                                       
CONECT    9    6    7    8                                                  
CONECT   10    4   11   12                                                  
CONECT   11    6   10   14                                                  
CONECT   12    5   10   15                                                  
CONECT   13    7   14   17                                                  
CONECT   14   11   13   15                                                  
CONECT   15   12   14                                                       
CONECT   16    8                                                            
CONECT   17    1   13                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

COMPND    HMDB0033452
HETATM    1  C1  UNL     1       2.938   2.878  -0.196  1.00  0.00           C  
HETATM    2  O1  UNL     1       1.585   2.485  -0.340  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.247   1.208   0.095  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.172   0.337   0.648  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.802  -0.923   1.069  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.797  -1.868   1.668  1.00  0.00           C  
HETATM    7  O2  UNL     1       3.386  -2.655   0.652  1.00  0.00           O  
HETATM    8  C6  UNL     1       0.475  -1.270   0.913  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.465  -0.420   0.365  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.085   0.843  -0.055  1.00  0.00           C  
HETATM   11  N1  UNL     1      -1.168   1.490  -0.554  1.00  0.00           N  
HETATM   12  C9  UNL     1      -2.255   0.695  -0.478  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.567   0.897  -0.850  1.00  0.00           C  
HETATM   14  C11 UNL     1      -4.467  -0.125  -0.642  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.041  -1.327  -0.067  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.722  -1.485   0.289  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.820  -0.488   0.091  1.00  0.00           C  
HETATM   18  H1  UNL     1       3.588   2.187  -0.798  1.00  0.00           H  
HETATM   19  H2  UNL     1       3.111   3.906  -0.547  1.00  0.00           H  
HETATM   20  H3  UNL     1       3.237   2.760   0.884  1.00  0.00           H  
HETATM   21  H4  UNL     1       3.198   0.673   0.742  1.00  0.00           H  
HETATM   22  H5  UNL     1       2.285  -2.599   2.342  1.00  0.00           H  
HETATM   23  H6  UNL     1       3.574  -1.339   2.225  1.00  0.00           H  
HETATM   24  H7  UNL     1       2.741  -3.304   0.289  1.00  0.00           H  
HETATM   25  H8  UNL     1       0.180  -2.251   1.239  1.00  0.00           H  
HETATM   26  H9  UNL     1      -1.147   2.462  -0.938  1.00  0.00           H  
HETATM   27  H10 UNL     1      -3.934   1.810  -1.296  1.00  0.00           H  
HETATM   28  H11 UNL     1      -5.508  -0.033  -0.910  1.00  0.00           H  
HETATM   29  H12 UNL     1      -4.752  -2.127   0.095  1.00  0.00           H  
HETATM   30  H13 UNL     1      -2.383  -2.416   0.736  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3
CONECT    3    4    4   10
CONECT    4    5   21
CONECT    5    6    8    8
CONECT    6    7   22   23
CONECT    7   24
CONECT    8    9   25
CONECT    9   10   10   17
CONECT   10   11
CONECT   11   12   26
CONECT   12   13   13   17
CONECT   13   14   27
CONECT   14   15   15   28
CONECT   15   16   29
CONECT   16   17   17   30
END

HMDB0033452
     RDKit          3D
Koenoline
 30 32  0  0  0  0  0  0  0  0999 V2000
    2.9380    2.8777   -0.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5849    2.4854   -0.3402 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2472    1.2083    0.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1721    0.3368    0.6484 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8016   -0.9234    1.0694 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7968   -1.8678    1.6676 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3859   -2.6548    0.6523 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4749   -1.2700    0.9132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4652   -0.4198    0.3648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0853    0.8426   -0.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1681    1.4896   -0.5540 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2548    0.6950   -0.4780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5673    0.8967   -0.8501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4666   -0.1253   -0.6417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0411   -1.3268   -0.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7224   -1.4851    0.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8203   -0.4877    0.0909 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5884    2.1867   -0.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1107    3.9062   -0.5466 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2368    2.7595    0.8837 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1976    0.6732    0.7418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2853   -2.5992    2.3417 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5738   -1.3390    2.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7410   -3.3044    0.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1800   -2.2508    1.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1473    2.4622   -0.9378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9338    1.8098   -1.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5080   -0.0325   -0.9101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7517   -2.1273    0.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3832   -2.4157    0.7359 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  1  0
  6  7  1  0
  5  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 10  3  1  0
 17 12  1  0
 17  9  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
 11 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Methoxy-9H-carbazole-3-methanol, 9ci	HMDB
Koenoline	MeSH

Chemical Formula

C₁₄H₁₃NO₂

Average Molecular Weight

227.2585

Monoisotopic Molecular Weight

227.094628665

IUPAC Name

(1-methoxy-9H-carbazol-3-yl)methanol

Traditional Name

(1-methoxy-9H-carbazol-3-yl)methanol

CAS Registry Number

3909-78-2

SMILES

COC1=CC(CO)=CC2=C1NC1=CC=CC=C21

InChI Identifier

InChI=1S/C14H13NO2/c1-17-13-7-9(8-16)6-11-10-4-2-3-5-12(10)15-14(11)13/h2-7,15-16H,8H2,1H3

InChI Key

KNKVHLASDDREQS-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
Indole
Anisole
Alkyl aryl ether
Benzenoid
Heteroaromatic compound
Pyrrole
Ether
Azacycle
Primary alcohol
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Alcohol
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0033452)

Cellular substructure

Membrane (HMDB: HMDB0033452)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033452)

Source

Exogenous

Food

Food (HMDB: HMDB0033452)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0033452)

Not Available

Nutrient (HMDB: HMDB0033452)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	142 °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	0.042 g/L	ALOGPS
logP	2.91	ALOGPS
logP	2.17	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	13.8	ChemAxon
pKa (Strongest Basic)	-2.9	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	2	ChemAxon
Refractivity	66.75 m³·mol⁻¹	ChemAxon
Polarizability	25.06 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	152.973	31661259
DarkChem	[M-H]-	152.527	31661259
DeepCCS	[M-2H]-	181.603	30932474
DeepCCS	[M+Na]+	156.907	30932474
AllCCS	[M+H]+	150.6	32859911
AllCCS	[M+H-H2O]+	146.5	32859911
AllCCS	[M+NH4]+	154.4	32859911
AllCCS	[M+Na]+	155.5	32859911
AllCCS	[M-H]-	155.0	32859911
AllCCS	[M+Na-2H]-	154.6	32859911
AllCCS	[M+HCOO]-	154.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Koenoline	COC1=CC(CO)=CC2=C1NC1=CC=CC=C21	3232.3	Standard polar	33892256
Koenoline	COC1=CC(CO)=CC2=C1NC1=CC=CC=C21	2317.3	Standard non polar	33892256
Koenoline	COC1=CC(CO)=CC2=C1NC1=CC=CC=C21	2489.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Koenoline,1TMS,isomer #1	COC1=CC(CO[Si](C)(C)C)=CC2=C1[NH]C1=CC=CC=C12	2537.1	Semi standard non polar	33892256
Koenoline,1TMS,isomer #2	COC1=CC(CO)=CC2=C1N([Si](C)(C)C)C1=CC=CC=C21	2513.6	Semi standard non polar	33892256
Koenoline,2TMS,isomer #1	COC1=CC(CO[Si](C)(C)C)=CC2=C1N([Si](C)(C)C)C1=CC=CC=C21	2597.6	Semi standard non polar	33892256
Koenoline,2TMS,isomer #1	COC1=CC(CO[Si](C)(C)C)=CC2=C1N([Si](C)(C)C)C1=CC=CC=C21	2364.5	Standard non polar	33892256
Koenoline,1TBDMS,isomer #1	COC1=CC(CO[Si](C)(C)C(C)(C)C)=CC2=C1[NH]C1=CC=CC=C12	2734.6	Semi standard non polar	33892256
Koenoline,1TBDMS,isomer #2	COC1=CC(CO)=CC2=C1N([Si](C)(C)C(C)(C)C)C1=CC=CC=C21	2708.7	Semi standard non polar	33892256
Koenoline,2TBDMS,isomer #1	COC1=CC(CO[Si](C)(C)C(C)(C)C)=CC2=C1N([Si](C)(C)C(C)(C)C)C1=CC=CC=C21	2880.0	Semi standard non polar	33892256
Koenoline,2TBDMS,isomer #1	COC1=CC(CO[Si](C)(C)C(C)(C)C)=CC2=C1N([Si](C)(C)C(C)(C)C)C1=CC=CC=C21	2777.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Koenoline GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ot-0940000000-d5a3f47034026c58c6f6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Koenoline GC-MS (1 TMS) - 70eV, Positive	splash10-00e9-7190000000-2a7970de7b7e2781b5b0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Koenoline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Koenoline 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 - Koenoline 10V, Positive-QTOF	splash10-01t9-0090000000-9050b4f0f06699739f56	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenoline 20V, Positive-QTOF	splash10-03di-0390000000-147f3c1506ef179befa7	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenoline 40V, Positive-QTOF	splash10-0gx0-0930000000-041da835b9272dddf23c	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenoline 10V, Negative-QTOF	splash10-004i-0190000000-fff1c1b09e149a358fdc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenoline 20V, Negative-QTOF	splash10-004j-0790000000-19585b09ed4a669d35c8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenoline 40V, Negative-QTOF	splash10-01q9-0910000000-a03a06cd4f0f636a7f43	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenoline 10V, Negative-QTOF	splash10-004i-0090000000-dad58f66aff90bcb1e15	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenoline 20V, Negative-QTOF	splash10-004i-0790000000-67cdc46b1bb3432539c9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenoline 40V, Negative-QTOF	splash10-0006-0900000000-fffd71dd8ca43100b37f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenoline 10V, Positive-QTOF	splash10-004i-0090000000-e78c68df31de6c2c9dfe	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenoline 20V, Positive-QTOF	splash10-004i-0190000000-a999caec113bd43ad0f6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenoline 40V, Positive-QTOF	splash10-00ls-0900000000-2c78a42c7e22fa7eb049	2021-09-23	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

FDB011490

KNApSAcK ID

C00024715

Chemspider ID

332795

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

375152

PDB ID

Not Available

ChEBI ID

171730

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 Koenoline (HMDB0033452)

MOL for HMDB0033452 (Koenoline)

3D MOL for HMDB0033452 (Koenoline)

3D SDF for HMDB0033452 (Koenoline)

3D-SDF for HMDB0033452 (Koenoline)

PDB for HMDB0033452 (Koenoline)

3D PDB for HMDB0033452 (Koenoline)

SMILES for HMDB0033452 (Koenoline)

INCHI for HMDB0033452 (Koenoline)

Structure for HMDB0033452 (Koenoline)

3D Structure for HMDB0033452 (Koenoline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra