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 17:35:27 UTC

Update Date

2022-03-07 02:52:28 UTC

HMDB ID

HMDB0030207

Secondary Accession Numbers

HMDB30207

Metabolite Identification

Common Name

Koenigine

Description

Koenigine 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 small amount of articles have been published on Koenigine.

Structure

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

HMDB0030207
     RDKit          3D
Koenigine
 42 45  0  0  0  0  0  0  0  0999 V2000
    5.9140    0.7162    1.6894 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8110    0.0043    0.4721 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5562   -0.2302   -0.0736 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3845    0.2008    0.5172 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1840   -0.0805   -0.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0937   -0.7752   -1.2882 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2662   -1.2043   -1.8756 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4821   -0.9263   -1.2608 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6544   -1.3606   -1.8570 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7945   -0.8927   -1.6412 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0535   -0.2968   -0.7203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3028   -0.1278   -0.5951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8113    0.5475    0.4878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9909    1.0758    1.4793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5848    1.8083    2.6489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3683    0.8994    1.3420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8942    0.2241    0.2612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1855    0.7025    0.5872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1296    0.2316   -0.3222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9719    1.3592   -0.9172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0908   -0.7703    0.3309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5164   -0.4908   -1.4724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2082   -0.6536   -1.5926 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3387    0.1388    2.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9793    0.7039    1.9936 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5582    1.7436    1.5683 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4220    0.7488    1.4491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1968   -1.7474   -2.8031 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6549   -1.8696   -2.7186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4026   -1.3643   -2.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7614    2.4172    3.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4573    2.4111    2.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8371    1.0440    3.4364 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0362    1.2882    2.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3721    0.9889   -1.8702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7816    1.6449   -0.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2800    2.2095   -1.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7881   -1.1141   -0.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4771   -1.6525    0.6112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5869   -0.3498    1.2126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1426   -0.9060   -2.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7688   -1.1822   -2.4352 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  2  0
  8  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 13 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 22 23  2  0
  8  3  1  0
 17 11  1  0
 17  5  1  0
 23 12  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 20 35  1  0
 20 36  1  0
 20 37  1  0
 21 38  1  0
 21 39  1  0
 21 40  1  0
 22 41  1  0
 23 42  1  0
M  END


  Mrv0541 05061305052D          

 23 26  0  0  0  0            999 V2000
    2.9119   -0.6967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8927   -3.2592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9533   -2.2004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3556   -1.0970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7486   -3.5499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9249   -3.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1066   -1.4807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9675   -1.9890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0459   -3.6371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2829   -1.4336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2012   -2.8602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2734   -2.4350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4776   -2.2176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3126   -3.2590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7399   -3.1911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7007   -2.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0249   -2.9073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8302   -2.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5539   -2.7659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5410   -3.5510    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4732   -3.5692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3948   -1.9211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0066   -2.0762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
 10  1  1  0  0  0  0
 10  7  1  0  0  0  0
 11  5  1  0  0  0  0
 12  8  2  0  0  0  0
 13  7  2  0  0  0  0
 13 12  1  0  0  0  0
 14  9  2  0  0  0  0
 14 12  1  0  0  0  0
 15  9  1  0  0  0  0
 16  8  1  0  0  0  0
 16 15  2  0  0  0  0
 17 11  2  0  0  0  0
 17 13  1  0  0  0  0
 18 10  2  0  0  0  0
 18 11  1  0  0  0  0
 19  2  1  0  0  0  0
 19  3  1  0  0  0  0
 19  6  1  0  0  0  0
 20 14  1  0  0  0  0
 20 17  1  0  0  0  0
 21 15  1  0  0  0  0
 22  4  1  0  0  0  0
 22 16  1  0  0  0  0
 23 18  1  0  0  0  0
 23 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030207

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=C2NC3=C4C=CC(C)(C)OC4=C(C)C=C3C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H19NO3/c1-10-7-13-12-8-16(22-4)15(21)9-14(12)20-17(13)11-5-6-19(2,3)23-18(10)11/h5-9,20-21H,1-4H3

> <INCHI_KEY>
CZZZOTXCAIDYOZ-UHFFFAOYSA-N

> <FORMULA>
C19H19NO3

> <MOLECULAR_WEIGHT>
309.3591

> <EXACT_MASS>
309.136493479

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
34.99753450600044

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <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-1,3,7,9,11,13,15-heptaen-14-ol

> <ALOGPS_LOGP>
4.37

> <JCHEM_LOGP>
4.043693893333334

> <ALOGPS_LOGS>
-4.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.679553426373385

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.31086846432884

> <JCHEM_PKA_STRONGEST_BASIC>
-4.606546090528492

> <JCHEM_POLAR_SURFACE_AREA>
54.480000000000004

> <JCHEM_REFRACTIVITY>
91.35090000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.39e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13-methoxy-5,5,8-trimethyl-6-oxa-17-azatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1,3,7,9,11,13,15-heptaen-14-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030207
     RDKit          3D
Koenigine
 42 45  0  0  0  0  0  0  0  0999 V2000
    5.9140    0.7162    1.6894 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8110    0.0043    0.4721 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5562   -0.2302   -0.0736 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3845    0.2008    0.5172 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1840   -0.0805   -0.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0937   -0.7752   -1.2882 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2662   -1.2043   -1.8756 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4821   -0.9263   -1.2608 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6544   -1.3606   -1.8570 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7945   -0.8927   -1.6412 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0535   -0.2968   -0.7203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3028   -0.1278   -0.5951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8113    0.5475    0.4878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9909    1.0758    1.4793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5848    1.8083    2.6489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3683    0.8994    1.3420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8942    0.2241    0.2612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1855    0.7025    0.5872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1296    0.2316   -0.3222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9719    1.3592   -0.9172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0908   -0.7703    0.3309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5164   -0.4908   -1.4724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2082   -0.6536   -1.5926 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3387    0.1388    2.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9793    0.7039    1.9936 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5582    1.7436    1.5683 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4220    0.7488    1.4491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1968   -1.7474   -2.8031 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6549   -1.8696   -2.7186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4026   -1.3643   -2.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7614    2.4172    3.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4573    2.4111    2.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8371    1.0440    3.4364 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0362    1.2882    2.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3721    0.9889   -1.8702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7816    1.6449   -0.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2800    2.2095   -1.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7881   -1.1141   -0.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4771   -1.6525    0.6112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5869   -0.3498    1.2126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1426   -0.9060   -2.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7688   -1.1822   -2.4352 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  2  0
  8  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 13 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 22 23  2  0
  8  3  1  0
 17 11  1  0
 17  5  1  0
 23 12  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 20 35  1  0
 20 36  1  0
 20 37  1  0
 21 38  1  0
 21 39  1  0
 21 40  1  0
 22 41  1  0
 23 42  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       5.436  -1.301   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.666  -6.084   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.779  -4.107   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.730  -2.048   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.131  -6.626   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.593  -6.539   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.666  -2.764   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.139  -3.713   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.286  -6.789   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.128  -2.676   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.976  -5.339   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.844  -4.545   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.358  -4.140   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.917  -6.083   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.581  -5.957   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.508  -4.419   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.513  -5.427   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.283  -3.963   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.901  -5.163   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       8.477  -6.629   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0      13.950  -6.663   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      13.804  -3.586   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.746  -3.876   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   19                                                            
CONECT    3   19                                                            
CONECT    4   22                                                            
CONECT    5    6   11                                                       
CONECT    6    5   19                                                       
CONECT    7   10   13                                                       
CONECT    8   12   16                                                       
CONECT    9   14   15                                                       
CONECT   10    1    7   18                                                  
CONECT   11    5   17   18                                                  
CONECT   12    8   13   14                                                  
CONECT   13    7   12   17                                                  
CONECT   14    9   12   20                                                  
CONECT   15    9   16   21                                                  
CONECT   16    8   15   22                                                  
CONECT   17   11   13   20                                                  
CONECT   18   10   11   23                                                  
CONECT   19    2    3    6   23                                             
CONECT   20   14   17                                                       
CONECT   21   15                                                            
CONECT   22    4   16                                                       
CONECT   23   18   19                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0030207
HETATM    1  C1  UNL     1       5.914   0.716   1.689  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.811   0.004   0.472  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.556  -0.230  -0.074  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.384   0.201   0.517  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.184  -0.081  -0.102  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.094  -0.775  -1.288  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.266  -1.204  -1.876  1.00  0.00           C  
HETATM    8  C7  UNL     1       4.482  -0.926  -1.261  1.00  0.00           C  
HETATM    9  O2  UNL     1       5.654  -1.361  -1.857  1.00  0.00           O  
HETATM   10  N1  UNL     1       0.794  -0.893  -1.641  1.00  0.00           N  
HETATM   11  C8  UNL     1       0.053  -0.297  -0.720  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.303  -0.128  -0.595  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.811   0.548   0.488  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.991   1.076   1.479  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.585   1.808   2.649  1.00  0.00           C  
HETATM   16  C13 UNL     1       0.368   0.899   1.342  1.00  0.00           C  
HETATM   17  C14 UNL     1       0.894   0.224   0.261  1.00  0.00           C  
HETATM   18  O3  UNL     1      -3.185   0.703   0.587  1.00  0.00           O  
HETATM   19  C15 UNL     1      -4.130   0.232  -0.322  1.00  0.00           C  
HETATM   20  C16 UNL     1      -4.972   1.359  -0.917  1.00  0.00           C  
HETATM   21  C17 UNL     1      -5.091  -0.770   0.331  1.00  0.00           C  
HETATM   22  C18 UNL     1      -3.516  -0.491  -1.472  1.00  0.00           C  
HETATM   23  C19 UNL     1      -2.208  -0.654  -1.593  1.00  0.00           C  
HETATM   24  H1  UNL     1       5.339   0.139   2.442  1.00  0.00           H  
HETATM   25  H2  UNL     1       6.979   0.704   1.994  1.00  0.00           H  
HETATM   26  H3  UNL     1       5.558   1.744   1.568  1.00  0.00           H  
HETATM   27  H4  UNL     1       3.422   0.749   1.449  1.00  0.00           H  
HETATM   28  H5  UNL     1       3.197  -1.747  -2.803  1.00  0.00           H  
HETATM   29  H6  UNL     1       5.655  -1.870  -2.719  1.00  0.00           H  
HETATM   30  H7  UNL     1       0.403  -1.364  -2.486  1.00  0.00           H  
HETATM   31  H8  UNL     1      -0.761   2.417   3.091  1.00  0.00           H  
HETATM   32  H9  UNL     1      -2.457   2.411   2.353  1.00  0.00           H  
HETATM   33  H10 UNL     1      -1.837   1.044   3.436  1.00  0.00           H  
HETATM   34  H11 UNL     1       1.036   1.288   2.079  1.00  0.00           H  
HETATM   35  H12 UNL     1      -5.372   0.989  -1.870  1.00  0.00           H  
HETATM   36  H13 UNL     1      -5.782   1.645  -0.204  1.00  0.00           H  
HETATM   37  H14 UNL     1      -4.280   2.210  -1.113  1.00  0.00           H  
HETATM   38  H15 UNL     1      -5.788  -1.114  -0.454  1.00  0.00           H  
HETATM   39  H16 UNL     1      -4.477  -1.653   0.611  1.00  0.00           H  
HETATM   40  H17 UNL     1      -5.587  -0.350   1.213  1.00  0.00           H  
HETATM   41  H18 UNL     1      -4.143  -0.906  -2.250  1.00  0.00           H  
HETATM   42  H19 UNL     1      -1.769  -1.182  -2.435  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   27
CONECT    5    6    6   17
CONECT    6    7   10
CONECT    7    8    8   28
CONECT    8    9
CONECT    9   29
CONECT   10   11   30
CONECT   11   12   12   17
CONECT   12   13   23
CONECT   13   14   14   18
CONECT   14   15   16
CONECT   15   31   32   33
CONECT   16   17   17   34
CONECT   18   19
CONECT   19   20   21   22
CONECT   20   35   36   37
CONECT   21   38   39   40
CONECT   22   23   23   41
CONECT   23   42
END

HMDB0030207
     RDKit          3D
Koenigine
 42 45  0  0  0  0  0  0  0  0999 V2000
    5.9140    0.7162    1.6894 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8110    0.0043    0.4721 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5562   -0.2302   -0.0736 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3845    0.2008    0.5172 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1840   -0.0805   -0.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0937   -0.7752   -1.2882 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2662   -1.2043   -1.8756 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4821   -0.9263   -1.2608 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6544   -1.3606   -1.8570 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7945   -0.8927   -1.6412 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0535   -0.2968   -0.7203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3028   -0.1278   -0.5951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8113    0.5475    0.4878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9909    1.0758    1.4793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5848    1.8083    2.6489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3683    0.8994    1.3420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8942    0.2241    0.2612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1855    0.7025    0.5872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1296    0.2316   -0.3222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9719    1.3592   -0.9172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0908   -0.7703    0.3309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5164   -0.4908   -1.4724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2082   -0.6536   -1.5926 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3387    0.1388    2.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9793    0.7039    1.9936 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5582    1.7436    1.5683 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4220    0.7488    1.4491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1968   -1.7474   -2.8031 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6549   -1.8696   -2.7186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4026   -1.3643   -2.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7614    2.4172    3.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4573    2.4111    2.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8371    1.0440    3.4364 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0362    1.2882    2.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3721    0.9889   -1.8702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7816    1.6449   -0.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2800    2.2095   -1.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7881   -1.1141   -0.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4771   -1.6525    0.6112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5869   -0.3498    1.2126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1426   -0.9060   -2.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7688   -1.1822   -2.4352 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  2  0
  8  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 13 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 22 23  2  0
  8  3  1  0
 17 11  1  0
 17  5  1  0
 23 12  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 20 35  1  0
 20 36  1  0
 20 37  1  0
 21 38  1  0
 21 39  1  0
 21 40  1  0
 22 41  1  0
 23 42  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]carbazol-9-ol, 9ci	HMDB
Kenigine	HMDB

Chemical Formula

C₁₉H₁₉NO₃

Average Molecular Weight

309.3591

Monoisotopic Molecular Weight

309.136493479

IUPAC Name

13-methoxy-5,5,8-trimethyl-6-oxa-17-azatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1,3,7,9,11,13,15-heptaen-14-ol

Traditional Name

13-methoxy-5,5,8-trimethyl-6-oxa-17-azatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1,3,7,9,11,13,15-heptaen-14-ol

CAS Registry Number

28513-33-9

SMILES

COC1=C(O)C=C2NC3=C4C=CC(C)(C)OC4=C(C)C=C3C2=C1

InChI Identifier

InChI=1S/C19H19NO3/c1-10-7-13-12-8-16(22-4)15(21)9-14(12)20-17(13)11-5-6-19(2,3)23-18(10)11/h5-9,20-21H,1-4H3

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0030207)

Cellular substructure

Membrane (HMDB: HMDB0030207)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030207)

Source

Endogenous

Endogenous (HMDB: HMDB0030207)

Plant

Plant (HMDB: HMDB0030207)

Exogenous

Food

Food (HMDB: HMDB0030207)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	183 - 185 °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	0.0054 g/L	ALOGPS
logP	4.37	ALOGPS
logP	4.04	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	9.31	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	54.48 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	91.35 m³·mol⁻¹	ChemAxon
Polarizability	35 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]+	173.136	31661259
DarkChem	[M-H]-	175.932	31661259
DeepCCS	[M+H]+	182.976	30932474
DeepCCS	[M-H]-	180.618	30932474
DeepCCS	[M-2H]-	214.72	30932474
DeepCCS	[M+Na]+	189.949	30932474
AllCCS	[M+H]+	173.4	32859911
AllCCS	[M+H-H2O]+	169.9	32859911
AllCCS	[M+NH4]+	176.7	32859911
AllCCS	[M+Na]+	177.6	32859911
AllCCS	[M-H]-	179.6	32859911
AllCCS	[M+Na-2H]-	178.8	32859911
AllCCS	[M+HCOO]-	178.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Koenigine	COC1=C(O)C=C2NC3=C4C=CC(C)(C)OC4=C(C)C=C3C2=C1	3994.8	Standard polar	33892256
Koenigine	COC1=C(O)C=C2NC3=C4C=CC(C)(C)OC4=C(C)C=C3C2=C1	2919.1	Standard non polar	33892256
Koenigine	COC1=C(O)C=C2NC3=C4C=CC(C)(C)OC4=C(C)C=C3C2=C1	2998.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Koenigine,1TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)[NH]C1=C3C=CC(C)(C)OC3=C(C)C=C12	3185.6	Semi standard non polar	33892256
Koenigine,1TMS,isomer #2	COC1=CC2=C(C=C1O)N([Si](C)(C)C)C1=C3C=CC(C)(C)OC3=C(C)C=C21	3118.2	Semi standard non polar	33892256
Koenigine,2TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)N([Si](C)(C)C)C1=C3C=CC(C)(C)OC3=C(C)C=C21	3090.3	Semi standard non polar	33892256
Koenigine,2TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)N([Si](C)(C)C)C1=C3C=CC(C)(C)OC3=C(C)C=C21	2712.6	Standard non polar	33892256
Koenigine,1TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)[NH]C1=C3C=CC(C)(C)OC3=C(C)C=C12	3340.5	Semi standard non polar	33892256
Koenigine,1TBDMS,isomer #2	COC1=CC2=C(C=C1O)N([Si](C)(C)C(C)(C)C)C1=C3C=CC(C)(C)OC3=C(C)C=C21	3260.0	Semi standard non polar	33892256
Koenigine,2TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1=C3C=CC(C)(C)OC3=C(C)C=C21	3395.6	Semi standard non polar	33892256
Koenigine,2TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1=C3C=CC(C)(C)OC3=C(C)C=C21	3143.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Koenigine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-0291000000-9181726a39da865b5be8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Koenigine GC-MS (1 TMS) - 70eV, Positive	splash10-01b9-1119000000-511ee32d5b4b851c8fd0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Koenigine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Koenigine 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 - Koenigine 10V, Positive-QTOF	splash10-03di-0029000000-6ace861290084dedf6a9	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenigine 20V, Positive-QTOF	splash10-03di-1096000000-ef8cb7772fa70c518512	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenigine 40V, Positive-QTOF	splash10-0udi-1090000000-9746852717055824945b	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenigine 10V, Negative-QTOF	splash10-0a4i-0019000000-983934a0570a6bee3859	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenigine 20V, Negative-QTOF	splash10-0a4i-1089000000-8bc8c641f0d0165e7adb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenigine 40V, Negative-QTOF	splash10-006x-0190000000-9a6ea3a6cc5719d23a12	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenigine 10V, Negative-QTOF	splash10-0a4i-0009000000-6f2b8145258635fcc7b9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenigine 20V, Negative-QTOF	splash10-0a4i-0039000000-2d6aa6a60639f4bb1a7f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenigine 40V, Negative-QTOF	splash10-0ik9-0090000000-a652b4085a953b6e4461	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenigine 10V, Positive-QTOF	splash10-03di-0009000000-9b0e111066a4aee0da17	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenigine 20V, Positive-QTOF	splash10-03di-0039000000-ccfc460b7b6116a61bf1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenigine 40V, Positive-QTOF	splash10-0udl-1190000000-c6bc26802bb54998886f	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

FDB002025

KNApSAcK ID

C00051146

Chemspider ID

4477289

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5318825

PDB ID

Not Available

ChEBI ID

168437

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 Koenigine (HMDB0030207)

MOL for HMDB0030207 (Koenigine)

3D MOL for HMDB0030207 (Koenigine)

3D SDF for HMDB0030207 (Koenigine)

3D-SDF for HMDB0030207 (Koenigine)

PDB for HMDB0030207 (Koenigine)

3D PDB for HMDB0030207 (Koenigine)

SMILES for HMDB0030207 (Koenigine)

INCHI for HMDB0030207 (Koenigine)

Structure for HMDB0030207 (Koenigine)

3D Structure for HMDB0030207 (Koenigine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra