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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

HMDB0030208

Secondary Accession Numbers

HMDB30208

Metabolite Identification

Common Name

Koenigicine

Description

Koenigicine, also known as kenimbidine, 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 Koenigicine.

Structure

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

HMDB0030208
     RDKit          3D
Koenigicine
 45 48  0  0  0  0  0  0  0  0999 V2000
    5.7528    2.5956   -0.5913 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5926    1.2397   -0.2846 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3289    0.7017   -0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2069    1.4938   -0.3363 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9366    0.9506   -0.2106 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6956    1.4566   -0.3219 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2239    0.4868   -0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6080    0.5761   -0.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3144   -0.6000    0.1498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6914   -1.7989    0.4192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4981   -3.0398    0.7014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3124   -1.8166    0.4199 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4356   -0.6887    0.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7852   -0.4010    0.0951 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8931   -1.1775    0.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1586   -0.6430    0.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2989   -1.4398    0.3214 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1374   -2.8052    0.6303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6844   -0.4763    0.1251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4110    0.6905   -0.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3868    1.0129    0.9851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3029    0.4467   -1.3693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5916    1.8904   -0.4097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2853    1.8207   -0.3971 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1100    2.8482   -1.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5133    3.2003    0.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8004    2.8246   -0.9270 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2939    2.5633   -0.5781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5054    2.4544   -0.5469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5574   -3.5856   -0.2451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0474   -3.6323    1.5219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5175   -2.6931    0.9722 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2208   -2.7267    0.6243 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7615   -2.2245    0.5048 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1150   -3.2640    0.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5208   -2.9077    1.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5690   -3.3452   -0.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8519    1.1595    1.9581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9318    1.9367    0.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1296    0.2148    1.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5490    1.4154   -1.8327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7135   -0.1947   -2.0815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2171   -0.1127   -1.0799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0992    2.8613   -0.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7079    2.7330   -0.6046 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
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
  9 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
 23 24  2  0
 16  3  1  0
 14  5  2  0
 13  7  1  0
 24  8  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  6 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 15 34  1  0
 18 35  1  0
 18 36  1  0
 18 37  1  0
 21 38  1  0
 21 39  1  0
 21 40  1  0
 22 41  1  0
 22 42  1  0
 22 43  1  0
 23 44  1  0
 24 45  1  0
M  END


  Mrv0541 05061305052D          

 24 27  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
    8.1673   -3.1232    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
    6.7007   -2.3671    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
    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
    7.3948   -1.9211    0.0000 O   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
    2.0066   -2.0762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  2  0  0  0  0
 11  1  1  0  0  0  0
 11  8  1  0  0  0  0
 12  6  1  0  0  0  0
 13  9  2  0  0  0  0
 14  8  2  0  0  0  0
 14 13  1  0  0  0  0
 15 10  2  0  0  0  0
 15 13  1  0  0  0  0
 16  9  1  0  0  0  0
 17 10  1  0  0  0  0
 17 16  2  0  0  0  0
 18 12  2  0  0  0  0
 18 14  1  0  0  0  0
 19 11  2  0  0  0  0
 19 12  1  0  0  0  0
 20  2  1  0  0  0  0
 20  3  1  0  0  0  0
 20  7  1  0  0  0  0
 21 15  1  0  0  0  0
 21 18  1  0  0  0  0
 22  4  1  0  0  0  0
 22 16  1  0  0  0  0
 23  5  1  0  0  0  0
 23 17  1  0  0  0  0
 24 19  1  0  0  0  0
 24 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030208

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(OC)C=C2C(NC3=C4C=CC(C)(C)OC4=C(C)C=C23)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H21NO3/c1-11-8-14-13-9-16(22-4)17(23-5)10-15(13)21-18(14)12-6-7-20(2,3)24-19(11)12/h6-10,21H,1-5H3

> <INCHI_KEY>
IUZVYLWUISSZCS-UHFFFAOYSA-N

> <FORMULA>
C20H21NO3

> <MOLECULAR_WEIGHT>
323.3856

> <EXACT_MASS>
323.152143543

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
37.12364780952923

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
13,14-dimethoxy-5,5,8-trimethyl-6-oxa-17-azatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1,3,7,9,11,13,15-heptaene

> <ALOGPS_LOGP>
5.20

> <JCHEM_LOGP>
4.189587949333334

> <ALOGPS_LOGS>
-5.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.85840486882294

> <JCHEM_PKA_STRONGEST_BASIC>
-4.431527077700978

> <JCHEM_POLAR_SURFACE_AREA>
43.480000000000004

> <JCHEM_REFRACTIVITY>
95.83320000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.19e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030208
     RDKit          3D
Koenigicine
 45 48  0  0  0  0  0  0  0  0999 V2000
    5.7528    2.5956   -0.5913 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5926    1.2397   -0.2846 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3289    0.7017   -0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2069    1.4938   -0.3363 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9366    0.9506   -0.2106 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6956    1.4566   -0.3219 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2239    0.4868   -0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6080    0.5761   -0.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3144   -0.6000    0.1498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6914   -1.7989    0.4192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4981   -3.0398    0.7014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3124   -1.8166    0.4199 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4356   -0.6887    0.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7852   -0.4010    0.0951 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8931   -1.1775    0.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1586   -0.6430    0.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2989   -1.4398    0.3214 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1374   -2.8052    0.6303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6844   -0.4763    0.1251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4110    0.6905   -0.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3868    1.0129    0.9851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3029    0.4467   -1.3693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5916    1.8904   -0.4097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2853    1.8207   -0.3971 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1100    2.8482   -1.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5133    3.2003    0.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8004    2.8246   -0.9270 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2939    2.5633   -0.5781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5054    2.4544   -0.5469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5574   -3.5856   -0.2451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0474   -3.6323    1.5219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5175   -2.6931    0.9722 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2208   -2.7267    0.6243 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7615   -2.2245    0.5048 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1150   -3.2640    0.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5208   -2.9077    1.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5690   -3.3452   -0.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8519    1.1595    1.9581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9318    1.9367    0.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1296    0.2148    1.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5490    1.4154   -1.8327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7135   -0.1947   -2.0815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2171   -0.1127   -1.0799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0992    2.8613   -0.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7079    2.7330   -0.6046 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
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
  9 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
 23 24  2  0
 16  3  1  0
 14  5  2  0
 13  7  1  0
 24  8  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  6 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 15 34  1  0
 18 35  1  0
 18 36  1  0
 18 37  1  0
 21 38  1  0
 21 39  1  0
 21 40  1  0
 22 41  1  0
 22 42  1  0
 22 43  1  0
 23 44  1  0
 24 45  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      15.246  -5.830   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.131  -6.626   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.593  -6.539   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.666  -2.764   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.139  -3.713   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.286  -6.789   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.128  -2.676   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.976  -5.339   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.844  -4.545   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.358  -4.140   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.917  -6.083   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      12.581  -5.957   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.513  -5.427   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.283  -3.963   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.901  -5.163   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       8.477  -6.629   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0      13.804  -3.586   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      13.950  -6.663   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       3.746  -3.876   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   20                                                            
CONECT    3   20                                                            
CONECT    4   22                                                            
CONECT    5   23                                                            
CONECT    6    7   12                                                       
CONECT    7    6   20                                                       
CONECT    8   11   14                                                       
CONECT    9   13   16                                                       
CONECT   10   15   17                                                       
CONECT   11    1    8   19                                                  
CONECT   12    6   18   19                                                  
CONECT   13    9   14   15                                                  
CONECT   14    8   13   18                                                  
CONECT   15   10   13   21                                                  
CONECT   16    9   17   22                                                  
CONECT   17   10   16   23                                                  
CONECT   18   12   14   21                                                  
CONECT   19   11   12   24                                                  
CONECT   20    2    3    7   24                                             
CONECT   21   15   18                                                       
CONECT   22    4   16                                                       
CONECT   23    5   17                                                       
CONECT   24   19   20                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0030208
HETATM    1  C1  UNL     1       5.753   2.596  -0.591  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.593   1.240  -0.285  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.329   0.702  -0.160  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.207   1.494  -0.336  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.937   0.951  -0.211  1.00  0.00           C  
HETATM    6  N1  UNL     1       0.696   1.457  -0.322  1.00  0.00           N  
HETATM    7  C5  UNL     1      -0.224   0.487  -0.101  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.608   0.576  -0.118  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.314  -0.600   0.150  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.691  -1.799   0.419  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.498  -3.040   0.701  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.312  -1.817   0.420  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.436  -0.689   0.163  1.00  0.00           C  
HETATM   14  C12 UNL     1       1.785  -0.401   0.095  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.893  -1.178   0.268  1.00  0.00           C  
HETATM   16  C14 UNL     1       4.159  -0.643   0.144  1.00  0.00           C  
HETATM   17  O2  UNL     1       5.299  -1.440   0.321  1.00  0.00           O  
HETATM   18  C15 UNL     1       5.137  -2.805   0.630  1.00  0.00           C  
HETATM   19  O3  UNL     1      -3.684  -0.476   0.125  1.00  0.00           O  
HETATM   20  C16 UNL     1      -4.411   0.691  -0.137  1.00  0.00           C  
HETATM   21  C17 UNL     1      -5.387   1.013   0.985  1.00  0.00           C  
HETATM   22  C18 UNL     1      -5.303   0.447  -1.369  1.00  0.00           C  
HETATM   23  C19 UNL     1      -3.592   1.890  -0.410  1.00  0.00           C  
HETATM   24  C20 UNL     1      -2.285   1.821  -0.397  1.00  0.00           C  
HETATM   25  H1  UNL     1       5.110   2.848  -1.463  1.00  0.00           H  
HETATM   26  H2  UNL     1       5.513   3.200   0.310  1.00  0.00           H  
HETATM   27  H3  UNL     1       6.800   2.825  -0.927  1.00  0.00           H  
HETATM   28  H4  UNL     1       3.294   2.563  -0.578  1.00  0.00           H  
HETATM   29  H5  UNL     1       0.505   2.454  -0.547  1.00  0.00           H  
HETATM   30  H6  UNL     1      -2.557  -3.586  -0.245  1.00  0.00           H  
HETATM   31  H7  UNL     1      -2.047  -3.632   1.522  1.00  0.00           H  
HETATM   32  H8  UNL     1      -3.518  -2.693   0.972  1.00  0.00           H  
HETATM   33  H9  UNL     1       0.221  -2.727   0.624  1.00  0.00           H  
HETATM   34  H10 UNL     1       2.761  -2.225   0.505  1.00  0.00           H  
HETATM   35  H11 UNL     1       6.115  -3.264   0.848  1.00  0.00           H  
HETATM   36  H12 UNL     1       4.521  -2.908   1.567  1.00  0.00           H  
HETATM   37  H13 UNL     1       4.569  -3.345  -0.156  1.00  0.00           H  
HETATM   38  H14 UNL     1      -4.852   1.159   1.958  1.00  0.00           H  
HETATM   39  H15 UNL     1      -5.932   1.937   0.709  1.00  0.00           H  
HETATM   40  H16 UNL     1      -6.130   0.215   1.140  1.00  0.00           H  
HETATM   41  H17 UNL     1      -5.549   1.415  -1.833  1.00  0.00           H  
HETATM   42  H18 UNL     1      -4.714  -0.195  -2.082  1.00  0.00           H  
HETATM   43  H19 UNL     1      -6.217  -0.113  -1.080  1.00  0.00           H  
HETATM   44  H20 UNL     1      -4.099   2.861  -0.628  1.00  0.00           H  
HETATM   45  H21 UNL     1      -1.708   2.733  -0.605  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4   16
CONECT    4    5   28
CONECT    5    6   14   14
CONECT    6    7   29
CONECT    7    8    8   13
CONECT    8    9   24
CONECT    9   10   10   19
CONECT   10   11   12
CONECT   11   30   31   32
CONECT   12   13   13   33
CONECT   13   14
CONECT   14   15
CONECT   15   16   16   34
CONECT   16   17
CONECT   17   18
CONECT   18   35   36   37
CONECT   19   20
CONECT   20   21   22   23
CONECT   21   38   39   40
CONECT   22   41   42   43
CONECT   23   24   24   44
CONECT   24   45
END

HMDB0030208
     RDKit          3D
Koenigicine
 45 48  0  0  0  0  0  0  0  0999 V2000
    5.7528    2.5956   -0.5913 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5926    1.2397   -0.2846 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3289    0.7017   -0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2069    1.4938   -0.3363 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9366    0.9506   -0.2106 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6956    1.4566   -0.3219 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2239    0.4868   -0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6080    0.5761   -0.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3144   -0.6000    0.1498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6914   -1.7989    0.4192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4981   -3.0398    0.7014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3124   -1.8166    0.4199 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4356   -0.6887    0.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7852   -0.4010    0.0951 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8931   -1.1775    0.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1586   -0.6430    0.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2989   -1.4398    0.3214 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1374   -2.8052    0.6303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6844   -0.4763    0.1251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4110    0.6905   -0.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3868    1.0129    0.9851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3029    0.4467   -1.3693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5916    1.8904   -0.4097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2853    1.8207   -0.3971 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1100    2.8482   -1.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5133    3.2003    0.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8004    2.8246   -0.9270 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2939    2.5633   -0.5781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5054    2.4544   -0.5469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5574   -3.5856   -0.2451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0474   -3.6323    1.5219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5175   -2.6931    0.9722 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2208   -2.7267    0.6243 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7615   -2.2245    0.5048 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1150   -3.2640    0.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5208   -2.9077    1.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5690   -3.3452   -0.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8519    1.1595    1.9581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9318    1.9367    0.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1296    0.2148    1.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5490    1.4154   -1.8327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7135   -0.1947   -2.0815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2171   -0.1127   -1.0799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0992    2.8613   -0.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7079    2.7330   -0.6046 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
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
  9 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
 23 24  2  0
 16  3  1  0
 14  5  2  0
 13  7  1  0
 24  8  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  6 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 15 34  1  0
 18 35  1  0
 18 36  1  0
 18 37  1  0
 21 38  1  0
 21 39  1  0
 21 40  1  0
 22 41  1  0
 22 42  1  0
 22 43  1  0
 23 44  1  0
 24 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,11-Dihydro-8,9-dimethoxy-3,3,5-trimethylpyrano[3,2-a]carbazole, 9ci	HMDB
Kenidine	HMDB
Kenigicine	HMDB
Kenimbidine	HMDB
Koenidine	HMDB
Koenimbidine	HMDB

Chemical Formula

C₂₀H₂₁NO₃

Average Molecular Weight

323.3856

Monoisotopic Molecular Weight

323.152143543

IUPAC Name

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

Traditional Name

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

CAS Registry Number

24123-92-0

SMILES

COC1=C(OC)C=C2C(NC3=C4C=CC(C)(C)OC4=C(C)C=C23)=C1

InChI Identifier

InChI=1S/C20H21NO3/c1-11-8-14-13-9-16(22-4)17(23-5)10-15(13)21-18(14)12-6-7-20(2,3)24-19(11)12/h6-10,21H,1-5H3

InChI Key

IUZVYLWUISSZCS-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: HMDB0030208)
Cell membrane (HMDB: HMDB0030208)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030208)

Source

Endogenous

Endogenous (HMDB: HMDB0030208)

Plant

Plant (HMDB: HMDB0030208)

Exogenous

Food

Food (HMDB: HMDB0030208)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0030208)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	224 - 225 °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	0.0012 g/L	ALOGPS
logP	5.2	ALOGPS
logP	4.19	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	14.86	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	43.48 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	95.83 m³·mol⁻¹	ChemAxon
Polarizability	37.12 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]+	177.044	31661259
DarkChem	[M-H]-	179.52	31661259
DeepCCS	[M-2H]-	221.644	30932474
DeepCCS	[M+Na]+	197.319	30932474
AllCCS	[M+H]+	177.0	32859911
AllCCS	[M+H-H2O]+	173.6	32859911
AllCCS	[M+NH4]+	180.2	32859911
AllCCS	[M+Na]+	181.1	32859911
AllCCS	[M-H]-	184.4	32859911
AllCCS	[M+Na-2H]-	183.7	32859911
AllCCS	[M+HCOO]-	183.1	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.	6.64 minutes	32390414
Predicted by Siyang on May 30, 2022	13.7246 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.38 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2370.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	291.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	189.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	183.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	143.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	732.7 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	597.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	127.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1209.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	545.4 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	1437.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	512.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	375.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	282.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	439.6 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	8.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Koenigicine	COC1=C(OC)C=C2C(NC3=C4C=CC(C)(C)OC4=C(C)C=C23)=C1	3844.2	Standard polar	33892256
Koenigicine	COC1=C(OC)C=C2C(NC3=C4C=CC(C)(C)OC4=C(C)C=C23)=C1	2992.8	Standard non polar	33892256
Koenigicine	COC1=C(OC)C=C2C(NC3=C4C=CC(C)(C)OC4=C(C)C=C23)=C1	3011.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Koenigicine,1TMS,isomer #1	COC1=CC2=C(C=C1OC)N([Si](C)(C)C)C1=C3C=CC(C)(C)OC3=C(C)C=C21	3136.9	Semi standard non polar	33892256
Koenigicine,1TMS,isomer #1	COC1=CC2=C(C=C1OC)N([Si](C)(C)C)C1=C3C=CC(C)(C)OC3=C(C)C=C21	2682.3	Standard non polar	33892256
Koenigicine,1TBDMS,isomer #1	COC1=CC2=C(C=C1OC)N([Si](C)(C)C(C)(C)C)C1=C3C=CC(C)(C)OC3=C(C)C=C21	3238.7	Semi standard non polar	33892256
Koenigicine,1TBDMS,isomer #1	COC1=CC2=C(C=C1OC)N([Si](C)(C)C(C)(C)C)C1=C3C=CC(C)(C)OC3=C(C)C=C21	2896.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Koenigicine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-0194000000-57473b23f526fd4b67b5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Koenigicine 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 - Koenigicine 10V, Positive-QTOF	splash10-00di-0029000000-9fbeac8c7d5a28d286fc	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenigicine 20V, Positive-QTOF	splash10-00di-1097000000-0034e482a246013beb24	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenigicine 40V, Positive-QTOF	splash10-02ti-1090000000-b63d18e80a326b200249	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenigicine 10V, Negative-QTOF	splash10-00di-0009000000-5dd19f7bd1def9c36c02	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenigicine 20V, Negative-QTOF	splash10-00di-0059000000-b1e9c056fb8cc14c3029	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenigicine 40V, Negative-QTOF	splash10-0gx9-0190000000-1a2a0a711f253625d983	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenigicine 10V, Positive-QTOF	splash10-00di-0009000000-7684723ce4870da7ab11	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenigicine 20V, Positive-QTOF	splash10-00di-0029000000-f80040819625b3561332	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenigicine 40V, Positive-QTOF	splash10-066r-0092000000-090bed63ed86d6377c75	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenigicine 10V, Negative-QTOF	splash10-00di-0009000000-b8817382b3fde66270d6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenigicine 20V, Negative-QTOF	splash10-00di-0069000000-5e910b54031a501df53a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Koenigicine 40V, Negative-QTOF	splash10-00b9-0092000000-3a1430a4597dd61e2fd2	2021-09-22	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

FDB002026

KNApSAcK ID

C00051145

Chemspider ID

244749

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

278055

PDB ID

Not Available

ChEBI ID

Not Available

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 Koenigicine (HMDB0030208)

MOL for HMDB0030208 (Koenigicine)

3D MOL for HMDB0030208 (Koenigicine)

3D SDF for HMDB0030208 (Koenigicine)

3D-SDF for HMDB0030208 (Koenigicine)

PDB for HMDB0030208 (Koenigicine)

3D PDB for HMDB0030208 (Koenigicine)

SMILES for HMDB0030208 (Koenigicine)

INCHI for HMDB0030208 (Koenigicine)

Structure for HMDB0030208 (Koenigicine)

3D Structure for HMDB0030208 (Koenigicine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra