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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 00:36:06 UTC

Update Date

2021-09-26 22:57:22 UTC

HMDB ID

HMDB0247598

Secondary Accession Numbers

None

Metabolite Identification

Common Name

9-Hydroxyellipticine

Description

9-Hydroxyellipticine, also known as 9-OH-e or 9HE, belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring. Based on a literature review a significant number of articles have been published on 9-Hydroxyellipticine. This compound has been identified in human blood as reported by (PMID: 31557052 ). 9-hydroxyellipticine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 9-Hydroxyellipticine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0247598
     RDKit          3D
9-Hydroxyellipticine
 34 37  0  0  0  0  0  0  0  0999 V2000
   -1.9053    2.7445    0.7173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4667    1.3750    0.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3640    0.3610    0.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7238    0.5793    0.2369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6709   -0.3943    0.0248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2161   -1.6090   -0.2926 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8887   -1.9145   -0.4114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9482   -0.9355   -0.1977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5933   -1.1813   -0.3031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0729   -2.5012   -0.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3300   -0.1471   -0.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1137    1.1347    0.2578 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9757    1.9146    0.4158 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0748    1.1727    0.1947 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4165    1.5112    0.2339 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3574    0.5456   -0.0381 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0076   -0.7500   -0.3491 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9994   -1.7129   -0.6222 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6747   -1.0861   -0.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7057   -0.1434   -0.1207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3792    3.1934   -0.2041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0694    3.3454    1.0963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6626    2.7012    1.5284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1079    1.5762    0.4977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7438   -0.1769    0.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6039   -2.9192   -0.6717 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5206   -2.8762    0.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4631   -2.4933   -1.6170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8769   -3.2412   -0.7834 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9445    2.9355    0.6710 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7158    2.5407    0.4803 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4314    0.7815   -0.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3275   -2.2244    0.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4626   -2.1059   -0.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 12  2  1  0
 20 14  1  0
  8  3  1  0
 20 11  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  7 26  1  0
 10 27  1  0
 10 28  1  0
 10 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 18 33  1  0
 19 34  1  0
M  END


  Mrv1533004241501462D          

 20 23  0  0  0  0            999 V2000
    3.4623    2.3118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2997    1.5030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9189    0.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7006    1.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3198    0.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1571   -0.1327    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3754   -0.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7562    0.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9745   -0.1146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8119   -0.9235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3553    0.4306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5359    0.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0583   -0.3374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2369   -0.2602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2406   -0.9330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1069    0.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3706    1.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1920    1.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7990    1.6440    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5180    1.2394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 12 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  2 20  1  0  0  0  0
 11 20  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0247598

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C2C=CN=CC2=C(C)C2=C1NC1=C2C=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H14N2O/c1-9-14-8-18-6-5-12(14)10(2)17-16(9)13-7-11(20)3-4-15(13)19-17/h3-8,19-20H,1-2H3

> <INCHI_KEY>
QZTWUDDGLIDXSE-UHFFFAOYSA-N

> <FORMULA>
C17H14N2O

> <MOLECULAR_WEIGHT>
262.312

> <EXACT_MASS>
262.110613079

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
29.25439673863042

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,11-dimethyl-6H-pyrido[4,3-b]carbazol-9-ol

> <ALOGPS_LOGP>
4.08

> <JCHEM_LOGP>
3.5859674759999995

> <ALOGPS_LOGS>
-4.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.65257535819223

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.670075952787439

> <JCHEM_PKA_STRONGEST_BASIC>
5.917735634768203

> <JCHEM_POLAR_SURFACE_AREA>
48.910000000000004

> <JCHEM_REFRACTIVITY>
79.82880000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.05e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-hydroxyellipticine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0247598
     RDKit          3D
9-Hydroxyellipticine
 34 37  0  0  0  0  0  0  0  0999 V2000
   -1.9053    2.7445    0.7173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4667    1.3750    0.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3640    0.3610    0.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7238    0.5793    0.2369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6709   -0.3943    0.0248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2161   -1.6090   -0.2926 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8887   -1.9145   -0.4114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9482   -0.9355   -0.1977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5933   -1.1813   -0.3031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0729   -2.5012   -0.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3300   -0.1471   -0.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1137    1.1347    0.2578 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9757    1.9146    0.4158 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0748    1.1727    0.1947 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4165    1.5112    0.2339 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3574    0.5456   -0.0381 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0076   -0.7500   -0.3491 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9994   -1.7129   -0.6222 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6747   -1.0861   -0.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7057   -0.1434   -0.1207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3792    3.1934   -0.2041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0694    3.3454    1.0963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6626    2.7012    1.5284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1079    1.5762    0.4977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7438   -0.1769    0.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6039   -2.9192   -0.6717 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5206   -2.8762    0.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4631   -2.4933   -1.6170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8769   -3.2412   -0.7834 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9445    2.9355    0.6710 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7158    2.5407    0.4803 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4314    0.7815   -0.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3275   -2.2244    0.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4626   -2.1059   -0.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 12  2  1  0
 20 14  1  0
  8  3  1  0
 20 11  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  7 26  1  0
 10 27  1  0
 10 28  1  0
 10 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 18 33  1  0
 19 34  1  0
M  END

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       6.463   4.315   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.159   2.806   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.315   1.788   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.774   2.280   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.930   1.262   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       9.627  -0.248   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       8.167  -0.740   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.012   0.278   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.552  -0.214   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.249  -1.724   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.397   0.804   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.867   0.626   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.976  -0.630   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.442  -0.486   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.449  -1.742   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.200   0.914   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.692   2.170   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.225   2.026   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       3.358   3.069   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       4.700   2.314   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   20                                                  
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   12   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19    2   11                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

COMPND    HMDB0247598
HETATM    1  C1  UNL     1      -1.905   2.745   0.717  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.467   1.375   0.362  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.364   0.361   0.139  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.724   0.579   0.237  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.671  -0.394   0.025  1.00  0.00           C  
HETATM    6  N1  UNL     1      -4.216  -1.609  -0.293  1.00  0.00           N  
HETATM    7  C6  UNL     1      -2.889  -1.914  -0.411  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.948  -0.936  -0.198  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.593  -1.181  -0.303  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.073  -2.501  -0.646  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.330  -0.147  -0.076  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.114   1.135   0.258  1.00  0.00           C  
HETATM   13  N2  UNL     1       0.976   1.915   0.416  1.00  0.00           N  
HETATM   14  C12 UNL     1       2.075   1.173   0.195  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.417   1.511   0.234  1.00  0.00           C  
HETATM   16  C14 UNL     1       4.357   0.546  -0.038  1.00  0.00           C  
HETATM   17  C15 UNL     1       4.008  -0.750  -0.349  1.00  0.00           C  
HETATM   18  O1  UNL     1       4.999  -1.713  -0.622  1.00  0.00           O  
HETATM   19  C16 UNL     1       2.675  -1.086  -0.388  1.00  0.00           C  
HETATM   20  C17 UNL     1       1.706  -0.143  -0.121  1.00  0.00           C  
HETATM   21  H1  UNL     1      -2.379   3.193  -0.204  1.00  0.00           H  
HETATM   22  H2  UNL     1      -1.069   3.345   1.096  1.00  0.00           H  
HETATM   23  H3  UNL     1      -2.663   2.701   1.528  1.00  0.00           H  
HETATM   24  H4  UNL     1      -4.108   1.576   0.498  1.00  0.00           H  
HETATM   25  H5  UNL     1      -5.744  -0.177   0.114  1.00  0.00           H  
HETATM   26  H6  UNL     1      -2.604  -2.919  -0.672  1.00  0.00           H  
HETATM   27  H7  UNL     1       0.521  -2.876   0.216  1.00  0.00           H  
HETATM   28  H8  UNL     1       0.463  -2.493  -1.617  1.00  0.00           H  
HETATM   29  H9  UNL     1      -0.877  -3.241  -0.783  1.00  0.00           H  
HETATM   30  H10 UNL     1       0.944   2.935   0.671  1.00  0.00           H  
HETATM   31  H11 UNL     1       3.716   2.541   0.480  1.00  0.00           H  
HETATM   32  H12 UNL     1       5.431   0.782  -0.015  1.00  0.00           H  
HETATM   33  H13 UNL     1       5.328  -2.224   0.187  1.00  0.00           H  
HETATM   34  H14 UNL     1       2.463  -2.106  -0.636  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    3   12
CONECT    3    4    8
CONECT    4    5    5   24
CONECT    5    6   25
CONECT    6    7    7
CONECT    7    8   26
CONECT    8    9    9
CONECT    9   10   11
CONECT   10   27   28   29
CONECT   11   12   12   20
CONECT   12   13
CONECT   13   14   30
CONECT   14   15   15   20
CONECT   15   16   31
CONECT   16   17   17   32
CONECT   17   18   19
CONECT   18   33
CONECT   19   20   20   34
END

HMDB0247598
     RDKit          3D
9-Hydroxyellipticine
 34 37  0  0  0  0  0  0  0  0999 V2000
   -1.9053    2.7445    0.7173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4667    1.3750    0.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3640    0.3610    0.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7238    0.5793    0.2369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6709   -0.3943    0.0248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2161   -1.6090   -0.2926 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8887   -1.9145   -0.4114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9482   -0.9355   -0.1977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5933   -1.1813   -0.3031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0729   -2.5012   -0.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3300   -0.1471   -0.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1137    1.1347    0.2578 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9757    1.9146    0.4158 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0748    1.1727    0.1947 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4165    1.5112    0.2339 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3574    0.5456   -0.0381 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0076   -0.7500   -0.3491 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9994   -1.7129   -0.6222 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6747   -1.0861   -0.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7057   -0.1434   -0.1207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3792    3.1934   -0.2041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0694    3.3454    1.0963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6626    2.7012    1.5284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1079    1.5762    0.4977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7438   -0.1769    0.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6039   -2.9192   -0.6717 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5206   -2.8762    0.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4631   -2.4933   -1.6170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8769   -3.2412   -0.7834 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9445    2.9355    0.6710 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7158    2.5407    0.4803 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4314    0.7815   -0.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3275   -2.2244    0.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4626   -2.1059   -0.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 12  2  1  0
 20 14  1  0
  8  3  1  0
 20 11  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  7 26  1  0
 10 27  1  0
 10 28  1  0
 10 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 18 33  1  0
 19 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5,11-Dimethyl-6H-pyrido[4,3-b]carbazol-9-ol	ChEBI
9-Hydroxy-5,11-dimethyl-6H-pyrido[4,3-b]carbazole	ChEBI
9-OH-e	ChEBI
9HE	ChEBI
9-Hydroxyellipticine, radical ion (1+)	HMDB
9-Hydroxyellipticine monohydrochloride	HMDB

Chemical Formula

C₁₇H₁₄N₂O

Average Molecular Weight

262.312

Monoisotopic Molecular Weight

262.110613079

IUPAC Name

5,11-dimethyl-6H-pyrido[4,3-b]carbazol-9-ol

Traditional Name

9-hydroxyellipticine

CAS Registry Number

Not Available

SMILES

CC1=C2C=CN=CC2=C(C)C2=C1NC1=C2C=C(O)C=C1

InChI Identifier

InChI=1S/C17H14N2O/c1-9-14-8-18-6-5-12(14)10(2)17-16(9)13-7-11(20)3-4-15(13)19-17/h3-8,19-20H,1-2H3

InChI Key

QZTWUDDGLIDXSE-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
Isoquinoline
Hydroxyindole
Indole
1-hydroxy-2-unsubstituted benzenoid
Pyridine
Benzenoid
Pyrrole
Heteroaromatic compound
Azacycle
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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
logP	4.08	ALOGPS
logP	3.59	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	9.67	ChemAxon
pKa (Strongest Basic)	5.92	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	48.91 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	79.83 m³·mol⁻¹	ChemAxon
Polarizability	29.25 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
DeepCCS	[M+H]+	164.338	30932474
DeepCCS	[M-H]-	161.98	30932474
DeepCCS	[M-2H]-	194.866	30932474
DeepCCS	[M+Na]+	170.431	30932474
AllCCS	[M+H]+	163.1	32859911
AllCCS	[M+H-H2O]+	159.6	32859911
AllCCS	[M+NH4]+	166.3	32859911
AllCCS	[M+Na]+	167.2	32859911
AllCCS	[M-H]-	164.0	32859911
AllCCS	[M+Na-2H]-	162.9	32859911
AllCCS	[M+HCOO]-	161.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	10.8496 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.85 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1579.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	272.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	128.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	161.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	112.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	399.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	318.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	73.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	684.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	300.4 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	1308.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	262.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	275.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	379.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	267.7 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	149.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
9-Hydroxyellipticine	CC1=C2C=CN=CC2=C(C)C2=C1NC1=C2C=C(O)C=C1	4082.1	Standard polar	33892256
9-Hydroxyellipticine	CC1=C2C=CN=CC2=C(C)C2=C1NC1=C2C=C(O)C=C1	2729.7	Standard non polar	33892256
9-Hydroxyellipticine	CC1=C2C=CN=CC2=C(C)C2=C1NC1=C2C=C(O)C=C1	3373.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
9-Hydroxyellipticine,2TMS,isomer #1	CC1=C2C=NC=CC2=C(C)C2=C1C1=CC(O[Si](C)(C)C)=CC=C1N2[Si](C)(C)C	3158.4	Semi standard non polar	33892256
9-Hydroxyellipticine,2TMS,isomer #1	CC1=C2C=NC=CC2=C(C)C2=C1C1=CC(O[Si](C)(C)C)=CC=C1N2[Si](C)(C)C	2673.7	Standard non polar	33892256
9-Hydroxyellipticine,2TMS,isomer #1	CC1=C2C=NC=CC2=C(C)C2=C1C1=CC(O[Si](C)(C)C)=CC=C1N2[Si](C)(C)C	2914.8	Standard polar	33892256
9-Hydroxyellipticine,2TBDMS,isomer #1	CC1=C2C=NC=CC2=C(C)C2=C1C1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1N2[Si](C)(C)C(C)(C)C	3521.6	Semi standard non polar	33892256
9-Hydroxyellipticine,2TBDMS,isomer #1	CC1=C2C=NC=CC2=C(C)C2=C1C1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1N2[Si](C)(C)C(C)(C)C	3057.7	Standard non polar	33892256
9-Hydroxyellipticine,2TBDMS,isomer #1	CC1=C2C=NC=CC2=C(C)C2=C1C1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1N2[Si](C)(C)C(C)(C)C	3134.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 9-Hydroxyellipticine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ila-0290000000-137436beb875812d4d26	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9-Hydroxyellipticine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9-Hydroxyellipticine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9-Hydroxyellipticine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9-Hydroxyellipticine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9-Hydroxyellipticine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	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 - 9-Hydroxyellipticine 10V, Positive-QTOF	splash10-03di-0090000000-e8a3fa9b5502c4fbee8b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxyellipticine 20V, Positive-QTOF	splash10-03di-0090000000-e8a3fa9b5502c4fbee8b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxyellipticine 40V, Positive-QTOF	splash10-01ot-0190000000-c0fd0fbb49264aa8c53c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxyellipticine 10V, Negative-QTOF	splash10-03di-0090000000-73cec9912228d6fe472d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxyellipticine 20V, Negative-QTOF	splash10-03di-0090000000-73cec9912228d6fe472d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxyellipticine 40V, Negative-QTOF	splash10-0rna-0190000000-b2f5f427af2e640493b4	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

82746

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

91643

PDB ID

Not Available

ChEBI ID

88297

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 9-Hydroxyellipticine (HMDB0247598)

MOL for HMDB0247598 (9-Hydroxyellipticine)

3D MOL for HMDB0247598 (9-Hydroxyellipticine)

3D SDF for HMDB0247598 (9-Hydroxyellipticine)

3D-SDF for HMDB0247598 (9-Hydroxyellipticine)

PDB for HMDB0247598 (9-Hydroxyellipticine)

3D PDB for HMDB0247598 (9-Hydroxyellipticine)

SMILES for HMDB0247598 (9-Hydroxyellipticine)

INCHI for HMDB0247598 (9-Hydroxyellipticine)

Structure for HMDB0247598 (9-Hydroxyellipticine)

3D Structure for HMDB0247598 (9-Hydroxyellipticine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra