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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 09:50:27 UTC

Update Date

2022-09-22 17:44:23 UTC

HMDB ID

HMDB0252138

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Evodiamine

Description

Isoevodiamine belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety. Based on a literature review very few articles have been published on Isoevodiamine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Evodiamine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Evodiamine 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

HMDB0252138
     RDKit          3D
Evodiamine
 40 44  0  0  0  0  0  0  0  0999 V2000
    0.8546   -1.5514    1.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3763   -0.3827    0.5518 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7649   -0.3003    0.2530 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6709   -1.0136    1.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0152   -0.9274    0.7516 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4584   -0.1533   -0.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5495    0.5465   -1.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2063    0.4696   -0.8046 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1817    1.1760   -1.5781 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5365    1.9019   -2.5666 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8153    1.0383   -1.2120 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1874    1.2160   -2.2390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4217    0.3911   -1.9857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8029    0.3047   -0.5713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8880    0.4635    0.4183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5472    0.3283    1.5767 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8543    0.0882    1.3513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9643   -0.1267    2.1632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2216   -0.3545    1.6668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3987   -0.3722    0.2973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2983   -0.1588   -0.5406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0480    0.0674   -0.0111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5274    0.7298    0.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2471   -1.5909    1.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2890   -2.4535    0.7726 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9768   -1.4989    2.3220 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3110   -1.6131    1.8755 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7651   -1.4548    1.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5038   -0.0620   -0.5753 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8476    1.1619   -1.9287 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1857    0.9419   -3.2482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4319    2.2980   -2.2748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3326   -0.6399   -2.3860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2532    0.8767   -2.5581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1709    0.3872    2.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8211   -0.1120    3.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0911   -0.5228    2.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3707   -0.5476   -0.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3922   -0.1642   -1.6172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9077    1.6137    0.7564 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
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 15 23  1  0
 23  2  1  0
  8  3  1  0
 23 11  1  0
 22 14  1  0
 22 17  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 16 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 21 39  1  0
 23 40  1  0
M  END

  Mrv1533004151519452D          

 23 27  0  0  0  0            999 V2000
    2.6077    1.4988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3356    0.7200    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8740    0.0949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6018   -0.6840    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1402   -1.3091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9508   -1.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2229   -0.3765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6845    0.2486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1127    0.9538    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157    0.7646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5936    1.2347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3397    0.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4079    0.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7299   -0.4097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9838   -0.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7913   -0.8377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5191   -1.6165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2529   -0.2126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4423   -0.3663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0961    0.2588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1761    1.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9866    1.1913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5250    0.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  7 15  1  0  0  0  0
 10 15  1  0  0  0  0
  4 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
  2 23  1  0  0  0  0
 18 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0252138

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C2N(CCC3=C2NC2=CC=CC=C32)C(=O)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C19H17N3O/c1-21-16-9-5-3-7-14(16)19(23)22-11-10-13-12-6-2-4-8-15(12)20-17(13)18(21)22/h2-9,18,20H,10-11H2,1H3

> <INCHI_KEY>
TXDUTHBFYKGSAH-UHFFFAOYSA-N

> <FORMULA>
C19H17N3O

> <MOLECULAR_WEIGHT>
303.365

> <EXACT_MASS>
303.137162179

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
33.72217522754726

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
21-methyl-3,13,21-triazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15,17,19-heptaen-14-one

> <ALOGPS_LOGP>
3.07

> <JCHEM_LOGP>
3.3167599676666666

> <ALOGPS_LOGS>
-3.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.914592872748702

> <JCHEM_PKA_STRONGEST_BASIC>
-1.7754121878232172

> <JCHEM_POLAR_SURFACE_AREA>
39.34

> <JCHEM_REFRACTIVITY>
91.01320000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.58e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
evodiamine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0252138
     RDKit          3D
Evodiamine
 40 44  0  0  0  0  0  0  0  0999 V2000
    0.8546   -1.5514    1.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3763   -0.3827    0.5518 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7649   -0.3003    0.2530 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6709   -1.0136    1.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0152   -0.9274    0.7516 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4584   -0.1533   -0.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5495    0.5465   -1.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2063    0.4696   -0.8046 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1817    1.1760   -1.5781 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5365    1.9019   -2.5666 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8153    1.0383   -1.2120 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1874    1.2160   -2.2390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4217    0.3911   -1.9857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8029    0.3047   -0.5713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8880    0.4635    0.4183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5472    0.3283    1.5767 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8543    0.0882    1.3513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9643   -0.1267    2.1632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2216   -0.3545    1.6668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3987   -0.3722    0.2973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2983   -0.1588   -0.5406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0480    0.0674   -0.0111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5274    0.7298    0.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2471   -1.5909    1.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2890   -2.4535    0.7726 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9768   -1.4989    2.3220 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3110   -1.6131    1.8755 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7651   -1.4548    1.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5038   -0.0620   -0.5753 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8476    1.1619   -1.9287 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1857    0.9419   -3.2482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4319    2.2980   -2.2748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3326   -0.6399   -2.3860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2532    0.8767   -2.5581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1709    0.3872    2.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8211   -0.1120    3.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0911   -0.5228    2.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3707   -0.5476   -0.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3922   -0.1642   -1.6172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9077    1.6137    0.7564 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
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 15 23  1  0
 23  2  1  0
  8  3  1  0
 23 11  1  0
 22 14  1  0
 22 17  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 16 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 21 39  1  0
 23 40  1  0
M  END

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  C   UNK     0       4.868   2.798   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       4.360   1.344   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       5.365   0.177   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       4.857  -1.277   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       5.862  -2.444   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.375  -2.157   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.883  -0.703   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.878   0.464   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       7.677   1.780   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       9.176   1.427   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.441   2.305   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.834   1.648   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.961   0.113   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.696  -0.765   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.303  -0.108   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.344  -1.564   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.836  -3.017   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.339  -0.397   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.826  -0.684   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.179   0.483   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.329   1.937   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.842   2.224   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.847   1.057   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5   16                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    7   10                                                  
CONECT   16    4   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22    2   18                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   54    0
END

COMPND    HMDB0252138
HETATM    1  C1  UNL     1       0.855  -1.551   1.227  1.00  0.00           C  
HETATM    2  N1  UNL     1       1.376  -0.383   0.552  1.00  0.00           N  
HETATM    3  C2  UNL     1       2.765  -0.300   0.253  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.671  -1.014   1.050  1.00  0.00           C  
HETATM    5  C4  UNL     1       5.015  -0.927   0.752  1.00  0.00           C  
HETATM    6  C5  UNL     1       5.458  -0.153  -0.312  1.00  0.00           C  
HETATM    7  C6  UNL     1       4.550   0.547  -1.091  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.206   0.470  -0.805  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.182   1.176  -1.578  1.00  0.00           C  
HETATM   10  O1  UNL     1       2.537   1.902  -2.567  1.00  0.00           O  
HETATM   11  N2  UNL     1       0.815   1.038  -1.212  1.00  0.00           N  
HETATM   12  C9  UNL     1      -0.187   1.216  -2.239  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.422   0.391  -1.986  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.803   0.305  -0.571  1.00  0.00           C  
HETATM   15  C12 UNL     1      -0.888   0.463   0.418  1.00  0.00           C  
HETATM   16  N3  UNL     1      -1.547   0.328   1.577  1.00  0.00           N  
HETATM   17  C13 UNL     1      -2.854   0.088   1.351  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.964  -0.127   2.163  1.00  0.00           C  
HETATM   19  C15 UNL     1      -5.222  -0.354   1.667  1.00  0.00           C  
HETATM   20  C16 UNL     1      -5.399  -0.372   0.297  1.00  0.00           C  
HETATM   21  C17 UNL     1      -4.298  -0.159  -0.541  1.00  0.00           C  
HETATM   22  C18 UNL     1      -3.048   0.067  -0.011  1.00  0.00           C  
HETATM   23  C19 UNL     1       0.527   0.730   0.160  1.00  0.00           C  
HETATM   24  H1  UNL     1      -0.247  -1.591   1.037  1.00  0.00           H  
HETATM   25  H2  UNL     1       1.289  -2.453   0.773  1.00  0.00           H  
HETATM   26  H3  UNL     1       0.977  -1.499   2.322  1.00  0.00           H  
HETATM   27  H4  UNL     1       3.311  -1.613   1.876  1.00  0.00           H  
HETATM   28  H5  UNL     1       5.765  -1.455   1.330  1.00  0.00           H  
HETATM   29  H6  UNL     1       6.504  -0.062  -0.575  1.00  0.00           H  
HETATM   30  H7  UNL     1       4.848   1.162  -1.929  1.00  0.00           H  
HETATM   31  H8  UNL     1       0.186   0.942  -3.248  1.00  0.00           H  
HETATM   32  H9  UNL     1      -0.432   2.298  -2.275  1.00  0.00           H  
HETATM   33  H10 UNL     1      -1.333  -0.640  -2.386  1.00  0.00           H  
HETATM   34  H11 UNL     1      -2.253   0.877  -2.558  1.00  0.00           H  
HETATM   35  H12 UNL     1      -1.171   0.387   2.561  1.00  0.00           H  
HETATM   36  H13 UNL     1      -3.821  -0.112   3.234  1.00  0.00           H  
HETATM   37  H14 UNL     1      -6.091  -0.523   2.296  1.00  0.00           H  
HETATM   38  H15 UNL     1      -6.371  -0.548  -0.151  1.00  0.00           H  
HETATM   39  H16 UNL     1      -4.392  -0.164  -1.617  1.00  0.00           H  
HETATM   40  H17 UNL     1       0.908   1.614   0.756  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   23
CONECT    3    4    4    8
CONECT    4    5   27
CONECT    5    6    6   28
CONECT    6    7   29
CONECT    7    8    8   30
CONECT    8    9
CONECT    9   10   10   11
CONECT   11   12   23
CONECT   12   13   31   32
CONECT   13   14   33   34
CONECT   14   15   15   22
CONECT   15   16   23
CONECT   16   17   35
CONECT   17   18   18   22
CONECT   18   19   36
CONECT   19   20   20   37
CONECT   20   21   38
CONECT   21   22   22   39
CONECT   23   40
END

HMDB0252138
     RDKit          3D
Evodiamine
 40 44  0  0  0  0  0  0  0  0999 V2000
    0.8546   -1.5514    1.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3763   -0.3827    0.5518 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7649   -0.3003    0.2530 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6709   -1.0136    1.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0152   -0.9274    0.7516 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4584   -0.1533   -0.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5495    0.5465   -1.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2063    0.4696   -0.8046 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1817    1.1760   -1.5781 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5365    1.9019   -2.5666 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8153    1.0383   -1.2120 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1874    1.2160   -2.2390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4217    0.3911   -1.9857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8029    0.3047   -0.5713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8880    0.4635    0.4183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5472    0.3283    1.5767 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8543    0.0882    1.3513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9643   -0.1267    2.1632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2216   -0.3545    1.6668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3987   -0.3722    0.2973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2983   -0.1588   -0.5406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0480    0.0674   -0.0111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5274    0.7298    0.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2471   -1.5909    1.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2890   -2.4535    0.7726 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9768   -1.4989    2.3220 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3110   -1.6131    1.8755 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7651   -1.4548    1.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5038   -0.0620   -0.5753 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8476    1.1619   -1.9287 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1857    0.9419   -3.2482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4319    2.2980   -2.2748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3326   -0.6399   -2.3860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2532    0.8767   -2.5581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1709    0.3872    2.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8211   -0.1120    3.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0911   -0.5228    2.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3707   -0.5476   -0.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3922   -0.1642   -1.6172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9077    1.6137    0.7564 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
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 15 23  1  0
 23  2  1  0
  8  3  1  0
 23 11  1  0
 22 14  1  0
 22 17  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 16 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 21 39  1  0
 23 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Evodiamine	MeSH
Evodiamine, (S)-isomer	MeSH
Isoevodiamine	MeSH

Chemical Formula

C₁₉H₁₇N₃O

Average Molecular Weight

303.365

Monoisotopic Molecular Weight

303.137162179

IUPAC Name

21-methyl-3,13,21-triazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15,17,19-heptaen-14-one

Traditional Name

evodiamine

CAS Registry Number

Not Available

SMILES

CN1C2N(CCC3=C2NC2=CC=CC=C32)C(=O)C2=CC=CC=C12

InChI Identifier

InChI=1S/C19H17N3O/c1-21-16-9-5-3-7-14(16)19(23)22-11-10-13-12-6-2-4-8-15(12)20-17(13)18(21)22/h2-9,18,20H,10-11H2,1H3

InChI Key

TXDUTHBFYKGSAH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyridoindoles

Direct Parent

Beta carbolines

Alternative Parents

Substituents

Beta-carboline
Diazanaphthalene
Quinazoline
3-alkylindole
Indole
Dialkylarylamine
Benzenoid
Pyrrole
Tertiary carboxylic acid amide
Vinylogous amide
Heteroaromatic compound
Lactam
Carboxamide group
Carboxylic acid derivative
Azacycle
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Organooxygen compound
Organonitrogen 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	3.07	ALOGPS
logP	3.32	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	14.91	ChemAxon
pKa (Strongest Basic)	-1.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	39.34 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	91.01 m³·mol⁻¹	ChemAxon
Polarizability	33.72 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	201.528	30932474
DeepCCS	[M+Na]+	177.094	30932474
AllCCS	[M+H]+	174.0	32859911
AllCCS	[M+H-H2O]+	170.8	32859911
AllCCS	[M+NH4]+	176.9	32859911
AllCCS	[M+Na]+	177.7	32859911
AllCCS	[M-H]-	174.7	32859911
AllCCS	[M+Na-2H]-	173.6	32859911
AllCCS	[M+HCOO]-	172.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Evodiamine	CN1C2N(CCC3=C2NC2=CC=CC=C32)C(=O)C2=CC=CC=C12	4251.7	Standard polar	33892256
Evodiamine	CN1C2N(CCC3=C2NC2=CC=CC=C32)C(=O)C2=CC=CC=C12	3076.1	Standard non polar	33892256
Evodiamine	CN1C2N(CCC3=C2NC2=CC=CC=C32)C(=O)C2=CC=CC=C12	3205.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Evodiamine,1TMS,isomer #1	CN1C2=CC=CC=C2C(=O)N2CCC3=C(C21)N([Si](C)(C)C)C1=CC=CC=C31	3025.5	Semi standard non polar	33892256
Evodiamine,1TMS,isomer #1	CN1C2=CC=CC=C2C(=O)N2CCC3=C(C21)N([Si](C)(C)C)C1=CC=CC=C31	2957.9	Standard non polar	33892256
Evodiamine,1TMS,isomer #1	CN1C2=CC=CC=C2C(=O)N2CCC3=C(C21)N([Si](C)(C)C)C1=CC=CC=C31	3741.8	Standard polar	33892256
Evodiamine,1TBDMS,isomer #1	CN1C2=CC=CC=C2C(=O)N2CCC3=C(C21)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C31	3219.6	Semi standard non polar	33892256
Evodiamine,1TBDMS,isomer #1	CN1C2=CC=CC=C2C(=O)N2CCC3=C(C21)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C31	3192.3	Standard non polar	33892256
Evodiamine,1TBDMS,isomer #1	CN1C2=CC=CC=C2C(=O)N2CCC3=C(C21)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C31	3812.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Evodiamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001c-0951000000-b2078f6746826873cf83	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Evodiamine 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Evodiamine 6V, Positive-QTOF	splash10-0gb9-0903000000-cd2c22b9158d54374f38	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Evodiamine 6V, Positive-QTOF	splash10-014i-0900000000-9800b9ca2aa56be1b4ad	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Evodiamine 6V, Positive-QTOF	splash10-014i-0900000000-8c13f5290f7848f731e7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Evodiamine 6V, Positive-QTOF	splash10-0006-0900000000-ff61cd1655f82c6e43e0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Evodiamine 6V, Positive-QTOF	splash10-0udi-0109000000-d9bf146f94cf9da8cd94	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Evodiamine 6V, Positive-QTOF	splash10-0gb9-0903000000-88c54ff95a9f74d4f06f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Evodiamine 6V, Positive-QTOF	splash10-0f89-0903000000-fe20f29a9010a06b4acc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Evodiamine 6V, Negative-QTOF	splash10-0gb9-0904000000-22737b523c2166bf036a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Evodiamine 6V, Positive-QTOF	splash10-0udi-0209000000-b9ebc6a6cb3c1a4f8539	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Evodiamine 6V, Positive-QTOF	splash10-0udi-0209000000-5dfa86f6de9ca32f95d0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Evodiamine 6V, Positive-QTOF	splash10-0006-0900000000-f712c89423b88ce63705	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Evodiamine 6V, Positive-QTOF	splash10-014i-0900000000-185be3047b17cb38e13e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Evodiamine 6V, Positive-QTOF	splash10-0006-0900000000-d97cdc913a6017c916b2	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Evodiamine 10V, Positive-QTOF	splash10-0udi-0009000000-c5c4c80cf9dc0ec785ef	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Evodiamine 20V, Positive-QTOF	splash10-0udi-0009000000-c5c4c80cf9dc0ec785ef	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Evodiamine 40V, Positive-QTOF	splash10-014i-0920000000-7cc15da142206cc5c9e5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Evodiamine 10V, Negative-QTOF	splash10-0udi-0009000000-2f2cc9c9ba414d09519b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Evodiamine 20V, Negative-QTOF	splash10-0udi-0009000000-66fa79cbf615668b03f0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Evodiamine 40V, Negative-QTOF	splash10-00di-0091000000-9cb117777b8aa8e1f979	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

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

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

133343

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

151289

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

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 Evodiamine (HMDB0252138)

MOL for HMDB0252138 (Evodiamine)

3D MOL for HMDB0252138 (Evodiamine)

3D SDF for HMDB0252138 (Evodiamine)

3D-SDF for HMDB0252138 (Evodiamine)

PDB for HMDB0252138 (Evodiamine)

3D PDB for HMDB0252138 (Evodiamine)

SMILES for HMDB0252138 (Evodiamine)

INCHI for HMDB0252138 (Evodiamine)

Structure for HMDB0252138 (Evodiamine)

3D Structure for HMDB0252138 (Evodiamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra