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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 01:37:26 UTC

Update Date

2021-09-26 22:58:34 UTC

HMDB ID

HMDB0248346

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Amonafide

Description

Amonafide, also known as as-1413amonafide or MFA-142, belongs to the class of organic compounds known as isoquinolones and derivatives. These are aromatic polycyclic compounds containing a ketone bearing isoquinoline moiety. Based on a literature review very few articles have been published on Amonafide. This compound has been identified in human blood as reported by (PMID: 31557052 ). Amonafide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Amonafide 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

HMDB0248346
     RDKit          3D
Amonafide
 38 40  0  0  0  0  0  0  0  0999 V2000
    4.6218    0.8361    1.2962 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2088   -0.3628    0.6522 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8648   -0.7067   -0.5584 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7925   -0.4857    0.4931 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1781    0.4989   -0.4711 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7484    0.2259   -0.5001 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1265   -0.6784   -1.3907 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8330   -1.2914   -2.2139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3270   -0.8868   -1.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9487   -1.7667   -2.2033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3138   -1.9790   -2.1737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1055   -1.3072   -1.2674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4980   -0.4190   -0.3931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3285    0.2410    0.5075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7289    1.1271    1.3816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5050    1.8401    2.3320 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3661    1.3287    1.3410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5386    0.6773    0.4509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1323   -0.2121   -0.4286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0898    0.9095    0.4279 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3688    1.7263    1.2522 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0547    0.8892    2.2706 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3705    1.7669    0.7598 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6823    0.7792    1.5839 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2017   -1.7821   -0.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7860   -0.1294   -0.7778 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2404   -0.7080   -1.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6150   -1.5283    0.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3247   -0.4238    1.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5685    0.4324   -1.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3811    1.5270   -0.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2998   -2.2876   -2.9135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7661   -2.6810   -2.8712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1802   -1.4696   -1.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3951    0.0796    0.5348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0052    2.7129    2.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5691    1.4814    3.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8699    2.0264    2.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 20  6  1  0
 19  9  2  0
 19 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  0
 14 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
M  END

  Mrv0541 02231218052D          

 21 23  0  0  0  0            999 V2000
    2.8115    0.4739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6298    0.4739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2206    0.4739    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9252    2.5078    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0629   -2.4103    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2206   -1.1533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2206    1.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5160   -0.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9252   -0.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5160    0.0672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2337   -2.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9252    0.0672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9252    1.6943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7757   -1.1588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6656   -1.1588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5031   -2.4299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7692   -2.0061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9381   -2.4299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6721   -2.0061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2206    2.9146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6298    2.9146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  2  0  0  0  0
  2 12  2  0  0  0  0
  3  7  1  0  0  0  0
  3 10  1  0  0  0  0
  3 12  1  0  0  0  0
  4 13  1  0  0  0  0
  4 20  1  0  0  0  0
  4 21  1  0  0  0  0
  5 17  1  0  0  0  0
  6  8  2  0  0  0  0
  6  9  1  0  0  0  0
  6 11  1  0  0  0  0
  7 13  1  0  0  0  0
  8 10  1  0  0  0  0
  8 14  1  0  0  0  0
  9 12  1  0  0  0  0
  9 15  2  0  0  0  0
 11 16  2  0  0  0  0
 11 18  1  0  0  0  0
 14 17  2  0  0  0  0
 15 19  1  0  0  0  0
 16 17  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0248346

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)CCN1C(=O)C2=CC=CC3=CC(N)=CC(C1=O)=C23

> <INCHI_IDENTIFIER>
InChI=1S/C16H17N3O2/c1-18(2)6-7-19-15(20)12-5-3-4-10-8-11(17)9-13(14(10)12)16(19)21/h3-5,8-9H,6-7,17H2,1-2H3

> <INCHI_KEY>
UPALIKSFLSVKIS-UHFFFAOYSA-N

> <FORMULA>
C16H17N3O2

> <MOLECULAR_WEIGHT>
283.3251

> <EXACT_MASS>
283.132076803

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
30.099216092582473

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
11-amino-3-[2-(dimethylamino)ethyl]-3-azatricyclo[7.3.1.0⁵,¹³]trideca-1(13),5,7,9,11-pentaene-2,4-dione

> <ALOGPS_LOGP>
0.90

> <JCHEM_LOGP>
1.0962944290000003

> <ALOGPS_LOGS>
-2.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.517468222802735

> <JCHEM_POLAR_SURFACE_AREA>
66.64

> <JCHEM_REFRACTIVITY>
83.3812

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.64e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
amonafide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0248346
     RDKit          3D
Amonafide
 38 40  0  0  0  0  0  0  0  0999 V2000
    4.6218    0.8361    1.2962 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2088   -0.3628    0.6522 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8648   -0.7067   -0.5584 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7925   -0.4857    0.4931 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1781    0.4989   -0.4711 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7484    0.2259   -0.5001 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1265   -0.6784   -1.3907 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8330   -1.2914   -2.2139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3270   -0.8868   -1.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9487   -1.7667   -2.2033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3138   -1.9790   -2.1737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1055   -1.3072   -1.2674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4980   -0.4190   -0.3931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3285    0.2410    0.5075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7289    1.1271    1.3816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5050    1.8401    2.3320 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3661    1.3287    1.3410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5386    0.6773    0.4509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1323   -0.2121   -0.4286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0898    0.9095    0.4279 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3688    1.7263    1.2522 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0547    0.8892    2.2706 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3705    1.7669    0.7598 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6823    0.7792    1.5839 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2017   -1.7821   -0.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7860   -0.1294   -0.7778 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2404   -0.7080   -1.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6150   -1.5283    0.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3247   -0.4238    1.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5685    0.4324   -1.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3811    1.5270   -0.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2998   -2.2876   -2.9135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7661   -2.6810   -2.8712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1802   -1.4696   -1.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3951    0.0796    0.5348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0052    2.7129    2.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5691    1.4814    3.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8699    2.0264    2.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 20  6  1  0
 19  9  2  0
 19 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  0
 14 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       5.248   0.885   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      10.509   0.885   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       7.878   0.885   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       9.194   4.681   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       3.851  -4.499   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       7.878  -2.153   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.878   2.403   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.563  -1.393   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.194  -1.393   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.563   0.125   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.903  -3.734   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.194   0.125   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.194   3.163   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.181  -2.163   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.576  -2.163   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.539  -4.536   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.169  -3.745   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.218  -4.536   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.588  -3.745   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.878   5.441   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.509   5.441   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2   12                                                            
CONECT    3    7   10   12                                                  
CONECT    4   13   20   21                                                  
CONECT    5   17                                                            
CONECT    6    8    9   11                                                  
CONECT    7    3   13                                                       
CONECT    8    6   10   14                                                  
CONECT    9    6   12   15                                                  
CONECT   10    1    3    8                                                  
CONECT   11    6   16   18                                                  
CONECT   12    2    3    9                                                  
CONECT   13    4    7                                                       
CONECT   14    8   17                                                       
CONECT   15    9   19                                                       
CONECT   16   11   17                                                       
CONECT   17    5   14   16                                                  
CONECT   18   11   19                                                       
CONECT   19   15   18                                                       
CONECT   20    4                                                            
CONECT   21    4                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0248346
HETATM    1  C1  UNL     1       4.622   0.836   1.296  1.00  0.00           C  
HETATM    2  N1  UNL     1       4.209  -0.363   0.652  1.00  0.00           N  
HETATM    3  C2  UNL     1       4.865  -0.707  -0.558  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.793  -0.486   0.493  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.178   0.499  -0.471  1.00  0.00           C  
HETATM    6  N2  UNL     1       0.748   0.226  -0.500  1.00  0.00           N  
HETATM    7  C5  UNL     1       0.126  -0.678  -1.391  1.00  0.00           C  
HETATM    8  O1  UNL     1       0.833  -1.291  -2.214  1.00  0.00           O  
HETATM    9  C6  UNL     1      -1.327  -0.887  -1.341  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.949  -1.767  -2.203  1.00  0.00           C  
HETATM   11  C8  UNL     1      -3.314  -1.979  -2.174  1.00  0.00           C  
HETATM   12  C9  UNL     1      -4.106  -1.307  -1.267  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.498  -0.419  -0.393  1.00  0.00           C  
HETATM   14  C11 UNL     1      -4.328   0.241   0.508  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.729   1.127   1.382  1.00  0.00           C  
HETATM   16  N3  UNL     1      -4.505   1.840   2.332  1.00  0.00           N  
HETATM   17  C13 UNL     1      -2.366   1.329   1.341  1.00  0.00           C  
HETATM   18  C14 UNL     1      -1.539   0.677   0.451  1.00  0.00           C  
HETATM   19  C15 UNL     1      -2.132  -0.212  -0.429  1.00  0.00           C  
HETATM   20  C16 UNL     1      -0.090   0.909   0.428  1.00  0.00           C  
HETATM   21  O2  UNL     1       0.369   1.726   1.252  1.00  0.00           O  
HETATM   22  H1  UNL     1       4.055   0.889   2.271  1.00  0.00           H  
HETATM   23  H2  UNL     1       4.370   1.767   0.760  1.00  0.00           H  
HETATM   24  H3  UNL     1       5.682   0.779   1.584  1.00  0.00           H  
HETATM   25  H4  UNL     1       5.202  -1.782  -0.458  1.00  0.00           H  
HETATM   26  H5  UNL     1       5.786  -0.129  -0.778  1.00  0.00           H  
HETATM   27  H6  UNL     1       4.240  -0.708  -1.471  1.00  0.00           H  
HETATM   28  H7  UNL     1       2.615  -1.528   0.094  1.00  0.00           H  
HETATM   29  H8  UNL     1       2.325  -0.424   1.486  1.00  0.00           H  
HETATM   30  H9  UNL     1       2.569   0.432  -1.480  1.00  0.00           H  
HETATM   31  H10 UNL     1       2.381   1.527  -0.102  1.00  0.00           H  
HETATM   32  H11 UNL     1      -1.300  -2.288  -2.914  1.00  0.00           H  
HETATM   33  H12 UNL     1      -3.766  -2.681  -2.871  1.00  0.00           H  
HETATM   34  H13 UNL     1      -5.180  -1.470  -1.238  1.00  0.00           H  
HETATM   35  H14 UNL     1      -5.395   0.080   0.535  1.00  0.00           H  
HETATM   36  H15 UNL     1      -5.005   2.713   2.068  1.00  0.00           H  
HETATM   37  H16 UNL     1      -4.569   1.481   3.296  1.00  0.00           H  
HETATM   38  H17 UNL     1      -1.870   2.026   2.025  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    4
CONECT    3   25   26   27
CONECT    4    5   28   29
CONECT    5    6   30   31
CONECT    6    7   20
CONECT    7    8    8    9
CONECT    9   10   19   19
CONECT   10   11   11   32
CONECT   11   12   33
CONECT   12   13   13   34
CONECT   13   14   19
CONECT   14   15   15   35
CONECT   15   16   17
CONECT   16   36   37
CONECT   17   18   18   38
CONECT   18   19   20
CONECT   20   21   21
END

HMDB0248346
     RDKit          3D
Amonafide
 38 40  0  0  0  0  0  0  0  0999 V2000
    4.6218    0.8361    1.2962 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2088   -0.3628    0.6522 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8648   -0.7067   -0.5584 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7925   -0.4857    0.4931 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1781    0.4989   -0.4711 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7484    0.2259   -0.5001 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1265   -0.6784   -1.3907 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8330   -1.2914   -2.2139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3270   -0.8868   -1.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9487   -1.7667   -2.2033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3138   -1.9790   -2.1737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1055   -1.3072   -1.2674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4980   -0.4190   -0.3931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3285    0.2410    0.5075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7289    1.1271    1.3816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5050    1.8401    2.3320 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3661    1.3287    1.3410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5386    0.6773    0.4509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1323   -0.2121   -0.4286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0898    0.9095    0.4279 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3688    1.7263    1.2522 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0547    0.8892    2.2706 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3705    1.7669    0.7598 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6823    0.7792    1.5839 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2017   -1.7821   -0.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7860   -0.1294   -0.7778 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2404   -0.7080   -1.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6150   -1.5283    0.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3247   -0.4238    1.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5685    0.4324   -1.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3811    1.5270   -0.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2998   -2.2876   -2.9135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7661   -2.6810   -2.8712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1802   -1.4696   -1.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3951    0.0796    0.5348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0052    2.7129    2.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5691    1.4814    3.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8699    2.0264    2.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 20  6  1  0
 19  9  2  0
 19 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  0
 14 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
AS-1413amonafide	HMDB
MFA-142	HMDB
m-FA 142	HMDB
m-FA-142	HMDB
5-Amino-2-(2-dimethylaminoethyl)benzo(de)isoquinolin-1,3-dione	HMDB
MFA 142	HMDB
Benzisoquinolinedione	HMDB
Nafidimide	HMDB

Chemical Formula

C₁₆H₁₇N₃O₂

Average Molecular Weight

283.3251

Monoisotopic Molecular Weight

283.132076803

IUPAC Name

11-amino-3-[2-(dimethylamino)ethyl]-3-azatricyclo[7.3.1.0⁵,¹³]trideca-1(13),5,7,9,11-pentaene-2,4-dione

Traditional Name

amonafide

CAS Registry Number

Not Available

SMILES

CN(C)CCN1C(=O)C2=CC=CC3=CC(N)=CC(C1=O)=C23

InChI Identifier

InChI=1S/C16H17N3O2/c1-18(2)6-7-19-15(20)12-5-3-4-10-8-11(17)9-13(14(10)12)16(19)21/h3-5,8-9H,6-7,17H2,1-2H3

InChI Key

UPALIKSFLSVKIS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoquinolones and derivatives. These are aromatic polycyclic compounds containing a ketone bearing isoquinoline moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoquinolines and derivatives

Sub Class

Isoquinolones and derivatives

Direct Parent

Isoquinolones and derivatives

Alternative Parents

Substituents

Isoquinolone
Naphthalene
Carboxylic acid imide, n-substituted
Benzenoid
Carboxylic acid imide
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid derivative
Azacycle
Amine
Organooxygen compound
Organonitrogen compound
Primary amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
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 (HMDB: HMDB0248346)

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	0.9	ALOGPS
logP	1.1	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Basic)	8.52	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	66.64 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	83.38 m³·mol⁻¹	ChemAxon
Polarizability	30.1 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	200.018	30932474
DeepCCS	[M+Na]+	175.583	30932474
AllCCS	[M+H]+	165.4	32859911
AllCCS	[M+H-H2O]+	162.0	32859911
AllCCS	[M+NH4]+	168.6	32859911
AllCCS	[M+Na]+	169.5	32859911
AllCCS	[M-H]-	170.2	32859911
AllCCS	[M+Na-2H]-	169.9	32859911
AllCCS	[M+HCOO]-	169.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	9.6523 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.72 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	441.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	231.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	108.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	174.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	52.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	243.2 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	302.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	753.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	599.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	67.0 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	790.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	178.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	245.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	539.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	520.1 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	111.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Amonafide	CN(C)CCN1C(=O)C2=CC=CC3=CC(N)=CC(C1=O)=C23	3908.9	Standard polar	33892256
Amonafide	CN(C)CCN1C(=O)C2=CC=CC3=CC(N)=CC(C1=O)=C23	2811.4	Standard non polar	33892256
Amonafide	CN(C)CCN1C(=O)C2=CC=CC3=CC(N)=CC(C1=O)=C23	2927.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Amonafide,1TMS,isomer #1	CN(C)CCN1C(=O)C2=C3C(=CC(N[Si](C)(C)C)=CC3=CC=C2)C1=O	2786.3	Semi standard non polar	33892256
Amonafide,1TMS,isomer #1	CN(C)CCN1C(=O)C2=C3C(=CC(N[Si](C)(C)C)=CC3=CC=C2)C1=O	2972.3	Standard non polar	33892256
Amonafide,1TMS,isomer #1	CN(C)CCN1C(=O)C2=C3C(=CC(N[Si](C)(C)C)=CC3=CC=C2)C1=O	3512.6	Standard polar	33892256
Amonafide,2TMS,isomer #1	CN(C)CCN1C(=O)C2=C3C(=CC(N([Si](C)(C)C)[Si](C)(C)C)=CC3=CC=C2)C1=O	2628.2	Semi standard non polar	33892256
Amonafide,2TMS,isomer #1	CN(C)CCN1C(=O)C2=C3C(=CC(N([Si](C)(C)C)[Si](C)(C)C)=CC3=CC=C2)C1=O	2933.7	Standard non polar	33892256
Amonafide,2TMS,isomer #1	CN(C)CCN1C(=O)C2=C3C(=CC(N([Si](C)(C)C)[Si](C)(C)C)=CC3=CC=C2)C1=O	3344.2	Standard polar	33892256
Amonafide,1TBDMS,isomer #1	CN(C)CCN1C(=O)C2=C3C(=CC(N[Si](C)(C)C(C)(C)C)=CC3=CC=C2)C1=O	2994.4	Semi standard non polar	33892256
Amonafide,1TBDMS,isomer #1	CN(C)CCN1C(=O)C2=C3C(=CC(N[Si](C)(C)C(C)(C)C)=CC3=CC=C2)C1=O	3141.2	Standard non polar	33892256
Amonafide,1TBDMS,isomer #1	CN(C)CCN1C(=O)C2=C3C(=CC(N[Si](C)(C)C(C)(C)C)=CC3=CC=C2)C1=O	3558.4	Standard polar	33892256
Amonafide,2TBDMS,isomer #1	CN(C)CCN1C(=O)C2=C3C(=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC3=CC=C2)C1=O	3097.7	Semi standard non polar	33892256
Amonafide,2TBDMS,isomer #1	CN(C)CCN1C(=O)C2=C3C(=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC3=CC=C2)C1=O	3332.3	Standard non polar	33892256
Amonafide,2TBDMS,isomer #1	CN(C)CCN1C(=O)C2=C3C(=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC3=CC=C2)C1=O	3431.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Amonafide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9150000000-e561ab18a08e16bfcc6d	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amonafide 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 - Amonafide 10V, Positive-QTOF	splash10-00lr-1090000000-4b95b84b13c909421f72	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amonafide 20V, Positive-QTOF	splash10-00dr-2090000000-288a906557fa09091168	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amonafide 40V, Positive-QTOF	splash10-00di-9240000000-8d63de23fd294fbcf1c5	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amonafide 10V, Negative-QTOF	splash10-001i-0090000000-99e59cbb9eb46b1cca37	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amonafide 20V, Negative-QTOF	splash10-001i-0090000000-6d056a9f512e4a46b8ba	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amonafide 40V, Negative-QTOF	splash10-03dl-4490000000-254b8fdc4732f4097e8c	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amonafide 10V, Positive-QTOF	splash10-001i-0090000000-e85e077a9db87aad9e9d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amonafide 20V, Positive-QTOF	splash10-001i-0090000000-7f9da2f3c5d1f2d8824f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amonafide 40V, Positive-QTOF	splash10-00di-2950000000-a294493f3fb0e48acfb2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amonafide 10V, Negative-QTOF	splash10-001i-0090000000-3f4d3a9d7c0734c60307	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amonafide 20V, Negative-QTOF	splash10-03di-0090000000-827e724f66ec6282237d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amonafide 40V, Negative-QTOF	splash10-03di-1090000000-fdc493e956ce8e1eabb0	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

DB05022

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

45804

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Amonafide

METLIN ID

Not Available

PubChem Compound

50515

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 Amonafide (HMDB0248346)

MOL for HMDB0248346 (Amonafide)

3D MOL for HMDB0248346 (Amonafide)

3D SDF for HMDB0248346 (Amonafide)

3D-SDF for HMDB0248346 (Amonafide)

PDB for HMDB0248346 (Amonafide)

3D PDB for HMDB0248346 (Amonafide)

SMILES for HMDB0248346 (Amonafide)

INCHI for HMDB0248346 (Amonafide)

Structure for HMDB0248346 (Amonafide)

3D Structure for HMDB0248346 (Amonafide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra