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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 11:09:49 UTC

Update Date

2021-09-26 23:05:57 UTC

HMDB ID

HMDB0252997

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine

Description

Gyki-52466 belongs to the class of organic compounds known as benzodiazepines. These are organic compounds containing a benzene ring fused to either isomers of diazepine(unsaturated seven-member heterocycle with two nitrogen atoms replacing two carbon atoms). Gyki-52466 is a strong basic compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-(8-methyl-9h-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine 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

HMDB0252997
     RDKit          3D
4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine
 37 40  0  0  0  0  0  0  0  0999 V2000
   -3.3955    3.0771    1.4344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2239    2.4055    0.7819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1051    2.5649    1.3734 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1706    2.0460    0.9848 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3718    0.9116    0.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7294    0.5441    0.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7197    1.2680    0.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0412    1.0553    0.4442 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4801    0.1477   -0.5093 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8619   -0.0151   -0.7444 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4931   -0.5489   -1.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1473   -0.3485   -0.9039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7024   -0.0167    0.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2803   -1.3421    0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1373   -2.3825   -0.0996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4388   -2.0762   -0.4860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8397   -0.7392   -0.5974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9918    0.2962   -0.3389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5898    1.6643   -0.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0874   -3.2865   -0.6871 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3204   -4.3449   -0.1533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0153   -3.7698   -0.0711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1062    3.9402    2.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0510    3.4384    0.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9006    2.3239    2.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4171    1.9977    1.4931 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7709    1.6376    1.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3170   -0.9139   -0.5166 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4212    0.7567   -1.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8155   -1.2655   -1.9276 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4220   -0.8927   -1.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7163   -1.5667    0.5004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8423   -0.5174   -0.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6876    1.6073   -0.5859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1769    2.1203   -1.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6696   -4.5286    0.8785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3334   -5.2481   -0.7947 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
  5 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 16 20  1  0
 20 21  1  0
 21 22  1  0
 19  2  1  0
 12  6  1  0
 18 13  1  0
 22 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  7 26  1  0
  8 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 14 32  1  0
 17 33  1  0
 19 34  1  0
 19 35  1  0
 21 36  1  0
 21 37  1  0
M  END


  Mrv1533004261514522D          

 22 25  0  0  0  0            999 V2000
   -0.2506   -0.9758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2638   -0.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0942    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2638    1.1558    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0681    1.3394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7131    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4276    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1421    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1421    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4276   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7131    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0681   -0.5144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9267   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4116    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9267    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2517    2.1437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6469    2.7048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8305    3.5092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6189    3.7523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2236    3.1912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0400    2.3869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8024    4.5566    0.0000 N   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
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  8 15  1  0  0  0  0
  5 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 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
 16 21  1  0  0  0  0
 19 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0252997

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=NN=C(C2=CC=C(N)C=C2)C2=CC3=C(OCO3)C=C2C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H15N3O2/c1-10-6-12-7-15-16(22-9-21-15)8-14(12)17(20-19-10)11-2-4-13(18)5-3-11/h2-5,7-8H,6,9,18H2,1H3

> <INCHI_KEY>
LFBZZHVSGAHQPP-UHFFFAOYSA-N

> <FORMULA>
C17H15N3O2

> <MOLECULAR_WEIGHT>
293.326

> <EXACT_MASS>
293.116426735

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
31.536058681323073

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{13-methyl-4,6-dioxa-11,12-diazatricyclo[7.5.0.0³,⁷]tetradeca-1,3(7),8,10,12-pentaen-10-yl}aniline

> <ALOGPS_LOGP>
2.89

> <JCHEM_LOGP>
2.2630421649999994

> <ALOGPS_LOGS>
-3.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
3.2377535019978665

> <JCHEM_POLAR_SURFACE_AREA>
69.2

> <JCHEM_REFRACTIVITY>
84.47370000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.31e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-{13-methyl-4,6-dioxa-11,12-diazatricyclo[7.5.0.0³,⁷]tetradeca-1,3(7),8,10,12-pentaen-10-yl}aniline

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0252997
     RDKit          3D
4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine
 37 40  0  0  0  0  0  0  0  0999 V2000
   -3.3955    3.0771    1.4344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2239    2.4055    0.7819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1051    2.5649    1.3734 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1706    2.0460    0.9848 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3718    0.9116    0.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7294    0.5441    0.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7197    1.2680    0.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0412    1.0553    0.4442 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4801    0.1477   -0.5093 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8619   -0.0151   -0.7444 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4931   -0.5489   -1.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1473   -0.3485   -0.9039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7024   -0.0167    0.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2803   -1.3421    0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1373   -2.3825   -0.0996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4388   -2.0762   -0.4860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8397   -0.7392   -0.5974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9918    0.2962   -0.3389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5898    1.6643   -0.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0874   -3.2865   -0.6871 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3204   -4.3449   -0.1533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0153   -3.7698   -0.0711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1062    3.9402    2.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0510    3.4384    0.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9006    2.3239    2.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4171    1.9977    1.4931 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7709    1.6376    1.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3170   -0.9139   -0.5166 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4212    0.7567   -1.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8155   -1.2655   -1.9276 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4220   -0.8927   -1.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7163   -1.5667    0.5004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8423   -0.5174   -0.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6876    1.6073   -0.5859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1769    2.1203   -1.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6696   -4.5286    0.8785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3334   -5.2481   -0.7947 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
  5 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 16 20  1  0
 20 21  1  0
 21 22  1  0
 19  2  1  0
 12  6  1  0
 18 13  1  0
 22 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  7 26  1  0
  8 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 14 32  1  0
 17 33  1  0
 19 34  1  0
 19 35  1  0
 21 36  1  0
 21 37  1  0
M  END

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0      -0.468  -1.822   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.492  -0.617   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -0.176   0.770   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       0.492   2.157   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       1.994   2.500   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.198   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.532   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.865   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.865   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.532  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.198   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.994  -0.960   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       7.330  -0.476   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.235   0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.330   2.016   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.337   4.002   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.208   5.049   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.550   6.550   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.022   7.004   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.151   5.957   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.808   4.455   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       3.365   8.506   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   16                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   15                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10    6   12                                                  
CONECT   12   11    2                                                       
CONECT   13    9   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    8                                                       
CONECT   16    5   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22   19                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0252997
HETATM    1  C1  UNL     1      -3.395   3.077   1.434  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.224   2.405   0.782  1.00  0.00           C  
HETATM    3  N1  UNL     1      -1.105   2.565   1.373  1.00  0.00           N  
HETATM    4  N2  UNL     1       0.171   2.046   0.985  1.00  0.00           N  
HETATM    5  C3  UNL     1       0.372   0.912   0.356  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.729   0.544   0.036  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.720   1.268   0.729  1.00  0.00           C  
HETATM    8  C6  UNL     1       4.041   1.055   0.444  1.00  0.00           C  
HETATM    9  C7  UNL     1       4.480   0.148  -0.509  1.00  0.00           C  
HETATM   10  N3  UNL     1       5.862  -0.015  -0.744  1.00  0.00           N  
HETATM   11  C8  UNL     1       3.493  -0.549  -1.176  1.00  0.00           C  
HETATM   12  C9  UNL     1       2.147  -0.348  -0.904  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.702  -0.017   0.041  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.280  -1.342   0.162  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.137  -2.382  -0.100  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.439  -2.076  -0.486  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.840  -0.739  -0.597  1.00  0.00           C  
HETATM   18  C15 UNL     1      -1.992   0.296  -0.339  1.00  0.00           C  
HETATM   19  C16 UNL     1      -2.590   1.664  -0.455  1.00  0.00           C  
HETATM   20  O1  UNL     1      -3.087  -3.286  -0.687  1.00  0.00           O  
HETATM   21  C17 UNL     1      -2.320  -4.345  -0.153  1.00  0.00           C  
HETATM   22  O2  UNL     1      -1.015  -3.770  -0.071  1.00  0.00           O  
HETATM   23  H1  UNL     1      -3.106   3.940   2.038  1.00  0.00           H  
HETATM   24  H2  UNL     1      -4.051   3.438   0.610  1.00  0.00           H  
HETATM   25  H3  UNL     1      -3.901   2.324   2.060  1.00  0.00           H  
HETATM   26  H4  UNL     1       2.417   1.998   1.493  1.00  0.00           H  
HETATM   27  H5  UNL     1       4.771   1.638   1.005  1.00  0.00           H  
HETATM   28  H6  UNL     1       6.317  -0.914  -0.517  1.00  0.00           H  
HETATM   29  H7  UNL     1       6.421   0.757  -1.142  1.00  0.00           H  
HETATM   30  H8  UNL     1       3.816  -1.265  -1.928  1.00  0.00           H  
HETATM   31  H9  UNL     1       1.422  -0.893  -1.484  1.00  0.00           H  
HETATM   32  H10 UNL     1       0.716  -1.567   0.500  1.00  0.00           H  
HETATM   33  H11 UNL     1      -3.842  -0.517  -0.894  1.00  0.00           H  
HETATM   34  H12 UNL     1      -3.688   1.607  -0.586  1.00  0.00           H  
HETATM   35  H13 UNL     1      -2.177   2.120  -1.359  1.00  0.00           H  
HETATM   36  H14 UNL     1      -2.670  -4.529   0.879  1.00  0.00           H  
HETATM   37  H15 UNL     1      -2.333  -5.248  -0.795  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    3   19
CONECT    3    4
CONECT    4    5    5
CONECT    5    6   13
CONECT    6    7    7   12
CONECT    7    8   26
CONECT    8    9    9   27
CONECT    9   10   11
CONECT   10   28   29
CONECT   11   12   12   30
CONECT   12   31
CONECT   13   14   14   18
CONECT   14   15   32
CONECT   15   16   16   22
CONECT   16   17   20
CONECT   17   18   18   33
CONECT   18   19
CONECT   19   34   35
CONECT   20   21
CONECT   21   22   36   37
END

HMDB0252997
     RDKit          3D
4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine
 37 40  0  0  0  0  0  0  0  0999 V2000
   -3.3955    3.0771    1.4344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2239    2.4055    0.7819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1051    2.5649    1.3734 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1706    2.0460    0.9848 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3718    0.9116    0.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7294    0.5441    0.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7197    1.2680    0.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0412    1.0553    0.4442 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4801    0.1477   -0.5093 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8619   -0.0151   -0.7444 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4931   -0.5489   -1.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1473   -0.3485   -0.9039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7024   -0.0167    0.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2803   -1.3421    0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1373   -2.3825   -0.0996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4388   -2.0762   -0.4860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8397   -0.7392   -0.5974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9918    0.2962   -0.3389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5898    1.6643   -0.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0874   -3.2865   -0.6871 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3204   -4.3449   -0.1533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0153   -3.7698   -0.0711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1062    3.9402    2.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0510    3.4384    0.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9006    2.3239    2.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4171    1.9977    1.4931 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7709    1.6376    1.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3170   -0.9139   -0.5166 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4212    0.7567   -1.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8155   -1.2655   -1.9276 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4220   -0.8927   -1.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7163   -1.5667    0.5004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8423   -0.5174   -0.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6876    1.6073   -0.5859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1769    2.1203   -1.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6696   -4.5286    0.8785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3334   -5.2481   -0.7947 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
  5 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 16 20  1  0
 20 21  1  0
 21 22  1  0
 19  2  1  0
 12  6  1  0
 18 13  1  0
 22 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  7 26  1  0
  8 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 14 32  1  0
 17 33  1  0
 19 34  1  0
 19 35  1  0
 21 36  1  0
 21 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-(8-Methyl-9H-1,3-dioxolo[4,5-H][2,3]benzodiazepin-5-yl)benzenamine	Kegg
1-(p-Aminophenyl)-4-methyl-7,8-methylenedioxy-5H-2,3-benzodiazepine hydrochloride	MeSH

Chemical Formula

C₁₇H₁₅N₃O₂

Average Molecular Weight

293.326

Monoisotopic Molecular Weight

293.116426735

IUPAC Name

4-{13-methyl-4,6-dioxa-11,12-diazatricyclo[7.5.0.0³,⁷]tetradeca-1,3(7),8,10,12-pentaen-10-yl}aniline

Traditional Name

4-{13-methyl-4,6-dioxa-11,12-diazatricyclo[7.5.0.0³,⁷]tetradeca-1,3(7),8,10,12-pentaen-10-yl}aniline

CAS Registry Number

Not Available

SMILES

CC1=NN=C(C2=CC=C(N)C=C2)C2=CC3=C(OCO3)C=C2C1

InChI Identifier

InChI=1S/C17H15N3O2/c1-10-6-12-7-15-16(22-9-21-15)8-14(12)17(20-19-10)11-2-4-13(18)5-3-11/h2-5,7-8H,6,9,18H2,1H3

InChI Key

LFBZZHVSGAHQPP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzodiazepines. These are organic compounds containing a benzene ring fused to either isomers of diazepine(unsaturated seven-member heterocycle with two nitrogen atoms replacing two carbon atoms).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodiazepines

Sub Class

Not Available

Direct Parent

Benzodiazepines

Alternative Parents

Substituents

Benzodiazepine
Benzodioxole
Aniline or substituted anilines
Monocyclic benzene moiety
Benzenoid
Acetal
Oxacycle
Azacycle
Primary amine
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzodiazepine (CHEBI:79560 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (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	2.89	ALOGPS
logP	2.26	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	3.24	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	69.2 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	84.47 m³·mol⁻¹	ChemAxon
Polarizability	31.54 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]+	167.688	30932474
DeepCCS	[M-H]-	165.33	30932474
DeepCCS	[M-2H]-	199.149	30932474
DeepCCS	[M+Na]+	174.376	30932474
AllCCS	[M+H]+	169.3	32859911
AllCCS	[M+H-H2O]+	165.6	32859911
AllCCS	[M+NH4]+	172.7	32859911
AllCCS	[M+Na]+	173.7	32859911
AllCCS	[M-H]-	174.5	32859911
AllCCS	[M+Na-2H]-	173.9	32859911
AllCCS	[M+HCOO]-	173.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine	CC1=NN=C(C2=CC=C(N)C=C2)C2=CC3=C(OCO3)C=C2C1	4073.8	Standard polar	33892256
4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine	CC1=NN=C(C2=CC=C(N)C=C2)C2=CC3=C(OCO3)C=C2C1	2848.5	Standard non polar	33892256
4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine	CC1=NN=C(C2=CC=C(N)C=C2)C2=CC3=C(OCO3)C=C2C1	3040.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine,1TMS,isomer #1	CC1=NN=C(C2=CC=C(N[Si](C)(C)C)C=C2)C2=CC3=C(C=C2C1)OCO3	3108.7	Semi standard non polar	33892256
4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine,1TMS,isomer #1	CC1=NN=C(C2=CC=C(N[Si](C)(C)C)C=C2)C2=CC3=C(C=C2C1)OCO3	2776.9	Standard non polar	33892256
4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine,1TMS,isomer #1	CC1=NN=C(C2=CC=C(N[Si](C)(C)C)C=C2)C2=CC3=C(C=C2C1)OCO3	4358.6	Standard polar	33892256
4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine,2TMS,isomer #1	CC1=NN=C(C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)C2=CC3=C(C=C2C1)OCO3	3049.4	Semi standard non polar	33892256
4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine,2TMS,isomer #1	CC1=NN=C(C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)C2=CC3=C(C=C2C1)OCO3	2874.9	Standard non polar	33892256
4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine,2TMS,isomer #1	CC1=NN=C(C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)C2=CC3=C(C=C2C1)OCO3	4351.6	Standard polar	33892256
4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine,1TBDMS,isomer #1	CC1=NN=C(C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)C2=CC3=C(C=C2C1)OCO3	3301.8	Semi standard non polar	33892256
4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine,1TBDMS,isomer #1	CC1=NN=C(C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)C2=CC3=C(C=C2C1)OCO3	2987.5	Standard non polar	33892256
4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine,1TBDMS,isomer #1	CC1=NN=C(C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)C2=CC3=C(C=C2C1)OCO3	4458.7	Standard polar	33892256
4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine,2TBDMS,isomer #1	CC1=NN=C(C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C2=CC3=C(C=C2C1)OCO3	3379.3	Semi standard non polar	33892256
4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine,2TBDMS,isomer #1	CC1=NN=C(C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C2=CC3=C(C=C2C1)OCO3	3303.1	Standard non polar	33892256
4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine,2TBDMS,isomer #1	CC1=NN=C(C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)C2=CC3=C(C=C2C1)OCO3	4486.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fb9-0290000000-1a3a4dab5619b7e5e917	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine 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 - 4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine 10V, Negative-QTOF	splash10-0006-0090000000-c7b26c91f7086b4cc21f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine 20V, Negative-QTOF	splash10-0006-0090000000-44e5993c0ac93feb6e8f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine 40V, Negative-QTOF	splash10-03dl-0090000000-da947b32e62f3ce06210	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine 10V, Positive-QTOF	splash10-0006-0090000000-ce7dac974a90f440783e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine 20V, Positive-QTOF	splash10-0006-0090000000-340b9025169635b686bd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine 40V, Positive-QTOF	splash10-0f9i-0190000000-c9ddffc41671807baee2	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

Not Available

KEGG Compound ID

C15040

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3538

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 4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine (HMDB0252997)

MOL for HMDB0252997 (4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine)

3D MOL for HMDB0252997 (4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine)

3D SDF for HMDB0252997 (4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine)

3D-SDF for HMDB0252997 (4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine)

PDB for HMDB0252997 (4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine)

3D PDB for HMDB0252997 (4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine)

SMILES for HMDB0252997 (4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine)

INCHI for HMDB0252997 (4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine)

Structure for HMDB0252997 (4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine)

3D Structure for HMDB0252997 (4-(8-Methyl-9H-1,3-dioxolo(4,5-h)(2,3)benzodiazepin-5-yl)benzenamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra