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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 15:24:48 UTC

Update Date

2021-09-26 23:10:38 UTC

HMDB ID

HMDB0255631

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Nitracrine

Description

Nitracrine, also known as ledakrin, belongs to the class of organic compounds known as acridines. These are organic compounds containing the acridine moiety, a linear tricyclic heterocycle which consists of two benzene rings joined by a pyridine ring. Based on a literature review a significant number of articles have been published on Nitracrine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Nitracrine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Nitracrine 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

HMDB0255631
     RDKit          3D
Nitracrine
 44 46  0  0  0  0  0  0  0  0999 V2000
    4.8768    1.2622    0.5452 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2208   -0.0346    0.7033 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0401   -1.0316    0.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8979    0.1012    0.1299 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0751   -1.1279    0.1771 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7138   -0.8802   -0.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0608    0.1386    0.3048 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4524    0.1068    0.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1105   -0.9740    0.7306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4047   -1.8249    1.5537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0369   -2.8700    2.2138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3863   -3.0527    2.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0789   -2.1965    1.2203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4528   -1.1489    0.5582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1041   -0.2946   -0.2164 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5101    0.7445   -0.8429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2879    1.6141   -1.5598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7821    2.7338   -2.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4489    2.9594   -2.0312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5930    2.0836   -1.2975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2761    2.4895   -1.1556 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.7580    1.9332   -1.2928 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1206    3.9008   -0.9292 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.1326    0.9785   -0.7085 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5670    1.2644   -0.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1223    2.0653    0.3054 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3609    1.5151    1.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0458   -0.9554    0.6020 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7056   -2.0644    0.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2486   -0.8494   -0.9745 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3916    0.9169    0.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9587    0.4150   -0.9421 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5171   -1.9530   -0.4583 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9318   -1.5120    1.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8940   -0.6173   -1.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1408   -1.8334   -0.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3835    0.7921    0.9326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3597   -1.6581    1.7135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4805   -3.5462    2.8648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8856   -3.8738    2.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1297   -2.3505    1.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3682    1.4101   -1.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4209    3.4161   -2.7354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9663    3.8080   -2.4675 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  1  0
  8  9  2  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
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 20 24  2  0
 24  8  1  0
 14  9  1  0
 24 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  7 37  1  0
 10 38  1  0
 11 39  1  0
 12 40  1  0
 13 41  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
M  CHG  2  21   1  23  -1
M  END

  Mrv1652309112117252D          

 24 26  0  0  0  0            999 V2000
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    5.0013    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.8875    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  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  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
 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
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
  8 17  1  0  0  0  0
 10 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
  9 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
M  CHG  2  22   1  24  -1
M  END
> <DATABASE_ID>
HMDB0255631

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)CCCNC1=C2C(C=CC=C2[N+]([O-])=O)=NC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C18H20N4O2/c1-21(2)12-6-11-19-18-13-7-3-4-8-14(13)20-15-9-5-10-16(17(15)18)22(23)24/h3-5,7-10H,6,11-12H2,1-2H3,(H,19,20)

> <INCHI_KEY>
YMVWGSQGCWCDGW-UHFFFAOYSA-N

> <FORMULA>
C18H20N4O2

> <MOLECULAR_WEIGHT>
324.384

> <EXACT_MASS>
324.1586259

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
35.08708504905641

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[3-(dimethylamino)propyl]-1-nitroacridin-9-amine

> <ALOGPS_LOGP>
3.91

> <JCHEM_LOGP>
2.997594131666667

> <ALOGPS_LOGS>
-4.17

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_BASIC>
9.401381414237145

> <JCHEM_POLAR_SURFACE_AREA>
71.3

> <JCHEM_REFRACTIVITY>
95.4563

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.21e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nitracrine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0255631
     RDKit          3D
Nitracrine
 44 46  0  0  0  0  0  0  0  0999 V2000
    4.8768    1.2622    0.5452 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2208   -0.0346    0.7033 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0401   -1.0316    0.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8979    0.1012    0.1299 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0751   -1.1279    0.1771 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7138   -0.8802   -0.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0608    0.1386    0.3048 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4524    0.1068    0.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1105   -0.9740    0.7306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4047   -1.8249    1.5537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0369   -2.8700    2.2138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3863   -3.0527    2.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0789   -2.1965    1.2203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4528   -1.1489    0.5582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1041   -0.2946   -0.2164 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5101    0.7445   -0.8429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2879    1.6141   -1.5598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7821    2.7338   -2.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4489    2.9594   -2.0312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5930    2.0836   -1.2975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2761    2.4895   -1.1556 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.7580    1.9332   -1.2928 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1206    3.9008   -0.9292 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.1326    0.9785   -0.7085 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5670    1.2644   -0.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1223    2.0653    0.3054 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3609    1.5151    1.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0458   -0.9554    0.6020 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7056   -2.0644    0.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2486   -0.8494   -0.9745 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3916    0.9169    0.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9587    0.4150   -0.9421 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5171   -1.9530   -0.4583 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9318   -1.5120    1.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8940   -0.6173   -1.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1408   -1.8334   -0.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3835    0.7921    0.9326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3597   -1.6581    1.7135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4805   -3.5462    2.8648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8856   -3.8738    2.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1297   -2.3505    1.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3682    1.4101   -1.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4209    3.4161   -2.7354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9663    3.8080   -2.4675 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  1  0
  8  9  2  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
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 20 24  2  0
 24  8  1  0
 14  9  1  0
 24 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  7 37  1  0
 10 38  1  0
 11 39  1  0
 12 40  1  0
 13 41  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
M  CHG  2  21   1  23  -1
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       2.667   4.620   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   5.390   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       8.002   4.620   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336   0.770   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       8.002   0.000   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.003   0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.669   3.080   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      10.669   4.620   0.000  0.00  0.00           N+1
HETATM   23  O   UNK     0       9.336   5.390   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      12.003   5.390   0.000  0.00  0.00           O-1
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   17                                                  
CONECT    9    8   10   21                                                  
CONECT   10    9   11   18                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12    8                                                  
CONECT   18   10   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20    9   22                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0255631
HETATM    1  C1  UNL     1       4.877   1.262   0.545  1.00  0.00           C  
HETATM    2  N1  UNL     1       4.221  -0.035   0.703  1.00  0.00           N  
HETATM    3  C2  UNL     1       5.040  -1.032   0.100  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.898   0.101   0.130  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.075  -1.128   0.177  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.714  -0.880  -0.399  1.00  0.00           C  
HETATM    7  N2  UNL     1      -0.061   0.139   0.305  1.00  0.00           N  
HETATM    8  C6  UNL     1      -1.452   0.107   0.078  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.110  -0.974   0.731  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.405  -1.825   1.554  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.037  -2.870   2.214  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.386  -3.053   2.041  1.00  0.00           C  
HETATM   13  C11 UNL     1      -4.079  -2.196   1.220  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.453  -1.149   0.558  1.00  0.00           C  
HETATM   15  N3  UNL     1      -4.104  -0.295  -0.216  1.00  0.00           N  
HETATM   16  C13 UNL     1      -3.510   0.744  -0.843  1.00  0.00           C  
HETATM   17  C14 UNL     1      -4.288   1.614  -1.560  1.00  0.00           C  
HETATM   18  C15 UNL     1      -3.782   2.734  -2.166  1.00  0.00           C  
HETATM   19  C16 UNL     1      -2.449   2.959  -2.031  1.00  0.00           C  
HETATM   20  C17 UNL     1      -1.593   2.084  -1.297  1.00  0.00           C  
HETATM   21  N4  UNL     1      -0.276   2.490  -1.156  1.00  0.00           N1+
HETATM   22  O1  UNL     1       0.758   1.933  -1.293  1.00  0.00           O  
HETATM   23  O2  UNL     1      -0.121   3.901  -0.929  1.00  0.00           O1-
HETATM   24  C18 UNL     1      -2.133   0.979  -0.708  1.00  0.00           C  
HETATM   25  H1  UNL     1       5.567   1.264  -0.327  1.00  0.00           H  
HETATM   26  H2  UNL     1       4.122   2.065   0.305  1.00  0.00           H  
HETATM   27  H3  UNL     1       5.361   1.515   1.495  1.00  0.00           H  
HETATM   28  H4  UNL     1       6.046  -0.955   0.602  1.00  0.00           H  
HETATM   29  H5  UNL     1       4.706  -2.064   0.277  1.00  0.00           H  
HETATM   30  H6  UNL     1       5.249  -0.849  -0.974  1.00  0.00           H  
HETATM   31  H7  UNL     1       2.392   0.917   0.670  1.00  0.00           H  
HETATM   32  H8  UNL     1       2.959   0.415  -0.942  1.00  0.00           H  
HETATM   33  H9  UNL     1       2.517  -1.953  -0.458  1.00  0.00           H  
HETATM   34  H10 UNL     1       1.932  -1.512   1.226  1.00  0.00           H  
HETATM   35  H11 UNL     1       0.894  -0.617  -1.485  1.00  0.00           H  
HETATM   36  H12 UNL     1       0.141  -1.833  -0.450  1.00  0.00           H  
HETATM   37  H13 UNL     1       0.383   0.792   0.933  1.00  0.00           H  
HETATM   38  H14 UNL     1      -0.360  -1.658   1.713  1.00  0.00           H  
HETATM   39  H15 UNL     1      -1.480  -3.546   2.865  1.00  0.00           H  
HETATM   40  H16 UNL     1      -3.886  -3.874   2.558  1.00  0.00           H  
HETATM   41  H17 UNL     1      -5.130  -2.351   1.097  1.00  0.00           H  
HETATM   42  H18 UNL     1      -5.368   1.410  -1.659  1.00  0.00           H  
HETATM   43  H19 UNL     1      -4.421   3.416  -2.735  1.00  0.00           H  
HETATM   44  H20 UNL     1      -1.966   3.808  -2.467  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    4
CONECT    3   28   29   30
CONECT    4    5   31   32
CONECT    5    6   33   34
CONECT    6    7   35   36
CONECT    7    8   37
CONECT    8    9    9   24
CONECT    9   10   14
CONECT   10   11   11   38
CONECT   11   12   39
CONECT   12   13   13   40
CONECT   13   14   41
CONECT   14   15   15
CONECT   15   16
CONECT   16   17   17   24
CONECT   17   18   42
CONECT   18   19   19   43
CONECT   19   20   44
CONECT   20   21   24   24
CONECT   21   22   22   23
END

HMDB0255631
     RDKit          3D
Nitracrine
 44 46  0  0  0  0  0  0  0  0999 V2000
    4.8768    1.2622    0.5452 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2208   -0.0346    0.7033 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0401   -1.0316    0.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8979    0.1012    0.1299 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0751   -1.1279    0.1771 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7138   -0.8802   -0.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0608    0.1386    0.3048 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4524    0.1068    0.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1105   -0.9740    0.7306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4047   -1.8249    1.5537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0369   -2.8700    2.2138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3863   -3.0527    2.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0789   -2.1965    1.2203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4528   -1.1489    0.5582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1041   -0.2946   -0.2164 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5101    0.7445   -0.8429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2879    1.6141   -1.5598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7821    2.7338   -2.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4489    2.9594   -2.0312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5930    2.0836   -1.2975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2761    2.4895   -1.1556 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.7580    1.9332   -1.2928 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1206    3.9008   -0.9292 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.1326    0.9785   -0.7085 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5670    1.2644   -0.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1223    2.0653    0.3054 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3609    1.5151    1.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0458   -0.9554    0.6020 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7056   -2.0644    0.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2486   -0.8494   -0.9745 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3916    0.9169    0.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9587    0.4150   -0.9421 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5171   -1.9530   -0.4583 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9318   -1.5120    1.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8940   -0.6173   -1.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1408   -1.8334   -0.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3835    0.7921    0.9326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3597   -1.6581    1.7135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4805   -3.5462    2.8648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8856   -3.8738    2.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1297   -2.3505    1.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3682    1.4101   -1.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4209    3.4161   -2.7354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9663    3.8080   -2.4675 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  1  0
  8  9  2  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
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 20 24  2  0
 24  8  1  0
 14  9  1  0
 24 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  7 37  1  0
 10 38  1  0
 11 39  1  0
 12 40  1  0
 13 41  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
M  CHG  2  21   1  23  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Ledakrin	HMDB

Chemical Formula

C₁₈H₂₀N₄O₂

Average Molecular Weight

324.384

Monoisotopic Molecular Weight

324.1586259

IUPAC Name

N-[3-(dimethylamino)propyl]-1-nitroacridin-9-amine

Traditional Name

nitracrine

CAS Registry Number

Not Available

SMILES

CN(C)CCCNC1=C2C(C=CC=C2[N+]([O-])=O)=NC2=CC=CC=C12

InChI Identifier

InChI=1S/C18H20N4O2/c1-21(2)12-6-11-19-18-13-7-3-4-8-14(13)20-15-9-5-10-16(17(15)18)22(23)24/h3-5,7-10H,6,11-12H2,1-2H3,(H,19,20)

InChI Key

YMVWGSQGCWCDGW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acridines. These are organic compounds containing the acridine moiety, a linear tricyclic heterocycle which consists of two benzene rings joined by a pyridine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Benzoquinolines

Direct Parent

Acridines

Alternative Parents

Substituents

Acridine
Nitroquinoline
Aminoquinoline
4-aminoquinoline
Nitroaromatic compound
Aminopyridine
Secondary aliphatic/aromatic amine
Pyridine
Benzenoid
Heteroaromatic compound
C-nitro compound
Organic nitro compound
Tertiary amine
Tertiary aliphatic amine
Organic oxoazanium
Azacycle
Organic 1,3-dipolar compound
Secondary amine
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Organic oxygen compound
Organopnictogen compound
Organic oxide
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	3.91	ALOGPS
logP	3	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Basic)	9.4	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.3 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	95.46 m³·mol⁻¹	ChemAxon
Polarizability	35.09 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	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	208.56	30932474
DeepCCS	[M+Na]+	184.799	30932474
AllCCS	[M+H]+	176.3	32859911
AllCCS	[M+H-H2O]+	173.1	32859911
AllCCS	[M+NH4]+	179.3	32859911
AllCCS	[M+Na]+	180.2	32859911
AllCCS	[M-H]-	181.7	32859911
AllCCS	[M+Na-2H]-	181.2	32859911
AllCCS	[M+HCOO]-	180.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nitracrine	CN(C)CCCNC1=C2C(C=CC=C2[N+]([O-])=O)=NC2=CC=CC=C12	3955.4	Standard polar	33892256
Nitracrine	CN(C)CCCNC1=C2C(C=CC=C2[N+]([O-])=O)=NC2=CC=CC=C12	2998.4	Standard non polar	33892256
Nitracrine	CN(C)CCCNC1=C2C(C=CC=C2[N+]([O-])=O)=NC2=CC=CC=C12	3094.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nitracrine,1TMS,isomer #1	CN(C)CCCN(C1=C2C=CC=CC2=NC2=CC=CC([N+](=O)[O-])=C12)[Si](C)(C)C	2943.0	Semi standard non polar	33892256
Nitracrine,1TMS,isomer #1	CN(C)CCCN(C1=C2C=CC=CC2=NC2=CC=CC([N+](=O)[O-])=C12)[Si](C)(C)C	2756.9	Standard non polar	33892256
Nitracrine,1TMS,isomer #1	CN(C)CCCN(C1=C2C=CC=CC2=NC2=CC=CC([N+](=O)[O-])=C12)[Si](C)(C)C	3579.4	Standard polar	33892256
Nitracrine,1TBDMS,isomer #1	CN(C)CCCN(C1=C2C=CC=CC2=NC2=CC=CC([N+](=O)[O-])=C12)[Si](C)(C)C(C)(C)C	3145.4	Semi standard non polar	33892256
Nitracrine,1TBDMS,isomer #1	CN(C)CCCN(C1=C2C=CC=CC2=NC2=CC=CC([N+](=O)[O-])=C12)[Si](C)(C)C(C)(C)C	2969.1	Standard non polar	33892256
Nitracrine,1TBDMS,isomer #1	CN(C)CCCN(C1=C2C=CC=CC2=NC2=CC=CC([N+](=O)[O-])=C12)[Si](C)(C)C(C)(C)C	3650.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Nitracrine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9072000000-8a70f45f853c9b51bcbb	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nitracrine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	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

19425

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

20628

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 Nitracrine (HMDB0255631)

MOL for HMDB0255631 (Nitracrine)

3D MOL for HMDB0255631 (Nitracrine)

3D SDF for HMDB0255631 (Nitracrine)

3D-SDF for HMDB0255631 (Nitracrine)

PDB for HMDB0255631 (Nitracrine)

3D PDB for HMDB0255631 (Nitracrine)

SMILES for HMDB0255631 (Nitracrine)

INCHI for HMDB0255631 (Nitracrine)

Structure for HMDB0255631 (Nitracrine)

3D Structure for HMDB0255631 (Nitracrine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra