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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:39 UTC

HMDB ID

HMDB0014550

Secondary Accession Numbers

HMDB14550

Metabolite Identification

Common Name

Gentian Violet

Description

Gentian Violet is only found in individuals that have used or taken this drug. It is a dye that is a mixture of violet rosanilinis with antibacterial, antifungal, and anthelmintic properties. [PubChem]In aqueous solutions Gentian violet (GV) dissociates into positive (GV+)and negative ions (Cl-) that penetrate through the wall and membrane of both gram-positive and gram-negative bacterial cells. The GV+ interacts with negatively charged components of bacterial cells including the lipopolysaccharide (on the cell wall), the peptidoglycan and DNA. A similar cell penetration and DNA binding process is thought to take place for fungal cells as well. Because Gentian violet is a mutagen and mitotic poison, cell growth is consequently inhibited. A photodynamic action of gentian violet, apparently mediated by a free-radical mechanism, has recently been described in bacteria and in the protozoan T. cruzi. Evidence also suggests that gentian violet dissipates the bacterial (and mitochondrial) membrane potential by inducing permeability. This is followed by respiratory inhibition. This anti-mitochondrial activity might explain gentian violet's efficacy towards both bacteria and yeast with relatively mild effects on mammalian cells.

Structure

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

3468
  Mrv0541 02231214392D          

 28 30  0  0  0  0            999 V2000
    8.0804    2.2688    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.2688    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -2.6813    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    5.2224    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  2 15  1  0  0  0  0
  2 23  1  0  0  0  0
  2 24  1  0  0  0  0
  3 16  2  0  0  0  0
  3 27  1  0  0  0  0
  3 28  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  2  0  0  0  0
  5  8  2  0  0  0  0
  5 10  1  0  0  0  0
  6  9  2  0  0  0  0
  6 11  1  0  0  0  0
  7 12  1  0  0  0  0
  7 13  1  0  0  0  0
  8 17  1  0  0  0  0
  9 18  1  0  0  0  0
 10 19  2  0  0  0  0
 11 20  2  0  0  0  0
 12 21  2  0  0  0  0
 13 22  2  0  0  0  0
 14 17  2  0  0  0  0
 14 19  1  0  0  0  0
 15 18  2  0  0  0  0
 15 20  1  0  0  0  0
 16 21  1  0  0  0  0
 16 22  1  0  0  0  0
M  CHG  1   3   1
M  END

HMDB0014550
     RDKit          3D
Gentian Violet
 58 60  0  0  0  0  0  0  0  0999 V2000
   -0.1506    6.4316   -0.4100 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5961    5.5106    0.4127 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6261    5.9243    1.3545 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3291    4.1313    0.3238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8871    3.4534   -0.7471 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6749    2.1052   -0.8516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0860    1.4284    0.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2454   -0.0299   -0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4075   -0.6536   -0.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4515   -2.1278   -0.1113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6072   -2.7798   -0.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8649   -2.0493    0.0248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9828   -2.6865    0.0484 N   0  0  0  0  0  4  0  0  0  0  0  0
   -6.2229   -1.9180    0.1754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0643   -4.1302   -0.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8444   -0.5896    0.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6754    0.0305    0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0071   -0.7669   -0.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7278   -1.0774    1.0170 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9338   -1.7385    0.9540 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4260   -2.0946   -0.2951 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6499   -2.7735   -0.4536 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6687   -4.1999   -0.5610 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8844   -2.0415   -0.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7249   -1.7952   -1.4645 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5017   -1.1230   -1.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6259    2.1334    1.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4221    3.4921    1.2652 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0938    7.4956   -0.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2329    6.2540   -0.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1222    6.2399   -1.4723 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2404    5.0620    1.6821 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0790    6.2572    2.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2768    6.7197    0.9550 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4764    3.9605   -1.4942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0934    1.5178   -1.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5398   -2.6808   -0.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6180   -3.8573   -0.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0637   -2.6181    0.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3459   -1.2726   -0.7107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2346   -1.3426    1.1237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0610   -4.4950    0.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0635   -4.4355   -1.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3209   -4.6580    0.5858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7727   -0.0188    0.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    1.1171    0.1820 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3504   -0.8013    1.9916 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5320   -2.0036    1.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7059   -4.6036   -0.4783 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0037   -4.6488    0.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2054   -4.4514   -1.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7751   -0.9810   -0.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2793   -1.9971   -1.5457 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6808   -2.4706    0.1543 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1278   -2.0789   -2.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9980   -0.9185   -2.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2214    1.6214    1.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8617    4.0227    2.1236 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  3
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  3
 13 14  1  0
 13 15  1  0
 12 16  1  0
 16 17  2  0
  8 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 21 25  1  0
 25 26  2  0
  7 27  1  0
 27 28  2  0
 28  4  1  0
 17  9  1  0
 26 18  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  3 33  1  0
  3 34  1  0
  5 35  1  0
  6 36  1  0
 10 37  1  0
 11 38  1  0
 14 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 17 46  1  0
 19 47  1  0
 20 48  1  0
 23 49  1  0
 23 50  1  0
 23 51  1  0
 24 52  1  0
 24 53  1  0
 24 54  1  0
 25 55  1  0
 26 56  1  0
 27 57  1  0
 28 58  1  0
M  CHG  1  13   1
M  END

3468
  Mrv0541 02231214392D          

 28 30  0  0  0  0            999 V2000
    8.0804    2.2688    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.2688    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -2.6813    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    5.2224    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  2 15  1  0  0  0  0
  2 23  1  0  0  0  0
  2 24  1  0  0  0  0
  3 16  2  0  0  0  0
  3 27  1  0  0  0  0
  3 28  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  2  0  0  0  0
  5  8  2  0  0  0  0
  5 10  1  0  0  0  0
  6  9  2  0  0  0  0
  6 11  1  0  0  0  0
  7 12  1  0  0  0  0
  7 13  1  0  0  0  0
  8 17  1  0  0  0  0
  9 18  1  0  0  0  0
 10 19  2  0  0  0  0
 11 20  2  0  0  0  0
 12 21  2  0  0  0  0
 13 22  2  0  0  0  0
 14 17  2  0  0  0  0
 14 19  1  0  0  0  0
 15 18  2  0  0  0  0
 15 20  1  0  0  0  0
 16 21  1  0  0  0  0
 16 22  1  0  0  0  0
M  CHG  1   3   1
M  END
> <DATABASE_ID>
HMDB0014550

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)C1=CC=C(C=C1)C(C1=CC=C(C=C1)N(C)C)=C1C=CC(C=C1)=[N+](C)C

> <INCHI_IDENTIFIER>
InChI=1S/C25H30N3/c1-26(2)22-13-7-19(8-14-22)25(20-9-15-23(16-10-20)27(3)4)21-11-17-24(18-12-21)28(5)6/h7-18H,1-6H3/q+1

> <INCHI_KEY>
LGLFFNDHMLKUMI-UHFFFAOYSA-N

> <FORMULA>
C25H30N3

> <MOLECULAR_WEIGHT>
372.5258

> <EXACT_MASS>
372.243972975

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
45.60353055534987

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-{bis[4-(dimethylamino)phenyl]methylidene}-N,N-dimethylcyclohexa-2,5-dien-1-iminium

> <ALOGPS_LOGP>
0.87

> <JCHEM_LOGP>
1.3955111288615885

> <ALOGPS_LOGS>
-5.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
4.826430924312215

> <JCHEM_POLAR_SURFACE_AREA>
9.49

> <JCHEM_REFRACTIVITY>
146.00389999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.93e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gentian violet

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014550
     RDKit          3D
Gentian Violet
 58 60  0  0  0  0  0  0  0  0999 V2000
   -0.1506    6.4316   -0.4100 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5961    5.5106    0.4127 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6261    5.9243    1.3545 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3291    4.1313    0.3238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8871    3.4534   -0.7471 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6749    2.1052   -0.8516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0860    1.4284    0.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2454   -0.0299   -0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4075   -0.6536   -0.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4515   -2.1278   -0.1113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6072   -2.7798   -0.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8649   -2.0493    0.0248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9828   -2.6865    0.0484 N   0  0  0  0  0  4  0  0  0  0  0  0
   -6.2229   -1.9180    0.1754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0643   -4.1302   -0.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8444   -0.5896    0.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6754    0.0305    0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0071   -0.7669   -0.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7278   -1.0774    1.0170 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9338   -1.7385    0.9540 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4260   -2.0946   -0.2951 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6499   -2.7735   -0.4536 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6687   -4.1999   -0.5610 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8844   -2.0415   -0.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7249   -1.7952   -1.4645 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5017   -1.1230   -1.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6259    2.1334    1.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4221    3.4921    1.2652 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0938    7.4956   -0.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2329    6.2540   -0.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1222    6.2399   -1.4723 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2404    5.0620    1.6821 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0790    6.2572    2.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2768    6.7197    0.9550 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4764    3.9605   -1.4942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0934    1.5178   -1.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5398   -2.6808   -0.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6180   -3.8573   -0.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0637   -2.6181    0.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3459   -1.2726   -0.7107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2346   -1.3426    1.1237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0610   -4.4950    0.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0635   -4.4355   -1.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3209   -4.6580    0.5858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7727   -0.0188    0.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    1.1171    0.1820 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3504   -0.8013    1.9916 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5320   -2.0036    1.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7059   -4.6036   -0.4783 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0037   -4.6488    0.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2054   -4.4514   -1.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7751   -0.9810   -0.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2793   -1.9971   -1.5457 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6808   -2.4706    0.1543 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1278   -2.0789   -2.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9980   -0.9185   -2.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2214    1.6214    1.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8617    4.0227    2.1236 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  3
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  3
 13 14  1  0
 13 15  1  0
 12 16  1  0
 16 17  2  0
  8 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 21 25  1  0
 25 26  2  0
  7 27  1  0
 27 28  2  0
 28  4  1  0
 17  9  1  0
 26 18  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  3 33  1  0
  3 34  1  0
  5 35  1  0
  6 36  1  0
 10 37  1  0
 11 38  1  0
 14 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 17 46  1  0
 19 47  1  0
 20 48  1  0
 23 49  1  0
 23 50  1  0
 23 51  1  0
 24 52  1  0
 24 53  1  0
 24 54  1  0
 25 55  1  0
 26 56  1  0
 27 57  1  0
 28 58  1  0
M  CHG  1  13   1
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 3468                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0      15.083   4.235   0.000  0.00  0.00           N+0
HETATM    2  N   UNK     0       4.414   4.235   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       9.748  -5.005   0.000  0.00  0.00           N+1
HETATM    4  C   UNK     0       9.748   1.155   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.082   1.925   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.415   1.925   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.748  -0.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.082   3.465   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.081   1.155   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.416   1.155   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.415   3.465   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.082  -1.155   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.415  -1.155   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.750   3.465   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.747   3.465   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.748  -3.465   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.416   4.235   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.747   1.925   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.750   1.925   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.081   4.235   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.082  -2.695   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.415  -2.695   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.414   5.775   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.080   3.465   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.083   5.775   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      16.417   3.465   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.415  -5.775   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.082  -5.775   0.000  0.00  0.00           C+0
CONECT    1   14   25   26                                                  
CONECT    2   15   23   24                                                  
CONECT    3   16   27   28                                                  
CONECT    4    5    6    7                                                  
CONECT    5    4    8   10                                                  
CONECT    6    4    9   11                                                  
CONECT    7    4   12   13                                                  
CONECT    8    5   17                                                       
CONECT    9    6   18                                                       
CONECT   10    5   19                                                       
CONECT   11    6   20                                                       
CONECT   12    7   21                                                       
CONECT   13    7   22                                                       
CONECT   14    1   17   19                                                  
CONECT   15    2   18   20                                                  
CONECT   16    3   21   22                                                  
CONECT   17    8   14                                                       
CONECT   18    9   15                                                       
CONECT   19   10   14                                                       
CONECT   20   11   15                                                       
CONECT   21   12   16                                                       
CONECT   22   13   16                                                       
CONECT   23    2                                                            
CONECT   24    2                                                            
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    3                                                            
CONECT   28    3                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

COMPND    HMDB0014550
HETATM    1  C1  UNL     1      -0.151   6.432  -0.410  1.00  0.00           C  
HETATM    2  N1  UNL     1       0.596   5.511   0.413  1.00  0.00           N  
HETATM    3  C2  UNL     1       1.626   5.924   1.354  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.329   4.131   0.324  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.887   3.453  -0.747  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.675   2.105  -0.852  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.086   1.428   0.095  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.245  -0.030  -0.012  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.407  -0.654  -0.002  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.451  -2.128  -0.111  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.607  -2.780  -0.098  1.00  0.00           C  
HETATM   12  C11 UNL     1      -3.865  -2.049   0.025  1.00  0.00           C  
HETATM   13  N2  UNL     1      -4.983  -2.687   0.048  1.00  0.00           N1+
HETATM   14  C12 UNL     1      -6.223  -1.918   0.175  1.00  0.00           C  
HETATM   15  C13 UNL     1      -5.064  -4.130  -0.040  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.844  -0.590   0.133  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.675   0.031   0.116  1.00  0.00           C  
HETATM   18  C16 UNL     1       1.007  -0.767  -0.122  1.00  0.00           C  
HETATM   19  C17 UNL     1       1.728  -1.077   1.017  1.00  0.00           C  
HETATM   20  C18 UNL     1       2.934  -1.739   0.954  1.00  0.00           C  
HETATM   21  C19 UNL     1       3.426  -2.095  -0.295  1.00  0.00           C  
HETATM   22  N3  UNL     1       4.650  -2.774  -0.454  1.00  0.00           N  
HETATM   23  C20 UNL     1       4.669  -4.200  -0.561  1.00  0.00           C  
HETATM   24  C21 UNL     1       5.884  -2.041  -0.501  1.00  0.00           C  
HETATM   25  C22 UNL     1       2.725  -1.795  -1.464  1.00  0.00           C  
HETATM   26  C23 UNL     1       1.502  -1.123  -1.349  1.00  0.00           C  
HETATM   27  C24 UNL     1      -0.626   2.133   1.144  1.00  0.00           C  
HETATM   28  C25 UNL     1      -0.422   3.492   1.265  1.00  0.00           C  
HETATM   29  H1  UNL     1       0.094   7.496  -0.210  1.00  0.00           H  
HETATM   30  H2  UNL     1      -1.233   6.254  -0.290  1.00  0.00           H  
HETATM   31  H3  UNL     1       0.122   6.240  -1.472  1.00  0.00           H  
HETATM   32  H4  UNL     1       2.240   5.062   1.682  1.00  0.00           H  
HETATM   33  H5  UNL     1       1.079   6.257   2.271  1.00  0.00           H  
HETATM   34  H6  UNL     1       2.277   6.720   0.955  1.00  0.00           H  
HETATM   35  H7  UNL     1       1.476   3.960  -1.494  1.00  0.00           H  
HETATM   36  H8  UNL     1       1.093   1.518  -1.680  1.00  0.00           H  
HETATM   37  H9  UNL     1      -0.540  -2.681  -0.206  1.00  0.00           H  
HETATM   38  H10 UNL     1      -2.618  -3.857  -0.176  1.00  0.00           H  
HETATM   39  H11 UNL     1      -7.064  -2.618   0.207  1.00  0.00           H  
HETATM   40  H12 UNL     1      -6.346  -1.273  -0.711  1.00  0.00           H  
HETATM   41  H13 UNL     1      -6.235  -1.343   1.124  1.00  0.00           H  
HETATM   42  H14 UNL     1      -6.061  -4.495   0.354  1.00  0.00           H  
HETATM   43  H15 UNL     1      -5.063  -4.436  -1.105  1.00  0.00           H  
HETATM   44  H16 UNL     1      -4.321  -4.658   0.586  1.00  0.00           H  
HETATM   45  H17 UNL     1      -4.773  -0.019   0.226  1.00  0.00           H  
HETATM   46  H18 UNL     1      -2.691   1.117   0.182  1.00  0.00           H  
HETATM   47  H19 UNL     1       1.350  -0.801   1.992  1.00  0.00           H  
HETATM   48  H20 UNL     1       3.532  -2.004   1.810  1.00  0.00           H  
HETATM   49  H21 UNL     1       5.706  -4.604  -0.478  1.00  0.00           H  
HETATM   50  H22 UNL     1       4.004  -4.649   0.201  1.00  0.00           H  
HETATM   51  H23 UNL     1       4.205  -4.451  -1.558  1.00  0.00           H  
HETATM   52  H24 UNL     1       5.775  -0.981  -0.181  1.00  0.00           H  
HETATM   53  H25 UNL     1       6.279  -1.997  -1.546  1.00  0.00           H  
HETATM   54  H26 UNL     1       6.681  -2.471   0.154  1.00  0.00           H  
HETATM   55  H27 UNL     1       3.128  -2.079  -2.434  1.00  0.00           H  
HETATM   56  H28 UNL     1       0.998  -0.919  -2.287  1.00  0.00           H  
HETATM   57  H29 UNL     1      -1.221   1.621   1.916  1.00  0.00           H  
HETATM   58  H30 UNL     1      -0.862   4.023   2.124  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3    4
CONECT    3   32   33   34
CONECT    4    5    5   28
CONECT    5    6   35
CONECT    6    7    7   36
CONECT    7    8   27
CONECT    8    9    9   18
CONECT    9   10   17
CONECT   10   11   11   37
CONECT   11   12   38
CONECT   12   13   13   16
CONECT   13   14   15
CONECT   14   39   40   41
CONECT   15   42   43   44
CONECT   16   17   17   45
CONECT   17   46
CONECT   18   19   19   26
CONECT   19   20   47
CONECT   20   21   21   48
CONECT   21   22   25
CONECT   22   23   24
CONECT   23   49   50   51
CONECT   24   52   53   54
CONECT   25   26   26   55
CONECT   26   56
CONECT   27   28   28   57
CONECT   28   58
END

HMDB0014550
     RDKit          3D
Gentian Violet
 58 60  0  0  0  0  0  0  0  0999 V2000
   -0.1506    6.4316   -0.4100 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5961    5.5106    0.4127 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6261    5.9243    1.3545 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3291    4.1313    0.3238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8871    3.4534   -0.7471 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6749    2.1052   -0.8516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0860    1.4284    0.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2454   -0.0299   -0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4075   -0.6536   -0.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4515   -2.1278   -0.1113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6072   -2.7798   -0.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8649   -2.0493    0.0248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9828   -2.6865    0.0484 N   0  0  0  0  0  4  0  0  0  0  0  0
   -6.2229   -1.9180    0.1754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0643   -4.1302   -0.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8444   -0.5896    0.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6754    0.0305    0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0071   -0.7669   -0.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7278   -1.0774    1.0170 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9338   -1.7385    0.9540 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4260   -2.0946   -0.2951 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6499   -2.7735   -0.4536 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6687   -4.1999   -0.5610 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8844   -2.0415   -0.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7249   -1.7952   -1.4645 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5017   -1.1230   -1.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6259    2.1334    1.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4221    3.4921    1.2652 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0938    7.4956   -0.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2329    6.2540   -0.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1222    6.2399   -1.4723 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2404    5.0620    1.6821 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0790    6.2572    2.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2768    6.7197    0.9550 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4764    3.9605   -1.4942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0934    1.5178   -1.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5398   -2.6808   -0.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6180   -3.8573   -0.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0637   -2.6181    0.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3459   -1.2726   -0.7107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2346   -1.3426    1.1237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0610   -4.4950    0.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0635   -4.4355   -1.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3209   -4.6580    0.5858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7727   -0.0188    0.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    1.1171    0.1820 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3504   -0.8013    1.9916 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5320   -2.0036    1.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7059   -4.6036   -0.4783 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0037   -4.6488    0.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2054   -4.4514   -1.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7751   -0.9810   -0.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2793   -1.9971   -1.5457 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6808   -2.4706    0.1543 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1278   -2.0789   -2.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9980   -0.9185   -2.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2214    1.6214    1.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8617    4.0227    2.1236 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  3
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  3
 13 14  1  0
 13 15  1  0
 12 16  1  0
 16 17  2  0
  8 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 21 25  1  0
 25 26  2  0
  7 27  1  0
 27 28  2  0
 28  4  1  0
 17  9  1  0
 26 18  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  3 33  1  0
  3 34  1  0
  5 35  1  0
  6 36  1  0
 10 37  1  0
 11 38  1  0
 14 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 17 46  1  0
 19 47  1  0
 20 48  1  0
 23 49  1  0
 23 50  1  0
 23 51  1  0
 24 52  1  0
 24 53  1  0
 24 54  1  0
 25 55  1  0
 26 56  1  0
 27 57  1  0
 28 58  1  0
M  CHG  1  13   1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Crystal violet carbocation	ChEBI
Crystal violet ion(1)	ChEBI
Crystal violet(1+)	ChEBI
Gentian violet carbocation	ChEBI
Gentian violet cation	ChEBI
Gentian violet(1+)	ChEBI
Crystal violet	HMDB

Chemical Formula

C₂₅H₃₀N₃

Average Molecular Weight

372.5258

Monoisotopic Molecular Weight

372.243972975

IUPAC Name

4-{bis[4-(dimethylamino)phenyl]methylidene}-N,N-dimethylcyclohexa-2,5-dien-1-iminium

Traditional Name

gentian violet

CAS Registry Number

14426-25-6

SMILES

CN(C)C1=CC=C(C=C1)C(C1=CC=C(C=C1)N(C)C)=C1C=CC(C=C1)=[N+](C)C

InChI Identifier

InChI=1S/C25H30N3/c1-26(2)22-13-7-19(8-14-22)25(20-9-15-23(16-10-20)27(3)4)21-11-17-24(18-12-21)28(5)6/h7-18H,1-6H3/q+1

InChI Key

LGLFFNDHMLKUMI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
Aniline or substituted anilines
Dialkylarylamine
Tertiary aliphatic/aromatic amine
Secondary ketimine
Azomethine
Tertiary amine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Organic cation
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

iminium ion (CHEBI:77181 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014550)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	215 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0019 g/L	Not Available
LogP	3.18	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0019 g/L	ALOGPS
logP	0.87	ALOGPS
logP	1.4	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Basic)	4.83	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.49 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	146 m³·mol⁻¹	ChemAxon
Polarizability	45.6 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	205.655	30932474
DeepCCS	[M-H]-	203.259	30932474
DeepCCS	[M-2H]-	236.144	30932474
DeepCCS	[M+Na]+	211.684	30932474
AllCCS	[M+H]+	194.4	32859911
AllCCS	[M+H-H2O]+	191.6	32859911
AllCCS	[M+NH4]+	197.0	32859911
AllCCS	[M+Na]+	197.8	32859911
AllCCS	[M-H]-	199.9	32859911
AllCCS	[M+Na-2H]-	200.5	32859911
AllCCS	[M+HCOO]-	201.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.35 minutes	32390414
Predicted by Siyang on May 30, 2022	20.7755 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.04 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	30.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3155.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	476.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	254.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	242.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	126.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	752.6 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	537.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	106.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2110.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	552.1 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	1807.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	574.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	431.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	351.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	470.8 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	8.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Gentian Violet	CN(C)C1=CC=C(C=C1)C(C1=CC=C(C=C1)N(C)C)=C1C=CC(C=C1)=[N+](C)C	4321.0	Standard polar	33892256
Gentian Violet	CN(C)C1=CC=C(C=C1)C(C1=CC=C(C=C1)N(C)C)=C1C=CC(C=C1)=[N+](C)C	3205.4	Standard non polar	33892256
Gentian Violet	CN(C)C1=CC=C(C=C1)C(C1=CC=C(C=C1)N(C)C)=C1C=CC(C=C1)=[N+](C)C	3798.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Gentian Violet GC-MS (Non-derivatized) - 70eV, Positive	splash10-0pi0-3049000000-80f825970014ad316343	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gentian Violet 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 - Gentian Violet 10V, Positive-QTOF	splash10-00di-0009000000-a180c3b409add4294548	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gentian Violet 20V, Positive-QTOF	splash10-00di-1009000000-280bb4ba1bf4de1f499c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gentian Violet 40V, Positive-QTOF	splash10-00di-9134000000-e868f5dd8c887ae09188	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gentian Violet 10V, Negative-QTOF	splash10-00di-0009000000-04443be1085d68e12981	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gentian Violet 20V, Negative-QTOF	splash10-00di-0009000000-6c18d897813c5e051baa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gentian Violet 40V, Negative-QTOF	splash10-00xr-9007000000-e9e03d7198bf6e7ffaf7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gentian Violet 10V, Positive-QTOF	splash10-00di-0009000000-d19ae55e6f44c6c20e81	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gentian Violet 20V, Positive-QTOF	splash10-00di-0009000000-fa424c62ab49e3723797	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gentian Violet 40V, Positive-QTOF	splash10-100c-0049000000-e89b52ae60e84c397fa5	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00406	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00406	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00406

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3349

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Crystal violet

METLIN ID

Not Available

PubChem Compound

3468

PDB ID

CVI

ChEBI ID

77181

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

Not Available

Transporters

Enzyme Details

1. Solute carrier family 22 member 1

General function:: Involved in ion transmembrane transporter activity
Specific function:: Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)- N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin- dependent kinase II and LCK tyrosine kinase
Gene Name:: SLC22A1
Uniprot ID:: O15245
Molecular weight:: 61187.4

References

Bednarczyk D, Ekins S, Wikel JH, Wright SH: Influence of molecular structure on substrate binding to the human organic cation transporter, hOCT1. Mol Pharmacol. 2003 Mar;63(3):489-98. [PubMed:12606755 ]

Showing metabocard for Gentian Violet (HMDB0014550)

MOL for HMDB0014550 (Gentian Violet)

3D MOL for HMDB0014550 (Gentian Violet)

3D SDF for HMDB0014550 (Gentian Violet)

3D-SDF for HMDB0014550 (Gentian Violet)

PDB for HMDB0014550 (Gentian Violet)

3D PDB for HMDB0014550 (Gentian Violet)

SMILES for HMDB0014550 (Gentian Violet)

INCHI for HMDB0014550 (Gentian Violet)

Structure for HMDB0014550 (Gentian Violet)

3D Structure for HMDB0014550 (Gentian Violet)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Transporters

References