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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:06:38 UTC

Update Date

2021-09-26 23:07:45 UTC

HMDB ID

HMDB0254034

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Leucomethylene blue

Description

Leucomethylene blue, also known as panatone or LMTX compound, belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring. Leucomethylene blue is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Leucomethylene blue. This compound has been identified in human blood as reported by (PMID: 31557052 ). Leucomethylene blue is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Leucomethylene blue 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

HMDB0254034
     RDKit          3D
Leucomethylene blue
 39 41  0  0  0  0  0  0  0  0999 V2000
   -5.4257    1.3578    0.8394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1417    0.1166    0.1825 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2287   -0.7340   -0.2496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7999   -0.2890   -0.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5347   -1.4964   -0.6881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2280   -1.8716   -0.9041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1418   -1.0753   -0.5015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4639    0.1044    0.1229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7540    0.5030    0.3510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0972    1.1431    0.6488 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.3856    0.2926    0.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5834    0.8964    0.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7896    0.3276    0.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0480    0.9602    0.4764 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2676    0.2830    0.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1128    2.2255    1.1372 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7516   -0.8906   -0.4763 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5779   -1.5293   -0.7945 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3568   -0.9140   -0.4532 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1474   -1.5552   -0.7724 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3170    2.1879    0.1183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4633    1.4114    1.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7639    1.4568    1.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1581   -1.7142    0.2608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1890   -0.8350   -1.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2144   -0.3089   -0.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3588   -2.1182   -1.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0500   -2.8237   -1.4068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9180    1.4644    0.8584 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5982    1.8600    0.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3319   -0.7036    0.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1460    0.9124    0.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1717    0.0288   -0.9860 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1063    2.6760    0.9440 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0845    2.0525    2.2497 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3183    2.9398    0.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6894   -1.3564   -0.7349 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5513   -2.4816   -1.2944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2299   -2.5033   -1.2717 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  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 13 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
  9  4  1  0
 19 11  1  0
 20  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  5 27  1  0
  6 28  1  0
  9 29  1  0
 12 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 20 39  1  0
M  END

  Mrv1652309112115062D          

 20 22  0  0  0  0            999 V2000
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 N   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
    4.2868   -0.0000    0.0000 C   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
    2.8579    0.8250    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
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  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
  4  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  6 13  1  0  0  0  0
 12 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
 11 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254034

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)C1=CC2=C(NC3=C(S2)C=C(C=C3)N(C)C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H19N3S/c1-18(2)11-5-7-13-15(9-11)20-16-10-12(19(3)4)6-8-14(16)17-13/h5-10,17H,1-4H3

> <INCHI_KEY>
QTWZICCBKBYHDM-UHFFFAOYSA-N

> <FORMULA>
C16H19N3S

> <MOLECULAR_WEIGHT>
285.41

> <EXACT_MASS>
285.129968798

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
33.48366277858987

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N3,N3,N7,N7-tetramethyl-10H-phenothiazine-3,7-diamine

> <ALOGPS_LOGP>
4.78

> <JCHEM_LOGP>
3.8447629563333328

> <ALOGPS_LOGS>
-3.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
5.250367898885235

> <JCHEM_POLAR_SURFACE_AREA>
18.509999999999998

> <JCHEM_REFRACTIVITY>
90.0275

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.10e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N3,N3,N7,N7-tetramethyl-10H-phenothiazine-3,7-diamine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0254034
     RDKit          3D
Leucomethylene blue
 39 41  0  0  0  0  0  0  0  0999 V2000
   -5.4257    1.3578    0.8394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1417    0.1166    0.1825 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2287   -0.7340   -0.2496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7999   -0.2890   -0.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5347   -1.4964   -0.6881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2280   -1.8716   -0.9041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1418   -1.0753   -0.5015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4639    0.1044    0.1229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7540    0.5030    0.3510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0972    1.1431    0.6488 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.3856    0.2926    0.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5834    0.8964    0.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7896    0.3276    0.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0480    0.9602    0.4764 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2676    0.2830    0.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1128    2.2255    1.1372 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7516   -0.8906   -0.4763 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5779   -1.5293   -0.7945 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3568   -0.9140   -0.4532 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1474   -1.5552   -0.7724 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3170    2.1879    0.1183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4633    1.4114    1.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7639    1.4568    1.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1581   -1.7142    0.2608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1890   -0.8350   -1.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2144   -0.3089   -0.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3588   -2.1182   -1.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0500   -2.8237   -1.4068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9180    1.4644    0.8584 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5982    1.8600    0.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3319   -0.7036    0.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1460    0.9124    0.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1717    0.0288   -0.9860 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1063    2.6760    0.9440 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0845    2.0525    2.2497 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3183    2.9398    0.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6894   -1.3564   -0.7349 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5513   -2.4816   -1.2944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2299   -2.5033   -1.2717 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  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 13 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
  9  4  1  0
 19 11  1  0
 20  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  5 27  1  0
  6 28  1  0
  9 29  1  0
 12 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 20 39  1  0
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      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       9.336  -0.770   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       4.001   2.310   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  S   UNK     0       4.001  -0.770   0.000  0.00  0.00           S+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      -1.334  -0.770   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    7   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12    6                                                       
CONECT   14   12   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16   11                                                       
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0254034
HETATM    1  C1  UNL     1      -5.426   1.358   0.839  1.00  0.00           C  
HETATM    2  N1  UNL     1      -5.142   0.117   0.182  1.00  0.00           N  
HETATM    3  C2  UNL     1      -6.229  -0.734  -0.250  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.800  -0.289  -0.050  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.535  -1.496  -0.688  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.228  -1.872  -0.904  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.142  -1.075  -0.501  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.464   0.104   0.123  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.754   0.503   0.351  1.00  0.00           C  
HETATM   10  S1  UNL     1      -0.097   1.143   0.649  1.00  0.00           S  
HETATM   11  C9  UNL     1       1.386   0.293   0.180  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.583   0.896   0.480  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.790   0.328   0.163  1.00  0.00           C  
HETATM   14  N2  UNL     1       5.048   0.960   0.476  1.00  0.00           N  
HETATM   15  C12 UNL     1       6.268   0.283   0.105  1.00  0.00           C  
HETATM   16  C13 UNL     1       5.113   2.226   1.137  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.752  -0.891  -0.476  1.00  0.00           C  
HETATM   18  C15 UNL     1       2.578  -1.529  -0.794  1.00  0.00           C  
HETATM   19  C16 UNL     1       1.357  -0.914  -0.453  1.00  0.00           C  
HETATM   20  N3  UNL     1       0.147  -1.555  -0.772  1.00  0.00           N  
HETATM   21  H1  UNL     1      -5.317   2.188   0.118  1.00  0.00           H  
HETATM   22  H2  UNL     1      -6.463   1.411   1.229  1.00  0.00           H  
HETATM   23  H3  UNL     1      -4.764   1.457   1.725  1.00  0.00           H  
HETATM   24  H4  UNL     1      -6.158  -1.714   0.261  1.00  0.00           H  
HETATM   25  H5  UNL     1      -6.189  -0.835  -1.352  1.00  0.00           H  
HETATM   26  H6  UNL     1      -7.214  -0.309  -0.003  1.00  0.00           H  
HETATM   27  H7  UNL     1      -4.359  -2.118  -1.003  1.00  0.00           H  
HETATM   28  H8  UNL     1      -2.050  -2.824  -1.407  1.00  0.00           H  
HETATM   29  H9  UNL     1      -2.918   1.464   0.858  1.00  0.00           H  
HETATM   30  H10 UNL     1       2.598   1.860   0.986  1.00  0.00           H  
HETATM   31  H11 UNL     1       6.332  -0.704   0.641  1.00  0.00           H  
HETATM   32  H12 UNL     1       7.146   0.912   0.272  1.00  0.00           H  
HETATM   33  H13 UNL     1       6.172   0.029  -0.986  1.00  0.00           H  
HETATM   34  H14 UNL     1       6.106   2.676   0.944  1.00  0.00           H  
HETATM   35  H15 UNL     1       5.084   2.053   2.250  1.00  0.00           H  
HETATM   36  H16 UNL     1       4.318   2.940   0.836  1.00  0.00           H  
HETATM   37  H17 UNL     1       4.689  -1.356  -0.735  1.00  0.00           H  
HETATM   38  H18 UNL     1       2.551  -2.482  -1.294  1.00  0.00           H  
HETATM   39  H19 UNL     1       0.230  -2.503  -1.272  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    4
CONECT    3   24   25   26
CONECT    4    5    5    9
CONECT    5    6   27
CONECT    6    7    7   28
CONECT    7    8   20
CONECT    8    9    9   10
CONECT    9   29
CONECT   10   11
CONECT   11   12   12   19
CONECT   12   13   30
CONECT   13   14   17   17
CONECT   14   15   16
CONECT   15   31   32   33
CONECT   16   34   35   36
CONECT   17   18   37
CONECT   18   19   19   38
CONECT   19   20
CONECT   20   39
END

HMDB0254034
     RDKit          3D
Leucomethylene blue
 39 41  0  0  0  0  0  0  0  0999 V2000
   -5.4257    1.3578    0.8394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1417    0.1166    0.1825 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2287   -0.7340   -0.2496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7999   -0.2890   -0.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5347   -1.4964   -0.6881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2280   -1.8716   -0.9041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1418   -1.0753   -0.5015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4639    0.1044    0.1229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7540    0.5030    0.3510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0972    1.1431    0.6488 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.3856    0.2926    0.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5834    0.8964    0.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7896    0.3276    0.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0480    0.9602    0.4764 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2676    0.2830    0.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1128    2.2255    1.1372 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7516   -0.8906   -0.4763 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5779   -1.5293   -0.7945 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3568   -0.9140   -0.4532 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1474   -1.5552   -0.7724 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3170    2.1879    0.1183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4633    1.4114    1.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7639    1.4568    1.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1581   -1.7142    0.2608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1890   -0.8350   -1.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2144   -0.3089   -0.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3588   -2.1182   -1.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0500   -2.8237   -1.4068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9180    1.4644    0.8584 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5982    1.8600    0.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3319   -0.7036    0.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1460    0.9124    0.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1717    0.0288   -0.9860 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1063    2.6760    0.9440 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0845    2.0525    2.2497 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3183    2.9398    0.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6894   -1.3564   -0.7349 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5513   -2.4816   -1.2944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2299   -2.5033   -1.2717 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  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 13 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
  9  4  1  0
 19 11  1  0
 20  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  5 27  1  0
  6 28  1  0
  9 29  1  0
 12 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 20 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Panatone	ChEBI
Reduced methylene blue	ChEBI
LMTX Compound	HMDB
Hydromethylthionine	HMDB
Hydromethylthionine mesylate	HMDB
Leuco-methylthioninium	HMDB
Leukomethylene blue	HMDB

Chemical Formula

C₁₆H₁₉N₃S

Average Molecular Weight

285.41

Monoisotopic Molecular Weight

285.129968798

IUPAC Name

N3,N3,N7,N7-tetramethyl-10H-phenothiazine-3,7-diamine

Traditional Name

N3,N3,N7,N7-tetramethyl-10H-phenothiazine-3,7-diamine

CAS Registry Number

Not Available

SMILES

CN(C)C1=CC2=C(NC3=C(S2)C=C(C=C3)N(C)C)C=C1

InChI Identifier

InChI=1S/C16H19N3S/c1-18(2)11-5-7-13-15(9-11)20-16-10-12(19(3)4)6-8-14(16)17-13/h5-10,17H,1-4H3

InChI Key

QTWZICCBKBYHDM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiazines

Sub Class

Phenothiazines

Direct Parent

Phenothiazines

Alternative Parents

Substituents

Phenothiazine
Diarylthioether
Aryl thioether
Tertiary aliphatic/aromatic amine
Dialkylarylamine
Para-thiazine
Benzenoid
Tertiary amine
Secondary amine
Azacycle
Thioether
Organic nitrogen compound
Organopnictogen compound
Organonitrogen compound
Hydrocarbon derivative
Amine
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	4.78	ALOGPS
logP	3.84	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Basic)	5.25	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	18.51 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	90.03 m³·mol⁻¹	ChemAxon
Polarizability	33.48 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	173.25	30932474
DeepCCS	[M-H]-	170.892	30932474
DeepCCS	[M-2H]-	203.83	30932474
DeepCCS	[M+Na]+	179.343	30932474
AllCCS	[M+H]+	166.7	32859911
AllCCS	[M+H-H2O]+	163.3	32859911
AllCCS	[M+NH4]+	169.8	32859911
AllCCS	[M+Na]+	170.7	32859911
AllCCS	[M-H]-	170.9	32859911
AllCCS	[M+Na-2H]-	170.3	32859911
AllCCS	[M+HCOO]-	169.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Leucomethylene blue	CN(C)C1=CC2=C(NC3=C(S2)C=C(C=C3)N(C)C)C=C1	3505.5	Standard polar	33892256
Leucomethylene blue	CN(C)C1=CC2=C(NC3=C(S2)C=C(C=C3)N(C)C)C=C1	2542.8	Standard non polar	33892256
Leucomethylene blue	CN(C)C1=CC2=C(NC3=C(S2)C=C(C=C3)N(C)C)C=C1	2928.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Leucomethylene blue,1TMS,isomer #1	CN(C)C1=CC=C2C(=C1)SC1=CC(N(C)C)=CC=C1N2[Si](C)(C)C	2760.7	Semi standard non polar	33892256
Leucomethylene blue,1TMS,isomer #1	CN(C)C1=CC=C2C(=C1)SC1=CC(N(C)C)=CC=C1N2[Si](C)(C)C	2637.0	Standard non polar	33892256
Leucomethylene blue,1TMS,isomer #1	CN(C)C1=CC=C2C(=C1)SC1=CC(N(C)C)=CC=C1N2[Si](C)(C)C	3153.6	Standard polar	33892256
Leucomethylene blue,1TBDMS,isomer #1	CN(C)C1=CC=C2C(=C1)SC1=CC(N(C)C)=CC=C1N2[Si](C)(C)C(C)(C)C	2986.1	Semi standard non polar	33892256
Leucomethylene blue,1TBDMS,isomer #1	CN(C)C1=CC=C2C(=C1)SC1=CC(N(C)C)=CC=C1N2[Si](C)(C)C(C)(C)C	2870.9	Standard non polar	33892256
Leucomethylene blue,1TBDMS,isomer #1	CN(C)C1=CC=C2C(=C1)SC1=CC(N(C)C)=CC=C1N2[Si](C)(C)C(C)(C)C	3234.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Leucomethylene blue GC-MS (Non-derivatized) - 70eV, Positive	splash10-00li-0590000000-d7b41dbfc4a828a354e6	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Leucomethylene blue 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 - Leucomethylene blue 10V, Positive-QTOF	splash10-000i-0090000000-d2b14d1825ef47bdb20d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leucomethylene blue 20V, Positive-QTOF	splash10-000i-0090000000-d2b14d1825ef47bdb20d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leucomethylene blue 40V, Positive-QTOF	splash10-0gdl-0290000000-7b6f4fe9a16ef9a31d45	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leucomethylene blue 10V, Negative-QTOF	splash10-001i-0090000000-38db1b15f0d5a2e05312	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leucomethylene blue 20V, Negative-QTOF	splash10-001i-0090000000-38db1b15f0d5a2e05312	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leucomethylene blue 40V, Negative-QTOF	splash10-00or-0190000000-7e4b70923d1a98ebf9da	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

144378

KEGG Compound ID

C05721

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

164695

PDB ID

Not Available

ChEBI ID

134180

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 Leucomethylene blue (HMDB0254034)

MOL for HMDB0254034 (Leucomethylene blue)

3D MOL for HMDB0254034 (Leucomethylene blue)

3D SDF for HMDB0254034 (Leucomethylene blue)

3D-SDF for HMDB0254034 (Leucomethylene blue)

PDB for HMDB0254034 (Leucomethylene blue)

3D PDB for HMDB0254034 (Leucomethylene blue)

SMILES for HMDB0254034 (Leucomethylene blue)

INCHI for HMDB0254034 (Leucomethylene blue)

Structure for HMDB0254034 (Leucomethylene blue)

3D Structure for HMDB0254034 (Leucomethylene blue)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra