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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 07:41:41 UTC

Update Date

2021-09-26 23:02:10 UTC

HMDB ID

HMDB0250602

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Cyamemazine

Description

Cyamemazine, also known as tercian, 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. Based on a literature review very few articles have been published on Cyamemazine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Cyamemazine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Cyamemazine 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

HMDB0250602
     RDKit          3D
Cyamemazine
 44 46  0  0  0  0  0  0  0  0999 V2000
    2.1618   -1.1018   -1.8010 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1375   -0.5781   -0.8015 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7481    0.5912   -0.0963 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9207    0.3323    0.6178 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8509   -0.4889    1.7639 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1788    0.4627   -0.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2016   -0.3851   -1.4161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2274    0.1361   -0.5128 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4425    1.5344   -0.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6981    2.3745   -1.2770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8634    3.7521   -1.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7829    4.2867   -0.4092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5322    3.5087    0.4328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3540    2.1527    0.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3369    1.1466    1.4948 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8806   -0.5255    1.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5216   -1.4957    1.9011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2417   -2.8421    1.7523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2763   -3.1924    0.8350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9268   -4.5712    0.6202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6472   -5.6741    0.4278 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6377   -2.2039    0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9203   -0.8403    0.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7884   -2.0221   -2.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0633   -1.4364   -1.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4672   -0.3211   -2.5041 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1002   -1.4241   -0.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9774    1.0635    0.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0111    1.3415   -0.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0079   -0.1686    2.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7978   -0.4520    2.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6359   -1.5690    1.5351 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0725    0.7291   -1.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7505    1.3311    0.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7899   -0.4667    0.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0887    0.2118   -2.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5584   -1.3588   -1.9018 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0069    1.9136   -1.9380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2561    4.3344   -1.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8949    5.3659   -0.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2663    3.9252    1.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2783   -1.2150    2.6199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7284   -3.6255    2.3052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9048   -2.5358   -0.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  2  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  3  0
 19 22  1  0
 22 23  2  0
 23  8  1  0
 14  9  1  0
 23 16  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  5 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  6 35  1  0
  7 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
 22 44  1  0
M  END

  Mrv0541 06171409292D          

 23 25  0  0  0  0            999 V2000
   -1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    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
   -2.8578    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5723    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0012   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0012    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5723   -0.4125    0.0000 C   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
   -0.7144    0.4125    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
   -1.4289    0.8250    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
   -2.8578    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5723    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5723    2.0625    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
   -4.2868   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8578    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    1.6500    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  9  8  2  0  0  0  0
 14  1  1  0  0  0  0
 14 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15  8  1  0  0  0  0
 15 10  2  0  0  0  0
 15 11  1  0  0  0  0
 16  6  2  0  0  0  0
 17 10  1  0  0  0  0
 18  7  2  0  0  0  0
 18 16  1  0  0  0  0
 19  9  1  0  0  0  0
 19 17  2  0  0  0  0
 20 11  3  0  0  0  0
 21  2  1  0  0  0  0
 21  3  1  0  0  0  0
 21 12  1  0  0  0  0
 22 13  1  0  0  0  0
 22 16  1  0  0  0  0
 22 17  1  0  0  0  0
 23 18  1  0  0  0  0
 23 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0250602

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(CN(C)C)CN1C2=CC=CC=C2SC2=C1C=C(C=C2)C#N

> <INCHI_IDENTIFIER>
InChI=1S/C19H21N3S/c1-14(12-21(2)3)13-22-16-6-4-5-7-18(16)23-19-9-8-15(11-20)10-17(19)22/h4-10,14H,12-13H2,1-3H3

> <INCHI_KEY>
SLFGIOIONGJGRT-UHFFFAOYSA-N

> <FORMULA>
C19H21N3S

> <MOLECULAR_WEIGHT>
323.455

> <EXACT_MASS>
323.145618377

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
36.47817716179923

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10-[3-(dimethylamino)-2-methylpropyl]-10H-phenothiazine-2-carbonitrile

> <ALOGPS_LOGP>
4.28

> <JCHEM_LOGP>
4.266375313666666

> <ALOGPS_LOGS>
-4.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.421368308892973

> <JCHEM_POLAR_SURFACE_AREA>
30.270000000000003

> <JCHEM_REFRACTIVITY>
99.08949999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.90e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cyamemazine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0250602
     RDKit          3D
Cyamemazine
 44 46  0  0  0  0  0  0  0  0999 V2000
    2.1618   -1.1018   -1.8010 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1375   -0.5781   -0.8015 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7481    0.5912   -0.0963 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9207    0.3323    0.6178 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8509   -0.4889    1.7639 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1788    0.4627   -0.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2016   -0.3851   -1.4161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2274    0.1361   -0.5128 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4425    1.5344   -0.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6981    2.3745   -1.2770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8634    3.7521   -1.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7829    4.2867   -0.4092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5322    3.5087    0.4328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3540    2.1527    0.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3369    1.1466    1.4948 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8806   -0.5255    1.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5216   -1.4957    1.9011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2417   -2.8421    1.7523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2763   -3.1924    0.8350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9268   -4.5712    0.6202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6472   -5.6741    0.4278 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6377   -2.2039    0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9203   -0.8403    0.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7884   -2.0221   -2.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0633   -1.4364   -1.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4672   -0.3211   -2.5041 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1002   -1.4241   -0.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9774    1.0635    0.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0111    1.3415   -0.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0079   -0.1686    2.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7978   -0.4520    2.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6359   -1.5690    1.5351 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0725    0.7291   -1.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7505    1.3311    0.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7899   -0.4667    0.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0887    0.2118   -2.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5584   -1.3588   -1.9018 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0069    1.9136   -1.9380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2561    4.3344   -1.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8949    5.3659   -0.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2663    3.9252    1.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2783   -1.2150    2.6199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7284   -3.6255    2.3052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9048   -2.5358   -0.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  2  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  3  0
 19 22  1  0
 22 23  2  0
 23  8  1  0
 14  9  1  0
 23 16  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  5 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  6 35  1  0
  7 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
 22 44  1  0
M  END

HEADER    PROTEIN                                 17-JUN-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-14         0                                  
HETATM    1  C   UNK     0      -2.667   3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   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   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.668   5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -9.336   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -8.002  -1.540   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   0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      -8.002  -4.620   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0       0.000   1.540   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0      -5.335   1.540   0.000  0.00  0.00           N+0
HETATM   23  S   UNK     0      -8.002   3.080   0.000  0.00  0.00           S+0
CONECT    1   14                                                            
CONECT    2   21                                                            
CONECT    3   21                                                            
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4   16                                                       
CONECT    7    5   18                                                       
CONECT    8    9   15                                                       
CONECT    9    8   19                                                       
CONECT   10   15   17                                                       
CONECT   11   15   20                                                       
CONECT   12   14   21                                                       
CONECT   13   14   22                                                       
CONECT   14    1   12   13                                                  
CONECT   15    8   10   11                                                  
CONECT   16    6   18   22                                                  
CONECT   17   10   19   22                                                  
CONECT   18    7   16   23                                                  
CONECT   19    9   17   23                                                  
CONECT   20   11                                                            
CONECT   21    2    3   12                                                  
CONECT   22   13   16   17                                                  
CONECT   23   18   19                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0250602
HETATM    1  C1  UNL     1       2.162  -1.102  -1.801  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.137  -0.578  -0.802  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.748   0.591  -0.096  1.00  0.00           C  
HETATM    4  N1  UNL     1       2.921   0.332   0.618  1.00  0.00           N  
HETATM    5  C4  UNL     1       2.851  -0.489   1.764  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.179   0.463  -0.003  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.202  -0.385  -1.416  1.00  0.00           C  
HETATM    8  N2  UNL     1      -1.227   0.136  -0.513  1.00  0.00           N  
HETATM    9  C7  UNL     1      -1.443   1.534  -0.432  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.698   2.374  -1.277  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.863   3.752  -1.270  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.783   4.287  -0.409  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.532   3.509   0.433  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.354   2.153   0.411  1.00  0.00           C  
HETATM   15  S1  UNL     1      -3.337   1.147   1.495  1.00  0.00           S  
HETATM   16  C13 UNL     1      -2.881  -0.526   1.179  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.522  -1.496   1.901  1.00  0.00           C  
HETATM   18  C15 UNL     1      -3.242  -2.842   1.752  1.00  0.00           C  
HETATM   19  C16 UNL     1      -2.276  -3.192   0.835  1.00  0.00           C  
HETATM   20  C17 UNL     1      -1.927  -4.571   0.620  1.00  0.00           C  
HETATM   21  N3  UNL     1      -1.647  -5.674   0.428  1.00  0.00           N  
HETATM   22  C18 UNL     1      -1.638  -2.204   0.113  1.00  0.00           C  
HETATM   23  C19 UNL     1      -1.920  -0.840   0.262  1.00  0.00           C  
HETATM   24  H1  UNL     1       1.788  -2.022  -2.306  1.00  0.00           H  
HETATM   25  H2  UNL     1       3.063  -1.436  -1.251  1.00  0.00           H  
HETATM   26  H3  UNL     1       2.467  -0.321  -2.504  1.00  0.00           H  
HETATM   27  H4  UNL     1       1.100  -1.424  -0.019  1.00  0.00           H  
HETATM   28  H5  UNL     1       0.977   1.063   0.579  1.00  0.00           H  
HETATM   29  H6  UNL     1       2.011   1.341  -0.906  1.00  0.00           H  
HETATM   30  H7  UNL     1       2.008  -0.169   2.417  1.00  0.00           H  
HETATM   31  H8  UNL     1       3.798  -0.452   2.359  1.00  0.00           H  
HETATM   32  H9  UNL     1       2.636  -1.569   1.535  1.00  0.00           H  
HETATM   33  H10 UNL     1       4.072   0.729  -1.093  1.00  0.00           H  
HETATM   34  H11 UNL     1       4.751   1.331   0.414  1.00  0.00           H  
HETATM   35  H12 UNL     1       4.790  -0.467   0.066  1.00  0.00           H  
HETATM   36  H13 UNL     1      -0.089   0.212  -2.356  1.00  0.00           H  
HETATM   37  H14 UNL     1      -0.558  -1.359  -1.902  1.00  0.00           H  
HETATM   38  H15 UNL     1       0.007   1.914  -1.938  1.00  0.00           H  
HETATM   39  H16 UNL     1      -0.256   4.334  -1.947  1.00  0.00           H  
HETATM   40  H17 UNL     1      -1.895   5.366  -0.421  1.00  0.00           H  
HETATM   41  H18 UNL     1      -3.266   3.925   1.122  1.00  0.00           H  
HETATM   42  H19 UNL     1      -4.278  -1.215   2.620  1.00  0.00           H  
HETATM   43  H20 UNL     1      -3.728  -3.625   2.305  1.00  0.00           H  
HETATM   44  H21 UNL     1      -0.905  -2.536  -0.564  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    7   27
CONECT    3    4   28   29
CONECT    4    5    6
CONECT    5   30   31   32
CONECT    6   33   34   35
CONECT    7    8   36   37
CONECT    8    9   23
CONECT    9   10   10   14
CONECT   10   11   38
CONECT   11   12   12   39
CONECT   12   13   40
CONECT   13   14   14   41
CONECT   14   15
CONECT   15   16
CONECT   16   17   17   23
CONECT   17   18   42
CONECT   18   19   19   43
CONECT   19   20   22
CONECT   20   21   21   21
CONECT   22   23   23   44
END

HMDB0250602
     RDKit          3D
Cyamemazine
 44 46  0  0  0  0  0  0  0  0999 V2000
    2.1618   -1.1018   -1.8010 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1375   -0.5781   -0.8015 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7481    0.5912   -0.0963 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9207    0.3323    0.6178 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8509   -0.4889    1.7639 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1788    0.4627   -0.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2016   -0.3851   -1.4161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2274    0.1361   -0.5128 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4425    1.5344   -0.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6981    2.3745   -1.2770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8634    3.7521   -1.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7829    4.2867   -0.4092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5322    3.5087    0.4328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3540    2.1527    0.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3369    1.1466    1.4948 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8806   -0.5255    1.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5216   -1.4957    1.9011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2417   -2.8421    1.7523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2763   -3.1924    0.8350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9268   -4.5712    0.6202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6472   -5.6741    0.4278 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6377   -2.2039    0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9203   -0.8403    0.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7884   -2.0221   -2.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0633   -1.4364   -1.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4672   -0.3211   -2.5041 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1002   -1.4241   -0.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9774    1.0635    0.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0111    1.3415   -0.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0079   -0.1686    2.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7978   -0.4520    2.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6359   -1.5690    1.5351 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0725    0.7291   -1.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7505    1.3311    0.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7899   -0.4667    0.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0887    0.2118   -2.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5584   -1.3588   -1.9018 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0069    1.9136   -1.9380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2561    4.3344   -1.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8949    5.3659   -0.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2663    3.9252    1.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2783   -1.2150    2.6199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7284   -3.6255    2.3052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9048   -2.5358   -0.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  2  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  3  0
 19 22  1  0
 22 23  2  0
 23  8  1  0
 14  9  1  0
 23 16  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  5 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  6 35  1  0
  7 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
 22 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Tercian	Kegg
Cyamemazine monohydrochloride	MeSH
10-(3-dimethylamino-2-Methylpropyl)phenothiazine-2-carbonitrile	MeSH
Cyamamazine	MeSH
Cyamepromazine	MeSH

Chemical Formula

C₁₉H₂₁N₃S

Average Molecular Weight

323.455

Monoisotopic Molecular Weight

323.145618377

IUPAC Name

10-[3-(dimethylamino)-2-methylpropyl]-10H-phenothiazine-2-carbonitrile

Traditional Name

cyamemazine

CAS Registry Number

Not Available

SMILES

CC(CN(C)C)CN1C2=CC=CC=C2SC2=C1C=C(C=C2)C#N

InChI Identifier

InChI=1S/C19H21N3S/c1-14(12-21(2)3)13-22-16-6-4-5-7-18(16)23-19-9-8-15(11-20)10-17(19)22/h4-10,14H,12-13H2,1-3H3

InChI Key

SLFGIOIONGJGRT-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
Alkyldiarylamine
Diarylthioether
Aryl thioether
Tertiary aliphatic/aromatic amine
Para-thiazine
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Carbonitrile
Nitrile
Azacycle
Thioether
Organonitrogen compound
Amine
Organopnictogen compound
Hydrocarbon derivative
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0250602)

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	4.28	ALOGPS
logP	4.27	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Basic)	9.42	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	30.27 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	99.09 m³·mol⁻¹	ChemAxon
Polarizability	36.48 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]+	169.741	30932474
DeepCCS	[M-H]-	167.384	30932474
DeepCCS	[M-2H]-	200.851	30932474
DeepCCS	[M+Na]+	176.079	30932474
AllCCS	[M+H]+	175.4	32859911
AllCCS	[M+H-H2O]+	172.3	32859911
AllCCS	[M+NH4]+	178.1	32859911
AllCCS	[M+Na]+	178.9	32859911
AllCCS	[M-H]-	179.6	32859911
AllCCS	[M+Na-2H]-	179.1	32859911
AllCCS	[M+HCOO]-	178.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cyamemazine	CC(CN(C)C)CN1C2=CC=CC=C2SC2=C1C=C(C=C2)C#N	3729.7	Standard polar	33892256
Cyamemazine	CC(CN(C)C)CN1C2=CC=CC=C2SC2=C1C=C(C=C2)C#N	2623.1	Standard non polar	33892256
Cyamemazine	CC(CN(C)C)CN1C2=CC=CC=C2SC2=C1C=C(C=C2)C#N	2642.4	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 - Cyamemazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-052r-4091000000-8fd4f49543d5acc4171d	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyamemazine 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 - Cyamemazine 10V, Positive-QTOF	splash10-00di-0459000000-e1b031ab308058c88888	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyamemazine 20V, Positive-QTOF	splash10-0ufr-3983000000-125d46ec1039bd960dbc	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyamemazine 40V, Positive-QTOF	splash10-0pc3-9420000000-f4b23fbdb473e415da46	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyamemazine 10V, Negative-QTOF	splash10-00di-0019000000-cb1db54ec97be2449448	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyamemazine 20V, Negative-QTOF	splash10-0229-0393000000-37c115004aec78d5d35c	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyamemazine 40V, Negative-QTOF	splash10-00di-4690000000-cea36bb79247000a195f	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyamemazine 10V, Positive-QTOF	splash10-00di-0109000000-e5bef22b7d81201bd614	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyamemazine 20V, Positive-QTOF	splash10-0ab9-9243000000-ec6b8b68f744c80c977c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyamemazine 40V, Positive-QTOF	splash10-0a4i-9180000000-f0d03c7e88d5c786da6d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyamemazine 10V, Negative-QTOF	splash10-00di-0009000000-e54ed851bfb2afca8090	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyamemazine 20V, Negative-QTOF	splash10-00di-0169000000-63a26edd4e5d9c71ef6b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyamemazine 40V, Negative-QTOF	splash10-000i-0290000000-c3eb114cf0bff62fde85	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

DB09000

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

56597

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cyamemazine

METLIN ID

Not Available

PubChem Compound

Not Available

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 Cyamemazine (HMDB0250602)

MOL for HMDB0250602 (Cyamemazine)

3D MOL for HMDB0250602 (Cyamemazine)

3D SDF for HMDB0250602 (Cyamemazine)

3D-SDF for HMDB0250602 (Cyamemazine)

PDB for HMDB0250602 (Cyamemazine)

3D PDB for HMDB0250602 (Cyamemazine)

SMILES for HMDB0250602 (Cyamemazine)

INCHI for HMDB0250602 (Cyamemazine)

Structure for HMDB0250602 (Cyamemazine)

3D Structure for HMDB0250602 (Cyamemazine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra