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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:49:14 UTC

Update Date

2021-09-26 23:08:30 UTC

HMDB ID

HMDB0254486

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Mesulergine

Description

({6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraen-4-yl}sulfamoyl)dimethylamine belongs to the class of organic compounds known as indoloquinolines. These are polycyclic aromatic compounds containing an indole fused to a quinoline. Based on a literature review very few articles have been published on ({6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraen-4-yl}sulfamoyl)dimethylamine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Mesulergine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Mesulergine 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

HMDB0254486
     RDKit          3D
Mesulergine
 51 54  0  0  0  0  0  0  0  0999 V2000
   -0.7769   -2.5062    0.6030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6216   -1.7173   -0.5714 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7073   -0.8776   -0.9115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7670    0.4500   -0.2702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6850    0.5364    0.8591 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9677    1.6574    0.5856 S   0  0  0  0  0  6  0  0  0  0  0  0
   -4.3107    2.3162    1.8909 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5269    2.7497   -0.3673 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3329    0.8756   -0.1183 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1835    0.9245   -1.5590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4988   -0.4848    0.3473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4366    1.0307    0.1324 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5924   -0.0069    0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8781    0.6374    0.7185 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9747    1.8125    1.4155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2359    2.3867    1.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3784    1.8013    1.0904 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2727    0.6136    0.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0142    0.0748    0.2284 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0589   -1.0980   -0.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4085   -1.2772   -0.7719 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1159   -0.2360   -0.2372 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5511   -0.0229   -0.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8213   -1.8345   -0.7627 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6118   -0.9929   -0.6508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1345   -2.5067    1.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9149   -3.5785    0.2827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6197   -2.2553    1.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7446   -0.8101   -2.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6549   -1.4386   -0.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1821    1.1723   -1.0366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1091   -0.3931    0.9761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4557    1.7087   -1.8578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1912    1.1011   -1.9787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8072   -0.0613   -1.8930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5921   -0.6913    0.4390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0138   -1.2058   -0.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0889   -0.6401    1.3762 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0021    1.6216   -0.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6354    1.7633    0.9320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2433   -0.4811    1.4464 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1107    2.2994    1.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3127    3.3121    2.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3665    2.2227    1.2140 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8062   -2.1111   -1.3277 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9469   -0.7093   -1.0807 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0435   -0.1423    0.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7241    1.0267   -0.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8017   -2.7595   -0.1500 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8700   -2.2050   -1.8297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5483   -0.3629   -1.5871 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
  5  6  1  0
  6  7  2  0
  6  8  2  0
  6  9  1  0
  9 10  1  0
  9 11  1  0
  4 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 20 24  1  0
 24 25  1  0
 25  2  1  0
 25 13  1  0
 19 14  1  0
 22 18  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
 10 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 15 42  1  0
 16 43  1  0
 17 44  1  0
 21 45  1  0
 23 46  1  0
 23 47  1  0
 23 48  1  0
 24 49  1  0
 24 50  1  0
 25 51  1  0
M  END


  Mrv1652309112115492D          

 25 28  0  0  0  0            999 V2000
    3.2789   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1794    1.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925    2.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5771    2.1840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9590    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.8250    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.0098    0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8348    1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -0.4125    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
  6 16  1  0  0  0  0
 16 17  2  0  0  0  0
  9 17  1  0  0  0  0
 12 17  1  0  0  0  0
 11 18  1  0  0  0  0
  4 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  2  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254486

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)S(=O)(=O)NC1CC2C(CC3=CN(C)C4=CC=CC2=C34)N(C)C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H26N4O2S/c1-20(2)25(23,24)19-13-9-15-14-6-5-7-16-18(14)12(10-21(16)3)8-17(15)22(4)11-13/h5-7,10,13,15,17,19H,8-9,11H2,1-4H3

> <INCHI_KEY>
JLVHTNZNKOSCNB-UHFFFAOYSA-N

> <FORMULA>
C18H26N4O2S

> <MOLECULAR_WEIGHT>
362.49

> <EXACT_MASS>
362.177647267

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
39.637374334948404

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
({6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraen-4-yl}sulfamoyl)dimethylamine

> <ALOGPS_LOGP>
1.56

> <JCHEM_LOGP>
1.0848037726666675

> <ALOGPS_LOGS>
-2.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.07535766032048

> <JCHEM_PKA_STRONGEST_BASIC>
6.9033456633459025

> <JCHEM_POLAR_SURFACE_AREA>
57.58

> <JCHEM_REFRACTIVITY>
100.29159999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.68e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
({6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraen-4-yl}sulfamoyl)dimethylamine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0254486
     RDKit          3D
Mesulergine
 51 54  0  0  0  0  0  0  0  0999 V2000
   -0.7769   -2.5062    0.6030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6216   -1.7173   -0.5714 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7073   -0.8776   -0.9115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7670    0.4500   -0.2702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6850    0.5364    0.8591 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9677    1.6574    0.5856 S   0  0  0  0  0  6  0  0  0  0  0  0
   -4.3107    2.3162    1.8909 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5269    2.7497   -0.3673 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3329    0.8756   -0.1183 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1835    0.9245   -1.5590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4988   -0.4848    0.3473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4366    1.0307    0.1324 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5924   -0.0069    0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8781    0.6374    0.7185 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9747    1.8125    1.4155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2359    2.3867    1.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3784    1.8013    1.0904 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2727    0.6136    0.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0142    0.0748    0.2284 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0589   -1.0980   -0.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4085   -1.2772   -0.7719 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1159   -0.2360   -0.2372 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5511   -0.0229   -0.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8213   -1.8345   -0.7627 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6118   -0.9929   -0.6508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1345   -2.5067    1.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9149   -3.5785    0.2827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6197   -2.2553    1.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7446   -0.8101   -2.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6549   -1.4386   -0.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1821    1.1723   -1.0366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1091   -0.3931    0.9761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4557    1.7087   -1.8578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1912    1.1011   -1.9787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8072   -0.0613   -1.8930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5921   -0.6913    0.4390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0138   -1.2058   -0.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0889   -0.6401    1.3762 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0021    1.6216   -0.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6354    1.7633    0.9320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2433   -0.4811    1.4464 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1107    2.2994    1.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3127    3.3121    2.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3665    2.2227    1.2140 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8062   -2.1111   -1.3277 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9469   -0.7093   -1.0807 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0435   -0.1423    0.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7241    1.0267   -0.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8017   -2.7595   -0.1500 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8700   -2.2050   -1.8297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5483   -0.3629   -1.5871 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
  5  6  1  0
  6  7  2  0
  6  8  2  0
  6  9  1  0
  9 10  1  0
  9 11  1  0
  4 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 20 24  1  0
 24 25  1  0
 25  2  1  0
 25 13  1  0
 19 14  1  0
 22 18  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
 10 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 15 42  1  0
 16 43  1  0
 17 44  1  0
 21 45  1  0
 23 46  1  0
 23 47  1  0
 23 48  1  0
 24 49  1  0
 24 50  1  0
 25 51  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       6.121  -2.310   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       6.121  -0.770   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.453  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.120  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.655  -0.476   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      -0.250   0.770   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       0.655   2.016   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.335   3.522   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.479   4.553   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.944   4.077   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.453   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.120   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.790   0.770   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       8.788   2.310   0.000  0.00  0.00           N+0
HETATM   20  S   UNK     0      10.122   1.540   0.000  0.00  0.00           S+0
HETATM   21  O   UNK     0       9.352   0.206   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      10.892   2.874   0.000  0.00  0.00           O+0
HETATM   23  N   UNK     0      11.455   0.770   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0      12.789   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.455  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   19                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   16                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   18                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    6   17                                                  
CONECT   17   16    9   12                                                  
CONECT   18   11                                                            
CONECT   19    4   20                                                       
CONECT   20   19   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0254486
HETATM    1  C1  UNL     1      -0.777  -2.506   0.603  1.00  0.00           C  
HETATM    2  N1  UNL     1      -0.622  -1.717  -0.571  1.00  0.00           N  
HETATM    3  C2  UNL     1      -1.707  -0.878  -0.912  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.767   0.450  -0.270  1.00  0.00           C  
HETATM    5  N2  UNL     1      -2.685   0.536   0.859  1.00  0.00           N  
HETATM    6  S1  UNL     1      -3.968   1.657   0.586  1.00  0.00           S  
HETATM    7  O1  UNL     1      -4.311   2.316   1.891  1.00  0.00           O  
HETATM    8  O2  UNL     1      -3.527   2.750  -0.367  1.00  0.00           O  
HETATM    9  N3  UNL     1      -5.333   0.876  -0.118  1.00  0.00           N  
HETATM   10  C4  UNL     1      -5.184   0.925  -1.559  1.00  0.00           C  
HETATM   11  C5  UNL     1      -5.499  -0.485   0.347  1.00  0.00           C  
HETATM   12  C6  UNL     1      -0.437   1.031   0.132  1.00  0.00           C  
HETATM   13  C7  UNL     1       0.592  -0.007   0.496  1.00  0.00           C  
HETATM   14  C8  UNL     1       1.878   0.637   0.719  1.00  0.00           C  
HETATM   15  C9  UNL     1       1.975   1.813   1.416  1.00  0.00           C  
HETATM   16  C10 UNL     1       3.236   2.387   1.595  1.00  0.00           C  
HETATM   17  C11 UNL     1       4.378   1.801   1.090  1.00  0.00           C  
HETATM   18  C12 UNL     1       4.273   0.614   0.387  1.00  0.00           C  
HETATM   19  C13 UNL     1       3.014   0.075   0.228  1.00  0.00           C  
HETATM   20  C14 UNL     1       3.059  -1.098  -0.485  1.00  0.00           C  
HETATM   21  C15 UNL     1       4.409  -1.277  -0.772  1.00  0.00           C  
HETATM   22  N4  UNL     1       5.116  -0.236  -0.237  1.00  0.00           N  
HETATM   23  C16 UNL     1       6.551  -0.023  -0.299  1.00  0.00           C  
HETATM   24  C17 UNL     1       1.821  -1.834  -0.763  1.00  0.00           C  
HETATM   25  C18 UNL     1       0.612  -0.993  -0.651  1.00  0.00           C  
HETATM   26  H1  UNL     1       0.134  -2.507   1.230  1.00  0.00           H  
HETATM   27  H2  UNL     1      -0.915  -3.578   0.283  1.00  0.00           H  
HETATM   28  H3  UNL     1      -1.620  -2.255   1.244  1.00  0.00           H  
HETATM   29  H4  UNL     1      -1.745  -0.810  -2.039  1.00  0.00           H  
HETATM   30  H5  UNL     1      -2.655  -1.439  -0.657  1.00  0.00           H  
HETATM   31  H6  UNL     1      -2.182   1.172  -1.037  1.00  0.00           H  
HETATM   32  H7  UNL     1      -3.109  -0.393   0.976  1.00  0.00           H  
HETATM   33  H8  UNL     1      -4.456   1.709  -1.858  1.00  0.00           H  
HETATM   34  H9  UNL     1      -6.191   1.101  -1.979  1.00  0.00           H  
HETATM   35  H10 UNL     1      -4.807  -0.061  -1.893  1.00  0.00           H  
HETATM   36  H11 UNL     1      -6.592  -0.691   0.439  1.00  0.00           H  
HETATM   37  H12 UNL     1      -5.014  -1.206  -0.324  1.00  0.00           H  
HETATM   38  H13 UNL     1      -5.089  -0.640   1.376  1.00  0.00           H  
HETATM   39  H14 UNL     1       0.002   1.622  -0.717  1.00  0.00           H  
HETATM   40  H15 UNL     1      -0.635   1.763   0.932  1.00  0.00           H  
HETATM   41  H16 UNL     1       0.243  -0.481   1.446  1.00  0.00           H  
HETATM   42  H17 UNL     1       1.111   2.299   1.825  1.00  0.00           H  
HETATM   43  H18 UNL     1       3.313   3.312   2.144  1.00  0.00           H  
HETATM   44  H19 UNL     1       5.366   2.223   1.214  1.00  0.00           H  
HETATM   45  H20 UNL     1       4.806  -2.111  -1.328  1.00  0.00           H  
HETATM   46  H21 UNL     1       6.947  -0.709  -1.081  1.00  0.00           H  
HETATM   47  H22 UNL     1       7.044  -0.142   0.679  1.00  0.00           H  
HETATM   48  H23 UNL     1       6.724   1.027  -0.656  1.00  0.00           H  
HETATM   49  H24 UNL     1       1.802  -2.760  -0.150  1.00  0.00           H  
HETATM   50  H25 UNL     1       1.870  -2.205  -1.830  1.00  0.00           H  
HETATM   51  H26 UNL     1       0.548  -0.363  -1.587  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   25
CONECT    3    4   29   30
CONECT    4    5   12   31
CONECT    5    6   32
CONECT    6    7    7    8    8
CONECT    6    9
CONECT    9   10   11
CONECT   10   33   34   35
CONECT   11   36   37   38
CONECT   12   13   39   40
CONECT   13   14   25   41
CONECT   14   15   15   19
CONECT   15   16   42
CONECT   16   17   17   43
CONECT   17   18   44
CONECT   18   19   19   22
CONECT   19   20
CONECT   20   21   21   24
CONECT   21   22   45
CONECT   22   23
CONECT   23   46   47   48
CONECT   24   25   49   50
CONECT   25   51
END

HMDB0254486
     RDKit          3D
Mesulergine
 51 54  0  0  0  0  0  0  0  0999 V2000
   -0.7769   -2.5062    0.6030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6216   -1.7173   -0.5714 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7073   -0.8776   -0.9115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7670    0.4500   -0.2702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6850    0.5364    0.8591 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9677    1.6574    0.5856 S   0  0  0  0  0  6  0  0  0  0  0  0
   -4.3107    2.3162    1.8909 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5269    2.7497   -0.3673 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3329    0.8756   -0.1183 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1835    0.9245   -1.5590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4988   -0.4848    0.3473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4366    1.0307    0.1324 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5924   -0.0069    0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8781    0.6374    0.7185 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9747    1.8125    1.4155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2359    2.3867    1.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3784    1.8013    1.0904 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2727    0.6136    0.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0142    0.0748    0.2284 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0589   -1.0980   -0.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4085   -1.2772   -0.7719 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1159   -0.2360   -0.2372 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5511   -0.0229   -0.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8213   -1.8345   -0.7627 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6118   -0.9929   -0.6508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1345   -2.5067    1.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9149   -3.5785    0.2827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6197   -2.2553    1.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7446   -0.8101   -2.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6549   -1.4386   -0.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1821    1.1723   -1.0366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1091   -0.3931    0.9761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4557    1.7087   -1.8578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1912    1.1011   -1.9787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8072   -0.0613   -1.8930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5921   -0.6913    0.4390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0138   -1.2058   -0.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0889   -0.6401    1.3762 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0021    1.6216   -0.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6354    1.7633    0.9320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2433   -0.4811    1.4464 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1107    2.2994    1.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3127    3.3121    2.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3665    2.2227    1.2140 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8062   -2.1111   -1.3277 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9469   -0.7093   -1.0807 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0435   -0.1423    0.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7241    1.0267   -0.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8017   -2.7595   -0.1500 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8700   -2.2050   -1.8297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5483   -0.3629   -1.5871 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
  5  6  1  0
  6  7  2  0
  6  8  2  0
  6  9  1  0
  9 10  1  0
  9 11  1  0
  4 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 20 24  1  0
 24 25  1  0
 25  2  1  0
 25 13  1  0
 19 14  1  0
 22 18  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
 10 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 15 42  1  0
 16 43  1  0
 17 44  1  0
 21 45  1  0
 23 46  1  0
 23 47  1  0
 23 48  1  0
 24 49  1  0
 24 50  1  0
 25 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
({6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0,.0,]hexadeca-1(16),9,12,14-tetraen-4-yl}sulphamoyl)dimethylamine	Generator

Chemical Formula

C₁₈H₂₆N₄O₂S

Average Molecular Weight

362.49

Monoisotopic Molecular Weight

362.177647267

IUPAC Name

({6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraen-4-yl}sulfamoyl)dimethylamine

Traditional Name

({6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraen-4-yl}sulfamoyl)dimethylamine

CAS Registry Number

Not Available

SMILES

CN(C)S(=O)(=O)NC1CC2C(CC3=CN(C)C4=CC=CC2=C34)N(C)C1

InChI Identifier

InChI=1S/C18H26N4O2S/c1-20(2)25(23,24)19-13-9-15-14-6-5-7-16-18(14)12(10-21(16)3)8-17(15)22(4)11-13/h5-7,10,13,15,17,19H,8-9,11H2,1-4H3

InChI Key

JLVHTNZNKOSCNB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoloquinolines. These are polycyclic aromatic compounds containing an indole fused to a quinoline.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Indoloquinolines

Direct Parent

Indoloquinolines

Alternative Parents

Substituents

Ergoline skeleton
Indoloquinoline
Benzoquinoline
Pyrroloquinoline
N-alkylindole
3-alkylindole
Indole
Indole or derivatives
Isoindole or derivatives
Alkaloid or derivatives
Aralkylamine
Benzenoid
N-methylpyrrole
Substituted pyrrole
Sulfuric acid diamide
Piperidine
Heteroaromatic compound
Organic sulfuric acid or derivatives
Pyrrole
Tertiary amine
Tertiary aliphatic amine
Azacycle
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Amine
Organic oxygen compound
Organonitrogen 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)

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	1.56	ALOGPS
logP	1.08	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	11.08	ChemAxon
pKa (Strongest Basic)	6.9	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	57.58 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	100.29 m³·mol⁻¹	ChemAxon
Polarizability	39.64 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	221.755	30932474
DeepCCS	[M+Na]+	197.128	30932474
AllCCS	[M+H]+	187.1	32859911
AllCCS	[M+H-H2O]+	184.3	32859911
AllCCS	[M+NH4]+	189.6	32859911
AllCCS	[M+Na]+	190.4	32859911
AllCCS	[M-H]-	188.1	32859911
AllCCS	[M+Na-2H]-	188.4	32859911
AllCCS	[M+HCOO]-	188.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Mesulergine	CN(C)S(=O)(=O)NC1CC2C(CC3=CN(C)C4=CC=CC2=C34)N(C)C1	5016.1	Standard polar	33892256
Mesulergine	CN(C)S(=O)(=O)NC1CC2C(CC3=CN(C)C4=CC=CC2=C34)N(C)C1	2966.2	Standard non polar	33892256
Mesulergine	CN(C)S(=O)(=O)NC1CC2C(CC3=CN(C)C4=CC=CC2=C34)N(C)C1	3271.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Mesulergine,1TMS,isomer #1	CN1CC(N([Si](C)(C)C)S(=O)(=O)N(C)C)CC2C3=CC=CC4=C3C(=CN4C)CC21	2936.3	Semi standard non polar	33892256
Mesulergine,1TMS,isomer #1	CN1CC(N([Si](C)(C)C)S(=O)(=O)N(C)C)CC2C3=CC=CC4=C3C(=CN4C)CC21	3071.4	Standard non polar	33892256
Mesulergine,1TMS,isomer #1	CN1CC(N([Si](C)(C)C)S(=O)(=O)N(C)C)CC2C3=CC=CC4=C3C(=CN4C)CC21	4147.5	Standard polar	33892256
Mesulergine,1TBDMS,isomer #1	CN1CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)N(C)C)CC2C3=CC=CC4=C3C(=CN4C)CC21	3172.5	Semi standard non polar	33892256
Mesulergine,1TBDMS,isomer #1	CN1CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)N(C)C)CC2C3=CC=CC4=C3C(=CN4C)CC21	3383.4	Standard non polar	33892256
Mesulergine,1TBDMS,isomer #1	CN1CC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)N(C)C)CC2C3=CC=CC4=C3C(=CN4C)CC21	4180.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Mesulergine GC-MS (Non-derivatized) - 70eV, Positive	splash10-03xu-5496000000-6debfeaa3f1a72ca51b7	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mesulergine 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 - Mesulergine 10V, Negative-QTOF	splash10-03di-2309000000-a31d31d9287cd4be66ab	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesulergine 20V, Negative-QTOF	splash10-08fr-9846000000-160e5e85304381a2b9ac	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesulergine 40V, Negative-QTOF	splash10-000i-0190000000-e4fb4f3f7fa55b24a8d9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesulergine 10V, Positive-QTOF	splash10-03di-0009000000-f73b509cb8f61a5db7be	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesulergine 20V, Positive-QTOF	splash10-000l-0190000000-b16e3e9c37bbc89957c7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mesulergine 40V, Positive-QTOF	splash10-000j-0790000000-cad4b9367668a62e6e08	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

4418664

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5251926

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 Mesulergine (HMDB0254486)

MOL for HMDB0254486 (Mesulergine)

3D MOL for HMDB0254486 (Mesulergine)

3D SDF for HMDB0254486 (Mesulergine)

3D-SDF for HMDB0254486 (Mesulergine)

PDB for HMDB0254486 (Mesulergine)

3D PDB for HMDB0254486 (Mesulergine)

SMILES for HMDB0254486 (Mesulergine)

INCHI for HMDB0254486 (Mesulergine)

Structure for HMDB0254486 (Mesulergine)

3D Structure for HMDB0254486 (Mesulergine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra