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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:54 UTC

HMDB ID

HMDB0015248

Secondary Accession Numbers

HMDB15248

Metabolite Identification

Common Name

Trimethaphan

Description

Trimethaphan is only found in individuals that have used or taken this drug. It is a nicotinic antagonist that has been used as a ganglionic blocker in hypertension, as an adjunct to anesthesia, and to induce hypotension during surgery. [PubChem]Trimethaphan is a ganglionic blocking agent prevents stimulation of postsynaptic receptors by competing with acetylcholine for these receptor sites. Additional effects may include direct peripheral vasodilation and release of histamine. Trimethaphan's hypotensive effect is due to reduction in sympathetic tone and vasodilation, and is primarily postural.

Structure

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

1116
  Mrv0541 02231215152D          

 26 30  0  0  1  0            999 V2000
    2.9779    1.7856    0.0000 S   0  3  0  0  0  0  0  0  0  0  0  0
    4.9509   -0.9300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6458   -0.2633    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7200    0.5172    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3904    0.5160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7228    1.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0578    1.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8029    1.7856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9028    1.0031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3131    2.2660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4659   -0.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1620   -0.9315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5051    0.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4988   -1.6847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6780    1.5775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3195   -1.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0151   -2.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0659    2.1306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4631    1.8310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6564   -2.5225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3520   -3.1060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2388    2.9373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6360    2.6377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1726   -3.1909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0239    3.1909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1  8  1  0  0  0  0
  1 10  1  0  0  0  0
  2 12  2  0  0  0  0
  3  5  1  0  0  0  0
  3 12  1  0  0  0  0
  3 13  1  0  0  0  0
  4  7  1  0  0  0  0
  4 12  1  0  0  0  0
  4 14  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  9  1  0  0  0  0
  7  8  1  0  0  0  0
  9 11  1  0  0  0  0
 10 11  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  2  0  0  0  0
 15 18  1  0  0  0  0
 16 19  2  0  0  0  0
 16 20  1  0  0  0  0
 17 21  1  0  0  0  0
 18 22  2  0  0  0  0
 19 23  1  0  0  0  0
 20 24  2  0  0  0  0
 21 25  2  0  0  0  0
 22 25  1  0  0  0  0
 23 26  2  0  0  0  0
 24 26  1  0  0  0  0
M  CHG  1   1   1
M  END

HMDB0015248
     RDKit          3D
Trimethaphan
 51 55  0  0  0  0  0  0  0  0999 V2000
   -0.6355   -1.7051    2.2112 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4367   -0.6693    1.5096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4694    0.1058    0.8504 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8724    0.1209    1.2233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6382   -0.9113    0.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7632   -2.1636    1.0749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4696   -3.1457    0.4398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0751   -2.8842   -0.7933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9592   -1.6376   -1.3664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2335   -0.6512   -0.6997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7670    0.7898   -0.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2640    2.1602   -0.5522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2478    2.7555   -1.3510 S   0  0  0  0  0  3  0  0  0  0  0  0
    0.7666    4.3007   -0.5878 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2373    3.9943   -0.3872 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3802    2.6360    0.1729 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4204    1.6851   -0.4701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5010    1.1641    0.5776 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8169   -0.0518    1.2204 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1437   -0.5381    1.5219 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7322   -1.3915    0.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0678   -1.7070    0.5253 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6777   -2.5096   -0.4204 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8833   -2.9929   -1.4267 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5397   -2.6916   -1.4908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9505   -1.8817   -0.5265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2753    1.1430    1.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0033   -0.0535    2.3221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3042   -2.3801    2.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5793   -4.1407    0.8668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6295   -3.7047   -1.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4305   -1.4407   -2.3220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1637    0.3056   -1.1735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5282    0.1759   -1.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4817    2.7229    0.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0537    2.1501   -1.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7009    5.1290   -1.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2390    4.4721    0.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8180    4.1923   -1.2930 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5959    4.7311    0.3831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3198    2.6202    1.2880 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4115    2.2677   -0.0623 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8591    0.9514   -1.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2721    2.0058    1.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0280   -1.1371    2.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8215    0.2938    1.8110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6883   -1.3198    1.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7206   -2.7622   -0.3981 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3644   -3.6327   -2.1828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9363   -3.0912   -2.3028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8927   -1.6784   -0.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  3 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 19  2  1  0
 26 21  1  0
 10  5  1  0
 18 11  1  0
 17 13  1  0
  4 27  1  0
  4 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 18 44  1  0
 20 45  1  0
 20 46  1  0
 22 47  1  0
 23 48  1  0
 24 49  1  0
 25 50  1  0
 26 51  1  0
M  CHG  1  13   1
M  END

1116
  Mrv0541 02231215152D          

 26 30  0  0  1  0            999 V2000
    2.9779    1.7856    0.0000 S   0  3  0  0  0  0  0  0  0  0  0  0
    4.9509   -0.9300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6458   -0.2633    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7200    0.5172    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3904    0.5160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7228    1.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0578    1.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8029    1.7856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9028    1.0031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3131    2.2660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4659   -0.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1620   -0.9315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5051    0.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4988   -1.6847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6780    1.5775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3195   -1.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0151   -2.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0659    2.1306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4631    1.8310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6564   -2.5225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3520   -3.1060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2388    2.9373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6360    2.6377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1726   -3.1909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0239    3.1909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1  8  1  0  0  0  0
  1 10  1  0  0  0  0
  2 12  2  0  0  0  0
  3  5  1  0  0  0  0
  3 12  1  0  0  0  0
  3 13  1  0  0  0  0
  4  7  1  0  0  0  0
  4 12  1  0  0  0  0
  4 14  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  9  1  0  0  0  0
  7  8  1  0  0  0  0
  9 11  1  0  0  0  0
 10 11  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  2  0  0  0  0
 15 18  1  0  0  0  0
 16 19  2  0  0  0  0
 16 20  1  0  0  0  0
 17 21  1  0  0  0  0
 18 22  2  0  0  0  0
 19 23  1  0  0  0  0
 20 24  2  0  0  0  0
 21 25  2  0  0  0  0
 22 25  1  0  0  0  0
 23 26  2  0  0  0  0
 24 26  1  0  0  0  0
M  CHG  1   1   1
M  END
> <DATABASE_ID>
HMDB0015248

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C1N(CC2=CC=CC=C2)C2C[S+]3CCCC3C2N1CC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H25N2OS/c25-22-23(14-17-8-3-1-4-9-17)19-16-26-13-7-12-20(26)21(19)24(22)15-18-10-5-2-6-11-18/h1-6,8-11,19-21H,7,12-16H2/q+1

> <INCHI_KEY>
CHQOEHPMXSHGCL-UHFFFAOYSA-N

> <FORMULA>
C22H25N2OS

> <MOLECULAR_WEIGHT>
365.512

> <EXACT_MASS>
365.168759122

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
40.13415435906711

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5-dibenzyl-4-oxo-8λ⁴-thia-3,5-diazatricyclo[6.3.0.0²,⁶]undecan-8-ylium

> <ALOGPS_LOGP>
4.40

> <JCHEM_LOGP>
2.324136726457387

> <ALOGPS_LOGS>
-4.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
-1.99444997108513

> <JCHEM_POLAR_SURFACE_AREA>
23.550000000000004

> <JCHEM_REFRACTIVITY>
105.43010000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.65e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trimethaphan

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015248
     RDKit          3D
Trimethaphan
 51 55  0  0  0  0  0  0  0  0999 V2000
   -0.6355   -1.7051    2.2112 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4367   -0.6693    1.5096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4694    0.1058    0.8504 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8724    0.1209    1.2233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6382   -0.9113    0.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7632   -2.1636    1.0749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4696   -3.1457    0.4398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0751   -2.8842   -0.7933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9592   -1.6376   -1.3664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2335   -0.6512   -0.6997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7670    0.7898   -0.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2640    2.1602   -0.5522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2478    2.7555   -1.3510 S   0  0  0  0  0  3  0  0  0  0  0  0
    0.7666    4.3007   -0.5878 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2373    3.9943   -0.3872 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3802    2.6360    0.1729 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4204    1.6851   -0.4701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5010    1.1641    0.5776 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8169   -0.0518    1.2204 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1437   -0.5381    1.5219 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7322   -1.3915    0.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0678   -1.7070    0.5253 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6777   -2.5096   -0.4204 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8833   -2.9929   -1.4267 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5397   -2.6916   -1.4908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9505   -1.8817   -0.5265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2753    1.1430    1.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0033   -0.0535    2.3221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3042   -2.3801    2.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5793   -4.1407    0.8668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6295   -3.7047   -1.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4305   -1.4407   -2.3220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1637    0.3056   -1.1735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5282    0.1759   -1.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4817    2.7229    0.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0537    2.1501   -1.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7009    5.1290   -1.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2390    4.4721    0.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8180    4.1923   -1.2930 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5959    4.7311    0.3831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3198    2.6202    1.2880 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4115    2.2677   -0.0623 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8591    0.9514   -1.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2721    2.0058    1.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0280   -1.1371    2.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8215    0.2938    1.8110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6883   -1.3198    1.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7206   -2.7622   -0.3981 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3644   -3.6327   -2.1828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9363   -3.0912   -2.3028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8927   -1.6784   -0.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  3 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 19  2  1  0
 26 21  1  0
 10  5  1  0
 18 11  1  0
 17 13  1  0
  4 27  1  0
  4 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 18 44  1  0
 20 45  1  0
 20 46  1  0
 22 47  1  0
 23 48  1  0
 24 49  1  0
 25 50  1  0
 26 51  1  0
M  CHG  1  13   1
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1116                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       5.559   3.333   0.000  0.00  0.00           S+1
HETATM    2  O   UNK     0       9.242  -1.736   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       6.805  -0.491   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       8.811   0.965   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       6.329   0.963   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.083   1.869   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.575   1.869   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.099   3.333   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.552   1.872   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.318   4.230   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.080   3.329   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.336  -0.490   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.902  -1.739   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.276   1.439   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.531  -3.145   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.599   2.945   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.063  -3.303   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.628  -4.392   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.456   3.977   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.064   3.418   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.692  -4.709   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.257  -5.798   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.779   5.483   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.387   4.924   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.789  -5.956   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.245   5.956   0.000  0.00  0.00           C+0
CONECT    1    6    8   10                                                  
CONECT    2   12                                                            
CONECT    3    5   12   13                                                  
CONECT    4    7   12   14                                                  
CONECT    5    3    6    7                                                  
CONECT    6    1    5    9                                                  
CONECT    7    4    5    8                                                  
CONECT    8    1    7                                                       
CONECT    9    6   11                                                       
CONECT   10    1   11                                                       
CONECT   11    9   10                                                       
CONECT   12    2    3    4                                                  
CONECT   13    3   15                                                       
CONECT   14    4   16                                                       
CONECT   15   13   17   18                                                  
CONECT   16   14   19   20                                                  
CONECT   17   15   21                                                       
CONECT   18   15   22                                                       
CONECT   19   16   23                                                       
CONECT   20   16   24                                                       
CONECT   21   17   25                                                       
CONECT   22   18   25                                                       
CONECT   23   19   26                                                       
CONECT   24   20   26                                                       
CONECT   25   21   22                                                       
CONECT   26   23   24                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   60    0
END

COMPND    HMDB0015248
HETATM    1  O1  UNL     1      -0.635  -1.705   2.211  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.437  -0.669   1.510  1.00  0.00           C  
HETATM    3  N1  UNL     1      -1.469   0.106   0.850  1.00  0.00           N  
HETATM    4  C2  UNL     1      -2.872   0.121   1.223  1.00  0.00           C  
HETATM    5  C3  UNL     1      -3.638  -0.911   0.514  1.00  0.00           C  
HETATM    6  C4  UNL     1      -3.763  -2.164   1.075  1.00  0.00           C  
HETATM    7  C5  UNL     1      -4.470  -3.146   0.440  1.00  0.00           C  
HETATM    8  C6  UNL     1      -5.075  -2.884  -0.793  1.00  0.00           C  
HETATM    9  C7  UNL     1      -4.959  -1.638  -1.366  1.00  0.00           C  
HETATM   10  C8  UNL     1      -4.233  -0.651  -0.700  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.767   0.790  -0.182  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.264   2.160  -0.552  1.00  0.00           C  
HETATM   13  S1  UNL     1       0.248   2.756  -1.351  1.00  0.00           S1+
HETATM   14  C11 UNL     1       0.767   4.301  -0.588  1.00  0.00           C  
HETATM   15  C12 UNL     1       2.237   3.994  -0.387  1.00  0.00           C  
HETATM   16  C13 UNL     1       2.380   2.636   0.173  1.00  0.00           C  
HETATM   17  C14 UNL     1       1.420   1.685  -0.470  1.00  0.00           C  
HETATM   18  C15 UNL     1       0.501   1.164   0.578  1.00  0.00           C  
HETATM   19  N2  UNL     1       0.817  -0.052   1.220  1.00  0.00           N  
HETATM   20  C16 UNL     1       2.144  -0.538   1.522  1.00  0.00           C  
HETATM   21  C17 UNL     1       2.732  -1.391   0.485  1.00  0.00           C  
HETATM   22  C18 UNL     1       4.068  -1.707   0.525  1.00  0.00           C  
HETATM   23  C19 UNL     1       4.678  -2.510  -0.420  1.00  0.00           C  
HETATM   24  C20 UNL     1       3.883  -2.993  -1.427  1.00  0.00           C  
HETATM   25  C21 UNL     1       2.540  -2.692  -1.491  1.00  0.00           C  
HETATM   26  C22 UNL     1       1.950  -1.882  -0.526  1.00  0.00           C  
HETATM   27  H1  UNL     1      -3.275   1.143   1.039  1.00  0.00           H  
HETATM   28  H2  UNL     1      -3.003  -0.053   2.322  1.00  0.00           H  
HETATM   29  H3  UNL     1      -3.304  -2.380   2.021  1.00  0.00           H  
HETATM   30  H4  UNL     1      -4.579  -4.141   0.867  1.00  0.00           H  
HETATM   31  H5  UNL     1      -5.629  -3.705  -1.261  1.00  0.00           H  
HETATM   32  H6  UNL     1      -5.430  -1.441  -2.322  1.00  0.00           H  
HETATM   33  H7  UNL     1      -4.164   0.306  -1.174  1.00  0.00           H  
HETATM   34  H8  UNL     1      -0.528   0.176  -1.071  1.00  0.00           H  
HETATM   35  H9  UNL     1      -1.482   2.723   0.353  1.00  0.00           H  
HETATM   36  H10 UNL     1      -2.054   2.150  -1.309  1.00  0.00           H  
HETATM   37  H11 UNL     1       0.701   5.129  -1.312  1.00  0.00           H  
HETATM   38  H12 UNL     1       0.239   4.472   0.355  1.00  0.00           H  
HETATM   39  H13 UNL     1       2.818   4.192  -1.293  1.00  0.00           H  
HETATM   40  H14 UNL     1       2.596   4.731   0.383  1.00  0.00           H  
HETATM   41  H15 UNL     1       2.320   2.620   1.288  1.00  0.00           H  
HETATM   42  H16 UNL     1       3.412   2.268  -0.062  1.00  0.00           H  
HETATM   43  H17 UNL     1       1.859   0.951  -1.136  1.00  0.00           H  
HETATM   44  H18 UNL     1       0.272   2.006   1.266  1.00  0.00           H  
HETATM   45  H19 UNL     1       2.028  -1.137   2.474  1.00  0.00           H  
HETATM   46  H20 UNL     1       2.821   0.294   1.811  1.00  0.00           H  
HETATM   47  H21 UNL     1       4.688  -1.320   1.326  1.00  0.00           H  
HETATM   48  H22 UNL     1       5.721  -2.762  -0.398  1.00  0.00           H  
HETATM   49  H23 UNL     1       4.364  -3.633  -2.183  1.00  0.00           H  
HETATM   50  H24 UNL     1       1.936  -3.091  -2.303  1.00  0.00           H  
HETATM   51  H25 UNL     1       0.893  -1.678  -0.622  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   19
CONECT    3    4   11
CONECT    4    5   27   28
CONECT    5    6    6   10
CONECT    6    7   29
CONECT    7    8    8   30
CONECT    8    9   31
CONECT    9   10   10   32
CONECT   10   33
CONECT   11   12   18   34
CONECT   12   13   35   36
CONECT   13   14   17
CONECT   14   15   37   38
CONECT   15   16   39   40
CONECT   16   17   41   42
CONECT   17   18   43
CONECT   18   19   44
CONECT   19   20
CONECT   20   21   45   46
CONECT   21   22   22   26
CONECT   22   23   47
CONECT   23   24   24   48
CONECT   24   25   49
CONECT   25   26   26   50
CONECT   26   51
END

HMDB0015248
     RDKit          3D
Trimethaphan
 51 55  0  0  0  0  0  0  0  0999 V2000
   -0.6355   -1.7051    2.2112 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4367   -0.6693    1.5096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4694    0.1058    0.8504 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8724    0.1209    1.2233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6382   -0.9113    0.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7632   -2.1636    1.0749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4696   -3.1457    0.4398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0751   -2.8842   -0.7933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9592   -1.6376   -1.3664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2335   -0.6512   -0.6997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7670    0.7898   -0.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2640    2.1602   -0.5522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2478    2.7555   -1.3510 S   0  0  0  0  0  3  0  0  0  0  0  0
    0.7666    4.3007   -0.5878 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2373    3.9943   -0.3872 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3802    2.6360    0.1729 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4204    1.6851   -0.4701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5010    1.1641    0.5776 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8169   -0.0518    1.2204 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1437   -0.5381    1.5219 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7322   -1.3915    0.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0678   -1.7070    0.5253 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6777   -2.5096   -0.4204 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8833   -2.9929   -1.4267 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5397   -2.6916   -1.4908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9505   -1.8817   -0.5265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2753    1.1430    1.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0033   -0.0535    2.3221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3042   -2.3801    2.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5793   -4.1407    0.8668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6295   -3.7047   -1.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4305   -1.4407   -2.3220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1637    0.3056   -1.1735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5282    0.1759   -1.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4817    2.7229    0.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0537    2.1501   -1.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7009    5.1290   -1.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2390    4.4721    0.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8180    4.1923   -1.2930 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5959    4.7311    0.3831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3198    2.6202    1.2880 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4115    2.2677   -0.0623 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8591    0.9514   -1.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2721    2.0058    1.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0280   -1.1371    2.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8215    0.2938    1.8110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6883   -1.3198    1.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7206   -2.7622   -0.3981 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3644   -3.6327   -2.1828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9363   -3.0912   -2.3028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8927   -1.6784   -0.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  3 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 19  2  1  0
 26 21  1  0
 10  5  1  0
 18 11  1  0
 17 13  1  0
  4 27  1  0
  4 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 18 44  1  0
 20 45  1  0
 20 46  1  0
 22 47  1  0
 23 48  1  0
 24 49  1  0
 25 50  1  0
 26 51  1  0
M  CHG  1  13   1
M  END

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Synonyms

Value	Source
Trimetaphan	ChEBI
Trimetaphanum	ChEBI
Thimethaphan	HMDB

Chemical Formula

C₂₂H₂₅N₂OS

Average Molecular Weight

365.512

Monoisotopic Molecular Weight

365.168759122

IUPAC Name

3,5-dibenzyl-4-oxo-8λ⁴-thia-3,5-diazatricyclo[6.3.0.0²,⁶]undecan-8-ylium

Traditional Name

trimethaphan

CAS Registry Number

7187-66-8

SMILES

O=C1N(CC2=CC=CC=C2)C2C[S+]3CCCC3C2N1CC1=CC=CC=C1

InChI Identifier

InChI=1S/C22H25N2OS/c25-22-23(14-17-8-3-1-4-9-17)19-16-26-13-7-12-20(26)21(19)24(22)15-18-10-5-2-6-11-18/h1-6,8-11,19-21H,7,12-16H2/q+1

InChI Key

CHQOEHPMXSHGCL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thienoimidazolidines. These are heterocyclic compounds containing a thiophene ring fused to an imidazolidine ring. Thiophene is 5-membered ring consisting of four carbon atoms and one sulfur atom. Imidazolidine is 5-membered saturated ring of three carbon atoms, and two nitrogen centers at the 1- and 3-positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Thienoimidazolidines

Sub Class

Not Available

Direct Parent

Thienoimidazolidines

Alternative Parents

Substituents

Thienoimidazolidine
Monocyclic benzene moiety
Imidazolidinone
Benzenoid
Imidazolidine
Thiolane
Thiophene
Carbonic acid derivative
Urea
Azacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

sulfonium compound (CHEBI:9728 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015248)
Membrane (HMDB: HMDB0015248)

Source

Exogenous

Exogenous (HMDB: HMDB0015248)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0066 g/L	Not Available
LogP	3.473	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0066 g/L	ALOGPS
logP	4.4	ALOGPS
logP	2.32	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	23.55 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	105.43 m³·mol⁻¹	ChemAxon
Polarizability	40.13 Å³	ChemAxon
Number of Rings	5	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]+	177.618	30932474
DeepCCS	[M-H]-	175.26	30932474
DeepCCS	[M-2H]-	209.157	30932474
DeepCCS	[M+Na]+	184.384	30932474
AllCCS	[M+H]+	187.1	32859911
AllCCS	[M+H-H2O]+	184.7	32859911
AllCCS	[M+NH4]+	189.4	32859911
AllCCS	[M+Na]+	190.1	32859911
AllCCS	[M-H]-	185.0	32859911
AllCCS	[M+Na-2H]-	184.8	32859911
AllCCS	[M+HCOO]-	184.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.35 minutes	32390414
Predicted by Siyang on May 30, 2022	15.9538 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.79 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	26.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3043.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	437.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	208.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	212.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	153.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	763.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	737.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	73.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1568.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	543.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1859.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	455.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	405.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	276.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	164.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	14.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Trimethaphan	O=C1N(CC2=CC=CC=C2)C2C[S+]3CCCC3C2N1CC1=CC=CC=C1	4230.5	Standard polar	33892256
Trimethaphan	O=C1N(CC2=CC=CC=C2)C2C[S+]3CCCC3C2N1CC1=CC=CC=C1	3142.3	Standard non polar	33892256
Trimethaphan	O=C1N(CC2=CC=CC=C2)C2C[S+]3CCCC3C2N1CC1=CC=CC=C1	3052.8	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 - Trimethaphan GC-MS (Non-derivatized) - 70eV, Positive	splash10-004l-9271000000-f658de0375569e641f0c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trimethaphan 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 - Trimethaphan 10V, Positive-QTOF	splash10-014i-2009000000-41c3789a24a1ea419575	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethaphan 20V, Positive-QTOF	splash10-0pbc-5902000000-f04d3df8ae575a3a0251	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethaphan 40V, Positive-QTOF	splash10-0006-9100000000-53ff7f774f006f61b641	2017-09-01	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01116	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01116	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01116

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

22044

KEGG Compound ID

C07174

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Trimetaphan camsilate

METLIN ID

Not Available

PubChem Compound

23576

PDB ID

Not Available

ChEBI ID

9728

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Cholinesterase

General function:: Involved in carboxylesterase activity
Specific function:: Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:: BCHE
Uniprot ID:: P06276
Molecular weight:: 68417.575

References

Nakamura K, Koide M, Imanaga T, Ogasawara H, Takahashi M, Yoshikawa M: Prolonged neuromuscular blockade following trimetaphan infusion. A case report and in vitro study of cholinesterase inhibition. Anaesthesia. 1980 Dec;35(12):1202-7. [PubMed:7457791 ]

Enzyme Details

2. Neuronal acetylcholine receptor subunit alpha-10

General function:: Involved in extracellular ligand-gated ion channel activity
Specific function:: Ionotropic receptor with a probable role in the modulation of auditory stimuli. Agonist binding may induce an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The channel is permeable to a range of divalent cations including calcium, the influx of which may activate a potassium current which hyperpolarizes the cell membrane. In the ear, this may lead to a reduction in basilar membrane motion, altering the activity of auditory nerve fibers and reducing the range of dynamic hearing. This may protect against acoustic trauma
Gene Name:: CHRNA10
Uniprot ID:: Q9GZZ6
Molecular weight:: 49704.3

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kurenny DE, Selyanko AA, Derkach VA, Gmiro VE, Skok VI: Mechanism of long-lasting block of ganglion nicotinic receptors by mono-ammonium compounds with long aliphatic chain. J Auton Nerv Syst. 1994 Aug;48(3):231-40. [PubMed:7963258 ]
Loiacono R, Stephenson J, Stevenson J, Mitchelson F: Multiple binding sites for nicotine receptor antagonists in inhibiting [3H](-)-nicotine binding in rat cortex. Neuropharmacology. 1993 Sep;32(9):847-53. [PubMed:8232788 ]

Showing metabocard for Trimethaphan (HMDB0015248)

MOL for HMDB0015248 (Trimethaphan)

3D MOL for HMDB0015248 (Trimethaphan)

3D SDF for HMDB0015248 (Trimethaphan)

3D-SDF for HMDB0015248 (Trimethaphan)

PDB for HMDB0015248 (Trimethaphan)

3D PDB for HMDB0015248 (Trimethaphan)

SMILES for HMDB0015248 (Trimethaphan)

INCHI for HMDB0015248 (Trimethaphan)

Structure for HMDB0015248 (Trimethaphan)

3D Structure for HMDB0015248 (Trimethaphan)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References