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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

HMDB0015222

Secondary Accession Numbers

HMDB15222

Metabolite Identification

Common Name

Pentolinium

Description

Pentolinium is only found in individuals that have used or taken this drug. It is a nicotinic antagonist that has been used as a ganglionic blocking agent in hypertension. [PubChem]Pentolinium binds to the nicotinic (ganglion) acetylcholine receptor. This receptor/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. Blockage of the receptor leads to smooth muscle relaxation and vasodilaton.

Structure

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

HMDB0015222
     RDKit          3D
Pentolinium
 49 50  0  0  0  0  0  0  0  0999 V2000
    2.4274   -1.0892   -0.7412 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9619   -0.1576    0.2480 N   0  0  0  0  0  4  0  0  0  0  0  0
    2.1600   -0.0489    1.4321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6925   -0.0169    1.2275 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1910    1.1286    0.4302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3132    1.1711    0.2490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8262   -0.0189   -0.4449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2373   -0.0582   -0.6755 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.5426    0.4645   -1.9969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0573    0.5472    0.3032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2375   -0.4193    1.4399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7850   -1.7243    0.8316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6621   -1.4470   -0.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2493   -0.6900    0.6917 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2407   -0.0364   -0.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6961    1.3871   -0.3731 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2211    1.1153   -0.3285 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9755   -0.5333   -1.5808 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7740   -1.8526   -0.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2995   -1.6427   -1.1996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4709   -0.8200    2.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4696    0.9188    1.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3418   -0.9825    0.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2207   -0.0648    2.2499 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5969    1.1057   -0.6020 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4660    2.1203    0.8587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7308    1.2239    1.2983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5270    2.1387   -0.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3220   -0.1285   -1.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5320   -0.9407    0.1393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2542    1.5399   -2.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5735    0.2656   -2.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8701   -0.0687   -2.7308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7379    1.5493    0.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0747    0.6975   -0.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6757   -0.1401    2.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3078   -0.5349    1.7299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5031   -2.5561    1.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8345   -2.0233    1.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9333   -2.1152   -1.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6759   -1.5307   -1.0912 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4498   -0.4236    1.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2526   -1.7912    0.5251 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2500    0.0774    0.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2607   -0.5334   -1.1968 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9659    1.8226   -1.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0163    2.0279    0.4479 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7884    1.1911   -1.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7750    1.8967    0.3236 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  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  2 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17  2  1  0
 13  8  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
M  CHG  2   2   1   8   1
M  END

1090
  Mrv0541 02231215142D          

 17 18  0  0  0  0            999 V2000
    6.7861    0.6406    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.8696   -1.1032    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    6.1186    1.1255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4535    1.1255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0626   -1.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9559   -0.2827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3011   -0.0269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6902   -1.1894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3736    1.9101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1986    1.9101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6501   -0.5602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2021    0.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4806    0.0593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1751   -0.5219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9956   -0.6081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2710   -0.0269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0412   -1.9101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  1  7  1  0  0  0  0
  1 16  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  2  8  1  0  0  0  0
  2 17  1  0  0  0  0
  3  9  1  0  0  0  0
  4 10  1  0  0  0  0
  5 11  1  0  0  0  0
  6 12  1  0  0  0  0
  7 13  1  0  0  0  0
  8 14  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  1  0  0  0  0
 13 15  1  0  0  0  0
 14 15  1  0  0  0  0
M  CHG  2   1   1   2   1
M  END
> <DATABASE_ID>
HMDB0015222

> <DATABASE_NAME>
hmdb

> <SMILES>
C[N+]1(CCCCC[N+]2(C)CCCC2)CCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C15H32N2/c1-16(12-6-7-13-16)10-4-3-5-11-17(2)14-8-9-15-17/h3-15H2,1-2H3/q+2

> <INCHI_KEY>
XSBSKEQEUFOSDD-UHFFFAOYSA-N

> <FORMULA>
C15H32N2

> <MOLECULAR_WEIGHT>
240.428

> <EXACT_MASS>
240.256549034

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
31.35545016829584

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
2

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-methyl-1-[5-(1-methylpyrrolidin-1-ium-1-yl)pentyl]pyrrolidin-1-ium

> <ALOGPS_LOGP>
-2.26

> <JCHEM_LOGP>
-6.28237323661016

> <ALOGPS_LOGS>
-7.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
99.0274

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.16e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pentolinium

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015222
     RDKit          3D
Pentolinium
 49 50  0  0  0  0  0  0  0  0999 V2000
    2.4274   -1.0892   -0.7412 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9619   -0.1576    0.2480 N   0  0  0  0  0  4  0  0  0  0  0  0
    2.1600   -0.0489    1.4321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6925   -0.0169    1.2275 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1910    1.1286    0.4302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3132    1.1711    0.2490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8262   -0.0189   -0.4449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2373   -0.0582   -0.6755 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.5426    0.4645   -1.9969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0573    0.5472    0.3032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2375   -0.4193    1.4399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7850   -1.7243    0.8316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6621   -1.4470   -0.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2493   -0.6900    0.6917 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2407   -0.0364   -0.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6961    1.3871   -0.3731 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2211    1.1153   -0.3285 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9755   -0.5333   -1.5808 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7740   -1.8526   -0.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2995   -1.6427   -1.1996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4709   -0.8200    2.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4696    0.9188    1.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3418   -0.9825    0.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2207   -0.0648    2.2499 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5969    1.1057   -0.6020 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4660    2.1203    0.8587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7308    1.2239    1.2983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5270    2.1387   -0.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3220   -0.1285   -1.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5320   -0.9407    0.1393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2542    1.5399   -2.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5735    0.2656   -2.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8701   -0.0687   -2.7308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7379    1.5493    0.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0747    0.6975   -0.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6757   -0.1401    2.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3078   -0.5349    1.7299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5031   -2.5561    1.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8345   -2.0233    1.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9333   -2.1152   -1.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6759   -1.5307   -1.0912 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4498   -0.4236    1.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2526   -1.7912    0.5251 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2500    0.0774    0.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2607   -0.5334   -1.1968 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9659    1.8226   -1.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0163    2.0279    0.4479 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7884    1.1911   -1.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7750    1.8967    0.3236 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  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  2 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17  2  1  0
 13  8  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
M  CHG  2   2   1   8   1
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1090                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0      12.667   1.196   0.000  0.00  0.00           N+1
HETATM    2  N   UNK     0       5.357  -2.059   0.000  0.00  0.00           N+1
HETATM    3  C   UNK     0      11.421   2.101   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.913   2.101   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.850  -2.379   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.518  -0.528   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.762  -0.050   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.888  -2.220   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.897   3.566   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.437   3.566   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.080  -1.046   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.111   0.099   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.230   0.111   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.794  -0.974   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.325  -1.135   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.573  -0.050   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.677  -3.566   0.000  0.00  0.00           C+0
CONECT    1    3    4    7   16                                             
CONECT    2    5    6    8   17                                             
CONECT    3    1    9                                                       
CONECT    4    1   10                                                       
CONECT    5    2   11                                                       
CONECT    6    2   12                                                       
CONECT    7    1   13                                                       
CONECT    8    2   14                                                       
CONECT    9    3   10                                                       
CONECT   10    4    9                                                       
CONECT   11    5   12                                                       
CONECT   12    6   11                                                       
CONECT   13    7   15                                                       
CONECT   14    8   15                                                       
CONECT   15   13   14                                                       
CONECT   16    1                                                            
CONECT   17    2                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0015222
HETATM    1  C1  UNL     1       2.427  -1.089  -0.741  1.00  0.00           C  
HETATM    2  N1  UNL     1       2.962  -0.158   0.248  1.00  0.00           N1+
HETATM    3  C2  UNL     1       2.160  -0.049   1.432  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.692  -0.017   1.227  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.191   1.129   0.430  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.313   1.171   0.249  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.826  -0.019  -0.445  1.00  0.00           C  
HETATM    8  N2  UNL     1      -3.237  -0.058  -0.676  1.00  0.00           N1+
HETATM    9  C7  UNL     1      -3.543   0.464  -1.997  1.00  0.00           C  
HETATM   10  C8  UNL     1      -4.057   0.547   0.303  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.238  -0.419   1.440  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.785  -1.724   0.832  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.662  -1.447  -0.652  1.00  0.00           C  
HETATM   14  C12 UNL     1       4.249  -0.690   0.692  1.00  0.00           C  
HETATM   15  C13 UNL     1       5.241  -0.036  -0.214  1.00  0.00           C  
HETATM   16  C14 UNL     1       4.696   1.387  -0.373  1.00  0.00           C  
HETATM   17  C15 UNL     1       3.221   1.115  -0.329  1.00  0.00           C  
HETATM   18  H1  UNL     1       1.975  -0.533  -1.581  1.00  0.00           H  
HETATM   19  H2  UNL     1       1.774  -1.853  -0.334  1.00  0.00           H  
HETATM   20  H3  UNL     1       3.299  -1.643  -1.200  1.00  0.00           H  
HETATM   21  H4  UNL     1       2.471  -0.820   2.190  1.00  0.00           H  
HETATM   22  H5  UNL     1       2.470   0.919   1.922  1.00  0.00           H  
HETATM   23  H6  UNL     1       0.342  -0.983   0.753  1.00  0.00           H  
HETATM   24  H7  UNL     1       0.221  -0.065   2.250  1.00  0.00           H  
HETATM   25  H8  UNL     1       0.597   1.106  -0.602  1.00  0.00           H  
HETATM   26  H9  UNL     1       0.466   2.120   0.859  1.00  0.00           H  
HETATM   27  H10 UNL     1      -1.731   1.224   1.298  1.00  0.00           H  
HETATM   28  H11 UNL     1      -1.527   2.139  -0.244  1.00  0.00           H  
HETATM   29  H12 UNL     1      -1.322  -0.129  -1.427  1.00  0.00           H  
HETATM   30  H13 UNL     1      -1.532  -0.941   0.139  1.00  0.00           H  
HETATM   31  H14 UNL     1      -3.254   1.540  -2.078  1.00  0.00           H  
HETATM   32  H15 UNL     1      -4.573   0.266  -2.309  1.00  0.00           H  
HETATM   33  H16 UNL     1      -2.870  -0.069  -2.731  1.00  0.00           H  
HETATM   34  H17 UNL     1      -3.738   1.549   0.640  1.00  0.00           H  
HETATM   35  H18 UNL     1      -5.075   0.697  -0.151  1.00  0.00           H  
HETATM   36  H19 UNL     1      -3.676  -0.140   2.346  1.00  0.00           H  
HETATM   37  H20 UNL     1      -5.308  -0.535   1.730  1.00  0.00           H  
HETATM   38  H21 UNL     1      -4.503  -2.556   1.029  1.00  0.00           H  
HETATM   39  H22 UNL     1      -2.835  -2.023   1.297  1.00  0.00           H  
HETATM   40  H23 UNL     1      -2.933  -2.115  -1.149  1.00  0.00           H  
HETATM   41  H24 UNL     1      -4.676  -1.531  -1.091  1.00  0.00           H  
HETATM   42  H25 UNL     1       4.450  -0.424   1.730  1.00  0.00           H  
HETATM   43  H26 UNL     1       4.253  -1.791   0.525  1.00  0.00           H  
HETATM   44  H27 UNL     1       6.250   0.077   0.241  1.00  0.00           H  
HETATM   45  H28 UNL     1       5.261  -0.533  -1.197  1.00  0.00           H  
HETATM   46  H29 UNL     1       4.966   1.823  -1.345  1.00  0.00           H  
HETATM   47  H30 UNL     1       5.016   2.028   0.448  1.00  0.00           H  
HETATM   48  H31 UNL     1       2.788   1.191  -1.373  1.00  0.00           H  
HETATM   49  H32 UNL     1       2.775   1.897   0.324  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   14   17
CONECT    3    4   21   22
CONECT    4    5   23   24
CONECT    5    6   25   26
CONECT    6    7   27   28
CONECT    7    8   29   30
CONECT    8    9   10   13
CONECT    9   31   32   33
CONECT   10   11   34   35
CONECT   11   12   36   37
CONECT   12   13   38   39
CONECT   13   40   41
CONECT   14   15   42   43
CONECT   15   16   44   45
CONECT   16   17   46   47
CONECT   17   48   49
END

HMDB0015222
     RDKit          3D
Pentolinium
 49 50  0  0  0  0  0  0  0  0999 V2000
    2.4274   -1.0892   -0.7412 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9619   -0.1576    0.2480 N   0  0  0  0  0  4  0  0  0  0  0  0
    2.1600   -0.0489    1.4321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6925   -0.0169    1.2275 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1910    1.1286    0.4302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3132    1.1711    0.2490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8262   -0.0189   -0.4449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2373   -0.0582   -0.6755 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.5426    0.4645   -1.9969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0573    0.5472    0.3032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2375   -0.4193    1.4399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7850   -1.7243    0.8316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6621   -1.4470   -0.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2493   -0.6900    0.6917 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2407   -0.0364   -0.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6961    1.3871   -0.3731 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2211    1.1153   -0.3285 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9755   -0.5333   -1.5808 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7740   -1.8526   -0.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2995   -1.6427   -1.1996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4709   -0.8200    2.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4696    0.9188    1.9222 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3418   -0.9825    0.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2207   -0.0648    2.2499 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5969    1.1057   -0.6020 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4660    2.1203    0.8587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7308    1.2239    1.2983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5270    2.1387   -0.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3220   -0.1285   -1.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5320   -0.9407    0.1393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2542    1.5399   -2.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5735    0.2656   -2.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8701   -0.0687   -2.7308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7379    1.5493    0.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0747    0.6975   -0.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6757   -0.1401    2.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3078   -0.5349    1.7299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5031   -2.5561    1.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8345   -2.0233    1.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9333   -2.1152   -1.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6759   -1.5307   -1.0912 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4498   -0.4236    1.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2526   -1.7912    0.5251 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2500    0.0774    0.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2607   -0.5334   -1.1968 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9659    1.8226   -1.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0163    2.0279    0.4479 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7884    1.1911   -1.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7750    1.8967    0.3236 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  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  2 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17  2  1  0
 13  8  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
M  CHG  2   2   1   8   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Pentolineum	ChEBI
Pentolonium	ChEBI
Pentolonum	ChEBI
Pentolinium tartrate	HMDB
Tartrate, pentolinium	HMDB
Tartrate, pentolonium	HMDB
Pentolonium tartrate	HMDB
Pentolinium	MeSH

Chemical Formula

C₁₅H₃₂N₂

Average Molecular Weight

240.428

Monoisotopic Molecular Weight

240.256549034

IUPAC Name

1-methyl-1-[5-(1-methylpyrrolidin-1-ium-1-yl)pentyl]pyrrolidin-1-ium

Traditional Name

pentolinium

CAS Registry Number

52-62-0

SMILES

C[N+]1(CCCCC[N+]2(C)CCCC2)CCCC1

InChI Identifier

InChI=1S/C15H32N2/c1-16(12-6-7-13-16)10-4-3-5-11-17(2)14-8-9-15-17/h3-15H2,1-2H3/q+2

InChI Key

XSBSKEQEUFOSDD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-alkylpyrrolidines. N-alkylpyrrolidines are compounds containing a pyrrolidine moiety that is substituted at the N1-position with an alkyl group. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolidines

Sub Class

N-alkylpyrrolidines

Direct Parent

N-alkylpyrrolidines

Alternative Parents

Substituents

N-alkylpyrrolidine
Tetraalkylammonium salt
Quaternary ammonium salt
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organic salt
Organonitrogen compound
Amine
Organic cation
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

organic cation (CHEBI:347401 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015222)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	213 °C (tartrate salt)	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.2e-05 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.2e-05 g/L	ALOGPS
logP	-2.3	ALOGPS
logP	-6.3	ChemAxon
logS	-7.4	ALOGPS
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	99.03 m³·mol⁻¹	ChemAxon
Polarizability	31.36 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	159.744	30932474
DeepCCS	[M-H]-	157.386	30932474
DeepCCS	[M-2H]-	191.088	30932474
DeepCCS	[M+Na]+	165.88	30932474
AllCCS	[M+H]+	162.1	32859911
AllCCS	[M+H-H2O]+	158.8	32859911
AllCCS	[M+NH4]+	165.2	32859911
AllCCS	[M+Na]+	166.1	32859911
AllCCS	[M-H]-	198.8	32859911
AllCCS	[M+Na-2H]-	199.3	32859911
AllCCS	[M+HCOO]-	199.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pentolinium	C[N+]1(CCCCC[N+]2(C)CCCC2)CCCC1	2084.0	Standard polar	33892256
Pentolinium	C[N+]1(CCCCC[N+]2(C)CCCC2)CCCC1	1531.5	Standard non polar	33892256
Pentolinium	C[N+]1(CCCCC[N+]2(C)CCCC2)CCCC1	1824.0	Semi standard non polar	33892256

Spectra

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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 DB01090	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01090	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01090

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5641

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pentolinium

METLIN ID

Not Available

PubChem Compound

5850

PDB ID

Not Available

ChEBI ID

347401

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. 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 ]
McKay DB, Burkman AM: Nicotinic and nonnicotinic receptor-mediated actions of vinblastine. Proc Soc Exp Biol Med. 1993 Jul;203(3):372-6. [PubMed:8516349 ]
Cachelin AB, Rust G: Beta-subunits co-determine the sensitivity of rat neuronal nicotinic receptors to antagonists. Pflugers Arch. 1995 Jan;429(3):449-51. [PubMed:7761270 ]

Showing metabocard for Pentolinium (HMDB0015222)

MOL for HMDB0015222 (Pentolinium)

3D MOL for HMDB0015222 (Pentolinium)

3D SDF for HMDB0015222 (Pentolinium)

3D-SDF for HMDB0015222 (Pentolinium)

PDB for HMDB0015222 (Pentolinium)

3D PDB for HMDB0015222 (Pentolinium)

SMILES for HMDB0015222 (Pentolinium)

INCHI for HMDB0015222 (Pentolinium)

Structure for HMDB0015222 (Pentolinium)

3D Structure for HMDB0015222 (Pentolinium)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

NMR Spectra

Enzymes

References