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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 02:51:55 UTC

HMDB ID

HMDB0015254

Secondary Accession Numbers

HMDB15254

Metabolite Identification

Common Name

Ambenonium

Description

Ambenonium is only found in individuals that have used or taken this drug. It is a cholinesterase inhibitor used in the management of myasthenia gravis. [Wikipedia ]Ambenonium exerts its actions against myasthenia gravis by competitive, reversible inhibition of acetylcholinesterase. The disease myasthenia gravis occurs when the body inappropriately produces antibodies against acetylcholine receptors, and thus inhibits proper acetylcholine signal transmission (when acetylcholine binds to acetylcholine receptors of striated muscle fibers, it stimulates those fibers to contract). Ambenonium reversibly binds acetylcholinesterase at the anionic site, which results in the blockage of the site of acetycholine binding, thereby inhibiting acetylcholine hydrolysis and enhancing cholinergic function through the accumulation of acetycholine at cholinergic synpases. In turn this facilitates transmission of impulses across the myoneural junction and effectively treats the disease.

Structure

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

1122
  Mrv0541 02231215152D          

 36 37  0  0  0  0            999 V2000
    9.5094    3.9188    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -3.9188    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    2.6813    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.6813    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    5.9370    1.0313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.0313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.7784    1.9668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3810   -1.9668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2060   -3.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.0804    3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1284    3.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6035    1.9668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5560   -1.9668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0310   -3.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949    4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2224   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949    5.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -5.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    5.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -5.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0791   -5.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 25  1  0  0  0  0
  2 26  1  0  0  0  0
  3 29  2  0  0  0  0
  4 30  2  0  0  0  0
  5  9  1  0  0  0  0
  5 11  1  0  0  0  0
  5 13  1  0  0  0  0
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  7 17  1  0  0  0  0
  7 29  1  0  0  0  0
  8 18  1  0  0  0  0
  8 30  1  0  0  0  0
  9 17  1  0  0  0  0
 10 18  1  0  0  0  0
 11 19  1  0  0  0  0
 12 20  1  0  0  0  0
 13 21  1  0  0  0  0
 14 22  1  0  0  0  0
 15 23  1  0  0  0  0
 16 24  1  0  0  0  0
 19 25  1  0  0  0  0
 19 27  2  0  0  0  0
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 27 33  1  0  0  0  0
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 29 30  1  0  0  0  0
 31 35  1  0  0  0  0
 32 36  1  0  0  0  0
 33 35  2  0  0  0  0
 34 36  2  0  0  0  0
M  CHG  2   5   1   6   1
M  END

HMDB0015254
     RDKit          3D
Ambenonium
 78 79  0  0  0  0  0  0  0  0999 V2000
   -5.9187   -1.3253   -2.2018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5001   -1.4411   -1.7053 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0602    1.0278   -0.6309 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9581    1.7356    0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8753    1.8419    1.3897 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0886    2.3345   -0.5155 N   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7172    0.2950    1.9593 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3048   -0.1950    2.2456 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1296    1.8111    0.8284 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9108    1.5406    2.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.0416   -0.3404   -2.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.5633   -4.8668   -0.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6239   -4.1195    0.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6208    0.5462   -1.3643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6725   -0.9776   -1.3280 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7594    3.6317   -0.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5584    3.8888    0.7333 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1375    1.9199    1.9703 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3670    0.3592   -0.4443 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3529    1.6567   -1.1026 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8659   -0.6399    0.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1204   -2.9129   -3.2622 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0822   -1.8661   -4.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1520   -2.1639    0.3288 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
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 22 23  2  0
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  3 29  1  0
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 27 22  1  0
 35 30  1  0
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  4 42  1  0
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  7 49  1  0
  7 50  1  0
  8 51  1  0
 13 52  1  0
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 15 56  1  0
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 24 70  1  0
 25 71  1  0
 26 72  1  0
 29 73  1  0
 29 74  1  0
 31 75  1  0
 32 76  1  0
 33 77  1  0
 34 78  1  0
M  CHG  2   3   1  16   1
M  END

1122
  Mrv0541 02231215152D          

 36 37  0  0  0  0            999 V2000
    9.5094    3.9188    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -3.9188    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    2.6813    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.6813    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    5.9370    1.0313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.0313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.7949    5.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -5.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    5.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  5  9  1  0  0  0  0
  5 11  1  0  0  0  0
  5 13  1  0  0  0  0
  5 14  1  0  0  0  0
  6 10  1  0  0  0  0
  6 12  1  0  0  0  0
  6 15  1  0  0  0  0
  6 16  1  0  0  0  0
  7 17  1  0  0  0  0
  7 29  1  0  0  0  0
  8 18  1  0  0  0  0
  8 30  1  0  0  0  0
  9 17  1  0  0  0  0
 10 18  1  0  0  0  0
 11 19  1  0  0  0  0
 12 20  1  0  0  0  0
 13 21  1  0  0  0  0
 14 22  1  0  0  0  0
 15 23  1  0  0  0  0
 16 24  1  0  0  0  0
 19 25  1  0  0  0  0
 19 27  2  0  0  0  0
 20 26  1  0  0  0  0
 20 28  2  0  0  0  0
 25 31  2  0  0  0  0
 26 32  2  0  0  0  0
 27 33  1  0  0  0  0
 28 34  1  0  0  0  0
 29 30  1  0  0  0  0
 31 35  1  0  0  0  0
 32 36  1  0  0  0  0
 33 35  2  0  0  0  0
 34 36  2  0  0  0  0
M  CHG  2   5   1   6   1
M  END
> <DATABASE_ID>
HMDB0015254

> <DATABASE_NAME>
hmdb

> <SMILES>
CC[N+](CC)(CCNC(=O)C(=O)NCC[N+](CC)(CC)CC1=CC=CC=C1Cl)CC1=CC=CC=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C28H40Cl2N4O2/c1-5-33(6-2,21-23-13-9-11-15-25(23)29)19-17-31-27(35)28(36)32-18-20-34(7-3,8-4)22-24-14-10-12-16-26(24)30/h9-16H,5-8,17-22H2,1-4H3/p+2

> <INCHI_KEY>
OMHBPUNFVFNHJK-UHFFFAOYSA-P

> <FORMULA>
C28H42Cl2N4O2

> <MOLECULAR_WEIGHT>
537.565

> <EXACT_MASS>
536.268482022

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
59.983826034638525

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
2

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2-chlorophenyl)methyl](2-{[(2-{[(2-chlorophenyl)methyl]diethylazaniumyl}ethyl)carbamoyl]formamido}ethyl)diethylazanium

> <ALOGPS_LOGP>
2.27

> <JCHEM_LOGP>
-3.633401447610157

> <ALOGPS_LOGS>
-8.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
16.48119147469844

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.78387342350433

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6154372428069315

> <JCHEM_POLAR_SURFACE_AREA>
58.2

> <JCHEM_REFRACTIVITY>
173.5709999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.42e-07 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ambenonium

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015254
     RDKit          3D
Ambenonium
 78 79  0  0  0  0  0  0  0  0999 V2000
   -5.9187   -1.3253   -2.2018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5001   -1.4411   -1.7053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3070   -1.5347   -0.3234 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.8931   -2.9496   -0.0529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0087   -3.8969   -0.2990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2194   -0.7718    0.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1899   -0.2639   -0.7004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1511    0.4564    0.0652 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0602    1.0278   -0.6309 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0583    0.9442   -1.8880 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9581    1.7356    0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8753    1.8419    1.3897 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0886    2.3345   -0.5155 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1105    3.0367    0.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8828    2.3402    1.2189 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7696    1.2345    0.8521 N   0  0  0  0  0  4  0  0  0  0  0  0
    4.7172    0.2950    1.9593 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3048   -0.1950    2.2456 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1296    1.8111    0.8284 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9108    1.5406    2.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4474    0.7413   -0.4110 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2508   -0.2613   -1.1000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3816   -0.8373   -0.6434 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0618   -1.7915   -1.4119 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6111   -2.1712   -2.6395 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4627   -1.5800   -3.0919 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7789   -0.6504   -2.3702 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2918    0.0624   -3.0319 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.4424   -1.2982    0.5191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0976   -0.0329    0.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7430    1.0522   -0.2082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4152    2.2569   -0.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4961    2.3859    0.6806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8884    1.3091    1.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1952    0.1473    1.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7327   -1.2106    2.3568 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -6.0416   -0.3404   -2.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1525   -2.0823   -2.9788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6945   -1.3888   -1.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1097   -2.3891   -2.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8807   -0.6625   -2.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0525   -3.2022   -0.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4959   -2.9603    0.9769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6065   -3.5429   -1.1562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5633   -4.8668   -0.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6239   -4.1195    0.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6773   -1.4111    0.9910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5746    0.0813    0.8555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6208    0.5462   -1.3643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6725   -0.9776   -1.3280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2631    0.5154    1.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1330    2.2619   -1.5433 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7594    3.6317   -0.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5584    3.8888    0.7333 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1375    1.9199    1.9703 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4917    3.1161    1.7743 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0085    0.8679    2.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3330   -0.5722    1.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8601    0.3190    3.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6652   -0.2316    1.3669 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4040   -1.2669    2.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9675    2.9444    0.8271 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7000    1.5365   -0.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9912    1.8520    1.9444 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9460    0.5106    2.4136 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5685    2.1697    2.9395 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3670    0.3592   -0.4443 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3529    1.6567   -1.1026 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8659   -0.6399    0.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9812   -2.2447   -1.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1204   -2.9129   -3.2622 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0822   -1.8661   -4.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1520   -2.1639    0.3288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1405   -1.5220    1.5980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9065    1.0010   -0.8706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1097    3.0947   -0.7487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0470    3.3232    0.7463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7408    1.4259    2.0975 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
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  1  0
 16 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
  3 29  1  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 27 22  1  0
 35 30  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  2 40  1  0
  2 41  1  0
  4 42  1  0
  4 43  1  0
  5 44  1  0
  5 45  1  0
  5 46  1  0
  6 47  1  0
  6 48  1  0
  7 49  1  0
  7 50  1  0
  8 51  1  0
 13 52  1  0
 14 53  1  0
 14 54  1  0
 15 55  1  0
 15 56  1  0
 17 57  1  0
 17 58  1  0
 18 59  1  0
 18 60  1  0
 18 61  1  0
 19 62  1  0
 19 63  1  0
 20 64  1  0
 20 65  1  0
 20 66  1  0
 21 67  1  0
 21 68  1  0
 23 69  1  0
 24 70  1  0
 25 71  1  0
 26 72  1  0
 29 73  1  0
 29 74  1  0
 31 75  1  0
 32 76  1  0
 33 77  1  0
 34 78  1  0
M  CHG  2   3   1  16   1
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1122                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0      17.751   7.315   0.000  0.00  0.00          Cl+0
HETATM    2 Cl   UNK     0       3.080  -7.315   0.000  0.00  0.00          Cl+0
HETATM    3  O   UNK     0      12.416  -0.385   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       8.415   0.385   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      13.750   5.005   0.000  0.00  0.00           N+1
HETATM    6  N   UNK     0       7.081  -5.005   0.000  0.00  0.00           N+1
HETATM    7  N   UNK     0      11.082   1.925   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       9.748  -1.925   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      12.416   4.235   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.415  -4.235   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.083   5.775   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.748  -5.775   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.980   6.339   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.520   3.671   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.311  -3.671   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.851  -6.339   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.416   2.695   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.415  -2.695   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.083   7.315   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.748  -7.315   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.440   6.339   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.060   3.671   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.771  -3.671   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.391  -6.339   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.417   8.085   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.414  -8.085   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.750   8.085   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.081  -8.085   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.082   0.385   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.748  -0.385   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.417   9.625   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.414  -9.625   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.750   9.625   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.081  -9.625   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      15.083  10.395   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.748 -10.395   0.000  0.00  0.00           C+0
CONECT    1   25                                                            
CONECT    2   26                                                            
CONECT    3   29                                                            
CONECT    4   30                                                            
CONECT    5    9   11   13   14                                             
CONECT    6   10   12   15   16                                             
CONECT    7   17   29                                                       
CONECT    8   18   30                                                       
CONECT    9    5   17                                                       
CONECT   10    6   18                                                       
CONECT   11    5   19                                                       
CONECT   12    6   20                                                       
CONECT   13    5   21                                                       
CONECT   14    5   22                                                       
CONECT   15    6   23                                                       
CONECT   16    6   24                                                       
CONECT   17    7    9                                                       
CONECT   18    8   10                                                       
CONECT   19   11   25   27                                                  
CONECT   20   12   26   28                                                  
CONECT   21   13                                                            
CONECT   22   14                                                            
CONECT   23   15                                                            
CONECT   24   16                                                            
CONECT   25    1   19   31                                                  
CONECT   26    2   20   32                                                  
CONECT   27   19   33                                                       
CONECT   28   20   34                                                       
CONECT   29    3    7   30                                                  
CONECT   30    4    8   29                                                  
CONECT   31   25   35                                                       
CONECT   32   26   36                                                       
CONECT   33   27   35                                                       
CONECT   34   28   36                                                       
CONECT   35   31   33                                                       
CONECT   36   32   34                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   74    0
END

COMPND    HMDB0015254
HETATM    1  C1  UNL     1      -5.919  -1.325  -2.202  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.500  -1.441  -1.705  1.00  0.00           C  
HETATM    3  N1  UNL     1      -4.307  -1.535  -0.323  1.00  0.00           N1+
HETATM    4  C3  UNL     1      -3.893  -2.950  -0.053  1.00  0.00           C  
HETATM    5  C4  UNL     1      -5.009  -3.897  -0.299  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.219  -0.772   0.223  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.190  -0.264  -0.700  1.00  0.00           C  
HETATM    8  N2  UNL     1      -1.151   0.456   0.065  1.00  0.00           N  
HETATM    9  C7  UNL     1      -0.060   1.028  -0.631  1.00  0.00           C  
HETATM   10  O1  UNL     1       0.058   0.944  -1.888  1.00  0.00           O  
HETATM   11  C8  UNL     1       0.958   1.736   0.135  1.00  0.00           C  
HETATM   12  O2  UNL     1       0.875   1.842   1.390  1.00  0.00           O  
HETATM   13  N3  UNL     1       2.089   2.335  -0.515  1.00  0.00           N  
HETATM   14  C9  UNL     1       3.111   3.037   0.201  1.00  0.00           C  
HETATM   15  C10 UNL     1       3.883   2.340   1.219  1.00  0.00           C  
HETATM   16  N4  UNL     1       4.770   1.234   0.852  1.00  0.00           N1+
HETATM   17  C11 UNL     1       4.717   0.295   1.959  1.00  0.00           C  
HETATM   18  C12 UNL     1       3.305  -0.195   2.246  1.00  0.00           C  
HETATM   19  C13 UNL     1       6.130   1.811   0.828  1.00  0.00           C  
HETATM   20  C14 UNL     1       6.911   1.541   2.065  1.00  0.00           C  
HETATM   21  C15 UNL     1       4.447   0.741  -0.411  1.00  0.00           C  
HETATM   22  C16 UNL     1       5.251  -0.261  -1.100  1.00  0.00           C  
HETATM   23  C17 UNL     1       6.382  -0.837  -0.643  1.00  0.00           C  
HETATM   24  C18 UNL     1       7.062  -1.792  -1.412  1.00  0.00           C  
HETATM   25  C19 UNL     1       6.611  -2.171  -2.639  1.00  0.00           C  
HETATM   26  C20 UNL     1       5.463  -1.580  -3.092  1.00  0.00           C  
HETATM   27  C21 UNL     1       4.779  -0.650  -2.370  1.00  0.00           C  
HETATM   28 CL1  UNL     1       3.292   0.062  -3.032  1.00  0.00          CL  
HETATM   29  C22 UNL     1      -5.442  -1.298   0.519  1.00  0.00           C  
HETATM   30  C23 UNL     1      -6.098  -0.033   0.530  1.00  0.00           C  
HETATM   31  C24 UNL     1      -5.743   1.052  -0.208  1.00  0.00           C  
HETATM   32  C25 UNL     1      -6.415   2.257  -0.153  1.00  0.00           C  
HETATM   33  C26 UNL     1      -7.496   2.386   0.681  1.00  0.00           C  
HETATM   34  C27 UNL     1      -7.888   1.309   1.446  1.00  0.00           C  
HETATM   35  C28 UNL     1      -7.195   0.147   1.356  1.00  0.00           C  
HETATM   36 CL2  UNL     1      -7.733  -1.211   2.357  1.00  0.00          CL  
HETATM   37  H1  UNL     1      -6.042  -0.340  -2.749  1.00  0.00           H  
HETATM   38  H2  UNL     1      -6.153  -2.082  -2.979  1.00  0.00           H  
HETATM   39  H3  UNL     1      -6.695  -1.389  -1.446  1.00  0.00           H  
HETATM   40  H4  UNL     1      -4.110  -2.389  -2.208  1.00  0.00           H  
HETATM   41  H5  UNL     1      -3.881  -0.662  -2.197  1.00  0.00           H  
HETATM   42  H6  UNL     1      -3.053  -3.202  -0.731  1.00  0.00           H  
HETATM   43  H7  UNL     1      -3.496  -2.960   0.977  1.00  0.00           H  
HETATM   44  H8  UNL     1      -5.607  -3.543  -1.156  1.00  0.00           H  
HETATM   45  H9  UNL     1      -4.563  -4.867  -0.610  1.00  0.00           H  
HETATM   46  H10 UNL     1      -5.624  -4.119   0.595  1.00  0.00           H  
HETATM   47  H11 UNL     1      -2.677  -1.411   0.991  1.00  0.00           H  
HETATM   48  H12 UNL     1      -3.575   0.081   0.856  1.00  0.00           H  
HETATM   49  H13 UNL     1      -2.621   0.546  -1.364  1.00  0.00           H  
HETATM   50  H14 UNL     1      -1.672  -0.978  -1.328  1.00  0.00           H  
HETATM   51  H15 UNL     1      -1.263   0.515   1.089  1.00  0.00           H  
HETATM   52  H16 UNL     1       2.133   2.262  -1.543  1.00  0.00           H  
HETATM   53  H17 UNL     1       3.759   3.632  -0.517  1.00  0.00           H  
HETATM   54  H18 UNL     1       2.558   3.889   0.733  1.00  0.00           H  
HETATM   55  H19 UNL     1       3.137   1.920   1.970  1.00  0.00           H  
HETATM   56  H20 UNL     1       4.492   3.116   1.774  1.00  0.00           H  
HETATM   57  H21 UNL     1       5.008   0.868   2.892  1.00  0.00           H  
HETATM   58  H22 UNL     1       5.333  -0.572   1.834  1.00  0.00           H  
HETATM   59  H23 UNL     1       2.860   0.319   3.131  1.00  0.00           H  
HETATM   60  H24 UNL     1       2.665  -0.232   1.367  1.00  0.00           H  
HETATM   61  H25 UNL     1       3.404  -1.267   2.603  1.00  0.00           H  
HETATM   62  H26 UNL     1       5.968   2.944   0.827  1.00  0.00           H  
HETATM   63  H27 UNL     1       6.700   1.536  -0.069  1.00  0.00           H  
HETATM   64  H28 UNL     1       7.991   1.852   1.944  1.00  0.00           H  
HETATM   65  H29 UNL     1       6.946   0.511   2.414  1.00  0.00           H  
HETATM   66  H30 UNL     1       6.568   2.170   2.939  1.00  0.00           H  
HETATM   67  H31 UNL     1       3.367   0.359  -0.444  1.00  0.00           H  
HETATM   68  H32 UNL     1       4.353   1.657  -1.103  1.00  0.00           H  
HETATM   69  H33 UNL     1       6.866  -0.640   0.319  1.00  0.00           H  
HETATM   70  H34 UNL     1       7.981  -2.245  -1.014  1.00  0.00           H  
HETATM   71  H35 UNL     1       7.120  -2.913  -3.262  1.00  0.00           H  
HETATM   72  H36 UNL     1       5.082  -1.866  -4.069  1.00  0.00           H  
HETATM   73  H37 UNL     1      -6.152  -2.164   0.329  1.00  0.00           H  
HETATM   74  H38 UNL     1      -5.141  -1.522   1.598  1.00  0.00           H  
HETATM   75  H39 UNL     1      -4.907   1.001  -0.871  1.00  0.00           H  
HETATM   76  H40 UNL     1      -6.110   3.095  -0.749  1.00  0.00           H  
HETATM   77  H41 UNL     1      -8.047   3.323   0.746  1.00  0.00           H  
HETATM   78  H42 UNL     1      -8.741   1.426   2.097  1.00  0.00           H  
CONECT    1    2   37   38   39
CONECT    2    3   40   41
CONECT    3    4    6   29
CONECT    4    5   42   43
CONECT    5   44   45   46
CONECT    6    7   47   48
CONECT    7    8   49   50
CONECT    8    9   51
CONECT    9   10   10   11
CONECT   11   12   12   13
CONECT   13   14   52
CONECT   14   15   53   54
CONECT   15   16   55   56
CONECT   16   17   19   21
CONECT   17   18   57   58
CONECT   18   59   60   61
CONECT   19   20   62   63
CONECT   20   64   65   66
CONECT   21   22   67   68
CONECT   22   23   23   27
CONECT   23   24   69
CONECT   24   25   25   70
CONECT   25   26   71
CONECT   26   27   27   72
CONECT   27   28
CONECT   29   30   73   74
CONECT   30   31   31   35
CONECT   31   32   75
CONECT   32   33   33   76
CONECT   33   34   77
CONECT   34   35   35   78
CONECT   35   36
END

HMDB0015254
     RDKit          3D
Ambenonium
 78 79  0  0  0  0  0  0  0  0999 V2000
   -5.9187   -1.3253   -2.2018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5001   -1.4411   -1.7053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3070   -1.5347   -0.3234 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.8931   -2.9496   -0.0529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0087   -3.8969   -0.2990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2194   -0.7718    0.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1899   -0.2639   -0.7004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1511    0.4564    0.0652 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0602    1.0278   -0.6309 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0583    0.9442   -1.8880 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9581    1.7356    0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8753    1.8419    1.3897 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0886    2.3345   -0.5155 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1105    3.0367    0.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8828    2.3402    1.2189 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7696    1.2345    0.8521 N   0  0  0  0  0  4  0  0  0  0  0  0
    4.7172    0.2950    1.9593 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3048   -0.1950    2.2456 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1296    1.8111    0.8284 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9108    1.5406    2.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4474    0.7413   -0.4110 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2508   -0.2613   -1.1000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3816   -0.8373   -0.6434 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0618   -1.7915   -1.4119 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6111   -2.1712   -2.6395 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4627   -1.5800   -3.0919 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7789   -0.6504   -2.3702 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2918    0.0624   -3.0319 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.4424   -1.2982    0.5191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0976   -0.0329    0.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7430    1.0522   -0.2082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4152    2.2569   -0.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4961    2.3859    0.6806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8884    1.3091    1.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1952    0.1473    1.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7327   -1.2106    2.3568 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -6.0416   -0.3404   -2.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1525   -2.0823   -2.9788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6945   -1.3888   -1.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1097   -2.3891   -2.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8807   -0.6625   -2.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0525   -3.2022   -0.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4959   -2.9603    0.9769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6065   -3.5429   -1.1562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5633   -4.8668   -0.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6239   -4.1195    0.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6773   -1.4111    0.9910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5746    0.0813    0.8555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6208    0.5462   -1.3643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6725   -0.9776   -1.3280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2631    0.5154    1.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1330    2.2619   -1.5433 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7594    3.6317   -0.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5584    3.8888    0.7333 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1375    1.9199    1.9703 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4917    3.1161    1.7743 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0085    0.8679    2.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3330   -0.5722    1.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8601    0.3190    3.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6652   -0.2316    1.3669 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4040   -1.2669    2.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9675    2.9444    0.8271 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7000    1.5365   -0.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9912    1.8520    1.9444 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9460    0.5106    2.4136 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5685    2.1697    2.9395 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3670    0.3592   -0.4443 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3529    1.6567   -1.1026 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8659   -0.6399    0.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9812   -2.2447   -1.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1204   -2.9129   -3.2622 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0822   -1.8661   -4.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1520   -2.1639    0.3288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1405   -1.5220    1.5980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9065    1.0010   -0.8706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1097    3.0947   -0.7487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0470    3.3232    0.7463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7408    1.4259    2.0975 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
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  1  0
 16 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
  3 29  1  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 27 22  1  0
 35 30  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  2 40  1  0
  2 41  1  0
  4 42  1  0
  4 43  1  0
  5 44  1  0
  5 45  1  0
  5 46  1  0
  6 47  1  0
  6 48  1  0
  7 49  1  0
  7 50  1  0
  8 51  1  0
 13 52  1  0
 14 53  1  0
 14 54  1  0
 15 55  1  0
 15 56  1  0
 17 57  1  0
 17 58  1  0
 18 59  1  0
 18 60  1  0
 18 61  1  0
 19 62  1  0
 19 63  1  0
 20 64  1  0
 20 65  1  0
 20 66  1  0
 21 67  1  0
 21 68  1  0
 23 69  1  0
 24 70  1  0
 25 71  1  0
 26 72  1  0
 29 73  1  0
 29 74  1  0
 31 75  1  0
 32 76  1  0
 33 77  1  0
 34 78  1  0
M  CHG  2   3   1  16   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Ambenonium base	ChEBI
Ambenonum	ChEBI
Mytelase	HMDB
Ambenonium chloride	HMDB
Chloride, ambenonium	HMDB
Sanofi winthrop brand OF ambenonium chloride	HMDB

Chemical Formula

C₂₈H₄₂Cl₂N₄O₂

Average Molecular Weight

537.565

Monoisotopic Molecular Weight

536.268482022

IUPAC Name

[(2-chlorophenyl)methyl](2-{[(2-{[(2-chlorophenyl)methyl]diethylazaniumyl}ethyl)carbamoyl]formamido}ethyl)diethylazanium

Traditional Name

ambenonium

CAS Registry Number

7648-98-8

SMILES

CC[N+](CC)(CCNC(=O)C(=O)NCC[N+](CC)(CC)CC1=CC=CC=C1Cl)CC1=CC=CC=C1Cl

InChI Identifier

InChI=1S/C28H40Cl2N4O2/c1-5-33(6-2,21-23-13-9-11-15-25(23)29)19-17-31-27(35)28(36)32-18-20-34(7-3,8-4)22-24-14-10-12-16-26(24)30/h9-16H,5-8,17-22H2,1-4H3/p+2

InChI Key

OMHBPUNFVFNHJK-UHFFFAOYSA-P

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acid amides

Alternative Parents

Substituents

Alpha-amino acid amide
Benzylamine
Phenylmethylamine
Aralkylamine
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Tetraalkylammonium salt
Quaternary ammonium salt
Carboxamide group
Secondary carboxylic acid amide
Organic nitrogen compound
Amine
Organonitrogen compound
Organochloride
Organohalogen compound
Organooxygen compound
Organic salt
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic cation
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

quaternary ammonium ion (CHEBI:2627 )

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: HMDB0015254)
Extracellular (HMDB: HMDB0015254)

Source

Exogenous

Exogenous (HMDB: HMDB0015254)

Not Available

EC 3.1.1.8 (cholinesterase) inhibitor (HMDB: HMDB0015254)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	196 - 199 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	9.4e-07 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	9.4e-07 g/L	ALOGPS
logP	2.27	ALOGPS
logP	-3.6	ChemAxon
logS	-8.8	ALOGPS
pKa (Strongest Acidic)	10.78	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.2 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	173.57 m³·mol⁻¹	ChemAxon
Polarizability	59.98 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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+H]+	209.165	30932474
DeepCCS	[M-H]-	206.807	30932474
DeepCCS	[M-2H]-	240.354	30932474
DeepCCS	[M+Na]+	215.581	30932474
AllCCS	[M+H]+	225.6	32859911
AllCCS	[M+H-H2O]+	224.2	32859911
AllCCS	[M+NH4]+	226.8	32859911
AllCCS	[M+Na]+	227.1	32859911
AllCCS	[M-H]-	223.5	32859911
AllCCS	[M+Na-2H]-	224.5	32859911
AllCCS	[M+HCOO]-	225.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ambenonium	CC[N+](CC)(CCNC(=O)C(=O)NCC[N+](CC)(CC)CC1=CC=CC=C1Cl)CC1=CC=CC=C1Cl	4849.3	Standard polar	33892256
Ambenonium	CC[N+](CC)(CCNC(=O)C(=O)NCC[N+](CC)(CC)CC1=CC=CC=C1Cl)CC1=CC=CC=C1Cl	2564.6	Standard non polar	33892256
Ambenonium	CC[N+](CC)(CCNC(=O)C(=O)NCC[N+](CC)(CC)CC1=CC=CC=C1Cl)CC1=CC=CC=C1Cl	3991.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ambenonium,1TMS,isomer #1	CC[N+](CC)(CCNC(=O)C(=O)N(CC[N+](CC)(CC)CC1=CC=CC=C1Cl)[Si](C)(C)C)CC1=CC=CC=C1Cl	3922.2	Semi standard non polar	33892256
Ambenonium,1TMS,isomer #1	CC[N+](CC)(CCNC(=O)C(=O)N(CC[N+](CC)(CC)CC1=CC=CC=C1Cl)[Si](C)(C)C)CC1=CC=CC=C1Cl	3896.5	Standard non polar	33892256
Ambenonium,1TMS,isomer #1	CC[N+](CC)(CCNC(=O)C(=O)N(CC[N+](CC)(CC)CC1=CC=CC=C1Cl)[Si](C)(C)C)CC1=CC=CC=C1Cl	4974.6	Standard polar	33892256
Ambenonium,2TMS,isomer #1	CC[N+](CC)(CCN(C(=O)C(=O)N(CC[N+](CC)(CC)CC1=CC=CC=C1Cl)[Si](C)(C)C)[Si](C)(C)C)CC1=CC=CC=C1Cl	3898.8	Semi standard non polar	33892256
Ambenonium,2TMS,isomer #1	CC[N+](CC)(CCN(C(=O)C(=O)N(CC[N+](CC)(CC)CC1=CC=CC=C1Cl)[Si](C)(C)C)[Si](C)(C)C)CC1=CC=CC=C1Cl	3913.1	Standard non polar	33892256
Ambenonium,2TMS,isomer #1	CC[N+](CC)(CCN(C(=O)C(=O)N(CC[N+](CC)(CC)CC1=CC=CC=C1Cl)[Si](C)(C)C)[Si](C)(C)C)CC1=CC=CC=C1Cl	4640.4	Standard polar	33892256
Ambenonium,1TBDMS,isomer #1	CC[N+](CC)(CCNC(=O)C(=O)N(CC[N+](CC)(CC)CC1=CC=CC=C1Cl)[Si](C)(C)C(C)(C)C)CC1=CC=CC=C1Cl	4110.3	Semi standard non polar	33892256
Ambenonium,1TBDMS,isomer #1	CC[N+](CC)(CCNC(=O)C(=O)N(CC[N+](CC)(CC)CC1=CC=CC=C1Cl)[Si](C)(C)C(C)(C)C)CC1=CC=CC=C1Cl	4100.9	Standard non polar	33892256
Ambenonium,1TBDMS,isomer #1	CC[N+](CC)(CCNC(=O)C(=O)N(CC[N+](CC)(CC)CC1=CC=CC=C1Cl)[Si](C)(C)C(C)(C)C)CC1=CC=CC=C1Cl	4954.0	Standard polar	33892256
Ambenonium,2TBDMS,isomer #1	CC[N+](CC)(CCN(C(=O)C(=O)N(CC[N+](CC)(CC)CC1=CC=CC=C1Cl)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC1=CC=CC=C1Cl	4268.5	Semi standard non polar	33892256
Ambenonium,2TBDMS,isomer #1	CC[N+](CC)(CCN(C(=O)C(=O)N(CC[N+](CC)(CC)CC1=CC=CC=C1Cl)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC1=CC=CC=C1Cl	4268.2	Standard non polar	33892256
Ambenonium,2TBDMS,isomer #1	CC[N+](CC)(CCN(C(=O)C(=O)N(CC[N+](CC)(CC)CC1=CC=CC=C1Cl)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC1=CC=CC=C1Cl	4621.4	Standard polar	33892256

Spectra

NMR Spectra

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

Biological Properties

Cellular Locations

Cytoplasm

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 DB01122	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01122	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01122

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2046

KEGG Compound ID

C07773

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ambenonium

METLIN ID

Not Available

PubChem Compound

2131

PDB ID

Not Available

ChEBI ID

2627

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. Acetylcholinesterase

General function:: Involved in carboxylesterase activity
Specific function:: Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name:: ACHE
Uniprot ID:: P22303
Molecular weight:: 67795.525

References

Lockhart B, Closier M, Howard K, Steward C, Lestage P: Differential inhibition of [3H]-oxotremorine-M and [3H]-quinuclinidyl benzilate binding to muscarinic receptors in rat brain membranes with acetylcholinesterase inhibitors. Naunyn Schmiedebergs Arch Pharmacol. 2001 Apr;363(4):429-38. [PubMed:11330337 ]
Hodge AS, Humphrey DR, Rosenberry TL: Ambenonium is a rapidly reversible noncovalent inhibitor of acetylcholinesterase, with one of the highest known affinities. Mol Pharmacol. 1992 May;41(5):937-42. [PubMed:1588924 ]
Papp MI, Komoly S, Szirmai IG, Kovacs T: Similarities between CSF-brain extracellular transfer and neurofibrillary tangle invasion in Alzheimer's disease. Neurobiol Aging. 2006 Mar;27(3):402-12. Epub 2005 Jun 27. [PubMed:15982786 ]
Kenakin TP, Beek D: Self-cancellation of drug properties as a mode of organ selectivity: the antimuscarinic effects of ambenonium. J Pharmacol Exp Ther. 1985 Mar;232(3):732-40. [PubMed:2857786 ]
Webb GD: Affinity of benzoquinonium and ambenonium derivatives for the acetylcholine receptor, tested on the electroplax, and for acetylcholinesterase in solution. Biochim Biophys Acta. 1965 May 25;102(1):172-84. [PubMed:5833399 ]
Bolognesi ML, Cavalli A, Andrisano V, Bartolini M, Banzi R, Antonello A, Rosini M, Melchiorre C: Design, synthesis and biological evaluation of ambenonium derivatives as AChE inhibitors. Farmaco. 2003 Sep;58(9):917-28. [PubMed:13679187 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

2. 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

Yamamoto K, Kohda Y, Sawada Y, Iga T: Pharmacokinetics of ambenonium, a reversible cholinesterase inhibitor, in rats. Biopharm Drug Dispos. 1991 Nov;12(8):613-25. [PubMed:1801966 ]

Showing metabocard for Ambenonium (HMDB0015254)

MOL for HMDB0015254 (Ambenonium)

3D MOL for HMDB0015254 (Ambenonium)

3D SDF for HMDB0015254 (Ambenonium)

3D-SDF for HMDB0015254 (Ambenonium)

PDB for HMDB0015254 (Ambenonium)

3D PDB for HMDB0015254 (Ambenonium)

SMILES for HMDB0015254 (Ambenonium)

INCHI for HMDB0015254 (Ambenonium)

Structure for HMDB0015254 (Ambenonium)

3D Structure for HMDB0015254 (Ambenonium)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

NMR Spectra

Enzymes

References

References