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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 17:05:36 UTC

Update Date

2022-11-23 22:29:18 UTC

HMDB ID

HMDB0256572

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Piperaquine

Description

piperaquine belongs to the class of organic compounds known as pyridinylpiperazines. Pyridinylpiperazines are compounds containing a pyridinylpiperazine skeleton, which consists of a pyridine linked (not fused) to a piperazine by a bond by a single bond that is not part of a ring. Based on a literature review a significant number of articles have been published on piperaquine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Piperaquine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Piperaquine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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


  Mrv1652306031606132D          

 37 42  0  0  0  0            999 V2000
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -8.6625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  2  0  0  0  0
  5  3  2  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  1  1  0  0  0  0
 11  1  1  0  0  0  0
 16 12  1  0  0  0  0
 17 13  1  0  0  0  0
 18 14  1  0  0  0  0
 19 15  1  0  0  0  0
 22  2  1  0  0  0  0
 22 20  2  0  0  0  0
 23  3  1  0  0  0  0
 23 21  2  0  0  0  0
 24  4  1  0  0  0  0
 25  5  1  0  0  0  0
 26 20  1  0  0  0  0
 26 24  2  0  0  0  0
 27 21  1  0  0  0  0
 27 25  2  0  0  0  0
 28  6  2  0  0  0  0
 28 24  1  0  0  0  0
 29  7  2  0  0  0  0
 29 25  1  0  0  0  0
 30 22  1  0  0  0  0
 31 23  1  0  0  0  0
 32  8  2  0  0  0  0
 32 26  1  0  0  0  0
 33  9  2  0  0  0  0
 33 27  1  0  0  0  0
 34 10  1  0  0  0  0
 34 12  1  0  0  0  0
 34 13  1  0  0  0  0
 35 11  1  0  0  0  0
 35 14  1  0  0  0  0
 35 15  1  0  0  0  0
 36 16  1  0  0  0  0
 36 17  1  0  0  0  0
 36 28  1  0  0  0  0
 37 18  1  0  0  0  0
 37 19  1  0  0  0  0
 37 29  1  0  0  0  0
M  END

HMDB0256572
     RDKit          3D
piperaquine
 69 74  0  0  0  0  0  0  0  0999 V2000
   -8.7675    2.5700   -3.7558 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -7.9903    1.8096   -2.3986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6069    1.8617   -2.2409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9604    1.2650   -1.1788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7091    0.5824   -0.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0595   -0.0228    0.8270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6703    0.0225    1.0446 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0439    1.2529    1.4560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6564    1.4202    0.9183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8236    0.2415    1.0292 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1710    0.0348   -0.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2685   -1.1445   -0.3129 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8757   -1.1858    0.6243 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8174   -0.1297    0.5771 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8982   -0.2791    1.5290 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1103   -0.9604    0.9130 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5128   -0.1294   -0.2089 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7919    0.5004   -0.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9087    1.8805   -0.2646 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1454    2.4676   -0.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2247    1.6787   -0.4840 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1384    0.3354   -0.5337 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2831   -0.4402   -0.6766 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2048   -1.8101   -0.7327 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7141   -2.7166   -0.9124 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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    6.8357   -1.6831   -0.5067 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9060   -0.2992   -0.4490 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    0.0252   -1.2353 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1560    0.4335   -0.6700 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.8619   -0.7061    1.7473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2254   -0.7410    1.5669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7908   -0.1339    0.5296 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0758    0.5380   -0.3907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7226    1.1332   -1.4489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0083    2.3979   -2.9895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8899    1.3198   -1.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9459    1.2248    2.5660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6603    2.1028    1.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6885    1.7852   -0.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1696    2.2457    1.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5886    0.9639   -0.4381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9595   -0.1101   -1.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0346   -1.2667   -1.3785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8802   -2.0748   -0.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1282    0.6826    1.9971 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7314   -1.9356    0.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8618   -1.0815    1.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0031    2.4591   -0.1561 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2587    3.5671   -0.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2489    0.0418   -0.7436 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9170   -3.4902   -0.6912 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8629   -2.1325   -0.4398 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3518   -0.9566   -1.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0782    1.5619   -0.6221 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4155    0.1559   -1.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8117   -0.6054    2.6233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5739   -1.3049   -0.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2701   -2.0630    1.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3625   -1.1863    2.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8126   -1.2789    2.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7941    1.0953   -1.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
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 13 14  1  0
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 23 24  1  0
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 10 31  1  0
 31 32  1  0
  6 33  2  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 36 37  2  0
 37  2  1  0
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 32  7  1  0
 30 14  1  0
 28 18  1  0
 28 22  1  0
  3 38  1  0
  4 39  1  0
  8 40  1  0
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 23 56  1  0
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 31 63  1  0
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 32 66  1  0
 33 67  1  0
 34 68  1  0
 37 69  1  0
M  END


  Mrv1652306031606132D          

 37 42  0  0  0  0            999 V2000
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  4  2  2  0  0  0  0
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  8  6  1  0  0  0  0
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 31 23  1  0  0  0  0
 32  8  2  0  0  0  0
 32 26  1  0  0  0  0
 33  9  2  0  0  0  0
 33 27  1  0  0  0  0
 34 10  1  0  0  0  0
 34 12  1  0  0  0  0
 34 13  1  0  0  0  0
 35 11  1  0  0  0  0
 35 14  1  0  0  0  0
 35 15  1  0  0  0  0
 36 16  1  0  0  0  0
 36 17  1  0  0  0  0
 36 28  1  0  0  0  0
 37 18  1  0  0  0  0
 37 19  1  0  0  0  0
 37 29  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0256572

> <DATABASE_NAME>
hmdb

> <SMILES>
ClC1=CC2=C(C=C1)C(=CC=N2)N1CCN(CCCN2CCN(CC2)C2=CC=NC3=C2C=CC(Cl)=C3)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C29H32Cl2N6/c30-22-2-4-24-26(20-22)32-8-6-28(24)36-16-12-34(13-17-36)10-1-11-35-14-18-37(19-15-35)29-7-9-33-27-21-23(31)3-5-25(27)29/h2-9,20-21H,1,10-19H2

> <INCHI_KEY>
UCRHFBCYFMIWHC-UHFFFAOYSA-N

> <FORMULA>
C29H32Cl2N6

> <MOLECULAR_WEIGHT>
535.52

> <EXACT_MASS>
534.2065505

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
59.55954399201663

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7-chloro-4-(4-{3-[4-(7-chloroquinolin-4-yl)piperazin-1-yl]propyl}piperazin-1-yl)quinoline

> <ALOGPS_LOGP>
5.53

> <JCHEM_LOGP>
5.268651966333335

> <ALOGPS_LOGS>
-4.51

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
3

> <JCHEM_PKA_STRONGEST_BASIC>
8.474282665831243

> <JCHEM_POLAR_SURFACE_AREA>
38.74000000000001

> <JCHEM_REFRACTIVITY>
153.42199999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.67e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
piperaquine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0256572
     RDKit          3D
piperaquine
 69 74  0  0  0  0  0  0  0  0999 V2000
   -8.7675    2.5700   -3.7558 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -7.9903    1.8096   -2.3986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6069    1.8617   -2.2409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9604    1.2650   -1.1788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7091    0.5824   -0.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0595   -0.0228    0.8270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6703    0.0225    1.0446 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0439    1.2529    1.4560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6564    1.4202    0.9183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8236    0.2415    1.0292 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1710    0.0348   -0.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2685   -1.1445   -0.3129 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8757   -1.1858    0.6243 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8174   -0.1297    0.5771 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8982   -0.2791    1.5290 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1103   -0.9604    0.9130 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5128   -0.1294   -0.2089 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7919    0.5004   -0.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9087    1.8805   -0.2646 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1454    2.4676   -0.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2247    1.6787   -0.4840 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1384    0.3354   -0.5337 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2831   -0.4402   -0.6766 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2048   -1.8101   -0.7327 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7141   -2.7166   -0.9124 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.9953   -2.4235   -0.6484 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8357   -1.6831   -0.5067 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9060   -0.2992   -0.4490 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    0.0252   -1.2353 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1560    0.4335   -0.6700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5269   -0.8793    1.5656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8429   -1.1364    0.8595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8619   -0.7061    1.7473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2254   -0.7410    1.5669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7908   -0.1339    0.5296 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0758    0.5380   -0.3907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7226    1.1332   -1.4489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0083    2.3979   -2.9895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8899    1.3198   -1.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9459    1.2248    2.5660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6603    2.1028    1.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6885    1.7852   -0.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1696    2.2457    1.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5886    0.9639   -0.4381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9595   -0.1101   -1.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0346   -1.2667   -1.3785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8802   -2.0748   -0.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4145   -2.1614    0.4303 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4879   -1.2634    1.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5310   -0.9761    2.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1282    0.6826    1.9971 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7314   -1.9356    0.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8618   -1.0815    1.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0031    2.4591   -0.1561 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2587    3.5671   -0.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2489    0.0418   -0.7436 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9170   -3.4902   -0.6912 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8629   -2.1325   -0.4398 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3518   -0.9566   -1.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7743    0.8358   -1.9620 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0782    1.5619   -0.6221 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4155    0.1559   -1.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9280   -1.7847    1.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8117   -0.6054    2.6233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5739   -1.3049   -0.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2701   -2.0630    1.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3625   -1.1863    2.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8126   -1.2789    2.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7941    1.0953   -1.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 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  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 26 27  1  0
 27 28  2  0
 17 29  1  0
 29 30  1  0
 10 31  1  0
 31 32  1  0
  6 33  2  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 36 37  2  0
 37  2  1  0
 36  5  1  0
 32  7  1  0
 30 14  1  0
 28 18  1  0
 28 22  1  0
  3 38  1  0
  4 39  1  0
  8 40  1  0
  8 41  1  0
  9 42  1  0
  9 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 12 47  1  0
 13 48  1  0
 13 49  1  0
 15 50  1  0
 15 51  1  0
 16 52  1  0
 16 53  1  0
 19 54  1  0
 20 55  1  0
 23 56  1  0
 26 57  1  0
 27 58  1  0
 29 59  1  0
 29 60  1  0
 30 61  1  0
 30 62  1  0
 31 63  1  0
 31 64  1  0
 32 65  1  0
 32 66  1  0
 33 67  1  0
 34 68  1  0
 37 69  1  0
M  END

HEADER    PROTEIN                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.000 -13.860   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.000 -12.320   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   30 Cl   UNK     0      -1.334 -16.170   0.000  0.00  0.00          Cl+0
HETATM   31 Cl   UNK     0       0.000   4.620   0.000  0.00  0.00          Cl+0
HETATM   32  N   UNK     0      -4.001 -11.550   0.000  0.00  0.00           N+0
HETATM   33  N   UNK     0       5.335   4.620   0.000  0.00  0.00           N+0
HETATM   34  N   UNK     0       2.667  -7.700   0.000  0.00  0.00           N+0
HETATM   35  N   UNK     0       5.335  -3.080   0.000  0.00  0.00           N+0
HETATM   36  N   UNK     0      -0.000  -9.240   0.000  0.00  0.00           N+0
HETATM   37  N   UNK     0       5.335   0.000   0.000  0.00  0.00           N+0
CONECT    1   10   11                                                       
CONECT    2    4   22                                                       
CONECT    3    5   23                                                       
CONECT    4    2   24                                                       
CONECT    5    3   25                                                       
CONECT    6    8   28                                                       
CONECT    7    9   29                                                       
CONECT    8    6   32                                                       
CONECT    9    7   33                                                       
CONECT   10    1   34                                                       
CONECT   11    1   35                                                       
CONECT   12   16   34                                                       
CONECT   13   17   34                                                       
CONECT   14   18   35                                                       
CONECT   15   19   35                                                       
CONECT   16   12   36                                                       
CONECT   17   13   36                                                       
CONECT   18   14   37                                                       
CONECT   19   15   37                                                       
CONECT   20   22   26                                                       
CONECT   21   23   27                                                       
CONECT   22    2   20   30                                                  
CONECT   23    3   21   31                                                  
CONECT   24    4   26   28                                                  
CONECT   25    5   27   29                                                  
CONECT   26   20   24   32                                                  
CONECT   27   21   25   33                                                  
CONECT   28    6   24   36                                                  
CONECT   29    7   25   37                                                  
CONECT   30   22                                                            
CONECT   31   23                                                            
CONECT   32    8   26                                                       
CONECT   33    9   27                                                       
CONECT   34   10   12   13                                                  
CONECT   35   11   14   15                                                  
CONECT   36   16   17   28                                                  
CONECT   37   18   19   29                                                  
MASTER        0    0    0    0    0    0    0    0   37    0   84    0
END

COMPND    HMDB0256572
HETATM    1 CL1  UNL     1      -8.767   2.570  -3.756  1.00  0.00          CL  
HETATM    2  C1  UNL     1      -7.990   1.810  -2.399  1.00  0.00           C  
HETATM    3  C2  UNL     1      -6.607   1.862  -2.241  1.00  0.00           C  
HETATM    4  C3  UNL     1      -5.960   1.265  -1.179  1.00  0.00           C  
HETATM    5  C4  UNL     1      -6.709   0.582  -0.225  1.00  0.00           C  
HETATM    6  C5  UNL     1      -6.059  -0.023   0.827  1.00  0.00           C  
HETATM    7  N1  UNL     1      -4.670   0.023   1.045  1.00  0.00           N  
HETATM    8  C6  UNL     1      -4.044   1.253   1.456  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.656   1.420   0.918  1.00  0.00           C  
HETATM   10  N2  UNL     1      -1.824   0.242   1.029  1.00  0.00           N  
HETATM   11  C8  UNL     1      -1.171   0.035  -0.219  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.269  -1.144  -0.313  1.00  0.00           C  
HETATM   13  C10 UNL     1       0.876  -1.186   0.624  1.00  0.00           C  
HETATM   14  N3  UNL     1       1.817  -0.130   0.577  1.00  0.00           N  
HETATM   15  C11 UNL     1       2.898  -0.279   1.529  1.00  0.00           C  
HETATM   16  C12 UNL     1       4.110  -0.960   0.913  1.00  0.00           C  
HETATM   17  N4  UNL     1       4.513  -0.129  -0.209  1.00  0.00           N  
HETATM   18  C13 UNL     1       5.792   0.500  -0.313  1.00  0.00           C  
HETATM   19  C14 UNL     1       5.909   1.881  -0.265  1.00  0.00           C  
HETATM   20  C15 UNL     1       7.145   2.468  -0.352  1.00  0.00           C  
HETATM   21  N5  UNL     1       8.225   1.679  -0.484  1.00  0.00           N  
HETATM   22  C16 UNL     1       8.138   0.335  -0.534  1.00  0.00           C  
HETATM   23  C17 UNL     1       9.283  -0.440  -0.677  1.00  0.00           C  
HETATM   24  C18 UNL     1       9.205  -1.810  -0.733  1.00  0.00           C  
HETATM   25 CL2  UNL     1      10.714  -2.717  -0.912  1.00  0.00          CL  
HETATM   26  C19 UNL     1       7.995  -2.423  -0.648  1.00  0.00           C  
HETATM   27  C20 UNL     1       6.836  -1.683  -0.507  1.00  0.00           C  
HETATM   28  C21 UNL     1       6.906  -0.299  -0.449  1.00  0.00           C  
HETATM   29  C22 UNL     1       3.499   0.025  -1.235  1.00  0.00           C  
HETATM   30  C23 UNL     1       2.156   0.433  -0.670  1.00  0.00           C  
HETATM   31  C24 UNL     1      -2.527  -0.879   1.566  1.00  0.00           C  
HETATM   32  C25 UNL     1      -3.843  -1.136   0.860  1.00  0.00           C  
HETATM   33  C26 UNL     1      -6.862  -0.706   1.747  1.00  0.00           C  
HETATM   34  C27 UNL     1      -8.225  -0.741   1.567  1.00  0.00           C  
HETATM   35  N6  UNL     1      -8.791  -0.134   0.530  1.00  0.00           N  
HETATM   36  C28 UNL     1      -8.076   0.538  -0.391  1.00  0.00           C  
HETATM   37  C29 UNL     1      -8.723   1.133  -1.449  1.00  0.00           C  
HETATM   38  H1  UNL     1      -6.008   2.398  -2.989  1.00  0.00           H  
HETATM   39  H2  UNL     1      -4.890   1.320  -1.091  1.00  0.00           H  
HETATM   40  H3  UNL     1      -3.946   1.225   2.566  1.00  0.00           H  
HETATM   41  H4  UNL     1      -4.660   2.103   1.131  1.00  0.00           H  
HETATM   42  H5  UNL     1      -2.688   1.785  -0.140  1.00  0.00           H  
HETATM   43  H6  UNL     1      -2.170   2.246   1.495  1.00  0.00           H  
HETATM   44  H7  UNL     1      -0.589   0.964  -0.438  1.00  0.00           H  
HETATM   45  H8  UNL     1      -1.959  -0.110  -1.008  1.00  0.00           H  
HETATM   46  H9  UNL     1       0.035  -1.267  -1.379  1.00  0.00           H  
HETATM   47  H10 UNL     1      -0.880  -2.075  -0.119  1.00  0.00           H  
HETATM   48  H11 UNL     1       1.414  -2.161   0.430  1.00  0.00           H  
HETATM   49  H12 UNL     1       0.488  -1.263   1.683  1.00  0.00           H  
HETATM   50  H13 UNL     1       2.531  -0.976   2.310  1.00  0.00           H  
HETATM   51  H14 UNL     1       3.128   0.683   1.997  1.00  0.00           H  
HETATM   52  H15 UNL     1       3.731  -1.936   0.542  1.00  0.00           H  
HETATM   53  H16 UNL     1       4.862  -1.082   1.688  1.00  0.00           H  
HETATM   54  H17 UNL     1       5.003   2.459  -0.156  1.00  0.00           H  
HETATM   55  H18 UNL     1       7.259   3.567  -0.315  1.00  0.00           H  
HETATM   56  H19 UNL     1      10.249   0.042  -0.744  1.00  0.00           H  
HETATM   57  H20 UNL     1       7.917  -3.490  -0.691  1.00  0.00           H  
HETATM   58  H21 UNL     1       5.863  -2.133  -0.440  1.00  0.00           H  
HETATM   59  H22 UNL     1       3.352  -0.957  -1.751  1.00  0.00           H  
HETATM   60  H23 UNL     1       3.774   0.836  -1.962  1.00  0.00           H  
HETATM   61  H24 UNL     1       2.078   1.562  -0.622  1.00  0.00           H  
HETATM   62  H25 UNL     1       1.416   0.156  -1.446  1.00  0.00           H  
HETATM   63  H26 UNL     1      -1.928  -1.785   1.597  1.00  0.00           H  
HETATM   64  H27 UNL     1      -2.812  -0.605   2.623  1.00  0.00           H  
HETATM   65  H28 UNL     1      -3.574  -1.305  -0.208  1.00  0.00           H  
HETATM   66  H29 UNL     1      -4.270  -2.063   1.272  1.00  0.00           H  
HETATM   67  H30 UNL     1      -6.363  -1.186   2.574  1.00  0.00           H  
HETATM   68  H31 UNL     1      -8.813  -1.279   2.301  1.00  0.00           H  
HETATM   69  H32 UNL     1      -9.794   1.095  -1.574  1.00  0.00           H  
CONECT    1    2
CONECT    2    3    3   37
CONECT    3    4   38
CONECT    4    5    5   39
CONECT    5    6   36
CONECT    6    7   33   33
CONECT    7    8   32
CONECT    8    9   40   41
CONECT    9   10   42   43
CONECT   10   11   31
CONECT   11   12   44   45
CONECT   12   13   46   47
CONECT   13   14   48   49
CONECT   14   15   30
CONECT   15   16   50   51
CONECT   16   17   52   53
CONECT   17   18   29
CONECT   18   19   19   28
CONECT   19   20   54
CONECT   20   21   21   55
CONECT   21   22
CONECT   22   23   23   28
CONECT   23   24   56
CONECT   24   25   26   26
CONECT   26   27   57
CONECT   27   28   28   58
CONECT   29   30   59   60
CONECT   30   61   62
CONECT   31   32   63   64
CONECT   32   65   66
CONECT   33   34   67
CONECT   34   35   35   68
CONECT   35   36
CONECT   36   37   37
CONECT   37   69
END

HMDB0256572
     RDKit          3D
piperaquine
 69 74  0  0  0  0  0  0  0  0999 V2000
   -8.7675    2.5700   -3.7558 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -7.9903    1.8096   -2.3986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6069    1.8617   -2.2409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9604    1.2650   -1.1788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7091    0.5824   -0.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0595   -0.0228    0.8270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6703    0.0225    1.0446 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0439    1.2529    1.4560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6564    1.4202    0.9183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8236    0.2415    1.0292 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1710    0.0348   -0.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2685   -1.1445   -0.3129 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8757   -1.1858    0.6243 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8174   -0.1297    0.5771 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8982   -0.2791    1.5290 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1103   -0.9604    0.9130 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5128   -0.1294   -0.2089 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7919    0.5004   -0.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9087    1.8805   -0.2646 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1454    2.4676   -0.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2247    1.6787   -0.4840 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1384    0.3354   -0.5337 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2831   -0.4402   -0.6766 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2048   -1.8101   -0.7327 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7141   -2.7166   -0.9124 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.9953   -2.4235   -0.6484 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8357   -1.6831   -0.5067 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9060   -0.2992   -0.4490 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    0.0252   -1.2353 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1560    0.4335   -0.6700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5269   -0.8793    1.5656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8429   -1.1364    0.8595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8619   -0.7061    1.7473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2254   -0.7410    1.5669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7908   -0.1339    0.5296 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0758    0.5380   -0.3907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7226    1.1332   -1.4489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0083    2.3979   -2.9895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8899    1.3198   -1.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9459    1.2248    2.5660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6603    2.1028    1.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6885    1.7852   -0.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1696    2.2457    1.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5886    0.9639   -0.4381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9595   -0.1101   -1.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0346   -1.2667   -1.3785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8802   -2.0748   -0.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4145   -2.1614    0.4303 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4879   -1.2634    1.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5310   -0.9761    2.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1282    0.6826    1.9971 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7314   -1.9356    0.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8618   -1.0815    1.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0031    2.4591   -0.1561 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2587    3.5671   -0.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2489    0.0418   -0.7436 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9170   -3.4902   -0.6912 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8629   -2.1325   -0.4398 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3518   -0.9566   -1.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7743    0.8358   -1.9620 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0782    1.5619   -0.6221 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4155    0.1559   -1.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9280   -1.7847    1.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8117   -0.6054    2.6233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5739   -1.3049   -0.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2701   -2.0630    1.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3625   -1.1863    2.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8126   -1.2789    2.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7941    1.0953   -1.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 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  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 26 27  1  0
 27 28  2  0
 17 29  1  0
 29 30  1  0
 10 31  1  0
 31 32  1  0
  6 33  2  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 36 37  2  0
 37  2  1  0
 36  5  1  0
 32  7  1  0
 30 14  1  0
 28 18  1  0
 28 22  1  0
  3 38  1  0
  4 39  1  0
  8 40  1  0
  8 41  1  0
  9 42  1  0
  9 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 12 47  1  0
 13 48  1  0
 13 49  1  0
 15 50  1  0
 15 51  1  0
 16 52  1  0
 16 53  1  0
 19 54  1  0
 20 55  1  0
 23 56  1  0
 26 57  1  0
 27 58  1  0
 29 59  1  0
 29 60  1  0
 30 61  1  0
 30 62  1  0
 31 63  1  0
 31 64  1  0
 32 65  1  0
 32 66  1  0
 33 67  1  0
 34 68  1  0
 37 69  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,3-Bis[4-(7-chloroquinolin-4-yl)piperazin-1-yl]propane	ChEBI
Piperaquinoline	ChEBI
1,3-Bis(4-(7'-chloro-4'-quinoline)-1-piperazine)	MeSH
1,3-Bis(1-(7-chloro-4'-quinolyl)-4'-piperazinyl)propane	MeSH

Chemical Formula

C₂₉H₃₂Cl₂N₆

Average Molecular Weight

535.52

Monoisotopic Molecular Weight

534.2065505

IUPAC Name

7-chloro-4-(4-{3-[4-(7-chloroquinolin-4-yl)piperazin-1-yl]propyl}piperazin-1-yl)quinoline

Traditional Name

piperaquine

CAS Registry Number

Not Available

SMILES

ClC1=CC2=C(C=C1)C(=CC=N2)N1CCN(CCCN2CCN(CC2)C2=CC=NC3=C2C=CC(Cl)=C3)CC1

InChI Identifier

InChI=1S/C29H32Cl2N6/c30-22-2-4-24-26(20-22)32-8-6-28(24)36-16-12-34(13-17-36)10-1-11-35-14-18-37(19-15-35)29-7-9-33-27-21-23(31)3-5-25(27)29/h2-9,20-21H,1,10-19H2

InChI Key

UCRHFBCYFMIWHC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyridinylpiperazines. Pyridinylpiperazines are compounds containing a pyridinylpiperazine skeleton, which consists of a pyridine linked (not fused) to a piperazine by a bond by a single bond that is not part of a ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazinanes

Sub Class

Piperazines

Direct Parent

Pyridinylpiperazines

Alternative Parents

Substituents

N-arylpiperazine
Pyridinylpiperazine
Aminoquinoline
4-aminoquinoline
Haloquinoline
Chloroquinoline
Quinoline
Dialkylarylamine
Tertiary aliphatic/aromatic amine
Aminopyridine
N-alkylpiperazine
Aryl chloride
Aryl halide
Benzenoid
Pyridine
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organonitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organopnictogen compound
Amine
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	5.53	ALOGPS
logP	5.27	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	8.47	ChemAxon
Physiological Charge	3	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	38.74 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	153.42 m³·mol⁻¹	ChemAxon
Polarizability	59.56 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	219.149	30932474
DeepCCS	[M-H]-	216.754	30932474
DeepCCS	[M-2H]-	249.637	30932474
DeepCCS	[M+Na]+	225.062	30932474
AllCCS	[M+H]+	225.3	32859911
AllCCS	[M+H-H2O]+	224.0	32859911
AllCCS	[M+NH4]+	226.6	32859911
AllCCS	[M+Na]+	226.9	32859911
AllCCS	[M-H]-	207.9	32859911
AllCCS	[M+Na-2H]-	208.7	32859911
AllCCS	[M+HCOO]-	209.7	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.	2.41 minutes	32390414
Predicted by Siyang on May 30, 2022	10.8077 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.94 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	688.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	200.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	169.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	174.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	90.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	311.3 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	317.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	532.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	676.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	57.7 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	918.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	191.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	289.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	603.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	403.9 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	38.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
piperaquine	ClC1=CC2=C(C=C1)C(=CC=N2)N1CCN(CCCN2CCN(CC2)C2=CC=NC3=C2C=CC(Cl)=C3)CC1	5041.3	Standard polar	33892256
piperaquine	ClC1=CC2=C(C=C1)C(=CC=N2)N1CCN(CCCN2CCN(CC2)C2=CC=NC3=C2C=CC(Cl)=C3)CC1	4403.9	Standard non polar	33892256
piperaquine	ClC1=CC2=C(C=C1)C(=CC=N2)N1CCN(CCCN2CCN(CC2)C2=CC=NC3=C2C=CC(Cl)=C3)CC1	5041.8	Semi standard non polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperaquine 10V, Positive-QTOF	splash10-000i-0000090000-40d0298556f035a4963a	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperaquine 20V, Positive-QTOF	splash10-000i-0061090000-ecdf8ed3a4dfb8517191	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperaquine 40V, Positive-QTOF	splash10-00kn-1392010000-3bc550beefebd13e0721	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperaquine 10V, Negative-QTOF	splash10-001i-0000090000-5e72099d2aeaf91b81bb	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperaquine 20V, Negative-QTOF	splash10-001i-0000090000-5574c2a1d5df4f47b36e	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperaquine 40V, Negative-QTOF	splash10-00kb-2292130000-af9efeea5070f4f58871	2019-02-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

109031

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Piperaquine

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

91231

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Piperaquine (HMDB0256572)

MOL for HMDB0256572 (Piperaquine)

3D MOL for HMDB0256572 (Piperaquine)

3D SDF for HMDB0256572 (Piperaquine)

3D-SDF for HMDB0256572 (Piperaquine)

PDB for HMDB0256572 (Piperaquine)

3D PDB for HMDB0256572 (Piperaquine)

SMILES for HMDB0256572 (Piperaquine)

INCHI for HMDB0256572 (Piperaquine)

Structure for HMDB0256572 (Piperaquine)

3D Structure for HMDB0256572 (Piperaquine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

MS/MS Spectra