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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:52:34 UTC

Update Date

2022-03-07 02:57:14 UTC

HMDB ID

HMDB0042003

Secondary Accession Numbers

HMDB42003

Metabolite Identification

Common Name

Pyronaridine

Description

Pyronaridine belongs to the family of Naphthyridines. These are compounds containing a naphthyridine moeity, a naphthalene in which a carbon atom has been replaced by a nitrogen in each of the two rings. The naphthyridine skeleton can also be described as an assembly two fused pyridine rings, which do not share their nitrogen atom.

Structure

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

  Mrv0541 09131211522D          

 37 42  0  0  0  0            999 V2000
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8945   -3.8795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3070   -3.1650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3234   -1.4045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7359   -0.6900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    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    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0875   -3.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7550   -2.5519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5165   -1.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1839   -0.0769    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
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    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
    3.5724    1.2375    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
    3.5724    2.0625    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
    2.8579    0.8250    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
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 Cl  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
    2.8579    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  5  4  1  0  0  0  0
  7  6  2  0  0  0  0
  9  8  1  0  0  0  0
 10  2  1  0  0  0  0
 11  3  1  0  0  0  0
 12  4  1  0  0  0  0
 13  5  1  0  0  0  0
 19 14  2  0  0  0  0
 19 17  1  0  0  0  0
 20 15  2  0  0  0  0
 20 18  1  0  0  0  0
 21  6  1  0  0  0  0
 21 16  2  0  0  0  0
 22 14  1  0  0  0  0
 22 15  1  0  0  0  0
 23  7  1  0  0  0  0
 24  8  2  0  0  0  0
 25 16  1  0  0  0  0
 25 23  2  0  0  0  0
 26  9  2  0  0  0  0
 27 23  1  0  0  0  0
 28 24  1  0  0  0  0
 28 27  2  0  0  0  0
 29 19  1  0  0  0  0
 29 20  1  0  0  0  0
 30 21  1  0  0  0  0
 31 22  2  0  0  0  0
 31 27  1  0  0  0  0
 32 24  1  0  0  0  0
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 33 26  1  0  0  0  0
 33 28  1  0  0  0  0
 34 10  1  0  0  0  0
 34 11  1  0  0  0  0
 34 17  1  0  0  0  0
 35 12  1  0  0  0  0
 35 13  1  0  0  0  0
 35 18  1  0  0  0  0
 36 29  2  0  0  0  0
 37  1  1  0  0  0  0
 37 26  1  0  0  0  0
M  END

HMDB0042003
     RDKit          3D
Pyronaridine
 69 74  0  0  0  0  0  0  0  0999 V2000
    3.3291   -0.8360    4.7210 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5533   -0.7340    3.5490 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0369   -0.3019    2.3328 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1224    0.4480    2.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6322    0.9050    0.9179 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0440    0.6006   -0.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5451    1.0477   -1.4823 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8834    0.6985   -2.6947 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3587    1.1250   -3.9270 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6941    0.7694   -5.0958 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2993    1.3099   -6.6484 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.5616   -0.0122   -4.9780 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0963   -0.4320   -3.7457 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7478   -0.0849   -2.5826 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2350   -0.5435   -1.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0643   -1.3465   -1.2509 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0851   -0.9582   -0.8325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3210    0.4039   -0.3288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4796    0.8079    0.0979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7402    2.1567    0.6026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6155    3.0600    0.5809 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0995    4.2900    1.2092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5768    5.1424    0.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5579    4.8193   -0.9871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2078    3.3840   -0.7472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5801   -0.1469    0.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7324    0.2002    0.4736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4113   -1.5134   -0.4210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5520   -2.4602   -0.4409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1150   -2.7035    0.8617 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2152   -3.6386    0.7962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5721   -4.9847    1.0683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5597   -4.6362    2.1356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1628   -3.2391    1.7912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1967   -1.8971   -0.8553 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8365   -0.2290   -0.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3704   -0.6545    1.1255 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7656    0.1212    5.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6654   -1.2926    5.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1394   -1.5670    4.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6223    0.7110    3.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5355    1.5264    0.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4053    1.6391   -1.5400 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2492    1.7383   -4.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0368   -0.2952   -5.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2073   -1.0466   -3.6383 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5294    1.0495   -0.3270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5516    2.6807    0.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1088    2.1503    1.6576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9735    4.1113    1.8654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3246    4.7884    1.8236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6201    4.8999   -0.2270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5652    6.2100    0.3447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9427    5.0044   -2.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3254    5.4780   -0.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9048    3.3033   -0.9046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6855    2.7194   -1.5073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3863   -2.0681   -1.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2100   -3.4295   -0.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9416   -3.4257    1.5990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6845   -3.6173   -0.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0737   -5.3961    0.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3216   -5.7320    1.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7033   -5.3487    2.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0721   -4.7024    3.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1647   -3.2702    1.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0936   -2.5913    2.7099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0969   -2.9131   -1.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5043   -1.2514    1.1911 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
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 12 13  1  0
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 34 30  1  0
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 33 65  1  0
 34 66  1  0
 34 67  1  0
 35 68  1  0
 37 69  1  0
M  END

  Mrv0541 09131211522D          

 37 42  0  0  0  0            999 V2000
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8945   -3.8795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3070   -3.1650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3234   -1.4045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7359   -0.6900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    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    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0875   -3.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7550   -2.5519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5165   -1.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1839   -0.0769    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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    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 Cl  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
    2.8579    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  5  4  1  0  0  0  0
  7  6  2  0  0  0  0
  9  8  1  0  0  0  0
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 35 13  1  0  0  0  0
 35 18  1  0  0  0  0
 36 29  2  0  0  0  0
 37  1  1  0  0  0  0
 37 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0042003

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C2NC3=C(C=CC(Cl)=C3)C(N=C3C=C(CN4CCCC4)C(=O)C(CN4CCCC4)=C3)=C2N1

> <INCHI_IDENTIFIER>
InChI=1S/C29H32ClN5O2/c1-37-26-9-8-24-28(33-26)27(23-7-6-21(30)16-25(23)32-24)31-22-14-19(17-34-10-2-3-11-34)29(36)20(15-22)18-35-12-4-5-13-35/h6-9,14-16,32-33H,2-5,10-13,17-18H2,1H3

> <INCHI_KEY>
YFYLPWJKCSESGB-UHFFFAOYSA-N

> <FORMULA>
C29H32ClN5O2

> <MOLECULAR_WEIGHT>
518.05

> <EXACT_MASS>
517.224453

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
57.320369109277536

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-({7-chloro-2-methoxy-1H,5H-benzo[b]1,5-naphthyridin-10-yl}imino)-2,6-bis(pyrrolidin-1-ylmethyl)cyclohexa-2,5-dien-1-one

> <ALOGPS_LOGP>
4.38

> <JCHEM_LOGP>
3.025789226333334

> <ALOGPS_LOGS>
-4.08

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
3

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.840248288065137

> <JCHEM_PKA_STRONGEST_BASIC>
8.635130342078096

> <JCHEM_POLAR_SURFACE_AREA>
69.2

> <JCHEM_REFRACTIVITY>
165.49439999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.28e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pyronaridine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0042003
     RDKit          3D
Pyronaridine
 69 74  0  0  0  0  0  0  0  0999 V2000
    3.3291   -0.8360    4.7210 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5533   -0.7340    3.5490 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0369   -0.3019    2.3328 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1224    0.4480    2.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6322    0.9050    0.9179 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0440    0.6006   -0.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5451    1.0477   -1.4823 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8834    0.6985   -2.6947 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3587    1.1250   -3.9270 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6941    0.7694   -5.0958 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2993    1.3099   -6.6484 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.5616   -0.0122   -4.9780 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0963   -0.4320   -3.7457 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7478   -0.0849   -2.5826 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2350   -0.5435   -1.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0643   -1.3465   -1.2509 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0851   -0.9582   -0.8325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3210    0.4039   -0.3288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4796    0.8079    0.0979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7402    2.1567    0.6026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6155    3.0600    0.5809 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0995    4.2900    1.2092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5768    5.1424    0.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5579    4.8193   -0.9871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2078    3.3840   -0.7472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5801   -0.1469    0.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7324    0.2002    0.4736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4113   -1.5134   -0.4210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5520   -2.4602   -0.4409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1150   -2.7035    0.8617 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2152   -3.6386    0.7962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5721   -4.9847    1.0683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5597   -4.6362    2.1356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1628   -3.2391    1.7912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1967   -1.8971   -0.8553 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8365   -0.2290   -0.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3704   -0.6545    1.1255 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7656    0.1212    5.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6654   -1.2926    5.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1394   -1.5670    4.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6223    0.7110    3.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5355    1.5264    0.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4053    1.6391   -1.5400 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2492    1.7383   -4.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0368   -0.2952   -5.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2073   -1.0466   -3.6383 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5294    1.0495   -0.3270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5516    2.6807    0.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1088    2.1503    1.6576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9735    4.1113    1.8654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3246    4.7884    1.8236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6201    4.8999   -0.2270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5652    6.2100    0.3447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9427    5.0044   -2.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3254    5.4780   -0.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9048    3.3033   -0.9046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6855    2.7194   -1.5073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3863   -2.0681   -1.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2100   -3.4295   -0.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9416   -3.4257    1.5990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6845   -3.6173   -0.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0737   -5.3961    0.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3216   -5.7320    1.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7033   -5.3487    2.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0721   -4.7024    3.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1647   -3.2702    1.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0936   -2.5913    2.7099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0969   -2.9131   -1.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5043   -1.2514    1.1911 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  3
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 19 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 28 35  2  0
 15 36  2  0
 36 37  1  0
 37  3  1  0
 36  6  1  0
 14  8  1  0
 35 17  1  0
 25 21  1  0
 34 30  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  4 41  1  0
  5 42  1  0
  7 43  1  0
  9 44  1  0
 12 45  1  0
 13 46  1  0
 18 47  1  0
 20 48  1  0
 20 49  1  0
 22 50  1  0
 22 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  0
 24 55  1  0
 25 56  1  0
 25 57  1  0
 29 58  1  0
 29 59  1  0
 31 60  1  0
 31 61  1  0
 32 62  1  0
 32 63  1  0
 33 64  1  0
 33 65  1  0
 34 66  1  0
 34 67  1  0
 35 68  1  0
 37 69  1  0
M  END

HEADER    PROTEIN                                 13-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-12         0                                  
HETATM    1  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.003  -7.242   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.773  -5.908   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.670  -2.622   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.440  -1.288   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.497  -6.922   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.743  -4.764   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.164  -2.302   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.410  -0.144   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       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   30 Cl   UNK     0      10.669   4.620   0.000  0.00  0.00          Cl+0
HETATM   31  N   UNK     0       5.335   0.000   0.000  0.00  0.00           N+0
HETATM   32  N   UNK     0       5.335   4.620   0.000  0.00  0.00           N+0
HETATM   33  N   UNK     0       2.667   1.540   0.000  0.00  0.00           N+0
HETATM   34  N   UNK     0       9.336  -5.390   0.000  0.00  0.00           N+0
HETATM   35  N   UNK     0      12.003  -0.770   0.000  0.00  0.00           N+0
HETATM   36  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1   37                                                            
CONECT    2    3   10                                                       
CONECT    3    2   11                                                       
CONECT    4    5   12                                                       
CONECT    5    4   13                                                       
CONECT    6    7   21                                                       
CONECT    7    6   23                                                       
CONECT    8    9   24                                                       
CONECT    9    8   26                                                       
CONECT   10    2   34                                                       
CONECT   11    3   34                                                       
CONECT   12    4   35                                                       
CONECT   13    5   35                                                       
CONECT   14   19   22                                                       
CONECT   15   20   22                                                       
CONECT   16   21   25                                                       
CONECT   17   19   34                                                       
CONECT   18   20   35                                                       
CONECT   19   14   17   29                                                  
CONECT   20   15   18   29                                                  
CONECT   21    6   16   30                                                  
CONECT   22   14   15   31                                                  
CONECT   23    7   25   27                                                  
CONECT   24    8   28   32                                                  
CONECT   25   16   23   32                                                  
CONECT   26    9   33   37                                                  
CONECT   27   23   28   31                                                  
CONECT   28   24   27   33                                                  
CONECT   29   19   20   36                                                  
CONECT   30   21                                                            
CONECT   31   22   27                                                       
CONECT   32   24   25                                                       
CONECT   33   26   28                                                       
CONECT   34   10   11   17                                                  
CONECT   35   12   13   18                                                  
CONECT   36   29                                                            
CONECT   37    1   26                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   84    0
END

COMPND    HMDB0042003
HETATM    1  C1  UNL     1       3.329  -0.836   4.721  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.553  -0.734   3.549  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.037  -0.302   2.333  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.122   0.448   2.217  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.632   0.905   0.918  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.044   0.601  -0.228  1.00  0.00           C  
HETATM    7  N1  UNL     1       4.545   1.048  -1.482  1.00  0.00           N  
HETATM    8  C6  UNL     1       3.883   0.698  -2.695  1.00  0.00           C  
HETATM    9  C7  UNL     1       4.359   1.125  -3.927  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.694   0.769  -5.096  1.00  0.00           C  
HETATM   11 CL1  UNL     1       4.299   1.310  -6.648  1.00  0.00          CL  
HETATM   12  C9  UNL     1       2.562  -0.012  -4.978  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.096  -0.432  -3.746  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.748  -0.085  -2.583  1.00  0.00           C  
HETATM   15  C12 UNL     1       2.235  -0.544  -1.287  1.00  0.00           C  
HETATM   16  N2  UNL     1       1.064  -1.346  -1.251  1.00  0.00           N  
HETATM   17  C13 UNL     1      -0.085  -0.958  -0.832  1.00  0.00           C  
HETATM   18  C14 UNL     1      -0.321   0.404  -0.329  1.00  0.00           C  
HETATM   19  C15 UNL     1      -1.480   0.808   0.098  1.00  0.00           C  
HETATM   20  C16 UNL     1      -1.740   2.157   0.603  1.00  0.00           C  
HETATM   21  N3  UNL     1      -0.615   3.060   0.581  1.00  0.00           N  
HETATM   22  C17 UNL     1      -1.099   4.290   1.209  1.00  0.00           C  
HETATM   23  C18 UNL     1      -1.577   5.142   0.050  1.00  0.00           C  
HETATM   24  C19 UNL     1      -0.558   4.819  -0.987  1.00  0.00           C  
HETATM   25  C20 UNL     1      -0.208   3.384  -0.747  1.00  0.00           C  
HETATM   26  C21 UNL     1      -2.580  -0.147   0.067  1.00  0.00           C  
HETATM   27  O2  UNL     1      -3.732   0.200   0.474  1.00  0.00           O  
HETATM   28  C22 UNL     1      -2.411  -1.513  -0.421  1.00  0.00           C  
HETATM   29  C23 UNL     1      -3.552  -2.460  -0.441  1.00  0.00           C  
HETATM   30  N4  UNL     1      -4.115  -2.703   0.862  1.00  0.00           N  
HETATM   31  C24 UNL     1      -5.215  -3.639   0.796  1.00  0.00           C  
HETATM   32  C25 UNL     1      -4.572  -4.985   1.068  1.00  0.00           C  
HETATM   33  C26 UNL     1      -3.560  -4.636   2.136  1.00  0.00           C  
HETATM   34  C27 UNL     1      -3.163  -3.239   1.791  1.00  0.00           C  
HETATM   35  C28 UNL     1      -1.197  -1.897  -0.855  1.00  0.00           C  
HETATM   36  C29 UNL     1       2.837  -0.229  -0.151  1.00  0.00           C  
HETATM   37  N5  UNL     1       2.370  -0.654   1.126  1.00  0.00           N  
HETATM   38  H1  UNL     1       3.766   0.121   5.042  1.00  0.00           H  
HETATM   39  H2  UNL     1       2.665  -1.293   5.497  1.00  0.00           H  
HETATM   40  H3  UNL     1       4.139  -1.567   4.522  1.00  0.00           H  
HETATM   41  H4  UNL     1       4.622   0.711   3.139  1.00  0.00           H  
HETATM   42  H5  UNL     1       5.535   1.526   0.853  1.00  0.00           H  
HETATM   43  H6  UNL     1       5.405   1.639  -1.540  1.00  0.00           H  
HETATM   44  H7  UNL     1       5.249   1.738  -4.005  1.00  0.00           H  
HETATM   45  H8  UNL     1       2.037  -0.295  -5.878  1.00  0.00           H  
HETATM   46  H9  UNL     1       1.207  -1.047  -3.638  1.00  0.00           H  
HETATM   47  H10 UNL     1       0.529   1.049  -0.327  1.00  0.00           H  
HETATM   48  H11 UNL     1      -2.552   2.681   0.016  1.00  0.00           H  
HETATM   49  H12 UNL     1      -2.109   2.150   1.658  1.00  0.00           H  
HETATM   50  H13 UNL     1      -1.973   4.111   1.865  1.00  0.00           H  
HETATM   51  H14 UNL     1      -0.325   4.788   1.824  1.00  0.00           H  
HETATM   52  H15 UNL     1      -2.620   4.900  -0.227  1.00  0.00           H  
HETATM   53  H16 UNL     1      -1.565   6.210   0.345  1.00  0.00           H  
HETATM   54  H17 UNL     1      -0.943   5.004  -2.014  1.00  0.00           H  
HETATM   55  H18 UNL     1       0.325   5.478  -0.840  1.00  0.00           H  
HETATM   56  H19 UNL     1       0.905   3.303  -0.905  1.00  0.00           H  
HETATM   57  H20 UNL     1      -0.686   2.719  -1.507  1.00  0.00           H  
HETATM   58  H21 UNL     1      -4.386  -2.068  -1.088  1.00  0.00           H  
HETATM   59  H22 UNL     1      -3.210  -3.430  -0.877  1.00  0.00           H  
HETATM   60  H23 UNL     1      -5.942  -3.426   1.599  1.00  0.00           H  
HETATM   61  H24 UNL     1      -5.684  -3.617  -0.201  1.00  0.00           H  
HETATM   62  H25 UNL     1      -4.074  -5.396   0.162  1.00  0.00           H  
HETATM   63  H26 UNL     1      -5.322  -5.732   1.418  1.00  0.00           H  
HETATM   64  H27 UNL     1      -2.703  -5.349   2.076  1.00  0.00           H  
HETATM   65  H28 UNL     1      -4.072  -4.702   3.123  1.00  0.00           H  
HETATM   66  H29 UNL     1      -2.165  -3.270   1.304  1.00  0.00           H  
HETATM   67  H30 UNL     1      -3.094  -2.591   2.710  1.00  0.00           H  
HETATM   68  H31 UNL     1      -1.097  -2.913  -1.212  1.00  0.00           H  
HETATM   69  H32 UNL     1       1.504  -1.251   1.191  1.00  0.00           H  
CONECT    1    2   38   39   40
CONECT    2    3
CONECT    3    4    4   37
CONECT    4    5   41
CONECT    5    6    6   42
CONECT    6    7   36
CONECT    7    8   43
CONECT    8    9    9   14
CONECT    9   10   44
CONECT   10   11   12   12
CONECT   12   13   45
CONECT   13   14   14   46
CONECT   14   15
CONECT   15   16   36   36
CONECT   16   17   17
CONECT   17   18   35
CONECT   18   19   19   47
CONECT   19   20   26
CONECT   20   21   48   49
CONECT   21   22   25
CONECT   22   23   50   51
CONECT   23   24   52   53
CONECT   24   25   54   55
CONECT   25   56   57
CONECT   26   27   27   28
CONECT   28   29   35   35
CONECT   29   30   58   59
CONECT   30   31   34
CONECT   31   32   60   61
CONECT   32   33   62   63
CONECT   33   34   64   65
CONECT   34   66   67
CONECT   35   68
CONECT   36   37
CONECT   37   69
END

HMDB0042003
     RDKit          3D
Pyronaridine
 69 74  0  0  0  0  0  0  0  0999 V2000
    3.3291   -0.8360    4.7210 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5533   -0.7340    3.5490 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0369   -0.3019    2.3328 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1224    0.4480    2.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6322    0.9050    0.9179 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0440    0.6006   -0.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5451    1.0477   -1.4823 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8834    0.6985   -2.6947 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3587    1.1250   -3.9270 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6941    0.7694   -5.0958 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2993    1.3099   -6.6484 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.5616   -0.0122   -4.9780 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0963   -0.4320   -3.7457 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7478   -0.0849   -2.5826 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2350   -0.5435   -1.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0643   -1.3465   -1.2509 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0851   -0.9582   -0.8325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3210    0.4039   -0.3288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4796    0.8079    0.0979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7402    2.1567    0.6026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6155    3.0600    0.5809 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0995    4.2900    1.2092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5768    5.1424    0.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5579    4.8193   -0.9871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2078    3.3840   -0.7472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5801   -0.1469    0.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7324    0.2002    0.4736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4113   -1.5134   -0.4210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5520   -2.4602   -0.4409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1150   -2.7035    0.8617 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2152   -3.6386    0.7962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5721   -4.9847    1.0683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5597   -4.6362    2.1356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1628   -3.2391    1.7912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1967   -1.8971   -0.8553 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8365   -0.2290   -0.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3704   -0.6545    1.1255 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7656    0.1212    5.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6654   -1.2926    5.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1394   -1.5670    4.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6223    0.7110    3.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5355    1.5264    0.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4053    1.6391   -1.5400 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2492    1.7383   -4.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0368   -0.2952   -5.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2073   -1.0466   -3.6383 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5294    1.0495   -0.3270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5516    2.6807    0.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1088    2.1503    1.6576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9735    4.1113    1.8654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3246    4.7884    1.8236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6201    4.8999   -0.2270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5652    6.2100    0.3447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9427    5.0044   -2.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3254    5.4780   -0.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9048    3.3033   -0.9046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6855    2.7194   -1.5073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3863   -2.0681   -1.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2100   -3.4295   -0.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9416   -3.4257    1.5990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6845   -3.6173   -0.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0737   -5.3961    0.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3216   -5.7320    1.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7033   -5.3487    2.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0721   -4.7024    3.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1647   -3.2702    1.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0936   -2.5913    2.7099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0969   -2.9131   -1.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5043   -1.2514    1.1911 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  3
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 19 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 28 35  2  0
 15 36  2  0
 36 37  1  0
 37  3  1  0
 36  6  1  0
 14  8  1  0
 35 17  1  0
 25 21  1  0
 34 30  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  4 41  1  0
  5 42  1  0
  7 43  1  0
  9 44  1  0
 12 45  1  0
 13 46  1  0
 18 47  1  0
 20 48  1  0
 20 49  1  0
 22 50  1  0
 22 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  0
 24 55  1  0
 25 56  1  0
 25 57  1  0
 29 58  1  0
 29 59  1  0
 31 60  1  0
 31 61  1  0
 32 62  1  0
 32 63  1  0
 33 64  1  0
 33 65  1  0
 34 66  1  0
 34 67  1  0
 35 68  1  0
 37 69  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Malaridine	HMDB
Pyronaridine phosphate salt	HMDB
Benzonaphthyridine 7351	HMDB
2-Methoxy-7-chloro-10-(3',5'-bis(pyrrolin-1-ylmethyl)-4'-hydroxyphenylamino)benzo(b)-1,5-naphthyridine	HMDB
4-((7-Chloro-2-methoxybenzo(b)-1,5-naphthyridin-10-yl)amino)-2,6-bis(1-pyrrolidinylmethyl)phenol	HMDB
Pyronaridine tetraphosphate	HMDB
4-((7-Chloro-2-methoxybenzo(b)(1,5)naphthyridin-10-yl)amino)-2,6-bis((pyrrolidin-1-yl)methyl)phenol	HMDB
Phenol, 4-((7-chloro-2-methoxybenzo(b)-1,5-naphthyridin-10-yl)amino)-2,6-bis(1-pyrrolidinylmethyl)-, phosphate (1:4)	HMDB
Pyronaridine	MeSH

Chemical Formula

C₂₉H₃₂ClN₅O₂

Average Molecular Weight

518.05

Monoisotopic Molecular Weight

517.224453

IUPAC Name

4-({7-chloro-2-methoxy-1H,5H-benzo[b]1,5-naphthyridin-10-yl}imino)-2,6-bis(pyrrolidin-1-ylmethyl)cyclohexa-2,5-dien-1-one

Traditional Name

pyronaridine

CAS Registry Number

74847-35-1

SMILES

COC1=CC=C2NC3=C(C=CC(Cl)=C3)C(N=C3C=C(CN4CCCC4)C(=O)C(CN4CCCC4)=C3)=C2N1

InChI Identifier

InChI=1S/C29H32ClN5O2/c1-37-26-9-8-24-28(33-26)27(23-7-6-21(30)16-25(23)32-24)31-22-14-19(17-34-10-2-3-11-34)29(36)20(15-22)18-35-12-4-5-13-35/h6-9,14-16,32-33H,2-5,10-13,17-18H2,1H3

InChI Key

YFYLPWJKCSESGB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroquinolones. Hydroquinolones are compounds containing a hydrogenated quinoline bearing a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinolones and derivatives

Direct Parent

Hydroquinolones

Alternative Parents

Substituents

Dihydroquinolone
Diazanaphthalene
Dihydroquinoline
Naphthyridine
P-quinonimine
Quinonimine
Dihydropyridine
Secondary aliphatic/aromatic amine
Aryl chloride
Aryl halide
Benzenoid
N-alkylpyrrolidine
Azomethine
Secondary ketimine
Pyrrolidine
Cyclic ketone
Tertiary aliphatic amine
Tertiary amine
Ketene acetal or derivatives
Ketimine
Ketone
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Secondary aliphatic amine
Secondary amine
Enamine
Imine
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Amine
Organooxygen compound
Organopnictogen compound
Organohalogen compound
Organochloride
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0042003)

Source

Exogenous

Exogenous (HMDB: HMDB0042003)

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
Water Solubility	0.043 g/L	ALOGPS
logP	4.38	ALOGPS
logP	3.03	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	16.84	ChemAxon
pKa (Strongest Basic)	8.64	ChemAxon
Physiological Charge	3	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	69.2 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	165.49 m³·mol⁻¹	ChemAxon
Polarizability	57.32 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	219.34	30932474
DeepCCS	[M-H]-	216.95	30932474
DeepCCS	[M-2H]-	250.187	30932474
DeepCCS	[M+Na]+	225.415	30932474
AllCCS	[M+H]+	221.5	32859911
AllCCS	[M+H-H2O]+	219.8	32859911
AllCCS	[M+NH4]+	223.0	32859911
AllCCS	[M+Na]+	223.5	32859911
AllCCS	[M-H]-	215.1	32859911
AllCCS	[M+Na-2H]-	216.5	32859911
AllCCS	[M+HCOO]-	218.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pyronaridine	COC1=CC=C2NC3=C(C=CC(Cl)=C3)C(N=C3C=C(CN4CCCC4)C(=O)C(CN4CCCC4)=C3)=C2N1	6350.8	Standard polar	33892256
Pyronaridine	COC1=CC=C2NC3=C(C=CC(Cl)=C3)C(N=C3C=C(CN4CCCC4)C(=O)C(CN4CCCC4)=C3)=C2N1	4056.4	Standard non polar	33892256
Pyronaridine	COC1=CC=C2NC3=C(C=CC(Cl)=C3)C(N=C3C=C(CN4CCCC4)C(=O)C(CN4CCCC4)=C3)=C2N1	4979.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Pyronaridine,1TMS,isomer #1	COC1=CC=C2C(=C(N=C3C=C(CN4CCCC4)C(=O)C(CN4CCCC4)=C3)C3=CC=C(Cl)C=C3N2[Si](C)(C)C)N1	4620.6	Semi standard non polar	33892256
Pyronaridine,1TMS,isomer #1	COC1=CC=C2C(=C(N=C3C=C(CN4CCCC4)C(=O)C(CN4CCCC4)=C3)C3=CC=C(Cl)C=C3N2[Si](C)(C)C)N1	4192.6	Standard non polar	33892256
Pyronaridine,1TMS,isomer #2	COC1=CC=C2NC3=CC(Cl)=CC=C3C(N=C3C=C(CN4CCCC4)C(=O)C(CN4CCCC4)=C3)=C2N1[Si](C)(C)C	4620.0	Semi standard non polar	33892256
Pyronaridine,1TMS,isomer #2	COC1=CC=C2NC3=CC(Cl)=CC=C3C(N=C3C=C(CN4CCCC4)C(=O)C(CN4CCCC4)=C3)=C2N1[Si](C)(C)C	4069.0	Standard non polar	33892256
Pyronaridine,2TMS,isomer #1	COC1=CC=C2C(=C(N=C3C=C(CN4CCCC4)C(=O)C(CN4CCCC4)=C3)C3=CC=C(Cl)C=C3N2[Si](C)(C)C)N1[Si](C)(C)C	4479.3	Semi standard non polar	33892256
Pyronaridine,2TMS,isomer #1	COC1=CC=C2C(=C(N=C3C=C(CN4CCCC4)C(=O)C(CN4CCCC4)=C3)C3=CC=C(Cl)C=C3N2[Si](C)(C)C)N1[Si](C)(C)C	3962.5	Standard non polar	33892256
Pyronaridine,1TBDMS,isomer #1	COC1=CC=C2C(=C(N=C3C=C(CN4CCCC4)C(=O)C(CN4CCCC4)=C3)C3=CC=C(Cl)C=C3N2[Si](C)(C)C(C)(C)C)N1	4793.4	Semi standard non polar	33892256
Pyronaridine,1TBDMS,isomer #1	COC1=CC=C2C(=C(N=C3C=C(CN4CCCC4)C(=O)C(CN4CCCC4)=C3)C3=CC=C(Cl)C=C3N2[Si](C)(C)C(C)(C)C)N1	4329.3	Standard non polar	33892256
Pyronaridine,1TBDMS,isomer #2	COC1=CC=C2NC3=CC(Cl)=CC=C3C(N=C3C=C(CN4CCCC4)C(=O)C(CN4CCCC4)=C3)=C2N1[Si](C)(C)C(C)(C)C	4860.1	Semi standard non polar	33892256
Pyronaridine,1TBDMS,isomer #2	COC1=CC=C2NC3=CC(Cl)=CC=C3C(N=C3C=C(CN4CCCC4)C(=O)C(CN4CCCC4)=C3)=C2N1[Si](C)(C)C(C)(C)C	4181.9	Standard non polar	33892256
Pyronaridine,2TBDMS,isomer #1	COC1=CC=C2C(=C(N=C3C=C(CN4CCCC4)C(=O)C(CN4CCCC4)=C3)C3=CC=C(Cl)C=C3N2[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C	4736.9	Semi standard non polar	33892256
Pyronaridine,2TBDMS,isomer #1	COC1=CC=C2C(=C(N=C3C=C(CN4CCCC4)C(=O)C(CN4CCCC4)=C3)C3=CC=C(Cl)C=C3N2[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C	4183.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Pyronaridine GC-MS (Non-derivatized) - 70eV, Positive	splash10-05a2-6150900000-7073415c2cdd28803cfd	2017-09-01	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyronaridine 10V, Positive-QTOF	splash10-00kb-0050590000-b0e6aacfaecd93b6a78c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyronaridine 20V, Positive-QTOF	splash10-0002-0190100000-1c6de0443fa28c6e9eab	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyronaridine 40V, Positive-QTOF	splash10-01tj-2469100000-bf1b8ab68b8d034f5729	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyronaridine 10V, Negative-QTOF	splash10-014i-6000490000-bbee5832e517c0176586	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyronaridine 20V, Negative-QTOF	splash10-01c0-7040960000-57c9bcd68dd05fd12ba5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyronaridine 40V, Negative-QTOF	splash10-00di-9000200000-6aaacbfd337dc3836a7d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyronaridine 10V, Negative-QTOF	splash10-014i-0000090000-d715feac25907e71b9f8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyronaridine 20V, Negative-QTOF	splash10-016r-2003390000-05822001e9b1fe6c4d46	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyronaridine 40V, Negative-QTOF	splash10-03di-1007940000-584300f097c4301715fd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyronaridine 10V, Positive-QTOF	splash10-014i-0000390000-15233bc0f7651f447f8f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyronaridine 20V, Positive-QTOF	splash10-004i-0009100000-75ba26b0e0202cbf7101	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pyronaridine 40V, Positive-QTOF	splash10-003r-1019100000-99ae31c68eb7565b48ff	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

4588649

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pyronaridine

METLIN ID

Not Available

PubChem Compound

5485198

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Pyronaridine (HMDB0042003)

MOL for HMDB0042003 (Pyronaridine)

3D MOL for HMDB0042003 (Pyronaridine)

3D SDF for HMDB0042003 (Pyronaridine)

3D-SDF for HMDB0042003 (Pyronaridine)

PDB for HMDB0042003 (Pyronaridine)

3D PDB for HMDB0042003 (Pyronaridine)

SMILES for HMDB0042003 (Pyronaridine)

INCHI for HMDB0042003 (Pyronaridine)

Structure for HMDB0042003 (Pyronaridine)

3D Structure for HMDB0042003 (Pyronaridine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra