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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 01:37:29 UTC

Update Date

2021-09-26 22:58:35 UTC

HMDB ID

HMDB0248347

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Amopyroquine

Description

Amopyroquine, also known as PAM 780, belongs to the class of organic compounds known as 4-aminoquinolines. These are organic compounds containing an amino group attached to the 4-position of a quinoline ring system. Based on a literature review very few articles have been published on Amopyroquine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Amopyroquine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Amopyroquine 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

HMDB0248347
     RDKit          3D
Amopyroquine
 45 48  0  0  0  0  0  0  0  0999 V2000
    2.0450    1.9226   -2.3878 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1522    1.3341   -1.5628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1777    1.6618   -1.5703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0852    1.0488   -0.7379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6802    0.0544    0.1668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8130   -0.4730    0.9046 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9863   -0.8380    0.1295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0284   -1.7034   -0.8823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2597   -2.0759   -1.4733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4028   -1.5689   -1.0138 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4307   -0.6776    0.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6489   -0.1075    0.4002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6034    0.8327    1.3735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1294    1.6486    1.9095 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.4493    1.2397    1.9840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2163    0.6630    1.5804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2417   -0.3192    0.5755 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6287   -0.2883    0.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5874    0.3220   -0.6234 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9566   -0.0859   -0.7818 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9709    0.0976    0.1018 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1123   -0.2328    1.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5670   -0.7770    1.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3272   -0.0338    0.5011 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3004    0.1029   -0.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0102    1.8564   -2.4596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4992    2.4672   -2.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1330    1.3694   -0.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8215   -0.6244    1.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1189   -2.1679   -1.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2274   -2.7689   -2.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6124   -0.4177   -0.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3796    1.9941    2.7950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2828    0.9319    1.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9166   -1.0527    0.9551 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8639   -1.2898   -0.8963 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2351    0.1122   -1.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0502    0.6733    2.1384 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4073   -0.9733    1.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9591   -0.5403    2.5946 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4934   -1.8351    1.3335 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7699    0.9073    0.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1582   -0.7104    0.1906 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4644    1.0467   -1.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2518   -0.7251   -1.2978 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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
  5 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  2  1  0
 25 21  1  0
 17  7  1  0
 17 11  1  0
  1 26  1  0
  3 27  1  0
  4 28  1  0
  6 29  1  0
  8 30  1  0
  9 31  1  0
 12 32  1  0
 15 33  1  0
 16 34  1  0
 18 35  1  0
 20 36  1  0
 20 37  1  0
 22 38  1  0
 22 39  1  0
 23 40  1  0
 23 41  1  0
 24 42  1  0
 24 43  1  0
 25 44  1  0
 25 45  1  0
M  END


  Mrv1652309112103372D          

 25 28  0  0  0  0            999 V2000
   -3.4491    1.5150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0366    2.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2296    2.0580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8971    0.9019    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
   -0.7145    1.2375    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
    0.0000    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   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
    1.4289    0.0000    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
    2.8579    0.0000    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
    2.8579   -1.6500    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   -1.6500    0.0000 N   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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 14 23  1  0  0  0  0
 18 24  1  0  0  0  0
  8 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0248347

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=C(CN2CCCC2)C=C(NC2=C3C=CC(Cl)=CC3=NC=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H20ClN3O/c21-15-3-5-17-18(7-8-22-19(17)12-15)23-16-4-6-20(25)14(11-16)13-24-9-1-2-10-24/h3-8,11-12,25H,1-2,9-10,13H2,(H,22,23)

> <INCHI_KEY>
YNWCUCSDUMVJKR-UHFFFAOYSA-N

> <FORMULA>
C20H20ClN3O

> <MOLECULAR_WEIGHT>
353.85

> <EXACT_MASS>
353.12949

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
38.17706675816243

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(7-chloroquinolin-4-yl)amino]-2-[(pyrrolidin-1-yl)methyl]phenol

> <ALOGPS_LOGP>
4.77

> <JCHEM_LOGP>
3.5017630916850213

> <ALOGPS_LOGS>
-4.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.089329747519121

> <JCHEM_PKA_STRONGEST_BASIC>
10.144486417598445

> <JCHEM_POLAR_SURFACE_AREA>
48.39

> <JCHEM_REFRACTIVITY>
101.33489999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.93e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
amopyroquine hydrochloride

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0248347
     RDKit          3D
Amopyroquine
 45 48  0  0  0  0  0  0  0  0999 V2000
    2.0450    1.9226   -2.3878 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1522    1.3341   -1.5628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1777    1.6618   -1.5703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0852    1.0488   -0.7379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6802    0.0544    0.1668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8130   -0.4730    0.9046 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9863   -0.8380    0.1295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0284   -1.7034   -0.8823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2597   -2.0759   -1.4733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4028   -1.5689   -1.0138 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4307   -0.6776    0.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6489   -0.1075    0.4002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6034    0.8327    1.3735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1294    1.6486    1.9095 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.4493    1.2397    1.9840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2163    0.6630    1.5804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2417   -0.3192    0.5755 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6287   -0.2883    0.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5874    0.3220   -0.6234 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9566   -0.0859   -0.7818 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9709    0.0976    0.1018 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1123   -0.2328    1.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5670   -0.7770    1.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3272   -0.0338    0.5011 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3004    0.1029   -0.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0102    1.8564   -2.4596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4992    2.4672   -2.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1330    1.3694   -0.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8215   -0.6244    1.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1189   -2.1679   -1.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2274   -2.7689   -2.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6124   -0.4177   -0.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3796    1.9941    2.7950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2828    0.9319    1.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9166   -1.0527    0.9551 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8639   -1.2898   -0.8963 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2351    0.1122   -1.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0502    0.6733    2.1384 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4073   -0.9733    1.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9591   -0.5403    2.5946 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4934   -1.8351    1.3335 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7699    0.9073    0.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1582   -0.7104    0.1906 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4644    1.0467   -1.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2518   -0.7251   -1.2978 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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
  5 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  2  1  0
 25 21  1  0
 17  7  1  0
 17 11  1  0
  1 26  1  0
  3 27  1  0
  4 28  1  0
  6 29  1  0
  8 30  1  0
  9 31  1  0
 12 32  1  0
 15 33  1  0
 16 34  1  0
 18 35  1  0
 20 36  1  0
 20 37  1  0
 22 38  1  0
 22 39  1  0
 23 40  1  0
 23 41  1  0
 24 42  1  0
 24 43  1  0
 25 44  1  0
 25 45  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      -6.438   2.828   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.668   4.162   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.162   3.842   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      -4.001   2.310   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -5.408   1.684   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       2.667   1.540   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   24 Cl   UNK     0       8.002  -3.080   0.000  0.00  0.00          Cl+0
HETATM   25  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4    1                                                       
CONECT    6    4    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9   25                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11    7                                                       
CONECT   13   11   14                                                       
CONECT   14   13   15   23                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   15   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   14                                                       
CONECT   24   18                                                            
CONECT   25    8                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0248347
HETATM    1  O1  UNL     1       2.045   1.923  -2.388  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.152   1.334  -1.563  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.178   1.662  -1.570  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.085   1.049  -0.738  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.680   0.054   0.167  1.00  0.00           C  
HETATM    6  N1  UNL     1      -1.813  -0.473   0.905  1.00  0.00           N  
HETATM    7  C5  UNL     1      -2.986  -0.838   0.130  1.00  0.00           C  
HETATM    8  C6  UNL     1      -3.028  -1.703  -0.882  1.00  0.00           C  
HETATM    9  C7  UNL     1      -4.260  -2.076  -1.473  1.00  0.00           C  
HETATM   10  N2  UNL     1      -5.403  -1.569  -1.014  1.00  0.00           N  
HETATM   11  C8  UNL     1      -5.431  -0.678   0.011  1.00  0.00           C  
HETATM   12  C9  UNL     1      -6.649  -0.108   0.400  1.00  0.00           C  
HETATM   13  C10 UNL     1      -6.603   0.833   1.374  1.00  0.00           C  
HETATM   14 CL1  UNL     1      -8.129   1.649   1.910  1.00  0.00          CL  
HETATM   15  C11 UNL     1      -5.449   1.240   1.984  1.00  0.00           C  
HETATM   16  C12 UNL     1      -4.216   0.663   1.580  1.00  0.00           C  
HETATM   17  C13 UNL     1      -4.242  -0.319   0.576  1.00  0.00           C  
HETATM   18  C14 UNL     1       0.629  -0.288   0.217  1.00  0.00           C  
HETATM   19  C15 UNL     1       1.587   0.322  -0.623  1.00  0.00           C  
HETATM   20  C16 UNL     1       2.957  -0.086  -0.782  1.00  0.00           C  
HETATM   21  N3  UNL     1       3.971   0.098   0.102  1.00  0.00           N  
HETATM   22  C17 UNL     1       4.112  -0.233   1.405  1.00  0.00           C  
HETATM   23  C18 UNL     1       5.567  -0.777   1.577  1.00  0.00           C  
HETATM   24  C19 UNL     1       6.327  -0.034   0.501  1.00  0.00           C  
HETATM   25  C20 UNL     1       5.300   0.103  -0.554  1.00  0.00           C  
HETATM   26  H1  UNL     1       3.010   1.856  -2.460  1.00  0.00           H  
HETATM   27  H2  UNL     1      -0.499   2.467  -2.244  1.00  0.00           H  
HETATM   28  H3  UNL     1      -2.133   1.369  -0.686  1.00  0.00           H  
HETATM   29  H4  UNL     1      -1.821  -0.624   1.927  1.00  0.00           H  
HETATM   30  H5  UNL     1      -2.119  -2.168  -1.276  1.00  0.00           H  
HETATM   31  H6  UNL     1      -4.227  -2.769  -2.309  1.00  0.00           H  
HETATM   32  H7  UNL     1      -7.612  -0.418  -0.092  1.00  0.00           H  
HETATM   33  H8  UNL     1      -5.380   1.994   2.795  1.00  0.00           H  
HETATM   34  H9  UNL     1      -3.283   0.932   1.982  1.00  0.00           H  
HETATM   35  H10 UNL     1       0.917  -1.053   0.955  1.00  0.00           H  
HETATM   36  H11 UNL     1       2.864  -1.290  -0.896  1.00  0.00           H  
HETATM   37  H12 UNL     1       3.235   0.112  -1.887  1.00  0.00           H  
HETATM   38  H13 UNL     1       4.050   0.673   2.138  1.00  0.00           H  
HETATM   39  H14 UNL     1       3.407  -0.973   1.855  1.00  0.00           H  
HETATM   40  H15 UNL     1       5.959  -0.540   2.595  1.00  0.00           H  
HETATM   41  H16 UNL     1       5.493  -1.835   1.334  1.00  0.00           H  
HETATM   42  H17 UNL     1       6.770   0.907   0.893  1.00  0.00           H  
HETATM   43  H18 UNL     1       7.158  -0.710   0.191  1.00  0.00           H  
HETATM   44  H19 UNL     1       5.464   1.047  -1.133  1.00  0.00           H  
HETATM   45  H20 UNL     1       5.252  -0.725  -1.298  1.00  0.00           H  
CONECT    1    2   26
CONECT    2    3    3   19
CONECT    3    4   27
CONECT    4    5    5   28
CONECT    5    6   18
CONECT    6    7   29
CONECT    7    8    8   17
CONECT    8    9   30
CONECT    9   10   10   31
CONECT   10   11
CONECT   11   12   12   17
CONECT   12   13   32
CONECT   13   14   15   15
CONECT   15   16   33
CONECT   16   17   17   34
CONECT   18   19   19   35
CONECT   19   20
CONECT   20   21   36   37
CONECT   21   22   25
CONECT   22   23   38   39
CONECT   23   24   40   41
CONECT   24   25   42   43
CONECT   25   44   45
END

HMDB0248347
     RDKit          3D
Amopyroquine
 45 48  0  0  0  0  0  0  0  0999 V2000
    2.0450    1.9226   -2.3878 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1522    1.3341   -1.5628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1777    1.6618   -1.5703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0852    1.0488   -0.7379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6802    0.0544    0.1668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8130   -0.4730    0.9046 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9863   -0.8380    0.1295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0284   -1.7034   -0.8823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2597   -2.0759   -1.4733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4028   -1.5689   -1.0138 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4307   -0.6776    0.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6489   -0.1075    0.4002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6034    0.8327    1.3735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1294    1.6486    1.9095 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.4493    1.2397    1.9840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2163    0.6630    1.5804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2417   -0.3192    0.5755 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6287   -0.2883    0.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5874    0.3220   -0.6234 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9566   -0.0859   -0.7818 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9709    0.0976    0.1018 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1123   -0.2328    1.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5670   -0.7770    1.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3272   -0.0338    0.5011 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3004    0.1029   -0.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0102    1.8564   -2.4596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4992    2.4672   -2.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1330    1.3694   -0.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8215   -0.6244    1.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1189   -2.1679   -1.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2274   -2.7689   -2.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6124   -0.4177   -0.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3796    1.9941    2.7950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2828    0.9319    1.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9166   -1.0527    0.9551 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8639   -1.2898   -0.8963 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2351    0.1122   -1.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0502    0.6733    2.1384 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4073   -0.9733    1.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9591   -0.5403    2.5946 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4934   -1.8351    1.3335 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7699    0.9073    0.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1582   -0.7104    0.1906 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4644    1.0467   -1.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2518   -0.7251   -1.2978 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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
  5 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  2  1  0
 25 21  1  0
 17  7  1  0
 17 11  1  0
  1 26  1  0
  3 27  1  0
  4 28  1  0
  6 29  1  0
  8 30  1  0
  9 31  1  0
 12 32  1  0
 15 33  1  0
 16 34  1  0
 18 35  1  0
 20 36  1  0
 20 37  1  0
 22 38  1  0
 22 39  1  0
 23 40  1  0
 23 41  1  0
 24 42  1  0
 24 43  1  0
 25 44  1  0
 25 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
PAM 780	HMDB
Amopyroquin	HMDB
Amopyroquine dihydrochloride	HMDB
Amopyroquine hydrochloride	HMDB

Chemical Formula

C₂₀H₂₀ClN₃O

Average Molecular Weight

353.85

Monoisotopic Molecular Weight

353.12949

IUPAC Name

4-[(7-chloroquinolin-4-yl)amino]-2-[(pyrrolidin-1-yl)methyl]phenol

Traditional Name

amopyroquine hydrochloride

CAS Registry Number

Not Available

SMILES

OC1=C(CN2CCCC2)C=C(NC2=C3C=CC(Cl)=CC3=NC=C2)C=C1

InChI Identifier

InChI=1S/C20H20ClN3O/c21-15-3-5-17-18(7-8-22-19(17)12-15)23-16-4-6-20(25)14(11-16)13-24-9-1-2-10-24/h3-8,11-12,25H,1-2,9-10,13H2,(H,22,23)

InChI Key

YNWCUCSDUMVJKR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4-aminoquinolines. These are organic compounds containing an amino group attached to the 4-position of a quinoline ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Aminoquinolines and derivatives

Direct Parent

4-aminoquinolines

Alternative Parents

Substituents

4-aminoquinoline
Haloquinoline
Chloroquinoline
Aminophenol
P-aminophenol
Phenylmethylamine
Benzylamine
Aniline or substituted anilines
1-hydroxy-2-unsubstituted benzenoid
Aminopyridine
Phenol
Aralkylamine
Pyridine
Aryl chloride
Monocyclic benzene moiety
Benzenoid
N-alkylpyrrolidine
Aryl halide
Heteroaromatic compound
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Azacycle
Secondary amine
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Amine
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
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)

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	4.77	ALOGPS
logP	3.5	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	9.09	ChemAxon
pKa (Strongest Basic)	10.14	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	48.39 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	101.33 m³·mol⁻¹	ChemAxon
Polarizability	38.18 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	188.568	30932474
DeepCCS	[M-H]-	186.037	30932474
DeepCCS	[M-2H]-	220.462	30932474
DeepCCS	[M+Na]+	196.752	30932474
AllCCS	[M+H]+	183.2	32859911
AllCCS	[M+H-H2O]+	180.3	32859911
AllCCS	[M+NH4]+	185.9	32859911
AllCCS	[M+Na]+	186.7	32859911
AllCCS	[M-H]-	184.9	32859911
AllCCS	[M+Na-2H]-	184.4	32859911
AllCCS	[M+HCOO]-	183.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Amopyroquine	OC1=C(CN2CCCC2)C=C(NC2=C3C=CC(Cl)=CC3=NC=C2)C=C1	4399.1	Standard polar	33892256
Amopyroquine	OC1=C(CN2CCCC2)C=C(NC2=C3C=CC(Cl)=CC3=NC=C2)C=C1	3298.7	Standard non polar	33892256
Amopyroquine	OC1=C(CN2CCCC2)C=C(NC2=C3C=CC(Cl)=CC3=NC=C2)C=C1	3541.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Amopyroquine,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C)C=C1CN1CCCC1	3182.1	Semi standard non polar	33892256
Amopyroquine,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C)C=C1CN1CCCC1	3035.5	Standard non polar	33892256
Amopyroquine,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C)C=C1CN1CCCC1	3861.1	Standard polar	33892256
Amopyroquine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C(C)(C)C)C=C1CN1CCCC1	3608.6	Semi standard non polar	33892256
Amopyroquine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C(C)(C)C)C=C1CN1CCCC1	3468.6	Standard non polar	33892256
Amopyroquine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C(C)(C)C)C=C1CN1CCCC1	3953.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Amopyroquine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00c0-9258000000-664e4b3b0461409a4b5e	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amopyroquine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amopyroquine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amopyroquine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amopyroquine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amopyroquine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	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 - Amopyroquine 10V, Positive-QTOF	splash10-001i-0093000000-8f9cf90df2649fc21577	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amopyroquine 20V, Positive-QTOF	splash10-001i-0090000000-3d6315be6d6ab1030512	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amopyroquine 40V, Positive-QTOF	splash10-05o0-0491000000-6b1f7dd8e47ce862b370	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amopyroquine 10V, Negative-QTOF	splash10-0udi-0029000000-f5226aeb8d5f27f24145	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amopyroquine 20V, Negative-QTOF	splash10-001i-2094000000-02c18ce8d4f5eabc0188	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amopyroquine 40V, Negative-QTOF	splash10-001i-4390000000-c6576bd5d9ec9810ed67	2021-10-12	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

23530

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25194

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

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 Amopyroquine (HMDB0248347)

MOL for HMDB0248347 (Amopyroquine)

3D MOL for HMDB0248347 (Amopyroquine)

3D SDF for HMDB0248347 (Amopyroquine)

3D-SDF for HMDB0248347 (Amopyroquine)

PDB for HMDB0248347 (Amopyroquine)

3D PDB for HMDB0248347 (Amopyroquine)

SMILES for HMDB0248347 (Amopyroquine)

INCHI for HMDB0248347 (Amopyroquine)

Structure for HMDB0248347 (Amopyroquine)

3D Structure for HMDB0248347 (Amopyroquine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra