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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (5)transporters (2) Show 7 proteins XML

enzymes (5)transporters (2) Show 7 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:54 UTC

HMDB ID

HMDB0015235

Secondary Accession Numbers

HMDB15235

Metabolite Identification

Common Name

Quinacrine

Description

quinacrine, also known as mepacrine, belongs to the class of organic compounds known as acridines. These are organic compounds containing the acridine moiety, a linear tricyclic heterocycle which consists of two benzene rings joined by a pyridine ring. Based on a literature review a small amount of articles have been published on quinacrine.

Structure

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

1103
  Mrv0541 02231215152D          

 28 30  0  0  1  0            999 V2000
    2.3097   -3.3052    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.1336   -1.6156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    2.0765    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -0.8106    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -3.2853    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073   -0.3981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073    0.4267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929    0.8392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929    1.6641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -1.6355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929   -0.8106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    2.9014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641    1.6641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9361   -2.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073   -2.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9361   -2.8728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073   -2.8728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641    3.3139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498    2.0765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6734   -1.6069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7699   -1.6069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6734   -3.3139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7699   -3.3139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4209   -2.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4209   -2.8900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0225   -2.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0225   -2.8900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8496   -2.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 27  1  0  0  0  0
  2 24  1  0  0  0  0
  2 28  1  0  0  0  0
  3  9  1  0  0  0  0
  3 12  1  0  0  0  0
  3 13  1  0  0  0  0
  4  6  1  0  0  0  0
  4 10  1  0  0  0  0
  5 16  2  0  0  0  0
  5 17  1  0  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10 14  2  0  0  0  0
 10 15  1  0  0  0  0
 12 18  1  0  0  0  0
 13 19  1  0  0  0  0
 14 16  1  0  0  0  0
 14 20  1  0  0  0  0
 15 17  2  0  0  0  0
 15 21  1  0  0  0  0
 16 22  1  0  0  0  0
 17 23  1  0  0  0  0
 20 24  2  0  0  0  0
 21 26  2  0  0  0  0
 22 25  2  0  0  0  0
 23 27  2  0  0  0  0
 24 25  1  0  0  0  0
 26 27  1  0  0  0  0
M  END

HMDB0243744
     RDKit          3D
(S)-Quinacrine
 58 60  0  0  0  0  0  0  0  0999 V2000
   -5.4824    2.5235   -1.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2491    1.9742   -0.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5321    0.9559    0.4835 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0243   -0.2673   -0.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3184   -1.2896    0.9502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3504    0.7421    1.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2025    0.1219    0.5044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0133   -0.1091    1.3993 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1594   -0.7004    0.6995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1532   -2.0379    0.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7814    0.1603   -0.2735 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0548   -0.2091   -0.7878 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2809   -0.8787   -1.9600 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1963   -1.1407   -2.7696 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4332   -1.8062   -3.9646 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6987   -2.1926   -4.3393 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9570   -3.0423   -5.8681 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.7639   -1.9308   -3.5397 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5687   -1.2684   -2.3375 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6030   -0.9753   -1.5308 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4002   -0.3145   -0.3759 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4849   -0.0036    0.4527 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2733    0.6773    1.6195 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0298    1.0834    2.0358 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7652    1.7710    3.2017 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8308    2.1015    4.0621 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9414    0.7812    1.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1558    0.0850    0.0313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0195    1.7638   -1.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1534    3.0499   -0.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1419    3.3019   -1.8679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7922    2.8400    0.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5239    1.6474   -1.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3261   -0.6584   -0.8618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9760   -0.0342   -0.6124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3422   -1.1099    1.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6034   -1.3826    1.7681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3890   -2.2831    0.4252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5080    0.2448    2.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9907    1.7819    1.5528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5759   -0.8956    0.2178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8818    0.7252   -0.3485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3179   -0.7456    2.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6727    0.8811    1.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9085   -0.9657    1.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8767   -1.9687   -0.7449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7954   -2.4718   -0.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5182   -2.7142    0.8932 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2987    1.0200   -0.5769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2157   -0.8209   -2.4748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5920   -2.0177   -4.6045 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7982   -2.2053   -3.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4706   -0.3150    0.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1167    0.9246    2.2723 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4710    2.3255    5.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5085    1.2334    4.1667 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4408    2.9440    3.6743 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9402    1.0946    1.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  2  0
 28 12  1  0
 19 13  1  0
 28 21  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  6 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  0
  8 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 10 48  1  0
 11 49  1  0
 14 50  1  0
 15 51  1  0
 18 52  1  0
 22 53  1  0
 23 54  1  0
 26 55  1  0
 26 56  1  0
 26 57  1  0
 27 58  1  0
M  END

1103
  Mrv0541 02231215152D          

 28 30  0  0  1  0            999 V2000
    2.3097   -3.3052    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.1336   -1.6156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    2.0765    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -0.8106    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -3.2853    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073   -0.3981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073    0.4267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929    0.8392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929    1.6641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -1.6355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7929   -0.8106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    2.9014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641    1.6641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9361   -2.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073   -2.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9361   -2.8728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5073   -2.8728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3641    3.3139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498    2.0765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6734   -1.6069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7699   -1.6069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6734   -3.3139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7699   -3.3139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4209   -2.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4209   -2.8900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0225   -2.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0225   -2.8900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8496   -2.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 27  1  0  0  0  0
  2 24  1  0  0  0  0
  2 28  1  0  0  0  0
  3  9  1  0  0  0  0
  3 12  1  0  0  0  0
  3 13  1  0  0  0  0
  4  6  1  0  0  0  0
  4 10  1  0  0  0  0
  5 16  2  0  0  0  0
  5 17  1  0  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10 14  2  0  0  0  0
 10 15  1  0  0  0  0
 12 18  1  0  0  0  0
 13 19  1  0  0  0  0
 14 16  1  0  0  0  0
 14 20  1  0  0  0  0
 15 17  2  0  0  0  0
 15 21  1  0  0  0  0
 16 22  1  0  0  0  0
 17 23  1  0  0  0  0
 20 24  2  0  0  0  0
 21 26  2  0  0  0  0
 22 25  2  0  0  0  0
 23 27  2  0  0  0  0
 24 25  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015235

> <DATABASE_NAME>
hmdb

> <SMILES>
CCN(CC)CCCC(C)NC1=C2C=C(OC)C=CC2=NC2=C1C=CC(Cl)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C23H30ClN3O/c1-5-27(6-2)13-7-8-16(3)25-23-19-11-9-17(24)14-22(19)26-21-12-10-18(28-4)15-20(21)23/h9-12,14-16H,5-8,13H2,1-4H3,(H,25,26)

> <INCHI_KEY>
GPKJTRJOBQGKQK-UHFFFAOYSA-N

> <FORMULA>
C23H30ClN3O

> <MOLECULAR_WEIGHT>
399.957

> <EXACT_MASS>
399.207740304

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
46.324000843001414

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-chloro-N-[5-(diethylamino)pentan-2-yl]-2-methoxyacridin-9-amine

> <ALOGPS_LOGP>
6.13

> <JCHEM_LOGP>
5.151536958

> <ALOGPS_LOGS>
-5.22

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_BASIC>
10.328892233193985

> <JCHEM_POLAR_SURFACE_AREA>
37.39

> <JCHEM_REFRACTIVITY>
118.96440000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.39e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-chloro-N-[5-(diethylamino)pentan-2-yl]-2-methoxyacridin-9-amine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0243744
     RDKit          3D
(S)-Quinacrine
 58 60  0  0  0  0  0  0  0  0999 V2000
   -5.4824    2.5235   -1.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2491    1.9742   -0.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5321    0.9559    0.4835 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0243   -0.2673   -0.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3184   -1.2896    0.9502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3504    0.7421    1.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2025    0.1219    0.5044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0133   -0.1091    1.3993 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1594   -0.7004    0.6995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1532   -2.0379    0.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7814    0.1603   -0.2735 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0548   -0.2091   -0.7878 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2809   -0.8787   -1.9600 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1963   -1.1407   -2.7696 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4332   -1.8062   -3.9646 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6987   -2.1926   -4.3393 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9570   -3.0423   -5.8681 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.7639   -1.9308   -3.5397 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5687   -1.2684   -2.3375 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6030   -0.9753   -1.5308 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4002   -0.3145   -0.3759 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4849   -0.0036    0.4527 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2733    0.6773    1.6195 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0298    1.0834    2.0358 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7652    1.7710    3.2017 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8308    2.1015    4.0621 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9414    0.7812    1.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1558    0.0850    0.0313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0195    1.7638   -1.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1534    3.0499   -0.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1419    3.3019   -1.8679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7922    2.8400    0.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5239    1.6474   -1.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3261   -0.6584   -0.8618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9760   -0.0342   -0.6124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3422   -1.1099    1.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6034   -1.3826    1.7681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3890   -2.2831    0.4252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5080    0.2448    2.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9907    1.7819    1.5528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5759   -0.8956    0.2178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8818    0.7252   -0.3485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3179   -0.7456    2.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6727    0.8811    1.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9085   -0.9657    1.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8767   -1.9687   -0.7449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7954   -2.4718   -0.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5182   -2.7142    0.8932 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2987    1.0200   -0.5769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2157   -0.8209   -2.4748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5920   -2.0177   -4.6045 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7982   -2.2053   -3.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4706   -0.3150    0.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1167    0.9246    2.2723 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4710    2.3255    5.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5085    1.2334    4.1667 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4408    2.9440    3.6743 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9402    1.0946    1.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  2  0
 28 12  1  0
 19 13  1  0
 28 21  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  6 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  0
  8 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 10 48  1  0
 11 49  1  0
 14 50  1  0
 15 51  1  0
 18 52  1  0
 22 53  1  0
 23 54  1  0
 26 55  1  0
 26 56  1  0
 26 57  1  0
 27 58  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1103                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       4.311  -6.170   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0      15.183  -3.016   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       5.747   3.876   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       9.747  -1.513   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       9.747  -6.132   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       8.414  -0.743   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.414   0.797   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.080   1.566   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.080   3.106   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.747  -3.053   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.080  -1.513   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.747   5.416   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.413   3.106   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.081  -3.823   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.414  -3.823   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.081  -5.363   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.414  -5.363   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.413   6.186   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.080   3.876   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.457  -3.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.037  -3.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.457  -6.186   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.037  -6.186   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.852  -3.791   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.852  -5.395   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.642  -3.791   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.642  -5.395   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      16.519  -3.780   0.000  0.00  0.00           C+0
CONECT    1   27                                                            
CONECT    2   24   28                                                       
CONECT    3    9   12   13                                                  
CONECT    4    6   10                                                       
CONECT    5   16   17                                                       
CONECT    6    4    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    3    8                                                       
CONECT   10    4   14   15                                                  
CONECT   11    6                                                            
CONECT   12    3   18                                                       
CONECT   13    3   19                                                       
CONECT   14   10   16   20                                                  
CONECT   15   10   17   21                                                  
CONECT   16    5   14   22                                                  
CONECT   17    5   15   23                                                  
CONECT   18   12                                                            
CONECT   19   13                                                            
CONECT   20   14   24                                                       
CONECT   21   15   26                                                       
CONECT   22   16   25                                                       
CONECT   23   17   27                                                       
CONECT   24    2   20   25                                                  
CONECT   25   22   24                                                       
CONECT   26   21   27                                                       
CONECT   27    1   23   26                                                  
CONECT   28    2                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

COMPND    HMDB0015235
HETATM    1  C1  UNL     1       5.429  -0.142   2.256  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.265   0.575   1.571  1.00  0.00           C  
HETATM    3  N1  UNL     1       3.845  -0.210   0.475  1.00  0.00           N  
HETATM    4  C3  UNL     1       4.737  -0.322  -0.607  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.955   0.960  -1.374  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.448  -0.289   0.210  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.827   0.972  -0.267  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.340   0.794  -0.508  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.008  -0.228  -1.522  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.557   0.076  -2.896  1.00  0.00           C  
HETATM   11  N2  UNL     1      -1.413  -0.436  -1.631  1.00  0.00           N  
HETATM   12  C10 UNL     1      -2.264  -0.842  -0.566  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.399  -2.169  -0.211  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.737  -3.171  -0.893  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.897  -4.489  -0.518  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.706  -4.875   0.530  1.00  0.00           C  
HETATM   17 CL1  UNL     1      -2.872  -6.579   0.966  1.00  0.00          CL  
HETATM   18  C15 UNL     1      -3.373  -3.891   1.219  1.00  0.00           C  
HETATM   19  C16 UNL     1      -3.214  -2.574   0.846  1.00  0.00           C  
HETATM   20  N3  UNL     1      -3.874  -1.597   1.514  1.00  0.00           N  
HETATM   21  C17 UNL     1      -3.767  -0.298   1.192  1.00  0.00           C  
HETATM   22  C18 UNL     1      -4.484   0.635   1.909  1.00  0.00           C  
HETATM   23  C19 UNL     1      -4.411   1.977   1.596  1.00  0.00           C  
HETATM   24  C20 UNL     1      -3.626   2.431   0.562  1.00  0.00           C  
HETATM   25  O1  UNL     1      -3.506   3.765   0.191  1.00  0.00           O  
HETATM   26  C21 UNL     1      -4.203   4.775   0.869  1.00  0.00           C  
HETATM   27  C22 UNL     1      -2.908   1.466  -0.150  1.00  0.00           C  
HETATM   28  C23 UNL     1      -2.952   0.120   0.133  1.00  0.00           C  
HETATM   29  H1  UNL     1       5.616  -1.122   1.770  1.00  0.00           H  
HETATM   30  H2  UNL     1       5.241  -0.326   3.326  1.00  0.00           H  
HETATM   31  H3  UNL     1       6.347   0.456   2.062  1.00  0.00           H  
HETATM   32  H4  UNL     1       4.551   1.618   1.311  1.00  0.00           H  
HETATM   33  H5  UNL     1       3.457   0.664   2.320  1.00  0.00           H  
HETATM   34  H6  UNL     1       5.733  -0.643  -0.223  1.00  0.00           H  
HETATM   35  H7  UNL     1       4.415  -1.130  -1.295  1.00  0.00           H  
HETATM   36  H8  UNL     1       4.656   1.859  -0.799  1.00  0.00           H  
HETATM   37  H9  UNL     1       6.021   1.051  -1.729  1.00  0.00           H  
HETATM   38  H10 UNL     1       4.344   0.912  -2.297  1.00  0.00           H  
HETATM   39  H11 UNL     1       2.309  -1.153  -0.493  1.00  0.00           H  
HETATM   40  H12 UNL     1       1.932  -0.584   1.156  1.00  0.00           H  
HETATM   41  H13 UNL     1       2.325   1.441  -1.127  1.00  0.00           H  
HETATM   42  H14 UNL     1       1.907   1.713   0.576  1.00  0.00           H  
HETATM   43  H15 UNL     1      -0.045   1.803  -0.791  1.00  0.00           H  
HETATM   44  H16 UNL     1      -0.119   0.528   0.463  1.00  0.00           H  
HETATM   45  H17 UNL     1       0.454  -1.220  -1.235  1.00  0.00           H  
HETATM   46  H18 UNL     1      -0.080  -0.460  -3.629  1.00  0.00           H  
HETATM   47  H19 UNL     1       0.530   1.144  -3.153  1.00  0.00           H  
HETATM   48  H20 UNL     1       1.581  -0.357  -3.020  1.00  0.00           H  
HETATM   49  H21 UNL     1      -1.892  -0.283  -2.573  1.00  0.00           H  
HETATM   50  H22 UNL     1      -1.094  -2.901  -1.736  1.00  0.00           H  
HETATM   51  H23 UNL     1      -1.366  -5.273  -1.068  1.00  0.00           H  
HETATM   52  H24 UNL     1      -4.026  -4.159   2.059  1.00  0.00           H  
HETATM   53  H25 UNL     1      -5.124   0.326   2.741  1.00  0.00           H  
HETATM   54  H26 UNL     1      -4.974   2.721   2.157  1.00  0.00           H  
HETATM   55  H27 UNL     1      -3.676   4.961   1.843  1.00  0.00           H  
HETATM   56  H28 UNL     1      -4.261   5.713   0.274  1.00  0.00           H  
HETATM   57  H29 UNL     1      -5.237   4.457   1.132  1.00  0.00           H  
HETATM   58  H30 UNL     1      -2.316   1.812  -0.968  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3   32   33
CONECT    3    4    6
CONECT    4    5   34   35
CONECT    5   36   37   38
CONECT    6    7   39   40
CONECT    7    8   41   42
CONECT    8    9   43   44
CONECT    9   10   11   45
CONECT   10   46   47   48
CONECT   11   12   49
CONECT   12   13   13   28
CONECT   13   14   19
CONECT   14   15   15   50
CONECT   15   16   51
CONECT   16   17   18   18
CONECT   18   19   52
CONECT   19   20   20
CONECT   20   21
CONECT   21   22   22   28
CONECT   22   23   53
CONECT   23   24   24   54
CONECT   24   25   27
CONECT   25   26
CONECT   26   55   56   57
CONECT   27   28   28   58
END

HMDB0243744
     RDKit          3D
(S)-Quinacrine
 58 60  0  0  0  0  0  0  0  0999 V2000
   -5.4824    2.5235   -1.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2491    1.9742   -0.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5321    0.9559    0.4835 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0243   -0.2673   -0.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3184   -1.2896    0.9502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3504    0.7421    1.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2025    0.1219    0.5044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0133   -0.1091    1.3993 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1594   -0.7004    0.6995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1532   -2.0379    0.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7814    0.1603   -0.2735 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0548   -0.2091   -0.7878 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2809   -0.8787   -1.9600 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1963   -1.1407   -2.7696 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4332   -1.8062   -3.9646 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6987   -2.1926   -4.3393 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9570   -3.0423   -5.8681 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.7639   -1.9308   -3.5397 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5687   -1.2684   -2.3375 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6030   -0.9753   -1.5308 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4002   -0.3145   -0.3759 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4849   -0.0036    0.4527 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2733    0.6773    1.6195 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0298    1.0834    2.0358 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7652    1.7710    3.2017 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8308    2.1015    4.0621 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9414    0.7812    1.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1558    0.0850    0.0313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0195    1.7638   -1.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1534    3.0499   -0.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1419    3.3019   -1.8679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7922    2.8400    0.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5239    1.6474   -1.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3261   -0.6584   -0.8618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9760   -0.0342   -0.6124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3422   -1.1099    1.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6034   -1.3826    1.7681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3890   -2.2831    0.4252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5080    0.2448    2.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9907    1.7819    1.5528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5759   -0.8956    0.2178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8818    0.7252   -0.3485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3179   -0.7456    2.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6727    0.8811    1.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9085   -0.9657    1.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8767   -1.9687   -0.7449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7954   -2.4718   -0.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5182   -2.7142    0.8932 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2987    1.0200   -0.5769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2157   -0.8209   -2.4748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5920   -2.0177   -4.6045 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7982   -2.2053   -3.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4706   -0.3150    0.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1167    0.9246    2.2723 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4710    2.3255    5.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5085    1.2334    4.1667 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4408    2.9440    3.6743 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9402    1.0946    1.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  2  0
 28 12  1  0
 19 13  1  0
 28 21  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  6 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  0
  8 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 10 48  1  0
 11 49  1  0
 14 50  1  0
 15 51  1  0
 18 52  1  0
 22 53  1  0
 23 54  1  0
 26 55  1  0
 26 56  1  0
 26 57  1  0
 27 58  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Methoxy-6-chloro-9-diethylaminopentylaminoacridine	ChEBI
3-Chloro-7-methoxy-9-(1-methyl-4-diethylaminobutylamino)acridine	ChEBI
6-Chloro-9-((4-(diethylamino)-1-methylbutyl)amino)-2-methoxyacridine	ChEBI
Mepacrine	ChEBI
N(4)-(6-Chloro-2-methoxy-9-acridinyl)-N(1),N(1)-diethyl-1,4-pentanediamine	ChEBI
Quinacrin	Kegg
Quinacrine dihydrochloride	HMDB, MeSH
Monomesylate, quinacrine	MeSH, HMDB
Quinacrine dimesylate	MeSH, HMDB
Quinacrine, (R)-isomer	MeSH, HMDB
Acrichine	MeSH, HMDB
Dihydrochloride, quinacrine	MeSH, HMDB
Dimesylate, quinacrine	MeSH, HMDB
Quinacrine hydrochloride	MeSH, HMDB
Quinacrine monoacetate	MeSH, HMDB
Quinacrine monomesylate	MeSH, HMDB
Atebrin	MeSH, HMDB
Monohydrochloride, quinacrine	MeSH, HMDB
Quinacrine dihyrochloride, (S)-isomer	MeSH, HMDB
Quinacrine monohydrochloride	MeSH, HMDB
Quinacrine, (+-)-isomer	MeSH, HMDB
Quinacrine, (S)-isomer	MeSH, HMDB
Atabrine	MeSH, HMDB
Hydrochloride, quinacrine	MeSH, HMDB
Monoacetate, quinacrine	MeSH, HMDB
Quinacrine dihydrochloride, dihydrate	MeSH, HMDB
Quinacrine dihyrochloride, (R)-isomer	MeSH, HMDB

Chemical Formula

C₂₃H₃₀ClN₃O

Average Molecular Weight

399.957

Monoisotopic Molecular Weight

399.207740304

IUPAC Name

6-chloro-N-[5-(diethylamino)pentan-2-yl]-2-methoxyacridin-9-amine

Traditional Name

6-chloro-N-[5-(diethylamino)pentan-2-yl]-2-methoxyacridin-9-amine

CAS Registry Number

83-89-6

SMILES

CCN(CC)CCCC(C)NC1=C2C=C(OC)C=CC2=NC2=C1C=CC(Cl)=C2

InChI Identifier

InChI=1S/C23H30ClN3O/c1-5-27(6-2)13-7-8-16(3)25-23-19-11-9-17(24)14-22(19)26-21-12-10-18(28-4)15-20(21)23/h9-12,14-16H,5-8,13H2,1-4H3,(H,25,26)

InChI Key

GPKJTRJOBQGKQK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acridines. These are organic compounds containing the acridine moiety, a linear tricyclic heterocycle which consists of two benzene rings joined by a pyridine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Benzoquinolines

Direct Parent

Acridines

Alternative Parents

Substituents

Acridine
Haloquinoline
Chloroquinoline
Anisole
Alkyl aryl ether
Aryl chloride
Aryl halide
Pyridine
Benzenoid
Secondary ketimine
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Ether
Azacycle
Amine
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary amino compound (CHEBI:8711 )
aromatic ether (CHEBI:8711 )
organochlorine compound (CHEBI:8711 )
acridines (CHEBI:8711 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015235)
Membrane (HMDB: HMDB0015235)

Source

Exogenous

Exogenous (HMDB: HMDB0015235)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	248 - 250 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0024 g/L	Not Available
LogP	5.5	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	195.668	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000989

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0024 g/L	ALOGPS
logP	6.13	ALOGPS
logP	5.15	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Basic)	10.33	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.39 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	118.96 m³·mol⁻¹	ChemAxon
Polarizability	46.32 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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]+	194.813	30932474
DeepCCS	[M-H]-	192.374	30932474
DeepCCS	[M-2H]-	226.894	30932474
DeepCCS	[M+Na]+	203.185	30932474
AllCCS	[M+H]+	197.0	32859911
AllCCS	[M+H-H2O]+	194.4	32859911
AllCCS	[M+NH4]+	199.3	32859911
AllCCS	[M+Na]+	200.0	32859911
AllCCS	[M-H]-	201.1	32859911
AllCCS	[M+Na-2H]-	201.6	32859911
AllCCS	[M+HCOO]-	202.3	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.	6.62 minutes	32390414
Predicted by Siyang on May 30, 2022	11.0907 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.04 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	109.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Quinacrine	CCN(CC)CCCC(C)NC1=C2C=C(OC)C=CC2=NC2=C1C=CC(Cl)=C2	4442.3	Standard polar	33892256
Quinacrine	CCN(CC)CCCC(C)NC1=C2C=C(OC)C=CC2=NC2=C1C=CC(Cl)=C2	3275.3	Standard non polar	33892256
Quinacrine	CCN(CC)CCCC(C)NC1=C2C=C(OC)C=CC2=NC2=C1C=CC(Cl)=C2	3326.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Quinacrine,1TMS,isomer #1	CCN(CC)CCCC(C)N(C1=C2C=CC(Cl)=CC2=NC2=CC=C(OC)C=C12)[Si](C)(C)C	3163.2	Semi standard non polar	33892256
Quinacrine,1TMS,isomer #1	CCN(CC)CCCC(C)N(C1=C2C=CC(Cl)=CC2=NC2=CC=C(OC)C=C12)[Si](C)(C)C	2820.3	Standard non polar	33892256
Quinacrine,1TMS,isomer #1	CCN(CC)CCCC(C)N(C1=C2C=CC(Cl)=CC2=NC2=CC=C(OC)C=C12)[Si](C)(C)C	3866.6	Standard polar	33892256
Quinacrine,1TBDMS,isomer #1	CCN(CC)CCCC(C)N(C1=C2C=CC(Cl)=CC2=NC2=CC=C(OC)C=C12)[Si](C)(C)C(C)(C)C	3336.3	Semi standard non polar	33892256
Quinacrine,1TBDMS,isomer #1	CCN(CC)CCCC(C)N(C1=C2C=CC(Cl)=CC2=NC2=CC=C(OC)C=C12)[Si](C)(C)C(C)(C)C	3077.7	Standard non polar	33892256
Quinacrine,1TBDMS,isomer #1	CCN(CC)CCCC(C)N(C1=C2C=CC(Cl)=CC2=NC2=CC=C(OC)C=C12)[Si](C)(C)C(C)(C)C	3927.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Quinacrine GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-9025000000-fbef6d955948eb7f2a3f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Quinacrine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Quinacrine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Quinacrine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinacrine LC-ESI-QTOF , negative-QTOF	splash10-0002-0009200000-6e09844cb8551172f45c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinacrine LC-ESI-QTOF , negative-QTOF	splash10-0002-0009200000-242960dc93e3658182f0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinacrine LC-ESI-QTOF , negative-QTOF	splash10-0002-0019100000-85abeddd06ff2cce1fc9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinacrine LC-ESI-QTOF , positive-QTOF	splash10-0udi-0000900000-171d21b8fffe35f493d3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinacrine LC-ESI-QTOF , positive-QTOF	splash10-0udl-0423900000-9f5ab94c444b1766bd01	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinacrine LC-ESI-QTOF , positive-QTOF	splash10-0006-0934000000-afa177ceaf2f17c89180	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinacrine LC-ESI-QTOF , positive-QTOF	splash10-0006-0964000000-cb8056f84bdb3a200fba	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinacrine LC-ESI-QTOF , positive-QTOF	splash10-0006-0591000000-00e303f9525d62f012d4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinacrine 10V, Positive-QTOF	splash10-0udi-0000900000-171d21b8fffe35f493d3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinacrine 20V, Positive-QTOF	splash10-0udl-0423900000-9f5ab94c444b1766bd01	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinacrine 40V, Positive-QTOF	splash10-0006-0964000000-cb8056f84bdb3a200fba	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinacrine 30V, Positive-QTOF	splash10-0006-0934000000-afa177ceaf2f17c89180	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinacrine 20V, Negative-QTOF	splash10-0002-0009200000-242960dc93e3658182f0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinacrine 30V, Negative-QTOF	splash10-0002-0019100000-85abeddd06ff2cce1fc9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinacrine 10V, Negative-QTOF	splash10-0002-0009200000-6e09844cb8551172f45c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinacrine 50V, Positive-QTOF	splash10-0006-0591000000-00e303f9525d62f012d4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinacrine 50V, Positive-QTOF	splash10-0006-0591000000-ec7a34b139a1f19af5f1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinacrine 20V, Positive-QTOF	splash10-0002-0009200000-d6edfe4dda8af03dcf55	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinacrine 10V, Positive-QTOF	splash10-0udi-0002900000-f41646003acc390ed8bb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinacrine 20V, Positive-QTOF	splash10-0zfu-4975600000-ad273f8cfc82a9f76e9e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinacrine 40V, Positive-QTOF	splash10-009f-9251000000-556ea0aa9d5a370006a7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinacrine 10V, Negative-QTOF	splash10-0002-0009000000-b9379b7c57314e49af30	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinacrine 20V, Negative-QTOF	splash10-0002-0019000000-79e7dea5a1914a86d008	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinacrine 40V, Negative-QTOF	splash10-00di-9065000000-35833408615f0d3aa74a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinacrine 10V, Positive-QTOF	splash10-0udi-0000900000-f4b3bd614216642b1025	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01103	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01103	21059682	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

232

KEGG Compound ID

C07339

BioCyc ID

ATABRINE

BiGG ID

Not Available

Wikipedia Link

Quinacrine

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

8711

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

Bhatt RV: Camp laparoscopic sterilization deaths in Gujarat State, India, 1978-1980. Asia Oceania J Obstet Gynaecol. 1991 Dec;17(4):297-301. [PubMed:1839351 ]
Zipper J, Cole LP, Goldsmith A, Wheeler R, Rivera M: Quinacrine hydrochloride pellets: preliminary data on a nonsurgical method of female sterilization. Int J Gynaecol Obstet. 1980;18(4):275-9. [PubMed:6109672 ]
Peterson HB, Lubell I, DeStefano F, Ory HW: The safety and efficacy of tubal sterilization: an international overview. Int J Gynaecol Obstet. 1983 Apr;21(2):139-44. [PubMed:6136433 ]
Toubi E, Kessel A, Rosner I, Rozenbaum M, Paran D, Shoenfeld Y: The reduction of serum B-lymphocyte activating factor levels following quinacrine add-on therapy in systemic lupus erythematosus. Scand J Immunol. 2006 Apr;63(4):299-303. [PubMed:16623930 ]
Canete R, Escobedo AA, Gonzalez ME, Almirall P: Randomized clinical study of five days apostrophe therapy with mebendazole compared to quinacrine in the treatment of symptomatic giardiasis in children. World J Gastroenterol. 2006 Oct 21;12(39):6366-70. [PubMed:17072963 ]

Enzymes

Enzyme Details

1. Cytosolic phospholipase A2

General function:: Involved in metabolic process
Specific function:: Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory response.
Gene Name:: PLA2G4A
Uniprot ID:: P47712
Molecular weight:: 85210.19

References

Hellstrand M, Eriksson E, Nilsson CL: Dopamine D(2) receptor-induced COX-2-mediated production of prostaglandin E(2) in D(2)-transfected Chinese hamster ovary cells without simultaneous administration of a Ca(2+)-mobilizing agent. Biochem Pharmacol. 2002 Jun 15;63(12):2151-8. [PubMed:12110374 ]
Ong WY, Lu XR, Ong BK, Horrocks LA, Farooqui AA, Lim SK: Quinacrine abolishes increases in cytoplasmic phospholipase A2 mRNA levels in the rat hippocampus after kainate-induced neuronal injury. Exp Brain Res. 2003 Feb;148(4):521-4. Epub 2002 Dec 11. [PubMed:12582837 ]
Kim BC, Kim JH: Exogenous C2-ceramide activates c-fos serum response element via Rac-dependent signalling pathway. Biochem J. 1998 Mar 1;330 ( Pt 2):1009-14. [PubMed:9480923 ]

Enzyme Details

2. 85/88 kDa calcium-independent phospholipase A2

General function:: Involved in metabolic process
Specific function:: Catalyzes the release of fatty acids from phospholipids. It has been implicated in normal phospholipid remodeling, nitric oxide-induced or vasopressin-induced arachidonic acid release and in leukotriene and prostaglandin production. May participate in fas mediated apoptosis and in regulating transmembrane ion flux in glucose-stimulated B-cells. Has a role in cardiolipin (CL) deacylation. Required for both speed and directionality of monocyte MCP1/CCL2-induced chemotaxis through regulation of F-actin polymerization at the pseudopods. Isoform ankyrin-iPLA2-1 and isoform ankyrin-iPLA2-2, which lack the catalytic domain, are probably involved in the negative regulation of iPLA2 activity.
Gene Name:: PLA2G6
Uniprot ID:: O60733
Molecular weight:: 84092.635

References

Nuttle LC, Ligon AL, Farrell KR, Hester RL: Inhibition of phospholipase A2 attenuates functional hyperemia in the hamster cremaster muscle. Am J Physiol. 1999 Apr;276(4 Pt 2):H1289-94. [PubMed:10199854 ]
Sastry BV, Hemontolor ME, Vidaver PS, Sastry WS, Janson VE: Influence of halothane on phospholipase A2 and enzymatic methylations in the rat retinal membranes. J Ocul Pharmacol Ther. 1999 Apr;15(2):165-78. [PubMed:10229494 ]
Lohmann CH, Sagun R Jr, Sylvia VL, Cochran DL, Dean DD, Boyan BD, Schwartz Z: Surface roughness modulates the response of MG63 osteoblast-like cells to 1,25-(OH)(2)D(3) through regulation of phospholipase A(2) activity and activation of protein kinase A. J Biomed Mater Res. 1999 Nov;47(2):139-51. [PubMed:10449625 ]
Schwartz Z, Sylvia VL, Del Toro F, Hardin RR, Dean DD, Boyan BD: 24R,25-(OH)(2)D(3) mediates its membrane receptor-dependent effects on protein kinase C and alkaline phosphatase via phospholipase A(2) and cyclooxygenase-1 but not cyclooxygenase-2 in growth plate chondrocytes. J Cell Physiol. 2000 Mar;182(3):390-401. [PubMed:10653606 ]
Sylvia VL, Del Toro F, Dean DD, Hardin RR, Schwartz Z, Boyan BD: Effects of 1alpha,25-(OH)(2)D(3) on rat growth zone chondrocytes are mediated via cyclooxygenase-1 and phospholipase A(2). J Cell Biochem Suppl. 2001;Suppl 36:32-45. [PubMed:11455568 ]

Enzyme Details

3. Histamine N-methyltransferase

General function:: Involved in histamine N-methyltransferase activity
Specific function:: Inactivates histamine by N-methylation. Plays an important role in degrading histamine and in regulating the airway response to histamine.
Gene Name:: HNMT
Uniprot ID:: P50135
Molecular weight:: 6045.9

References

Grassmann S, Apelt J, Sippl W, Ligneau X, Pertz HH, Zhao YH, Arrang JM, Ganellin CR, Schwartz JC, Schunack W, Stark H: Imidazole derivatives as a novel class of hybrid compounds with inhibitory histamine N-methyltransferase potencies and histamine hH3 receptor affinities. Bioorg Med Chem. 2003 May 15;11(10):2163-74. [PubMed:12713826 ]
Hui JY, Taylor SL: Inhibition of in vivo histamine metabolism in rats by foodborne and pharmacologic inhibitors of diamine oxidase, histamine N-methyltransferase, and monoamine oxidase. Toxicol Appl Pharmacol. 1985 Nov;81(2):241-9. [PubMed:3933141 ]

Enzyme Details

4. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

5. Cytochrome P450 3A5

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A5
Uniprot ID:: P20815
Molecular weight:: 57108.065

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Enzyme Details

1. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Tiberghien F, Loor F: Ranking of P-glycoprotein substrates and inhibitors by a calcein-AM fluorometry screening assay. Anticancer Drugs. 1996 Jul;7(5):568-78. [PubMed:8862725 ]

Enzyme Details

2. Solute carrier family 22 member 2

General function:: Involved in ion transmembrane transporter activity
Specific function:: Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, cisplatin and oxaliplatin. Cisplatin may develop a nephrotoxic action. Transport of creatinine is inhibited by fluoroquinolones such as DX-619 and LVFX. This transporter is a major determinant of the anticancer activity of oxaliplatin and may contribute to antitumor specificity
Gene Name:: SLC22A2
Uniprot ID:: O15244
Molecular weight:: 62564.0

References

Sweet DH, Pritchard JB: rOCT2 is a basolateral potential-driven carrier, not an organic cation/proton exchanger. Am J Physiol. 1999 Dec;277(6 Pt 2):F890-8. [PubMed:10600936 ]
Dohgu S, Yamauchi A, Takata F, Sawada Y, Higuchi S, Naito M, Tsuruo T, Shirabe S, Niwa M, Katamine S, Kataoka Y: Uptake and efflux of quinacrine, a candidate for the treatment of prion diseases, at the blood-brain barrier. Cell Mol Neurobiol. 2004 Apr;24(2):205-17. [PubMed:15176436 ]
Beck WT, Cirtain MC, Glover CJ, Felsted RL, Safa AR: Effects of indole alkaloids on multidrug resistance and labeling of P-glycoprotein by a photoaffinity analog of vinblastine. Biochem Biophys Res Commun. 1988 Jun 30;153(3):959-66. [PubMed:2898941 ]

Showing metabocard for Quinacrine (HMDB0015235)

MOL for HMDB0015235 (Quinacrine)

3D MOL for HMDB0015235 (Quinacrine)

3D SDF for HMDB0015235 (Quinacrine)

3D-SDF for HMDB0015235 (Quinacrine)

PDB for HMDB0015235 (Quinacrine)

3D PDB for HMDB0015235 (Quinacrine)

SMILES for HMDB0015235 (Quinacrine)

INCHI for HMDB0015235 (Quinacrine)

Structure for HMDB0015235 (Quinacrine)

3D Structure for HMDB0015235 (Quinacrine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

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References

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References

Transporters

References

References