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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 10:11:55 UTC

Update Date

2021-09-26 23:04:49 UTC

HMDB ID

HMDB0252319

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Floxacrine

Description

Floxacrine, also known as HOE 991, belongs to the class of organic compounds known as phenylquinolines. These are heterocyclic compounds containing a quinoline moiety substituted with a phenyl group. Based on a literature review a small amount of articles have been published on Floxacrine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Floxacrine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Floxacrine 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

  Mrv1652309112112122D          

 28 31  0  0  0  0            999 V2000
    3.5724    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
    4.2868    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 O   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
    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 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    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
    2.1434   -1.2375    0.0000 O   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
    0.0000   -0.0000    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
    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 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   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
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    2.8875    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.5572    1.7605    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.7322    3.1895    0.0000 F   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  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  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
  6 11  1  0  0  0  0
 11 12  2  0  0  0  0
 10 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
  9 16  1  0  0  0  0
 14 17  1  0  0  0  0
  8 18  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
M  END

HMDB0252319
     RDKit          3D
Floxacrine
 41 44  0  0  0  0  0  0  0  0999 V2000
   -0.8891   -2.0901    2.8232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6303   -1.1805    1.9899 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7208   -0.6115    1.8037 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0511   -0.6958    0.3193 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4828   -0.4052    0.0972 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0067    0.6822    0.7726 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3359    1.0578    0.6923 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1712    0.2950   -0.1119 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6142    0.6103   -0.2335 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9636    1.6837    0.5776 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.0074    0.8930   -1.5247 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.2947   -0.5110    0.2434 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.6673   -0.7880   -0.7907 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3161   -1.1471   -0.6907 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1116    0.1444   -0.4728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888   -0.0210   -0.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6874   -0.6268    1.1400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0199   -0.7193    1.4894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3027   -1.2820    2.5590 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0184   -0.2034    0.6796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3554   -0.2809    1.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3364    0.2459    0.1941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0330    0.1722    0.5909 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.9149    0.8489   -0.9702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5739    0.9245   -1.3011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5861    0.3987   -0.4821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2716    0.4862   -0.8202 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0086    1.1135   -2.0199 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6377    0.4852    2.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5056   -1.0832    2.4141 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8613   -1.7605   -0.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3890    1.3045    1.3995 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7708    1.8910    1.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3002   -1.3847   -1.4178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9151   -1.9963   -1.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4028    1.2218   -0.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2013   -0.2201   -1.5472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6384   -0.7581    1.9296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6385    1.2914   -1.6613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2795    1.3919   -2.2198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2546    0.6234   -2.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  9 12  1  0
  8 13  1  0
 13 14  2  0
  4 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 17  2  1  0
 26 20  1  0
 14  5  1  0
 27 16  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  6 32  1  0
  7 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 21 38  1  0
 24 39  1  0
 25 40  1  0
 28 41  1  0
M  END

  Mrv1652309112112122D          

 28 31  0  0  0  0            999 V2000
    3.5724    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
    4.2868    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 O   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
    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 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    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
    2.1434   -1.2375    0.0000 O   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
    0.0000   -0.0000    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
    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 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   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
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    2.8875    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.5572    1.7605    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.7322    3.1895    0.0000 F   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  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  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
  6 11  1  0  0  0  0
 11 12  2  0  0  0  0
 10 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
  9 16  1  0  0  0  0
 14 17  1  0  0  0  0
  8 18  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0252319

> <DATABASE_NAME>
hmdb

> <SMILES>
ON1C2=C(C(=O)CC(C2)C2=CC=C(C=C2)C(F)(F)F)C(=O)C2=C1C=CC(Cl)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C20H13ClF3NO3/c21-13-5-6-15-14(9-13)19(27)18-16(25(15)28)7-11(8-17(18)26)10-1-3-12(4-2-10)20(22,23)24/h1-6,9,11,28H,7-8H2

> <INCHI_KEY>
AWHZKKVSUJJVNL-UHFFFAOYSA-N

> <FORMULA>
C20H13ClF3NO3

> <MOLECULAR_WEIGHT>
407.77

> <EXACT_MASS>
407.0536055

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
37.7816205489933

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-chloro-10-hydroxy-3-[4-(trifluoromethyl)phenyl]-1,2,3,4,9,10-hexahydroacridine-1,9-dione

> <ALOGPS_LOGP>
3.99

> <JCHEM_LOGP>
4.895425779666666

> <ALOGPS_LOGS>
-4.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.488046000461125

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.957405544189399

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2548220013837668

> <JCHEM_POLAR_SURFACE_AREA>
57.61

> <JCHEM_REFRACTIVITY>
109.23170000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.33e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
floxacrine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0252319
     RDKit          3D
Floxacrine
 41 44  0  0  0  0  0  0  0  0999 V2000
   -0.8891   -2.0901    2.8232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6303   -1.1805    1.9899 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7208   -0.6115    1.8037 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0511   -0.6958    0.3193 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4828   -0.4052    0.0972 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0067    0.6822    0.7726 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3359    1.0578    0.6923 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1712    0.2950   -0.1119 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6142    0.6103   -0.2335 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9636    1.6837    0.5776 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.0074    0.8930   -1.5247 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.2947   -0.5110    0.2434 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.6673   -0.7880   -0.7907 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3161   -1.1471   -0.6907 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1116    0.1444   -0.4728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888   -0.0210   -0.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6874   -0.6268    1.1400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0199   -0.7193    1.4894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3027   -1.2820    2.5590 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0184   -0.2034    0.6796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3554   -0.2809    1.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3364    0.2459    0.1941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0330    0.1722    0.5909 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.9149    0.8489   -0.9702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5739    0.9245   -1.3011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5861    0.3987   -0.4821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2716    0.4862   -0.8202 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0086    1.1135   -2.0199 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6377    0.4852    2.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5056   -1.0832    2.4141 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8613   -1.7605   -0.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3890    1.3045    1.3995 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7708    1.8910    1.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3002   -1.3847   -1.4178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9151   -1.9963   -1.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4028    1.2218   -0.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2013   -0.2201   -1.5472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6384   -0.7581    1.9296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6385    1.2914   -1.6613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2795    1.3919   -2.2198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2546    0.6234   -2.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  9 12  1  0
  8 13  1  0
 13 14  2  0
  4 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 17  2  1  0
 26 20  1  0
 14  5  1  0
 27 16  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  6 32  1  0
  7 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 21 38  1  0
 24 39  1  0
 25 40  1  0
 28 41  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       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       4.001   2.310   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17 Cl   UNK     0      -1.334  -0.770   0.000  0.00  0.00          Cl+0
HETATM   18  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM   26  F   UNK     0      14.670   5.390   0.000  0.00  0.00           F+0
HETATM   27  F   UNK     0      14.107   3.286   0.000  0.00  0.00           F+0
HETATM   28  F   UNK     0      12.567   5.954   0.000  0.00  0.00           F+0
CONECT    1    2    7                                                       
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   11                                                  
CONECT    7    6    1    8                                                  
CONECT    8    7    9   18                                                  
CONECT    9    8   10   16                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10    6   12                                                  
CONECT   12   11                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15    9                                                       
CONECT   17   14                                                            
CONECT   18    8                                                            
CONECT   19    2   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23   19                                                       
CONECT   25   22   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

COMPND    HMDB0252319
HETATM    1  O1  UNL     1      -0.889  -2.090   2.823  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.630  -1.180   1.990  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.721  -0.612   1.804  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.051  -0.696   0.319  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.483  -0.405   0.097  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.007   0.682   0.773  1.00  0.00           C  
HETATM    7  C6  UNL     1       4.336   1.058   0.692  1.00  0.00           C  
HETATM    8  C7  UNL     1       5.171   0.295  -0.112  1.00  0.00           C  
HETATM    9  C8  UNL     1       6.614   0.610  -0.234  1.00  0.00           C  
HETATM   10  F1  UNL     1       6.964   1.684   0.578  1.00  0.00           F  
HETATM   11  F2  UNL     1       7.007   0.893  -1.525  1.00  0.00           F  
HETATM   12  F3  UNL     1       7.295  -0.511   0.243  1.00  0.00           F  
HETATM   13  C9  UNL     1       4.667  -0.788  -0.791  1.00  0.00           C  
HETATM   14  C10 UNL     1       3.316  -1.147  -0.691  1.00  0.00           C  
HETATM   15  C11 UNL     1       0.112   0.144  -0.473  1.00  0.00           C  
HETATM   16  C12 UNL     1      -1.289  -0.021  -0.023  1.00  0.00           C  
HETATM   17  C13 UNL     1      -1.687  -0.627   1.140  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.020  -0.719   1.489  1.00  0.00           C  
HETATM   19  O2  UNL     1      -3.303  -1.282   2.559  1.00  0.00           O  
HETATM   20  C15 UNL     1      -4.018  -0.203   0.680  1.00  0.00           C  
HETATM   21  C16 UNL     1      -5.355  -0.281   1.015  1.00  0.00           C  
HETATM   22  C17 UNL     1      -6.336   0.246   0.194  1.00  0.00           C  
HETATM   23 CL1  UNL     1      -8.033   0.172   0.591  1.00  0.00          CL  
HETATM   24  C18 UNL     1      -5.915   0.849  -0.970  1.00  0.00           C  
HETATM   25  C19 UNL     1      -4.574   0.925  -1.301  1.00  0.00           C  
HETATM   26  C20 UNL     1      -3.586   0.399  -0.482  1.00  0.00           C  
HETATM   27  N1  UNL     1      -2.272   0.486  -0.820  1.00  0.00           N  
HETATM   28  O3  UNL     1      -2.009   1.114  -2.020  1.00  0.00           O  
HETATM   29  H1  UNL     1       0.638   0.485   2.032  1.00  0.00           H  
HETATM   30  H2  UNL     1       1.506  -1.083   2.414  1.00  0.00           H  
HETATM   31  H3  UNL     1       0.861  -1.761  -0.008  1.00  0.00           H  
HETATM   32  H4  UNL     1       2.389   1.304   1.400  1.00  0.00           H  
HETATM   33  H5  UNL     1       4.771   1.891   1.210  1.00  0.00           H  
HETATM   34  H6  UNL     1       5.300  -1.385  -1.418  1.00  0.00           H  
HETATM   35  H7  UNL     1       2.915  -1.996  -1.222  1.00  0.00           H  
HETATM   36  H8  UNL     1       0.403   1.222  -0.423  1.00  0.00           H  
HETATM   37  H9  UNL     1       0.201  -0.220  -1.547  1.00  0.00           H  
HETATM   38  H10 UNL     1      -5.638  -0.758   1.930  1.00  0.00           H  
HETATM   39  H11 UNL     1      -6.638   1.291  -1.661  1.00  0.00           H  
HETATM   40  H12 UNL     1      -4.280   1.392  -2.220  1.00  0.00           H  
HETATM   41  H13 UNL     1      -2.255   0.623  -2.890  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   17
CONECT    3    4   29   30
CONECT    4    5   15   31
CONECT    5    6    6   14
CONECT    6    7   32
CONECT    7    8    8   33
CONECT    8    9   13
CONECT    9   10   11   12
CONECT   13   14   14   34
CONECT   14   35
CONECT   15   16   36   37
CONECT   16   17   17   27
CONECT   17   18
CONECT   18   19   19   20
CONECT   20   21   21   26
CONECT   21   22   38
CONECT   22   23   24   24
CONECT   24   25   39
CONECT   25   26   26   40
CONECT   26   27
CONECT   27   28
CONECT   28   41
END

HMDB0252319
     RDKit          3D
Floxacrine
 41 44  0  0  0  0  0  0  0  0999 V2000
   -0.8891   -2.0901    2.8232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6303   -1.1805    1.9899 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7208   -0.6115    1.8037 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0511   -0.6958    0.3193 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4828   -0.4052    0.0972 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0067    0.6822    0.7726 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3359    1.0578    0.6923 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1712    0.2950   -0.1119 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6142    0.6103   -0.2335 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9636    1.6837    0.5776 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.0074    0.8930   -1.5247 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.2947   -0.5110    0.2434 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.6673   -0.7880   -0.7907 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3161   -1.1471   -0.6907 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1116    0.1444   -0.4728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888   -0.0210   -0.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6874   -0.6268    1.1400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0199   -0.7193    1.4894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3027   -1.2820    2.5590 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0184   -0.2034    0.6796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3554   -0.2809    1.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3364    0.2459    0.1941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0330    0.1722    0.5909 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.9149    0.8489   -0.9702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5739    0.9245   -1.3011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5861    0.3987   -0.4821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2716    0.4862   -0.8202 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0086    1.1135   -2.0199 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6377    0.4852    2.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5056   -1.0832    2.4141 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8613   -1.7605   -0.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3890    1.3045    1.3995 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7708    1.8910    1.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3002   -1.3847   -1.4178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9151   -1.9963   -1.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4028    1.2218   -0.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2013   -0.2201   -1.5472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6384   -0.7581    1.9296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6385    1.2914   -1.6613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2795    1.3919   -2.2198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2546    0.6234   -2.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  9 12  1  0
  8 13  1  0
 13 14  2  0
  4 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 17  2  1  0
 26 20  1  0
 14  5  1  0
 27 16  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  6 32  1  0
  7 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 21 38  1  0
 24 39  1  0
 25 40  1  0
 28 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7-Chloro-10-hydroxy-3-(4-trifluoromethylphenyl)-3,4-dihydroacridine-1,9(2H,10H)-dione	HMDB
HOE 991	HMDB

Chemical Formula

C₂₀H₁₃ClF₃NO₃

Average Molecular Weight

407.77

Monoisotopic Molecular Weight

407.0536055

IUPAC Name

7-chloro-10-hydroxy-3-[4-(trifluoromethyl)phenyl]-1,2,3,4,9,10-hexahydroacridine-1,9-dione

Traditional Name

floxacrine

CAS Registry Number

Not Available

SMILES

ON1C2=C(C(=O)CC(C2)C2=CC=C(C=C2)C(F)(F)F)C(=O)C2=C1C=CC(Cl)=C2

InChI Identifier

InChI=1S/C20H13ClF3NO3/c21-13-5-6-15-14(9-13)19(27)18-16(25(15)28)7-11(8-17(18)26)10-1-3-12(4-2-10)20(22,23)24/h1-6,9,11,28H,7-8H2

InChI Key

AWHZKKVSUJJVNL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylquinolines. These are heterocyclic compounds containing a quinoline moiety substituted with a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Phenylquinolines

Direct Parent

Phenylquinolines

Alternative Parents

Substituents

Phenylquinoline
Acridine
Benzoquinoline
Dihydroquinolone
Haloquinoline
Chloroquinoline
Dihydroquinoline
Trifluoromethylbenzene
Aryl ketone
Aryl alkyl ketone
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Pyridine
Benzenoid
Vinylogous amide
Heteroaromatic compound
Ketone
Azacycle
Alkyl fluoride
Organochloride
Organohalogen compound
Organofluoride
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Alkyl halide
Organonitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.99	ALOGPS
logP	4.9	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	13.96	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	57.61 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	109.23 m³·mol⁻¹	ChemAxon
Polarizability	37.78 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]+	189.825	30932474
DeepCCS	[M-H]-	187.467	30932474
DeepCCS	[M-2H]-	221.124	30932474
DeepCCS	[M+Na]+	196.352	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Floxacrine	ON1C2=C(C(=O)CC(C2)C2=CC=C(C=C2)C(F)(F)F)C(=O)C2=C1C=CC(Cl)=C2	3761.0	Standard polar	33892256
Floxacrine	ON1C2=C(C(=O)CC(C2)C2=CC=C(C=C2)C(F)(F)F)C(=O)C2=C1C=CC(Cl)=C2	2941.6	Standard non polar	33892256
Floxacrine	ON1C2=C(C(=O)CC(C2)C2=CC=C(C=C2)C(F)(F)F)C(=O)C2=C1C=CC(Cl)=C2	3185.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Floxacrine GC-MS (Non-derivatized) - 70eV, Positive	splash10-059i-0968000000-54e898141d2663114772	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Floxacrine 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Floxacrine 10V, Positive-QTOF	splash10-0a4i-0000900000-35a3fe464ffd2ab340df	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Floxacrine 20V, Positive-QTOF	splash10-0a4i-0000900000-88b3c299518b13fd358b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Floxacrine 40V, Positive-QTOF	splash10-000i-0569100000-5f0122c0a1b44d8681ed	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Floxacrine 10V, Negative-QTOF	splash10-0a4i-0000900000-0c13855130ba04e42fe8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Floxacrine 20V, Negative-QTOF	splash10-0a59-4000900000-c38908b0e72439d9fef9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Floxacrine 40V, Negative-QTOF	splash10-001i-9268400000-b7c64818a6085f31adc1	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

61959

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

68708

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 Floxacrine (HMDB0252319)

MOL for HMDB0252319 (Floxacrine)

3D MOL for HMDB0252319 (Floxacrine)

3D SDF for HMDB0252319 (Floxacrine)

3D-SDF for HMDB0252319 (Floxacrine)

PDB for HMDB0252319 (Floxacrine)

3D PDB for HMDB0252319 (Floxacrine)

SMILES for HMDB0252319 (Floxacrine)

INCHI for HMDB0252319 (Floxacrine)

Structure for HMDB0252319 (Floxacrine)

3D Structure for HMDB0252319 (Floxacrine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra