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

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:57 UTC

HMDB ID

HMDB0015349

Secondary Accession Numbers

HMDB15349

Metabolite Identification

Common Name

Halofantrine

Description

Halofantrine is a drug used to treat malaria. It belongs to the phenanthrene class of compounds that includes quinine and lumefantrine. It appears to inhibit polymerisation of heme molecules (by the parasite enzyme 'heme polymerase'), resulting in the parasite being poisoned by its own waste. Halofantrine has been shown to preferentially block open and inactivated HERG channels leading to some degree of cardiotoxicity.

Structure

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

1218
  Mrv0541 02231215202D          

 33 35  0  0  1  0            999 V2000
    7.4502    1.8251    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.9997    4.3598    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.7781    2.9730    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.9477    1.5472    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.6754    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.5608   -0.6473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7043   -1.8848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9897   -1.4723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9897   -0.6473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2753   -0.2348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7043   -2.7098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4187   -1.4723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2753    0.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4187   -3.1223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1332   -1.8848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5608    1.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5608    1.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9897    1.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2753    2.2402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9897    1.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4187   -3.9473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8476   -1.4723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8233    0.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8233    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0758    1.8449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2621    3.0995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0758    0.9856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7405    2.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1332   -4.3598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5622   -1.8848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0029    3.5348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7472    3.1052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3629    2.2601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 28  1  0  0  0  0
  2 31  1  0  0  0  0
  3 33  1  0  0  0  0
  4 33  1  0  0  0  0
  5 33  1  0  0  0  0
  6 10  1  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 13  1  0  0  0  0
 11 14  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  2  0  0  0  0
 13 18  1  0  0  0  0
 14 21  1  0  0  0  0
 15 22  1  0  0  0  0
 16 17  1  0  0  0  0
 16 23  1  0  0  0  0
 17 19  2  0  0  0  0
 17 24  1  0  0  0  0
 18 20  2  0  0  0  0
 19 20  1  0  0  0  0
 19 26  1  0  0  0  0
 20 28  1  0  0  0  0
 21 29  1  0  0  0  0
 22 30  1  0  0  0  0
 23 27  2  0  0  0  0
 24 25  2  0  0  0  0
 25 27  1  0  0  0  0
 25 33  1  0  0  0  0
 26 31  2  0  0  0  0
 28 32  2  0  0  0  0
 31 32  1  0  0  0  0
M  END

HMDB0253039
     RDKit          3D
Halofantrina
 63 65  0  0  0  0  0  0  0  0999 V2000
   -5.2672   -4.4310    0.2477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0428   -3.6144    0.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2913   -2.1401   -0.2383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9773   -1.4486   -0.2734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9520   -0.0459   -0.4572 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4194    0.6252    0.7014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3747    2.0778    0.8403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1568    2.9543   -0.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6566    2.7264    0.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7844    0.4420   -1.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5312    0.1581   -0.2608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6692    0.7840   -0.9242 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7451    0.2474   -2.2165 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9429    0.3346   -0.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9821   -0.7235    0.5418 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2163   -1.1659    1.0715 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2546   -2.2644    1.9128 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7679   -3.0984    2.3204 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.4370   -2.7379    2.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6116   -2.0855    2.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0962   -2.6899    2.8257 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.6104   -0.9703    1.2835 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4092   -0.5305    0.7668 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3207    0.5648   -0.0976 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4703    1.2487   -0.4165 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4570    2.3552   -1.2511 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7106    3.0622   -1.5800 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4238    2.2242   -2.4147 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.5372    4.3271   -2.0366 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.5005    3.0960   -0.4014 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.2484    2.7476   -1.7470 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0448    2.1091   -1.4704 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1283    1.0053   -0.6259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0106   -5.3871    0.7685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0086   -3.8495    0.8664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6589   -4.6073   -0.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2186   -4.0181   -0.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5682   -3.4799    1.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0741   -1.7283    0.3668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7038   -2.2965   -1.2948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3442   -1.9720   -1.0590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4240   -1.7275    0.6845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9718    0.1469    1.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5202    0.3091    0.7914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7049    2.3046    1.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2856    2.4566    0.8942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0326    4.0159    0.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8781    2.9390   -1.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1952    3.7062   -0.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9110    2.4462    1.0863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0553    2.0016   -0.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7798    1.4754   -1.3576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6248   -0.1672   -2.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4373   -0.9349   -0.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6266    0.6462    0.7203 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5232    1.8613   -0.8746 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5832   -0.7467   -2.0986 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1614   -1.2997    0.8635 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3830   -3.6134    3.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5488   -0.5439    1.0850 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4173    0.9111   -0.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2005    3.6077   -2.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0862    2.4007   -1.8772 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
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  5 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
 26 31  2  0
 31 32  1  0
 32 33  2  0
 33 14  1  0
 23 16  1  0
 33 24  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
  2 38  1  0
  3 39  1  0
  3 40  1  0
  4 41  1  0
  4 42  1  0
  6 43  1  0
  6 44  1  0
  7 45  1  0
  7 46  1  0
  8 47  1  0
  8 48  1  0
  9 49  1  0
  9 50  1  0
  9 51  1  0
 10 52  1  0
 10 53  1  0
 11 54  1  0
 11 55  1  0
 12 56  1  0
 13 57  1  0
 15 58  1  0
 19 59  1  0
 22 60  1  0
 25 61  1  0
 31 62  1  0
 32 63  1  0
M  END

1218
  Mrv0541 02231215202D          

 33 35  0  0  1  0            999 V2000
    7.4502    1.8251    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.9997    4.3598    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.7781    2.9730    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.9477    1.5472    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.6754    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.5608   -0.6473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7043   -1.8848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9897   -1.4723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9897   -0.6473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2753   -0.2348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7043   -2.7098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4187   -1.4723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2753    0.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4187   -3.1223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1332   -1.8848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5608    1.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5608    1.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9897    1.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2753    2.2402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9897    1.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4187   -3.9473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8476   -1.4723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8233    0.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8233    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0758    1.8449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2621    3.0995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0758    0.9856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7405    2.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1332   -4.3598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5622   -1.8848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0029    3.5348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7472    3.1052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3629    2.2601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 28  1  0  0  0  0
  2 31  1  0  0  0  0
  3 33  1  0  0  0  0
  4 33  1  0  0  0  0
  5 33  1  0  0  0  0
  6 10  1  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 13  1  0  0  0  0
 11 14  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  2  0  0  0  0
 13 18  1  0  0  0  0
 14 21  1  0  0  0  0
 15 22  1  0  0  0  0
 16 17  1  0  0  0  0
 16 23  1  0  0  0  0
 17 19  2  0  0  0  0
 17 24  1  0  0  0  0
 18 20  2  0  0  0  0
 19 20  1  0  0  0  0
 19 26  1  0  0  0  0
 20 28  1  0  0  0  0
 21 29  1  0  0  0  0
 22 30  1  0  0  0  0
 23 27  2  0  0  0  0
 24 25  2  0  0  0  0
 25 27  1  0  0  0  0
 25 33  1  0  0  0  0
 26 31  2  0  0  0  0
 28 32  2  0  0  0  0
 31 32  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015349

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCN(CCCC)CCC(O)C1=C2C=CC(=CC2=C2C=C(Cl)C=C(Cl)C2=C1)C(F)(F)F

> <INCHI_IDENTIFIER>
InChI=1S/C26H30Cl2F3NO/c1-3-5-10-32(11-6-4-2)12-9-25(33)23-16-22-21(14-18(27)15-24(22)28)20-13-17(26(29,30)31)7-8-19(20)23/h7-8,13-16,25,33H,3-6,9-12H2,1-2H3

> <INCHI_KEY>
FOHHNHSLJDZUGQ-UHFFFAOYSA-N

> <FORMULA>
C26H30Cl2F3NO

> <MOLECULAR_WEIGHT>
500.424

> <EXACT_MASS>
499.165654616

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
51.53248165383641

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(dibutylamino)-1-[1,3-dichloro-6-(trifluoromethyl)phenanthren-9-yl]propan-1-ol

> <ALOGPS_LOGP>
7.34

> <JCHEM_LOGP>
8.056956757

> <ALOGPS_LOGS>
-6.66

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.470627226532233

> <JCHEM_PKA_STRONGEST_BASIC>
10.052483453652846

> <JCHEM_POLAR_SURFACE_AREA>
23.47

> <JCHEM_REFRACTIVITY>
131.6595

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.11e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
halofantrine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0253039
     RDKit          3D
Halofantrina
 63 65  0  0  0  0  0  0  0  0999 V2000
   -5.2672   -4.4310    0.2477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0428   -3.6144    0.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2913   -2.1401   -0.2383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9773   -1.4486   -0.2734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9520   -0.0459   -0.4572 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4194    0.6252    0.7014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3747    2.0778    0.8403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1568    2.9543   -0.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6566    2.7264    0.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7844    0.4420   -1.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5312    0.1581   -0.2608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6692    0.7840   -0.9242 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7451    0.2474   -2.2165 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9429    0.3346   -0.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9821   -0.7235    0.5418 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2163   -1.1659    1.0715 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2546   -2.2644    1.9128 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7679   -3.0984    2.3204 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.4370   -2.7379    2.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6116   -2.0855    2.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0962   -2.6899    2.8257 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.6104   -0.9703    1.2835 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4092   -0.5305    0.7668 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3207    0.5648   -0.0976 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4703    1.2487   -0.4165 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4570    2.3552   -1.2511 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7106    3.0622   -1.5800 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4238    2.2242   -2.4147 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.5372    4.3271   -2.0366 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.5005    3.0960   -0.4014 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.2484    2.7476   -1.7470 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0448    2.1091   -1.4704 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1283    1.0053   -0.6259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0106   -5.3871    0.7685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0086   -3.8495    0.8664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6589   -4.6073   -0.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2186   -4.0181   -0.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5682   -3.4799    1.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0741   -1.7283    0.3668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7038   -2.2965   -1.2948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3442   -1.9720   -1.0590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4240   -1.7275    0.6845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9718    0.1469    1.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5202    0.3091    0.7914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7049    2.3046    1.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2856    2.4566    0.8942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0326    4.0159    0.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8781    2.9390   -1.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1952    3.7062   -0.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9110    2.4462    1.0863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0553    2.0016   -0.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7798    1.4754   -1.3576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6248   -0.1672   -2.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4373   -0.9349   -0.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6266    0.6462    0.7203 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5232    1.8613   -0.8746 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5832   -0.7467   -2.0986 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1614   -1.2997    0.8635 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3830   -3.6134    3.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5488   -0.5439    1.0850 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4173    0.9111   -0.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2005    3.6077   -2.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0862    2.4007   -1.8772 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
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  5 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
 26 31  2  0
 31 32  1  0
 32 33  2  0
 33 14  1  0
 23 16  1  0
 33 24  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
  2 38  1  0
  3 39  1  0
  3 40  1  0
  4 41  1  0
  4 42  1  0
  6 43  1  0
  6 44  1  0
  7 45  1  0
  7 46  1  0
  8 47  1  0
  8 48  1  0
  9 49  1  0
  9 50  1  0
  9 51  1  0
 10 52  1  0
 10 53  1  0
 11 54  1  0
 11 55  1  0
 12 56  1  0
 13 57  1  0
 15 58  1  0
 19 59  1  0
 22 60  1  0
 25 61  1  0
 31 62  1  0
 32 63  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1218                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0      13.907   3.407   0.000  0.00  0.00          Cl+0
HETATM    2 Cl   UNK     0      11.199   8.138   0.000  0.00  0.00          Cl+0
HETATM    3  F   UNK     0       5.186   5.550   0.000  0.00  0.00           F+0
HETATM    4  F   UNK     0       3.636   2.888   0.000  0.00  0.00           F+0
HETATM    5  F   UNK     0       3.080   4.994   0.000  0.00  0.00           F+0
HETATM    6  O   UNK     0       8.513  -1.208   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0      12.515  -3.518   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      11.181  -2.748   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.181  -1.208   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.847  -0.438   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.515  -5.058   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.848  -2.748   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.847   1.102   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.848  -5.828   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.182  -3.518   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.513   1.872   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.513   3.412   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.181   1.872   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.847   4.182   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.181   3.412   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.848  -7.368   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.516  -2.748   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.137   1.048   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.137   4.235   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.741   3.444   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.823   5.786   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.741   1.840   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.582   4.192   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      15.182  -8.138   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      17.849  -3.518   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.205   6.598   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.595   5.796   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.411   4.219   0.000  0.00  0.00           C+0
CONECT    1   28                                                            
CONECT    2   31                                                            
CONECT    3   33                                                            
CONECT    4   33                                                            
CONECT    5   33                                                            
CONECT    6   10                                                            
CONECT    7    8   11   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    6    9   13                                                  
CONECT   11    7   14                                                       
CONECT   12    7   15                                                       
CONECT   13   10   16   18                                                  
CONECT   14   11   21                                                       
CONECT   15   12   22                                                       
CONECT   16   13   17   23                                                  
CONECT   17   16   19   24                                                  
CONECT   18   13   20                                                       
CONECT   19   17   20   26                                                  
CONECT   20   18   19   28                                                  
CONECT   21   14   29                                                       
CONECT   22   15   30                                                       
CONECT   23   16   27                                                       
CONECT   24   17   25                                                       
CONECT   25   24   27   33                                                  
CONECT   26   19   31                                                       
CONECT   27   23   25                                                       
CONECT   28    1   20   32                                                  
CONECT   29   21                                                            
CONECT   30   22                                                            
CONECT   31    2   26   32                                                  
CONECT   32   28   31                                                       
CONECT   33    3    4    5   25                                             
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

COMPND    HMDB0253039
HETATM    1  C1  UNL     1      -5.267  -4.431   0.248  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.043  -3.614   0.177  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.291  -2.140  -0.238  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.977  -1.449  -0.273  1.00  0.00           C  
HETATM    5  N1  UNL     1      -2.952  -0.046  -0.457  1.00  0.00           N  
HETATM    6  C5  UNL     1      -3.419   0.625   0.701  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.375   2.078   0.840  1.00  0.00           C  
HETATM    8  C7  UNL     1      -4.157   2.954  -0.046  1.00  0.00           C  
HETATM    9  C8  UNL     1      -5.657   2.726   0.042  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.784   0.442  -1.095  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.531   0.158  -0.261  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.669   0.784  -0.924  1.00  0.00           C  
HETATM   13  O1  UNL     1       0.745   0.247  -2.216  1.00  0.00           O  
HETATM   14  C12 UNL     1       1.943   0.335  -0.290  1.00  0.00           C  
HETATM   15  C13 UNL     1       1.982  -0.723   0.542  1.00  0.00           C  
HETATM   16  C14 UNL     1       3.216  -1.166   1.071  1.00  0.00           C  
HETATM   17  C15 UNL     1       3.255  -2.264   1.913  1.00  0.00           C  
HETATM   18 CL1  UNL     1       1.768  -3.098   2.320  1.00  0.00          CL  
HETATM   19  C16 UNL     1       4.437  -2.738   2.452  1.00  0.00           C  
HETATM   20  C17 UNL     1       5.612  -2.086   2.133  1.00  0.00           C  
HETATM   21 CL2  UNL     1       7.096  -2.690   2.826  1.00  0.00          CL  
HETATM   22  C18 UNL     1       5.610  -0.970   1.284  1.00  0.00           C  
HETATM   23  C19 UNL     1       4.409  -0.530   0.767  1.00  0.00           C  
HETATM   24  C20 UNL     1       4.321   0.565  -0.098  1.00  0.00           C  
HETATM   25  C21 UNL     1       5.470   1.249  -0.416  1.00  0.00           C  
HETATM   26  C22 UNL     1       5.457   2.355  -1.251  1.00  0.00           C  
HETATM   27  C23 UNL     1       6.711   3.062  -1.580  1.00  0.00           C  
HETATM   28  F1  UNL     1       7.424   2.224  -2.415  1.00  0.00           F  
HETATM   29  F2  UNL     1       6.537   4.327  -2.037  1.00  0.00           F  
HETATM   30  F3  UNL     1       7.501   3.096  -0.401  1.00  0.00           F  
HETATM   31  C24 UNL     1       4.248   2.748  -1.747  1.00  0.00           C  
HETATM   32  C25 UNL     1       3.045   2.109  -1.470  1.00  0.00           C  
HETATM   33  C26 UNL     1       3.128   1.005  -0.626  1.00  0.00           C  
HETATM   34  H1  UNL     1      -5.011  -5.387   0.769  1.00  0.00           H  
HETATM   35  H2  UNL     1      -6.009  -3.849   0.866  1.00  0.00           H  
HETATM   36  H3  UNL     1      -5.659  -4.607  -0.773  1.00  0.00           H  
HETATM   37  H4  UNL     1      -3.219  -4.018  -0.420  1.00  0.00           H  
HETATM   38  H5  UNL     1      -3.568  -3.480   1.221  1.00  0.00           H  
HETATM   39  H6  UNL     1      -5.074  -1.728   0.367  1.00  0.00           H  
HETATM   40  H7  UNL     1      -4.704  -2.297  -1.295  1.00  0.00           H  
HETATM   41  H8  UNL     1      -2.344  -1.972  -1.059  1.00  0.00           H  
HETATM   42  H9  UNL     1      -2.424  -1.728   0.684  1.00  0.00           H  
HETATM   43  H10 UNL     1      -2.972   0.147   1.609  1.00  0.00           H  
HETATM   44  H11 UNL     1      -4.520   0.309   0.791  1.00  0.00           H  
HETATM   45  H12 UNL     1      -3.705   2.305   1.901  1.00  0.00           H  
HETATM   46  H13 UNL     1      -2.286   2.457   0.894  1.00  0.00           H  
HETATM   47  H14 UNL     1      -4.033   4.016   0.359  1.00  0.00           H  
HETATM   48  H15 UNL     1      -3.878   2.939  -1.100  1.00  0.00           H  
HETATM   49  H16 UNL     1      -6.195   3.706  -0.145  1.00  0.00           H  
HETATM   50  H17 UNL     1      -5.911   2.446   1.086  1.00  0.00           H  
HETATM   51  H18 UNL     1      -6.055   2.002  -0.672  1.00  0.00           H  
HETATM   52  H19 UNL     1      -1.780   1.475  -1.358  1.00  0.00           H  
HETATM   53  H20 UNL     1      -1.625  -0.167  -2.032  1.00  0.00           H  
HETATM   54  H21 UNL     1      -0.437  -0.935  -0.083  1.00  0.00           H  
HETATM   55  H22 UNL     1      -0.627   0.646   0.720  1.00  0.00           H  
HETATM   56  H23 UNL     1       0.523   1.861  -0.875  1.00  0.00           H  
HETATM   57  H24 UNL     1       0.583  -0.747  -2.099  1.00  0.00           H  
HETATM   58  H25 UNL     1       1.161  -1.300   0.864  1.00  0.00           H  
HETATM   59  H26 UNL     1       4.383  -3.613   3.093  1.00  0.00           H  
HETATM   60  H27 UNL     1       6.549  -0.544   1.085  1.00  0.00           H  
HETATM   61  H28 UNL     1       6.417   0.911  -0.015  1.00  0.00           H  
HETATM   62  H29 UNL     1       4.200   3.608  -2.422  1.00  0.00           H  
HETATM   63  H30 UNL     1       2.086   2.401  -1.877  1.00  0.00           H  
CONECT    1    2   34   35   36
CONECT    2    3   37   38
CONECT    3    4   39   40
CONECT    4    5   41   42
CONECT    5    6   10
CONECT    6    7   43   44
CONECT    7    8   45   46
CONECT    8    9   47   48
CONECT    9   49   50   51
CONECT   10   11   52   53
CONECT   11   12   54   55
CONECT   12   13   14   56
CONECT   13   57
CONECT   14   15   15   33
CONECT   15   16   58
CONECT   16   17   17   23
CONECT   17   18   19
CONECT   19   20   20   59
CONECT   20   21   22
CONECT   22   23   23   60
CONECT   23   24
CONECT   24   25   25   33
CONECT   25   26   61
CONECT   26   27   31   31
CONECT   27   28   29   30
CONECT   31   32   62
CONECT   32   33   33   63
END

HMDB0253039
     RDKit          3D
Halofantrina
 63 65  0  0  0  0  0  0  0  0999 V2000
   -5.2672   -4.4310    0.2477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0428   -3.6144    0.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2913   -2.1401   -0.2383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9773   -1.4486   -0.2734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9520   -0.0459   -0.4572 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4194    0.6252    0.7014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3747    2.0778    0.8403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1568    2.9543   -0.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6566    2.7264    0.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7844    0.4420   -1.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5312    0.1581   -0.2608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6692    0.7840   -0.9242 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7451    0.2474   -2.2165 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9429    0.3346   -0.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9821   -0.7235    0.5418 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2163   -1.1659    1.0715 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2546   -2.2644    1.9128 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7679   -3.0984    2.3204 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.4370   -2.7379    2.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6116   -2.0855    2.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0962   -2.6899    2.8257 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.6104   -0.9703    1.2835 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4092   -0.5305    0.7668 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3207    0.5648   -0.0976 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4703    1.2487   -0.4165 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4570    2.3552   -1.2511 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7106    3.0622   -1.5800 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4238    2.2242   -2.4147 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.5372    4.3271   -2.0366 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.5005    3.0960   -0.4014 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.2484    2.7476   -1.7470 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0448    2.1091   -1.4704 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1283    1.0053   -0.6259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0106   -5.3871    0.7685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0086   -3.8495    0.8664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6589   -4.6073   -0.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2186   -4.0181   -0.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5682   -3.4799    1.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0741   -1.7283    0.3668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7038   -2.2965   -1.2948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3442   -1.9720   -1.0590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4240   -1.7275    0.6845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9718    0.1469    1.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5202    0.3091    0.7914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7049    2.3046    1.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2856    2.4566    0.8942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0326    4.0159    0.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8781    2.9390   -1.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1952    3.7062   -0.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9110    2.4462    1.0863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0553    2.0016   -0.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7798    1.4754   -1.3576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6248   -0.1672   -2.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4373   -0.9349   -0.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6266    0.6462    0.7203 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5232    1.8613   -0.8746 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5832   -0.7467   -2.0986 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1614   -1.2997    0.8635 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3830   -3.6134    3.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5488   -0.5439    1.0850 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4173    0.9111   -0.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2005    3.6077   -2.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0862    2.4007   -1.8772 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
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  5 10  1  0
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  1 35  1  0
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 32 63  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Halofantrine hydrochloride	MeSH, HMDB
1-(1,3-dichloro-6-Trifluoromethyl-9-phenanthryl)-3-di(N-butyl)aminopropanol HCL	MeSH, HMDB
Halfan	MeSH, HMDB
Halofantrine	MeSH

Chemical Formula

C₂₆H₃₀Cl₂F₃NO

Average Molecular Weight

500.424

Monoisotopic Molecular Weight

499.165654616

IUPAC Name

3-(dibutylamino)-1-[1,3-dichloro-6-(trifluoromethyl)phenanthren-9-yl]propan-1-ol

Traditional Name

halofantrine

CAS Registry Number

69756-53-2

SMILES

CCCCN(CCCC)CCC(O)C1=C2C=CC(=CC2=C2C=C(Cl)C=C(Cl)C2=C1)C(F)(F)F

InChI Identifier

InChI=1S/C26H30Cl2F3NO/c1-3-5-10-32(11-6-4-2)12-9-25(33)23-16-22-21(14-18(27)15-24(22)28)20-13-17(26(29,30)31)7-8-19(20)23/h7-8,13-16,25,33H,3-6,9-12H2,1-2H3

InChI Key

FOHHNHSLJDZUGQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Not Available

Direct Parent

Phenanthrenes and derivatives

Alternative Parents

Substituents

Phenanthrene
Chloronaphthalene
Naphthalene
Aralkylamine
Aryl chloride
Aryl halide
1,3-aminoalcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Organic nitrogen compound
Aromatic alcohol
Organooxygen compound
Organonitrogen compound
Organofluoride
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Amine
Alkyl halide
Alkyl fluoride
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

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

Membrane (HMDB: HMDB0015349)

Source

Exogenous

Exogenous (HMDB: HMDB0015349)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.00011 g/L	Not Available
LogP	8.9	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00011 g/L	ALOGPS
logP	7.34	ALOGPS
logP	8.06	ChemAxon
logS	-6.7	ALOGPS
pKa (Strongest Acidic)	14.47	ChemAxon
pKa (Strongest Basic)	10.05	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	23.47 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	131.66 m³·mol⁻¹	ChemAxon
Polarizability	51.53 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	213.405	30932474
DeepCCS	[M-H]-	211.046	30932474
DeepCCS	[M-2H]-	244.346	30932474
DeepCCS	[M+Na]+	220.208	30932474
AllCCS	[M+H]+	213.0	32859911
AllCCS	[M+H-H2O]+	211.2	32859911
AllCCS	[M+NH4]+	214.5	32859911
AllCCS	[M+Na]+	215.0	32859911
AllCCS	[M-H]-	211.4	32859911
AllCCS	[M+Na-2H]-	212.5	32859911
AllCCS	[M+HCOO]-	213.8	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.	9.94 minutes	32390414
Predicted by Siyang on May 30, 2022	22.7487 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.14 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	38.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Halofantrine	CCCCN(CCCC)CCC(O)C1=C2C=CC(=CC2=C2C=C(Cl)C=C(Cl)C2=C1)C(F)(F)F	3762.2	Standard polar	33892256
Halofantrine	CCCCN(CCCC)CCC(O)C1=C2C=CC(=CC2=C2C=C(Cl)C=C(Cl)C2=C1)C(F)(F)F	3218.1	Standard non polar	33892256
Halofantrine	CCCCN(CCCC)CCC(O)C1=C2C=CC(=CC2=C2C=C(Cl)C=C(Cl)C2=C1)C(F)(F)F	3157.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Halofantrine,1TMS,isomer #1	CCCCN(CCCC)CCC(O[Si](C)(C)C)C1=CC2=C(Cl)C=C(Cl)C=C2C2=CC(C(F)(F)F)=CC=C12	3055.4	Semi standard non polar	33892256
Halofantrine,1TBDMS,isomer #1	CCCCN(CCCC)CCC(O[Si](C)(C)C(C)(C)C)C1=CC2=C(Cl)C=C(Cl)C=C2C2=CC(C(F)(F)F)=CC=C12	3276.2	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 - Halofantrine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-4908300000-fda0bab8f57ca3a07e80	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Halofantrine GC-MS (1 TMS) - 70eV, Positive	splash10-014i-6300920000-cec8c95eb66963cbe215	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Halofantrine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Halofantrine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Halofantrine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Halofantrine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	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 - Halofantrine 10V, Positive-QTOF	splash10-0f89-0001960000-6de4854d3e09f97f38e8	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Halofantrine 20V, Positive-QTOF	splash10-0k9x-5906620000-1bd03c8b89b4e08b59a8	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Halofantrine 40V, Positive-QTOF	splash10-0a4l-9214100000-762ef2ced883607d0dbb	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Halofantrine 10V, Negative-QTOF	splash10-0002-0000900000-be08a4af62726ab4a275	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Halofantrine 20V, Negative-QTOF	splash10-002b-0603900000-9b2c085d0f8792872f2e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Halofantrine 40V, Negative-QTOF	splash10-00b9-9703100000-e44bd620e4350dd3fb8a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Halofantrine 10V, Positive-QTOF	splash10-0udi-0101090000-d48d790575986c9cda2f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Halofantrine 20V, Positive-QTOF	splash10-0uk9-0107930000-d721c8f598515e938db7	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Halofantrine 40V, Positive-QTOF	splash10-0w2a-9608100000-51ab02c084d77ef25ac9	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Halofantrine 10V, Negative-QTOF	splash10-0002-0000900000-24430f93d0a912beb13b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Halofantrine 20V, Negative-QTOF	splash10-0002-0201900000-509c10191484c06e55aa	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Halofantrine 40V, Negative-QTOF	splash10-03fr-1209200000-92e844f4cbc22f33c349	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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 DB01218	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01218	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01218

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

34303

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Halofantrine

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. 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

2. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

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

3. 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 ]

Enzyme Details

4. Cytochrome P450 2C8

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. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:: CYP2C8
Uniprot ID:: P10632
Molecular weight:: 55824.275

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. Potassium voltage-gated channel subfamily H member 2

General function:: Involved in ion channel activity
Specific function:: Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel. Channel properties are modulated by cAMP and subunit assembly. Mediates the rapidly activating component of the delayed rectifying potassium current in heart (IKr). Isoform 3 has no channel activity by itself, but modulates channel characteristics when associated with isoform 1
Gene Name:: KCNH2
Uniprot ID:: Q12809
Molecular weight:: 126653.5

References

Tie H, Walker BD, Singleton CB, Valenzuela SM, Bursill JA, Wyse KR, Breit SN, Campbell TJ: Inhibition of HERG potassium channels by the antimalarial agent halofantrine. Br J Pharmacol. 2000 Aug;130(8):1967-75. [PubMed:10952689 ]
Mbai M, Rajamani S, January CT: The anti-malarial drug halofantrine and its metabolite N-desbutylhalofantrine block HERG potassium channels. Cardiovasc Res. 2002 Sep;55(4):799-805. [PubMed:12176129 ]

Showing metabocard for Halofantrine (HMDB0015349)

MOL for HMDB0015349 (Halofantrine)

3D MOL for HMDB0015349 (Halofantrine)

3D SDF for HMDB0015349 (Halofantrine)

3D-SDF for HMDB0015349 (Halofantrine)

PDB for HMDB0015349 (Halofantrine)

3D PDB for HMDB0015349 (Halofantrine)

SMILES for HMDB0015349 (Halofantrine)

INCHI for HMDB0015349 (Halofantrine)

Structure for HMDB0015349 (Halofantrine)

3D Structure for HMDB0015349 (Halofantrine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References