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

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:04 UTC

HMDB ID

HMDB0015653

Secondary Accession Numbers

HMDB15653

Metabolite Identification

Common Name

Lumefantrine

Description

Lumefantrine, also known as benflumetol, belongs to the class of organic compounds known as fluorenes. Fluorenes are compounds containing a fluorene moiety, which consists of two benzene rings connected through either a cyclopentane, cyclopentene, or cyclopenta-1,3-diene. Lumefantrine is a blood schizonticide active against erythrocytic stages of Plasmodium falciparum. Lumefantrine is a very strong basic compound (based on its pKa). Common side effects in children include pyrexia, cough, vomiting, anorexia, and headache. Possible serious adverse effects include QT prolongation, bullous eruption, urticaria, splenomegaly (9%), hepatomegaly (adults, 9%; children, 6%), hypersensitivty reaction, and angioedema. and may be used to treat infections caused by P. falciparum and unidentified Plasmodium species, including infections acquired in chloroquine-resistant areas. Lumefantrine is an antimalarial agent used to treat acute uncomplicated malaria.

Structure

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


  Mrv0541 02241212482D          

 35 38  0  0  0  0            999 V2000
    4.9441   -4.4555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9441   -3.6305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.6585   -2.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3730   -1.9805    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0875   -2.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

HMDB0015653
     RDKit          3D
Lumefantrine
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M  END


  Mrv0541 02241212482D          

 35 38  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
HMDB0015653

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCN(CCCC)CC(O)C1=C2C(=CC(Cl)=C1)\C(=C/C1=CC=C(Cl)C=C1)C1=C2C=CC(Cl)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H32Cl3NO/c1-3-5-13-34(14-6-4-2)19-29(35)28-18-23(33)17-27-25(15-20-7-9-21(31)10-8-20)26-16-22(32)11-12-24(26)30(27)28/h7-12,15-18,29,35H,3-6,13-14,19H2,1-2H3/b25-15-

> <INCHI_KEY>
DYLGFOYVTXJFJP-MYYYXRDXSA-N

> <FORMULA>
C30H32Cl3NO

> <MOLECULAR_WEIGHT>
528.94

> <EXACT_MASS>
527.154947772

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
60.69151807154687

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(dibutylamino)-1-[(9Z)-2,7-dichloro-9-[(4-chlorophenyl)methylidene]-9H-fluoren-4-yl]ethan-1-ol

> <ALOGPS_LOGP>
8.34

> <JCHEM_LOGP>
9.191258858333333

> <ALOGPS_LOGS>
-7.23

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.10168381554502

> <JCHEM_PKA_STRONGEST_BASIC>
9.782283537249677

> <JCHEM_POLAR_SURFACE_AREA>
23.47

> <JCHEM_REFRACTIVITY>
160.8105

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.09e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lumefantrine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015653
     RDKit          3D
Lumefantrine
 67 70  0  0  0  0  0  0  0  0999 V2000
   -5.7605   -3.6041   -0.1437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5037   -2.8274   -0.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6860   -1.3336   -0.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3335   -0.7068   -0.3071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0800    0.6170   -0.5905 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4685    1.7310    0.0776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9579    2.0371    0.0378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1670    3.3421    0.8098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3931    4.4743    0.1359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7714    0.7698   -1.2839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7063    0.3581   -0.3727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8081   -0.8300    0.3271 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6757    0.8080   -0.5322 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0761    2.1195   -0.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3945    2.4590   -0.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8595    4.1528    0.0216 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.3570    1.5062   -0.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9879    0.1693   -0.1793 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6627   -0.1977   -0.4277 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5924   -1.6427   -0.5891 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5887   -2.4989   -0.9127 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8187   -3.8752   -1.0502 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0572   -4.4425   -0.8753 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3066   -6.1748   -1.0517 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0750   -3.5680   -0.5551 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8468   -2.2117   -0.4191 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7448   -1.0685   -0.1609 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0291   -1.1866   -0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9923   -0.1385    0.1718 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5245    0.1123    1.4440 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5370    1.0254    1.6250 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0194    1.6945    0.5065 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3209    2.8535    0.7664 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.4896    1.4417   -0.7329 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4803    0.5338   -0.9245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4558   -3.2050   -0.8922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4695   -4.6685   -0.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1995   -3.6575    0.8706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1179   -2.8259    0.9644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6861   -3.1826   -0.7322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1929   -1.2010   -1.3896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3692   -0.9662    0.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9528   -0.8980    0.7689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6300   -1.3598   -0.9407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2051    1.7453    1.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9909    2.6456   -0.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3410    2.1163   -0.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4727    1.2775    0.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2396    3.5490    0.8910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7427    3.2205    1.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9214    5.4337    0.3057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3437    4.3033   -0.9703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3726    4.4831    0.5343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6954    1.8737   -1.4448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8168    0.3378   -2.2784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0075    1.0547    0.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5104   -0.7985    1.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3203    2.8820   -0.4829 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3789    1.7213    0.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3943   -2.2343   -1.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0058   -4.5390   -1.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0702   -3.9658   -0.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4395   -2.2246   -0.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1602   -0.4067    2.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9643    1.2334    2.5951 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9130    1.9984   -1.5752 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0869    0.3593   -1.9106 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
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 32 34  1  0
 34 35  2  0
 19 13  1  0
 26 20  1  0
 35 29  1  0
 27 18  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  0
  2 40  1  0
  3 41  1  0
  3 42  1  0
  4 43  1  0
  4 44  1  0
  6 45  1  0
  6 46  1  0
  7 47  1  0
  7 48  1  0
  8 49  1  0
  8 50  1  0
  9 51  1  0
  9 52  1  0
  9 53  1  0
 10 54  1  0
 10 55  1  0
 11 56  1  0
 12 57  1  0
 14 58  1  0
 17 59  1  0
 21 60  1  0
 22 61  1  0
 25 62  1  0
 28 63  1  0
 30 64  1  0
 31 65  1  0
 34 66  1  0
 35 67  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       9.229  -8.317   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.229  -6.777   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.563  -6.007   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.563  -4.467   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      11.896  -3.697   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      13.230  -4.467   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.230  -6.007   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.564  -6.777   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.564  -8.317   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.896  -2.157   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.230  -1.387   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.230   0.153   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.564   0.923   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.028   0.447   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.933   1.693   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      18.465   1.532   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      19.091   0.125   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      18.186  -1.121   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.655  -0.960   0.000  0.00  0.00           C+0
HETATM   20 Cl   UNK     0      20.623  -0.036   0.000  0.00  0.00          Cl+0
HETATM   21  C   UNK     0      16.028   2.939   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.504   4.403   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.474   5.548   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.967   5.228   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.937   6.372   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.413   7.837   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.919   8.157   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      15.950   7.013   0.000  0.00  0.00           C+0
HETATM   29 Cl   UNK     0      12.382   8.981   0.000  0.00  0.00          Cl+0
HETATM   30  C   UNK     0      14.564   2.463   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.230   3.233   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.896   2.463   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.896   0.923   0.000  0.00  0.00           C+0
HETATM   34 Cl   UNK     0      10.563   3.233   0.000  0.00  0.00          Cl+0
HETATM   35  O   UNK     0      14.564  -2.157   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    5   11                                                       
CONECT   11   10   12   35                                                  
CONECT   12   11   13   33                                                  
CONECT   13   12   14   30                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20   17                                                            
CONECT   21   15   22   30                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27   23                                                       
CONECT   29   26                                                            
CONECT   30   21   13   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32   12                                                       
CONECT   34   32                                                            
CONECT   35   11                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

COMPND    HMDB0015653
HETATM    1  C1  UNL     1      -5.761  -3.604  -0.144  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.504  -2.827  -0.074  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.686  -1.334  -0.430  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.333  -0.707  -0.307  1.00  0.00           C  
HETATM    5  N1  UNL     1      -3.080   0.617  -0.590  1.00  0.00           N  
HETATM    6  C5  UNL     1      -3.468   1.731   0.078  1.00  0.00           C  
HETATM    7  C6  UNL     1      -4.958   2.037   0.038  1.00  0.00           C  
HETATM    8  C7  UNL     1      -5.167   3.342   0.810  1.00  0.00           C  
HETATM    9  C8  UNL     1      -4.393   4.474   0.136  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.771   0.770  -1.284  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.706   0.358  -0.373  1.00  0.00           C  
HETATM   12  O1  UNL     1      -0.808  -0.830   0.327  1.00  0.00           O  
HETATM   13  C11 UNL     1       0.676   0.808  -0.532  1.00  0.00           C  
HETATM   14  C12 UNL     1       1.076   2.120  -0.398  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.395   2.459  -0.153  1.00  0.00           C  
HETATM   16 CL1  UNL     1       2.859   4.153   0.022  1.00  0.00          CL  
HETATM   17  C14 UNL     1       3.357   1.506  -0.037  1.00  0.00           C  
HETATM   18  C15 UNL     1       2.988   0.169  -0.179  1.00  0.00           C  
HETATM   19  C16 UNL     1       1.663  -0.198  -0.428  1.00  0.00           C  
HETATM   20  C17 UNL     1       1.592  -1.643  -0.589  1.00  0.00           C  
HETATM   21  C18 UNL     1       0.589  -2.499  -0.913  1.00  0.00           C  
HETATM   22  C19 UNL     1       0.819  -3.875  -1.050  1.00  0.00           C  
HETATM   23  C20 UNL     1       2.057  -4.442  -0.875  1.00  0.00           C  
HETATM   24 CL2  UNL     1       2.307  -6.175  -1.052  1.00  0.00          CL  
HETATM   25  C21 UNL     1       3.075  -3.568  -0.555  1.00  0.00           C  
HETATM   26  C22 UNL     1       2.847  -2.212  -0.419  1.00  0.00           C  
HETATM   27  C23 UNL     1       3.745  -1.069  -0.161  1.00  0.00           C  
HETATM   28  C24 UNL     1       5.029  -1.187  -0.005  1.00  0.00           C  
HETATM   29  C25 UNL     1       5.992  -0.139   0.172  1.00  0.00           C  
HETATM   30  C26 UNL     1       6.524   0.112   1.444  1.00  0.00           C  
HETATM   31  C27 UNL     1       7.537   1.025   1.625  1.00  0.00           C  
HETATM   32  C28 UNL     1       8.019   1.694   0.506  1.00  0.00           C  
HETATM   33 CL3  UNL     1       9.321   2.853   0.766  1.00  0.00          CL  
HETATM   34  C29 UNL     1       7.490   1.442  -0.733  1.00  0.00           C  
HETATM   35  C30 UNL     1       6.480   0.534  -0.924  1.00  0.00           C  
HETATM   36  H1  UNL     1      -6.456  -3.205  -0.892  1.00  0.00           H  
HETATM   37  H2  UNL     1      -5.470  -4.669  -0.403  1.00  0.00           H  
HETATM   38  H3  UNL     1      -6.199  -3.658   0.871  1.00  0.00           H  
HETATM   39  H4  UNL     1      -4.118  -2.826   0.964  1.00  0.00           H  
HETATM   40  H5  UNL     1      -3.686  -3.183  -0.732  1.00  0.00           H  
HETATM   41  H6  UNL     1      -5.193  -1.201  -1.390  1.00  0.00           H  
HETATM   42  H7  UNL     1      -5.369  -0.966   0.371  1.00  0.00           H  
HETATM   43  H8  UNL     1      -2.953  -0.898   0.769  1.00  0.00           H  
HETATM   44  H9  UNL     1      -2.630  -1.360  -0.941  1.00  0.00           H  
HETATM   45  H10 UNL     1      -3.205   1.745   1.174  1.00  0.00           H  
HETATM   46  H11 UNL     1      -2.991   2.646  -0.405  1.00  0.00           H  
HETATM   47  H12 UNL     1      -5.341   2.116  -0.985  1.00  0.00           H  
HETATM   48  H13 UNL     1      -5.473   1.277   0.666  1.00  0.00           H  
HETATM   49  H14 UNL     1      -6.240   3.549   0.891  1.00  0.00           H  
HETATM   50  H15 UNL     1      -4.743   3.221   1.834  1.00  0.00           H  
HETATM   51  H16 UNL     1      -4.921   5.434   0.306  1.00  0.00           H  
HETATM   52  H17 UNL     1      -4.344   4.303  -0.970  1.00  0.00           H  
HETATM   53  H18 UNL     1      -3.373   4.483   0.534  1.00  0.00           H  
HETATM   54  H19 UNL     1      -1.695   1.874  -1.445  1.00  0.00           H  
HETATM   55  H20 UNL     1      -1.817   0.338  -2.278  1.00  0.00           H  
HETATM   56  H21 UNL     1      -1.007   1.055   0.572  1.00  0.00           H  
HETATM   57  H22 UNL     1      -0.510  -0.799   1.261  1.00  0.00           H  
HETATM   58  H23 UNL     1       0.320   2.882  -0.483  1.00  0.00           H  
HETATM   59  H24 UNL     1       4.379   1.721   0.187  1.00  0.00           H  
HETATM   60  H25 UNL     1      -0.394  -2.234  -1.164  1.00  0.00           H  
HETATM   61  H26 UNL     1      -0.006  -4.539  -1.301  1.00  0.00           H  
HETATM   62  H27 UNL     1       4.070  -3.966  -0.406  1.00  0.00           H  
HETATM   63  H28 UNL     1       5.440  -2.225  -0.000  1.00  0.00           H  
HETATM   64  H29 UNL     1       6.160  -0.407   2.308  1.00  0.00           H  
HETATM   65  H30 UNL     1       7.964   1.233   2.595  1.00  0.00           H  
HETATM   66  H31 UNL     1       7.913   1.998  -1.575  1.00  0.00           H  
HETATM   67  H32 UNL     1       6.087   0.359  -1.911  1.00  0.00           H  
CONECT    1    2   36   37   38
CONECT    2    3   39   40
CONECT    3    4   41   42
CONECT    4    5   43   44
CONECT    5    6   10
CONECT    6    7   45   46
CONECT    7    8   47   48
CONECT    8    9   49   50
CONECT    9   51   52   53
CONECT   10   11   54   55
CONECT   11   12   13   56
CONECT   12   57
CONECT   13   14   14   19
CONECT   14   15   58
CONECT   15   16   17   17
CONECT   17   18   59
CONECT   18   19   19   27
CONECT   19   20
CONECT   20   21   21   26
CONECT   21   22   60
CONECT   22   23   23   61
CONECT   23   24   25
CONECT   25   26   26   62
CONECT   26   27
CONECT   27   28   28
CONECT   28   29   63
CONECT   29   30   30   35
CONECT   30   31   64
CONECT   31   32   32   65
CONECT   32   33   34
CONECT   34   35   35   66
CONECT   35   67
END

HMDB0015653
     RDKit          3D
Lumefantrine
 67 70  0  0  0  0  0  0  0  0999 V2000
   -5.7605   -3.6041   -0.1437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5037   -2.8274   -0.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6860   -1.3336   -0.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3335   -0.7068   -0.3071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0800    0.6170   -0.5905 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4685    1.7310    0.0776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9579    2.0371    0.0378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1670    3.3421    0.8098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3931    4.4743    0.1359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7714    0.7698   -1.2839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7063    0.3581   -0.3727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8081   -0.8300    0.3271 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6757    0.8080   -0.5322 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0761    2.1195   -0.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3945    2.4590   -0.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8595    4.1528    0.0216 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.3570    1.5062   -0.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9879    0.1693   -0.1793 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6627   -0.1977   -0.4277 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5924   -1.6427   -0.5891 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5887   -2.4989   -0.9127 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8187   -3.8752   -1.0502 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0572   -4.4425   -0.8753 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3066   -6.1748   -1.0517 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0750   -3.5680   -0.5551 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8468   -2.2117   -0.4191 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7448   -1.0685   -0.1609 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0291   -1.1866   -0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9923   -0.1385    0.1718 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5245    0.1123    1.4440 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5370    1.0254    1.6250 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0194    1.6945    0.5065 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3209    2.8535    0.7664 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.4896    1.4417   -0.7329 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4803    0.5338   -0.9245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4558   -3.2050   -0.8922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4695   -4.6685   -0.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1995   -3.6575    0.8706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1179   -2.8259    0.9644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6861   -3.1826   -0.7322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1929   -1.2010   -1.3896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3692   -0.9662    0.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9528   -0.8980    0.7689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6300   -1.3598   -0.9407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2051    1.7453    1.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9909    2.6456   -0.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3410    2.1163   -0.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4727    1.2775    0.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2396    3.5490    0.8910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7427    3.2205    1.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9214    5.4337    0.3057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3437    4.3033   -0.9703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3726    4.4831    0.5343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6954    1.8737   -1.4448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8168    0.3378   -2.2784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0075    1.0547    0.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5104   -0.7985    1.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3203    2.8820   -0.4829 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3789    1.7213    0.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3943   -2.2343   -1.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0058   -4.5390   -1.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0702   -3.9658   -0.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4395   -2.2246   -0.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1602   -0.4067    2.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9643    1.2334    2.5951 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9130    1.9984   -1.5752 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0869    0.3593   -1.9106 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
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 32 34  1  0
 34 35  2  0
 19 13  1  0
 26 20  1  0
 35 29  1  0
 27 18  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  0
  2 40  1  0
  3 41  1  0
  3 42  1  0
  4 43  1  0
  4 44  1  0
  6 45  1  0
  6 46  1  0
  7 47  1  0
  7 48  1  0
  8 49  1  0
  8 50  1  0
  9 51  1  0
  9 52  1  0
  9 53  1  0
 10 54  1  0
 10 55  1  0
 11 56  1  0
 12 57  1  0
 14 58  1  0
 17 59  1  0
 21 60  1  0
 22 61  1  0
 25 62  1  0
 28 63  1  0
 30 64  1  0
 31 65  1  0
 34 66  1  0
 35 67  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+-)-2,7-Dichloro-9-((Z)-p-chlorobenzylidene)-alpha-((dibutylamino)methyl)fluorene-4-methanol	ChEBI
2-Dibutylamino-1-[2,7-dichloro-9-(4-chloro-benzylidene)-9H-fluoren-4-yl]-ethanol	ChEBI
2-Dibutylamino-1-{2,7-dichloro-9-[1-(4-chloro-phenyl)-meth-(Z)-ylidene]-9H-fluoren-4-yl}-ethanol	ChEBI
Benflumetol	ChEBI
DL-Benflumelol	ChEBI
(+-)-2,7-Dichloro-9-((Z)-p-chlorobenzylidene)-a-((dibutylamino)methyl)fluorene-4-methanol	Generator
(+-)-2,7-Dichloro-9-((Z)-p-chlorobenzylidene)-α-((dibutylamino)methyl)fluorene-4-methanol	Generator
Benflumetol, (+)-isomer	HMDB
Benflumetol, (+-)-isomer	HMDB
Benflumetol, (-)-isomer	HMDB

Chemical Formula

C₃₀H₃₂Cl₃NO

Average Molecular Weight

528.94

Monoisotopic Molecular Weight

527.154947772

IUPAC Name

2-(dibutylamino)-1-[(9Z)-2,7-dichloro-9-[(4-chlorophenyl)methylidene]-9H-fluoren-4-yl]ethan-1-ol

Traditional Name

lumefantrine

CAS Registry Number

82186-77-4

SMILES

CCCCN(CCCC)CC(O)C1=C2C(=CC(Cl)=C1)\C(=C/C1=CC=C(Cl)C=C1)C1=C2C=CC(Cl)=C1

InChI Identifier

InChI=1S/C30H32Cl3NO/c1-3-5-13-34(14-6-4-2)19-29(35)28-18-23(33)17-27-25(15-20-7-9-21(31)10-8-20)26-16-22(32)11-12-24(26)30(27)28/h7-12,15-18,29,35H,3-6,13-14,19H2,1-2H3/b25-15-

InChI Key

DYLGFOYVTXJFJP-MYYYXRDXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fluorenes. Fluorenes are compounds containing a fluorene moiety, which consists of two benzene rings connected through either a cyclopentane, cyclopentene, or cyclopenta-1,3-diene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Fluorenes

Sub Class

Not Available

Direct Parent

Fluorenes

Alternative Parents

Substituents

Fluorene
Chlorobenzene
Aralkylamine
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
1,2-aminoalcohol
Tertiary aliphatic amine
Secondary alcohol
Tertiary amine
Organochloride
Organohalogen compound
Alcohol
Aromatic alcohol
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Amine
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

tertiary amine (CHEBI:156095 )
secondary alcohol (CHEBI:156095 )
monochlorobenzenes (CHEBI:156095 )
fluorenes (CHEBI:156095 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015653)

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.1e-05 g/L	ALOGPS
logP	8.34	ALOGPS
logP	9.19	ChemAxon
logS	-7.2	ALOGPS
pKa (Strongest Acidic)	14.1	ChemAxon
pKa (Strongest Basic)	9.78	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	10	ChemAxon
Refractivity	160.81 m³·mol⁻¹	ChemAxon
Polarizability	60.69 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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]+	226.653	30932474
DeepCCS	[M-H]-	224.258	30932474
DeepCCS	[M-2H]-	257.141	30932474
DeepCCS	[M+Na]+	232.566	30932474
AllCCS	[M+H]+	223.8	32859911
AllCCS	[M+H-H2O]+	222.2	32859911
AllCCS	[M+NH4]+	225.3	32859911
AllCCS	[M+Na]+	225.7	32859911
AllCCS	[M-H]-	215.3	32859911
AllCCS	[M+Na-2H]-	216.3	32859911
AllCCS	[M+HCOO]-	217.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lumefantrine	CCCCN(CCCC)CC(O)C1=C2C(=CC(Cl)=C1)\C(=C/C1=CC=C(Cl)C=C1)C1=C2C=CC(Cl)=C1	5379.9	Standard polar	33892256
Lumefantrine	CCCCN(CCCC)CC(O)C1=C2C(=CC(Cl)=C1)\C(=C/C1=CC=C(Cl)C=C1)C1=C2C=CC(Cl)=C1	3739.5	Standard non polar	33892256
Lumefantrine	CCCCN(CCCC)CC(O)C1=C2C(=CC(Cl)=C1)\C(=C/C1=CC=C(Cl)C=C1)C1=C2C=CC(Cl)=C1	3889.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lumefantrine,1TMS,isomer #1	CCCCN(CCCC)CC(O[Si](C)(C)C)C1=CC(Cl)=CC2=C1C1=CC=C(Cl)C=C1/C2=C/C1=CC=C(Cl)C=C1	3840.0	Semi standard non polar	33892256
Lumefantrine,1TBDMS,isomer #1	CCCCN(CCCC)CC(O[Si](C)(C)C(C)(C)C)C1=CC(Cl)=CC2=C1C1=CC=C(Cl)C=C1/C2=C/C1=CC=C(Cl)C=C1	4035.7	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 - Lumefantrine GC-MS (Non-derivatized) - 70eV, Positive	splash10-000l-5908110000-30364837a4164a8491be	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lumefantrine GC-MS (1 TMS) - 70eV, Positive	splash10-0bt9-5300960000-f57d30fd0683000ba1df	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lumefantrine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lumefantrine GC-MS ("Lumefantrine,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	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 - Lumefantrine 10V, Positive-QTOF	splash10-03fr-0000190000-2026e5ba94f08f73450d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumefantrine 20V, Positive-QTOF	splash10-03e9-3309470000-dd7cd2616b9942c35f6d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumefantrine 40V, Positive-QTOF	splash10-0a4i-9214100000-82786f2daa0ffb34e593	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumefantrine 10V, Negative-QTOF	splash10-004i-0000090000-75a6769f5d87d37f6531	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumefantrine 20V, Negative-QTOF	splash10-004i-0602290000-621f19a6f82ad39466a4	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumefantrine 40V, Negative-QTOF	splash10-0ul1-5209000000-229aedab58de48c7d7fa	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumefantrine 10V, Positive-QTOF	splash10-004i-0000090000-f3e5f6566ad7bc0d6931	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumefantrine 20V, Positive-QTOF	splash10-004i-3100290000-5859b739d14324e74b77	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumefantrine 40V, Positive-QTOF	splash10-01q1-9301010000-442ed46841c560639476	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumefantrine 10V, Negative-QTOF	splash10-004i-0000090000-6f1797933f6c478c462e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumefantrine 20V, Negative-QTOF	splash10-004i-0205690000-b150da224a2d334104c3	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumefantrine 40V, Negative-QTOF	splash10-0f89-7509400000-ffd74bf582f10032d904	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 DB06708	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB06708	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB06708

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4941944

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lumefantrine

METLIN ID

Not Available

PubChem Compound

6437380

PDB ID

Not Available

ChEBI ID

156095

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

(). Artemether and Lumefantrine (2010). AHFS Drug Information [Electronic versionb]. Retrieved October 24, 2010.. .
(). Artemether/Lumefantrine (2010). DrugPointsÃ‚Â® System [Electronic version]. Retrieved October 24, 2010.. .
(). Novartis. Coartem (artemether/lumefantrine) tablets prescribing information. East Hanover, NJ; 2010 Feb.. .

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

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

Showing metabocard for Lumefantrine (HMDB0015653)

MOL for HMDB0015653 (Lumefantrine)

3D MOL for HMDB0015653 (Lumefantrine)

3D SDF for HMDB0015653 (Lumefantrine)

3D-SDF for HMDB0015653 (Lumefantrine)

PDB for HMDB0015653 (Lumefantrine)

3D PDB for HMDB0015653 (Lumefantrine)

SMILES for HMDB0015653 (Lumefantrine)

INCHI for HMDB0015653 (Lumefantrine)

Structure for HMDB0015653 (Lumefantrine)

3D Structure for HMDB0015653 (Lumefantrine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes