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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 14:07:42 UTC

Update Date

2021-10-01 22:39:36 UTC

HMDB ID

HMDB0254735

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Miltefosine

Description

Miltefosine, also known as impavido, belongs to the class of organic compounds known as phosphocholines. Phosphocholines are compounds containing a [2-(trimethylazaniumyl)ethoxy]phosphonic acid or derivative. Miltefosine is a drug which is used for the treatment of mucosal (caused by leishmania braziliensis), cutaneous (caused by l. braziliensis, l. guyanensis, and l. panamensis), and visceral leishmaniasis (caused by l. donovani). in comparing leishmania drug susceptibility, it has been found that l. donovani is the most susceptible to miltefosine while l. major is the least susceptible. off-label use includes treatment of free-living amebae (fla) infections (unlabeled use; cdc, 2013). . Based on a literature review a significant number of articles have been published on Miltefosine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Miltefosine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Miltefosine 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

  Mrv0541 02241517482D          

 27 26  0  0  0  0            999 V2000
    5.9960   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7144   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4124   -5.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5874   -3.9848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7105   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1394   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8539   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5684   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2828   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9973   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7118   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4262   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1407   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8552   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5697   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2841   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9986   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2854   -5.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7131   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5710   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9999   -4.6993    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   17.7295   -5.4137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5545   -3.9848    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   17.4275   -4.2868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8565   -5.1118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1420   -4.6993    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 20 18  1  0  0  0  0
 21 19  1  0  0  0  0
 22  2  1  0  0  0  0
 22  3  1  0  0  0  0
 22  4  1  0  0  0  0
 22 19  1  0  0  0  0
 25 20  1  0  0  0  0
 26 21  1  0  0  0  0
 27 23  2  0  0  0  0
 27 24  1  0  0  0  0
 27 25  1  0  0  0  0
 27 26  1  0  0  0  0
M  CHG  2  22   1  24  -1
M  END

HMDB0254735
     RDKit          3D
Miltefosine
 73 72  0  0  0  0  0  0  0  0999 V2000
   10.9296   -0.7751   -0.0242 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9368    0.1393   -0.7775 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6347   -0.0263   -0.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5295    0.8822   -0.6052 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2904    0.7094    0.1783 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5027   -0.5246    0.1919 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9051   -0.7332   -1.2282 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1072    0.4715   -1.5756 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8809    0.8706   -0.8805 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6623    0.0141   -0.9454 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3604   -0.9416    0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0136   -0.1424    1.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2593    0.6817    1.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4210   -0.1864    1.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6739    0.4293    0.5463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7824   -0.3047   -0.8375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0928    0.1814   -1.1705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9391   -1.3105   -0.9538 P   0  0  0  0  0  5  0  0  0  0  0  0
   -4.0799   -2.3627   -0.3093 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6017   -1.8059   -2.4388 O   0  0  0  0  0  1  0  0  0  0  0  0
   -6.2487   -0.9242    0.0265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4428    0.5167   -0.1024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9805    0.4774   -0.3787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6539   -0.1562    0.6787 N   0  0  0  0  0  4  0  0  0  0  0  0
  -10.0835   -0.0865    0.3053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3920   -1.6006    0.7222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4019    0.3909    1.9659 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4965   -1.7458    0.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0093   -0.2687    1.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8815   -0.7472   -0.5471 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8504   -0.3589   -1.7930 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2957    1.1472   -0.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6672    0.0149    1.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3296   -1.1103   -0.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3755    0.6811   -1.6751 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8877    1.9119   -0.4552 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6195    1.6093   -0.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5641    0.9189    1.2845 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8074   -0.6288    0.9938 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2467   -1.3944    0.2409 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3559   -1.6467   -1.2166 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8010   -0.7579   -1.8927 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7931    1.3402   -1.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7678    0.2547   -2.6881 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2537    0.7855    0.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6469    1.9459   -0.9770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7387    0.5233   -1.2603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8832   -0.6931   -1.8611 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0339   -1.7248    0.3275 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3769   -1.4199   -0.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7793   -0.8208    2.2338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7597    0.5816    1.6776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0824    1.3969    0.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2937    1.3192    2.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7386   -0.4023    2.2696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3232   -1.2437    0.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5641    0.3017    1.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5663    1.4947    0.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7335   -1.3417   -0.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0685    0.1663   -1.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2778    1.0445    0.8162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8852    0.8632   -0.9186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2649    1.4596   -0.6321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9806   -0.2105   -1.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6354   -0.5857    1.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3397    0.9593    0.0571 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0924   -0.6550   -0.6816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1851   -2.0088   -0.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6139   -1.9115    1.4268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3407   -2.1114    1.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3920    1.4894    1.9622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3990   -0.0035    2.3382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1441   -0.0437    2.6636 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
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  6 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  0
  8 44  1  0
  9 45  1  0
  9 46  1  0
 10 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  0
 12 52  1  0
 13 53  1  0
 13 54  1  0
 14 55  1  0
 14 56  1  0
 15 57  1  0
 15 58  1  0
 16 59  1  0
 16 60  1  0
 22 61  1  0
 22 62  1  0
 23 63  1  0
 23 64  1  0
 25 65  1  0
 25 66  1  0
 25 67  1  0
 26 68  1  0
 26 69  1  0
 26 70  1  0
 27 71  1  0
 27 72  1  0
 27 73  1  0
M  CHG  2  20  -1  24   1
M  END

  Mrv0541 02241517482D          

 27 26  0  0  0  0            999 V2000
    5.9960   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7144   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4124   -5.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5874   -3.9848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7105   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1394   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8539   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5684   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2828   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9973   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7118   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4262   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1407   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8552   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5697   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2841   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9986   -4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2854   -5.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7131   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5710   -4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9999   -4.6993    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   17.7295   -5.4137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5545   -3.9848    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   17.4275   -4.2868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8565   -5.1118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1420   -4.6993    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 20 18  1  0  0  0  0
 21 19  1  0  0  0  0
 22  2  1  0  0  0  0
 22  3  1  0  0  0  0
 22  4  1  0  0  0  0
 22 19  1  0  0  0  0
 25 20  1  0  0  0  0
 26 21  1  0  0  0  0
 27 23  2  0  0  0  0
 27 24  1  0  0  0  0
 27 25  1  0  0  0  0
 27 26  1  0  0  0  0
M  CHG  2  22   1  24  -1
M  END
> <DATABASE_ID>
HMDB0254735

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCCCCCCCCCOP([O-])(=O)OCC[N+](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C21H46NO4P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-20-25-27(23,24)26-21-19-22(2,3)4/h5-21H2,1-4H3

> <INCHI_KEY>
PQLXHQMOHUQAKB-UHFFFAOYSA-N

> <FORMULA>
C21H46NO4P

> <MOLECULAR_WEIGHT>
407.576

> <EXACT_MASS>
407.316445963

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
50.584318757311486

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
hexadecyl 2-(trimethylazaniumyl)ethyl phosphate

> <ALOGPS_LOGP>
2.68

> <JCHEM_LOGP>
2.2508485231949216

> <ALOGPS_LOGS>
-6.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8803148742183158

> <JCHEM_POLAR_SURFACE_AREA>
58.59

> <JCHEM_REFRACTIVITY>
125.51309999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.20e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
miltex

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0254735
     RDKit          3D
Miltefosine
 73 72  0  0  0  0  0  0  0  0999 V2000
   10.9296   -0.7751   -0.0242 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9368    0.1393   -0.7775 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6347   -0.0263   -0.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5295    0.8822   -0.6052 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2904    0.7094    0.1783 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5027   -0.5246    0.1919 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9051   -0.7332   -1.2282 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1072    0.4715   -1.5756 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8809    0.8706   -0.8805 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6623    0.0141   -0.9454 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3604   -0.9416    0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0136   -0.1424    1.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2593    0.6817    1.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4210   -0.1864    1.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6739    0.4293    0.5463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7824   -0.3047   -0.8375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0928    0.1814   -1.1705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9391   -1.3105   -0.9538 P   0  0  0  0  0  5  0  0  0  0  0  0
   -4.0799   -2.3627   -0.3093 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6017   -1.8059   -2.4388 O   0  0  0  0  0  1  0  0  0  0  0  0
   -6.2487   -0.9242    0.0265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4428    0.5167   -0.1024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9805    0.4774   -0.3787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6539   -0.1562    0.6787 N   0  0  0  0  0  4  0  0  0  0  0  0
  -10.0835   -0.0865    0.3053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3920   -1.6006    0.7222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4019    0.3909    1.9659 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4965   -1.7458    0.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0093   -0.2687    1.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8815   -0.7472   -0.5471 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8504   -0.3589   -1.7930 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2957    1.1472   -0.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6672    0.0149    1.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3296   -1.1103   -0.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3755    0.6811   -1.6751 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8877    1.9119   -0.4552 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6195    1.6093   -0.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5641    0.9189    1.2845 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8074   -0.6288    0.9938 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2467   -1.3944    0.2409 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3559   -1.6467   -1.2166 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8010   -0.7579   -1.8927 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7931    1.3402   -1.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7678    0.2547   -2.6881 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2537    0.7855    0.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6469    1.9459   -0.9770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7387    0.5233   -1.2603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8832   -0.6931   -1.8611 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0339   -1.7248    0.3275 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3769   -1.4199   -0.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7793   -0.8208    2.2338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7597    0.5816    1.6776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0824    1.3969    0.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2937    1.3192    2.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7386   -0.4023    2.2696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3232   -1.2437    0.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5641    0.3017    1.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5663    1.4947    0.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7335   -1.3417   -0.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0685    0.1663   -1.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2778    1.0445    0.8162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8852    0.8632   -0.9186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2649    1.4596   -0.6321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9806   -0.2105   -1.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6354   -0.5857    1.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3397    0.9593    0.0571 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0924   -0.6550   -0.6816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1851   -2.0088   -0.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6139   -1.9115    1.4268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3407   -2.1114    1.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3920    1.4894    1.9622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3990   -0.0035    2.3382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1441   -0.0437    2.6636 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
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  6 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  0
  8 44  1  0
  9 45  1  0
  9 46  1  0
 10 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  0
 12 52  1  0
 13 53  1  0
 13 54  1  0
 14 55  1  0
 14 56  1  0
 15 57  1  0
 15 58  1  0
 16 59  1  0
 16 60  1  0
 22 61  1  0
 22 62  1  0
 23 63  1  0
 23 64  1  0
 25 65  1  0
 25 66  1  0
 25 67  1  0
 26 68  1  0
 26 69  1  0
 26 70  1  0
 27 71  1  0
 27 72  1  0
 27 73  1  0
M  CHG  2  20  -1  24   1
M  END

HEADER    PROTEIN                                 24-FEB-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-15         0                                  
HETATM    1  C   UNK     0      11.193  -8.002   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      40.534  -8.002   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      39.970 -10.106   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      38.430  -7.438   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.526  -8.772   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.860  -8.002   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.194  -8.772   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.527  -8.002   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.861  -8.772   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      19.195  -8.002   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      20.528  -8.772   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.862  -8.002   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.196  -8.772   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      24.529  -8.002   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      25.863  -8.772   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      27.197  -8.002   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      28.530  -8.772   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      29.864  -8.002   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      37.866  -9.542   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      31.198  -8.772   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      36.533  -8.772   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      39.200  -8.772   0.000  0.00  0.00           N+1
HETATM   23  O   UNK     0      33.095 -10.106   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      34.635  -7.438   0.000  0.00  0.00           O-1
HETATM   25  O   UNK     0      32.531  -8.002   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      35.199  -9.542   0.000  0.00  0.00           O+0
HETATM   27  P   UNK     0      33.865  -8.772   0.000  0.00  0.00           P+0
CONECT    1    5                                                            
CONECT    2   22                                                            
CONECT    3   22                                                            
CONECT    4   22                                                            
CONECT    5    1    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   20                                                       
CONECT   19   21   22                                                       
CONECT   20   18   25                                                       
CONECT   21   19   26                                                       
CONECT   22    2    3    4   19                                             
CONECT   23   27                                                            
CONECT   24   27                                                            
CONECT   25   20   27                                                       
CONECT   26   21   27                                                       
CONECT   27   23   24   25   26                                             
MASTER        0    0    0    0    0    0    0    0   27    0   52    0
END

COMPND    HMDB0254735
HETATM    1  C1  UNL     1      10.930  -0.775  -0.024  1.00  0.00           C  
HETATM    2  C2  UNL     1       9.937   0.139  -0.778  1.00  0.00           C  
HETATM    3  C3  UNL     1       8.635  -0.026  -0.039  1.00  0.00           C  
HETATM    4  C4  UNL     1       7.530   0.882  -0.605  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.290   0.709   0.178  1.00  0.00           C  
HETATM    6  C6  UNL     1       5.503  -0.525   0.192  1.00  0.00           C  
HETATM    7  C7  UNL     1       4.905  -0.733  -1.228  1.00  0.00           C  
HETATM    8  C8  UNL     1       4.107   0.471  -1.576  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.881   0.871  -0.880  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.662   0.014  -0.945  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.360  -0.942   0.150  1.00  0.00           C  
HETATM   12  C12 UNL     1       1.014  -0.142   1.422  1.00  0.00           C  
HETATM   13  C13 UNL     1      -0.259   0.682   1.135  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.421  -0.186   1.169  1.00  0.00           C  
HETATM   15  C15 UNL     1      -2.674   0.429   0.546  1.00  0.00           C  
HETATM   16  C16 UNL     1      -2.782  -0.305  -0.837  1.00  0.00           C  
HETATM   17  O1  UNL     1      -4.093   0.181  -1.171  1.00  0.00           O  
HETATM   18  P1  UNL     1      -4.939  -1.311  -0.954  1.00  0.00           P  
HETATM   19  O2  UNL     1      -4.080  -2.363  -0.309  1.00  0.00           O  
HETATM   20  O3  UNL     1      -5.602  -1.806  -2.439  1.00  0.00           O1-
HETATM   21  O4  UNL     1      -6.249  -0.924   0.027  1.00  0.00           O  
HETATM   22  C17 UNL     1      -6.443   0.517  -0.102  1.00  0.00           C  
HETATM   23  C18 UNL     1      -7.981   0.477  -0.379  1.00  0.00           C  
HETATM   24  N1  UNL     1      -8.654  -0.156   0.679  1.00  0.00           N1+
HETATM   25  C19 UNL     1     -10.084  -0.086   0.305  1.00  0.00           C  
HETATM   26  C20 UNL     1      -8.392  -1.601   0.722  1.00  0.00           C  
HETATM   27  C21 UNL     1      -8.402   0.391   1.966  1.00  0.00           C  
HETATM   28  H1  UNL     1      10.496  -1.746   0.101  1.00  0.00           H  
HETATM   29  H2  UNL     1      11.009  -0.269   1.005  1.00  0.00           H  
HETATM   30  H3  UNL     1      11.881  -0.747  -0.547  1.00  0.00           H  
HETATM   31  H4  UNL     1       9.850  -0.359  -1.793  1.00  0.00           H  
HETATM   32  H5  UNL     1      10.296   1.147  -0.920  1.00  0.00           H  
HETATM   33  H6  UNL     1       8.667   0.015   1.017  1.00  0.00           H  
HETATM   34  H7  UNL     1       8.330  -1.110  -0.318  1.00  0.00           H  
HETATM   35  H8  UNL     1       7.375   0.681  -1.675  1.00  0.00           H  
HETATM   36  H9  UNL     1       7.888   1.912  -0.455  1.00  0.00           H  
HETATM   37  H10 UNL     1       5.620   1.609  -0.009  1.00  0.00           H  
HETATM   38  H11 UNL     1       6.564   0.919   1.285  1.00  0.00           H  
HETATM   39  H12 UNL     1       4.807  -0.629   0.994  1.00  0.00           H  
HETATM   40  H13 UNL     1       6.247  -1.394   0.241  1.00  0.00           H  
HETATM   41  H14 UNL     1       4.356  -1.647  -1.217  1.00  0.00           H  
HETATM   42  H15 UNL     1       5.801  -0.758  -1.893  1.00  0.00           H  
HETATM   43  H16 UNL     1       4.793   1.340  -1.766  1.00  0.00           H  
HETATM   44  H17 UNL     1       3.768   0.255  -2.688  1.00  0.00           H  
HETATM   45  H18 UNL     1       3.254   0.786   0.276  1.00  0.00           H  
HETATM   46  H19 UNL     1       2.647   1.946  -0.977  1.00  0.00           H  
HETATM   47  H20 UNL     1       0.739   0.523  -1.260  1.00  0.00           H  
HETATM   48  H21 UNL     1       1.883  -0.693  -1.861  1.00  0.00           H  
HETATM   49  H22 UNL     1       2.034  -1.725   0.328  1.00  0.00           H  
HETATM   50  H23 UNL     1       0.377  -1.420  -0.173  1.00  0.00           H  
HETATM   51  H24 UNL     1       0.779  -0.821   2.234  1.00  0.00           H  
HETATM   52  H25 UNL     1       1.760   0.582   1.678  1.00  0.00           H  
HETATM   53  H26 UNL     1      -0.082   1.397   0.374  1.00  0.00           H  
HETATM   54  H27 UNL     1      -0.294   1.319   2.132  1.00  0.00           H  
HETATM   55  H28 UNL     1      -1.739  -0.402   2.270  1.00  0.00           H  
HETATM   56  H29 UNL     1      -1.323  -1.244   0.794  1.00  0.00           H  
HETATM   57  H30 UNL     1      -3.564   0.302   1.128  1.00  0.00           H  
HETATM   58  H31 UNL     1      -2.566   1.495   0.260  1.00  0.00           H  
HETATM   59  H32 UNL     1      -2.734  -1.342  -0.738  1.00  0.00           H  
HETATM   60  H33 UNL     1      -2.068   0.166  -1.576  1.00  0.00           H  
HETATM   61  H34 UNL     1      -6.278   1.045   0.816  1.00  0.00           H  
HETATM   62  H35 UNL     1      -5.885   0.863  -0.919  1.00  0.00           H  
HETATM   63  H36 UNL     1      -8.265   1.460  -0.632  1.00  0.00           H  
HETATM   64  H37 UNL     1      -7.981  -0.211  -1.309  1.00  0.00           H  
HETATM   65  H38 UNL     1     -10.635  -0.586   1.067  1.00  0.00           H  
HETATM   66  H39 UNL     1     -10.340   0.959   0.057  1.00  0.00           H  
HETATM   67  H40 UNL     1     -10.092  -0.655  -0.682  1.00  0.00           H  
HETATM   68  H41 UNL     1      -8.185  -2.009  -0.311  1.00  0.00           H  
HETATM   69  H42 UNL     1      -7.614  -1.911   1.427  1.00  0.00           H  
HETATM   70  H43 UNL     1      -9.341  -2.111   1.046  1.00  0.00           H  
HETATM   71  H44 UNL     1      -8.392   1.489   1.962  1.00  0.00           H  
HETATM   72  H45 UNL     1      -7.399  -0.003   2.338  1.00  0.00           H  
HETATM   73  H46 UNL     1      -9.144  -0.044   2.664  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3   31   32
CONECT    3    4   33   34
CONECT    4    5   35   36
CONECT    5    6   37   38
CONECT    6    7   39   40
CONECT    7    8   41   42
CONECT    8    9   43   44
CONECT    9   10   45   46
CONECT   10   11   47   48
CONECT   11   12   49   50
CONECT   12   13   51   52
CONECT   13   14   53   54
CONECT   14   15   55   56
CONECT   15   16   57   58
CONECT   16   17   59   60
CONECT   17   18
CONECT   18   19   19   20   21
CONECT   21   22
CONECT   22   23   61   62
CONECT   23   24   63   64
CONECT   24   25   26   27
CONECT   25   65   66   67
CONECT   26   68   69   70
CONECT   27   71   72   73
END

HMDB0254735
     RDKit          3D
Miltefosine
 73 72  0  0  0  0  0  0  0  0999 V2000
   10.9296   -0.7751   -0.0242 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9368    0.1393   -0.7775 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6347   -0.0263   -0.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5295    0.8822   -0.6052 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2904    0.7094    0.1783 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5027   -0.5246    0.1919 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9051   -0.7332   -1.2282 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1072    0.4715   -1.5756 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8809    0.8706   -0.8805 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6623    0.0141   -0.9454 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3604   -0.9416    0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0136   -0.1424    1.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2593    0.6817    1.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4210   -0.1864    1.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6739    0.4293    0.5463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7824   -0.3047   -0.8375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0928    0.1814   -1.1705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9391   -1.3105   -0.9538 P   0  0  0  0  0  5  0  0  0  0  0  0
   -4.0799   -2.3627   -0.3093 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6017   -1.8059   -2.4388 O   0  0  0  0  0  1  0  0  0  0  0  0
   -6.2487   -0.9242    0.0265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4428    0.5167   -0.1024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9805    0.4774   -0.3787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6539   -0.1562    0.6787 N   0  0  0  0  0  4  0  0  0  0  0  0
  -10.0835   -0.0865    0.3053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3920   -1.6006    0.7222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4019    0.3909    1.9659 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4965   -1.7458    0.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0093   -0.2687    1.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8815   -0.7472   -0.5471 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8504   -0.3589   -1.7930 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2957    1.1472   -0.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6672    0.0149    1.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3296   -1.1103   -0.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3755    0.6811   -1.6751 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8877    1.9119   -0.4552 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6195    1.6093   -0.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5641    0.9189    1.2845 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8074   -0.6288    0.9938 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2467   -1.3944    0.2409 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3559   -1.6467   -1.2166 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8010   -0.7579   -1.8927 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7931    1.3402   -1.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7678    0.2547   -2.6881 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2537    0.7855    0.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6469    1.9459   -0.9770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7387    0.5233   -1.2603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8832   -0.6931   -1.8611 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0339   -1.7248    0.3275 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3769   -1.4199   -0.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7793   -0.8208    2.2338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7597    0.5816    1.6776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0824    1.3969    0.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2937    1.3192    2.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7386   -0.4023    2.2696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3232   -1.2437    0.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5641    0.3017    1.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5663    1.4947    0.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7335   -1.3417   -0.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0685    0.1663   -1.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2778    1.0445    0.8162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8852    0.8632   -0.9186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2649    1.4596   -0.6321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9806   -0.2105   -1.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6354   -0.5857    1.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3397    0.9593    0.0571 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0924   -0.6550   -0.6816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1851   -2.0088   -0.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6139   -1.9115    1.4268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3407   -2.1114    1.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3920    1.4894    1.9622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3990   -0.0035    2.3382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1441   -0.0437    2.6636 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
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  6 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  0
  8 44  1  0
  9 45  1  0
  9 46  1  0
 10 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  0
 12 52  1  0
 13 53  1  0
 13 54  1  0
 14 55  1  0
 14 56  1  0
 15 57  1  0
 15 58  1  0
 16 59  1  0
 16 60  1  0
 22 61  1  0
 22 62  1  0
 23 63  1  0
 23 64  1  0
 25 65  1  0
 25 66  1  0
 25 67  1  0
 26 68  1  0
 26 69  1  0
 26 70  1  0
 27 71  1  0
 27 72  1  0
 27 73  1  0
M  CHG  2  20  -1  24   1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Hexadecylphosphocholine	ChEBI
Hexadecylphosphorylcholine	ChEBI
Miltefosina	ChEBI
Miltefosinum	ChEBI
Monohexadecylphosphocholine	ChEBI
Monohexadecylphosphorylcholine	ChEBI
Impavido	Kegg
HDPC	MeSH
Miltex	MeSH
N-Hexadecylphosphorylcholine	MeSH

Chemical Formula

C₂₁H₄₆NO₄P

Average Molecular Weight

407.576

Monoisotopic Molecular Weight

407.316445963

IUPAC Name

hexadecyl 2-(trimethylazaniumyl)ethyl phosphate

Traditional Name

miltex

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCCOP([O-])(=O)OCC[N+](C)(C)C

InChI Identifier

InChI=1S/C21H46NO4P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-20-25-27(23,24)26-21-19-22(2,3)4/h5-21H2,1-4H3

InChI Key

PQLXHQMOHUQAKB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phosphocholines. Phosphocholines are compounds containing a [2-(trimethylazaniumyl)ethoxy]phosphonic acid or derivative.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Quaternary ammonium salts

Direct Parent

Phosphocholines

Alternative Parents

Substituents

Phosphocholine
Dialkyl phosphate
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Tetraalkylammonium salt
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Organooxygen compound
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

phosphocholines (CHEBI:75283 )
phospholipid (CHEBI:75283 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0254735)

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	2.68	ALOGPS
logP	2.25	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	1.88	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	58.59 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	125.51 m³·mol⁻¹	ChemAxon
Polarizability	50.58 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	204.92	30932474
DeepCCS	[M-H]-	201.319	30932474
DeepCCS	[M-2H]-	237.443	30932474
DeepCCS	[M+Na]+	213.735	30932474
AllCCS	[M+H]+	215.6	32859911
AllCCS	[M+H-H2O]+	213.7	32859911
AllCCS	[M+NH4]+	217.4	32859911
AllCCS	[M+Na]+	217.9	32859911
AllCCS	[M-H]-	210.7	32859911
AllCCS	[M+Na-2H]-	212.5	32859911
AllCCS	[M+HCOO]-	214.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Miltefosine	CCCCCCCCCCCCCCCCOP([O-])(=O)OCC[N+](C)(C)C	3010.9	Standard polar	33892256
Miltefosine	CCCCCCCCCCCCCCCCOP([O-])(=O)OCC[N+](C)(C)C	2515.3	Standard non polar	33892256
Miltefosine	CCCCCCCCCCCCCCCCOP([O-])(=O)OCC[N+](C)(C)C	2700.1	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 - Miltefosine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dj-9432000000-642b57f37f036f7f50c3	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Miltefosine 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 - Miltefosine 10V, Positive-QTOF	splash10-0550-9061400000-e095141ca899b073c533	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Miltefosine 20V, Positive-QTOF	splash10-004i-5690000000-7d225d53e68dce85d25b	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Miltefosine 40V, Positive-QTOF	splash10-000i-9410000000-f258e2588380399fafa5	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Miltefosine 10V, Negative-QTOF	splash10-0a4i-0003900000-1691b838c8f926e3c434	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Miltefosine 20V, Negative-QTOF	splash10-0kor-2019200000-4631320f9dcefaac10a7	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Miltefosine 40V, Negative-QTOF	splash10-004i-9011000000-f7696a7826d1d702049d	2019-02-23	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

DB09031

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3473

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Miltefosine

METLIN ID

Not Available

PubChem Compound

3599

PDB ID

Not Available

ChEBI ID

75283

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 ]

Enzymes

Enzyme Details

1. Phospholipid-transporting ATPase ABCA3

General function:: Not Available
Specific function:: Catalyzes the ATP-dependent transport of phospholipids such as phosphatidylcholine and phosphoglycerol from the cytoplasm into the lumen side of lamellar bodies, in turn participates in the lamellar bodies biogenesis and homeostasis of pulmonary surfactant (PubMed:16959783, PubMed:17574245, PubMed:28887056, PubMed:31473345, PubMed:27177387). Transports preferentially phosphatidylcholine containing short acyl chains (PubMed:27177387). In addition plays a role as an efflux transporter of miltefosine across macrophage membranes and free cholesterol (FC) through intralumenal vesicles by removing FC from the cell as a component of surfactant and protects cells from free cholesterol toxicity (PubMed:26903515, PubMed:25817392, PubMed:27177387).
Gene Name:: ABCA3
Uniprot ID:: Q99758
Molecular weight:: 191360.235

Showing metabocard for Miltefosine (HMDB0254735)

MOL for HMDB0254735 (Miltefosine)

3D MOL for HMDB0254735 (Miltefosine)

3D SDF for HMDB0254735 (Miltefosine)

3D-SDF for HMDB0254735 (Miltefosine)

PDB for HMDB0254735 (Miltefosine)

3D PDB for HMDB0254735 (Miltefosine)

SMILES for HMDB0254735 (Miltefosine)

INCHI for HMDB0254735 (Miltefosine)

Structure for HMDB0254735 (Miltefosine)

3D Structure for HMDB0254735 (Miltefosine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes