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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (10) Show 10 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2007-05-23 11:19:36 UTC

Update Date

2021-09-14 14:59:29 UTC

HMDB ID

HMDB0006482

Secondary Accession Numbers

HMDB0012083
HMDB06482
HMDB12083

Metabolite Identification

Common Name

LysoSM(d18:1)

Description

D-erythro-sphingosylphosphorylcholine is an intermediate in Sphingolipid metabolism. D-erythro-sphingosylphosphorylcholine is the 5th to last step in the synthesis of Digalactosylceramidesulfate and is converted from Sphingosine via the enzyme sphingosine cholinephosphotransferase ( EC 2.7.8.10). It is then converted to Sphingomyelin via the enzyme sphingosine N-acyltransferase (EC 2.3.1.24).

Structure

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


  Mrv0541 02231220402D          

 31 30  0  0  1  0            999 V2000
    3.8225   -9.9687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5383   -9.5586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2514   -9.9734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9672   -9.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6804   -9.9780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3962   -9.5679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1093   -9.9827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8251   -9.5725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5382   -9.9873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2541   -9.5772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9672   -9.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6830   -9.5818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3961   -9.9966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1119   -9.5865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8250  -10.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5408   -9.5911    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.2540  -10.0059    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.9698   -9.5957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5435   -8.7661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2513  -10.8309    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6829  -10.0106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3987   -9.6004    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   18.1118  -10.0152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4014   -8.7755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4075  -10.5325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8277   -9.6051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5408  -10.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2566   -9.6098    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   19.5434   -9.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9697  -10.0246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2593   -8.7848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  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  2  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
 16 19  1  1  0  0  0
 17 20  1  6  0  0  0
 21 18  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 22  2  0  0  0  0
 25 22  1  0  0  0  0
 26 23  1  0  0  0  0
 27 26  1  0  0  0  0
 28 27  1  0  0  0  0
 30 28  1  0  0  0  0
 31 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  CHG  1  28   1
M  END

     RDKit          3D

 81 80  0  0  0  0  0  0  0  0999 V2000
   10.8731    0.3289    0.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4830    0.8757    0.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4678    0.2389   -0.6031 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3629   -1.2435   -0.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9640   -1.7022    0.9253 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7100   -1.2350    1.5011 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3916   -1.4933    0.8958 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0916   -0.8963   -0.4186 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6679   -1.2536   -0.8656 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4313   -0.6221   -2.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5654    0.8839   -2.1826 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5890    1.5000   -1.2275 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1471    1.2162   -1.5579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3373    1.9183   -0.4970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4820    1.2820    0.3137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2808    1.9768    1.3606 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0634    2.9852    0.8222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1025    0.9883    2.1393 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7672    1.6889    3.2192 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1128    0.3067    1.2399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9933    1.2463    0.6754 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0998    0.4783   -0.3125 P   0  0  2  0  0  5  0  0  0  0  0  0
   -4.9518   -1.0127   -0.2899 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9369    1.0283   -1.9062 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6967    0.8587    0.1687 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5312   -0.2594    0.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9052    0.1535    0.4709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8641   -0.9236    0.3746 N   0  0  2  0  0  4  0  0  0  0  0  0
  -10.2836   -1.1449   -0.9798 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0244   -0.5655    1.1641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3386   -2.1648    0.9428 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9576   -0.2921   -0.7981 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6300    1.1466    0.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1579   -0.2223    1.0352 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5076    1.9593    0.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1349    0.7839    1.3625 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4890    0.6943   -0.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6836    0.4519   -1.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4238   -1.6991   -0.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7788   -1.6978   -1.2073 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8707   -2.8472    0.8355 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8118   -1.6265    1.6769 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6990   -1.6202    2.5961 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7354   -0.0831    1.6719 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1470   -2.6119    0.9120 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6201   -1.0971    1.6479 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7447   -1.0896   -1.2603 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0491    0.2321   -0.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6257   -2.3458   -1.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9100   -0.9172   -0.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0875   -1.0628   -2.9965 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3819   -0.8538   -2.5113 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6001    1.2301   -2.0070 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3298    1.2464   -3.2245 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7867    1.1098   -0.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7404    2.6157   -1.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9634    0.1244   -1.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8724    1.5839   -2.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4475    2.9834   -0.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5723    0.2206    0.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5964    2.4720    2.0974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8631    3.1824    1.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4549    0.2113    2.5603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8814    1.1038    4.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2736    2.5631    3.4742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7111   -0.4176    1.8293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5865   -0.1829    0.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3980    1.8985   -1.9630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5218   -0.5909   -1.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1082   -1.0469    0.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8249    0.5315    1.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2494    0.9663   -0.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3443   -2.2471   -1.1778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5377   -0.7070   -1.7036 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2975   -0.7506   -1.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3027    0.4816    0.9234 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8513   -1.2790    0.9796 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7197   -0.6029    2.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5913   -2.5919    0.2549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9233   -1.9196    1.9376 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2246   -2.8278    1.0780 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  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 22 21  1  1
 22 23  2  0
 22 24  1  0
 22 25  1  0
 25 26  1  0
 26 27  1  0
 28 27  1  6
 28 29  1  0
 28 30  1  0
 28 31  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  4 40  1  0
  5 41  1  0
  5 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
 10 51  1  0
 10 52  1  0
 11 53  1  0
 11 54  1  0
 12 55  1  0
 12 56  1  0
 13 57  1  0
 13 58  1  0
 14 59  1  0
 15 60  1  0
 16 61  1  1
 17 62  1  0
 18 63  1  1
 19 64  1  0
 19 65  1  0
 20 66  1  0
 20 67  1  0
 24 68  1  0
 26 69  1  0
 26 70  1  0
 27 71  1  0
 27 72  1  0
 29 73  1  0
 29 74  1  0
 29 75  1  0
 30 76  1  0
 30 77  1  0
 30 78  1  0
 31 79  1  0
 31 80  1  0
 31 81  1  0
M  CHG  1  28   1
M  END


  Mrv0541 02231220402D          

 31 30  0  0  1  0            999 V2000
    3.8225   -9.9687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5383   -9.5586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2514   -9.9734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9672   -9.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6804   -9.9780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3962   -9.5679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1093   -9.9827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8251   -9.5725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5382   -9.9873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2541   -9.5772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9672   -9.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6830   -9.5818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3961   -9.9966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1119   -9.5865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8250  -10.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5408   -9.5911    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.2540  -10.0059    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.9698   -9.5957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5435   -8.7661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2513  -10.8309    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6829  -10.0106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3987   -9.6004    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   18.1118  -10.0152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4014   -8.7755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4075  -10.5325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8277   -9.6051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5408  -10.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2566   -9.6098    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   19.5434   -9.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9697  -10.0246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2593   -8.7848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  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  2  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
 16 19  1  1  0  0  0
 17 20  1  6  0  0  0
 21 18  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 22  2  0  0  0  0
 25 22  1  0  0  0  0
 26 23  1  0  0  0  0
 27 26  1  0  0  0  0
 28 27  1  0  0  0  0
 30 28  1  0  0  0  0
 31 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  CHG  1  28   1
M  END
> <DATABASE_ID>
HMDB0006482

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)COP(=O)(O)OCC[N+](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C23H49N2O5P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(26)22(24)21-30-31(27,28)29-20-19-25(2,3)4/h17-18,22-23,26H,5-16,19-21,24H2,1-4H3/p+1/b18-17+/t22-,23+/m0/s1

> <INCHI_KEY>
JLVSPVFPBBFMBE-HXSWCURESA-O

> <FORMULA>
C23H50N2O5P

> <MOLECULAR_WEIGHT>
465.6273

> <EXACT_MASS>
465.345734232

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
55.36941130539543

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2S,3R,4E)-2-amino-3-hydroxyoctadec-4-en-1-yl]oxy}[2-(trimethylazaniumyl)ethoxy]phosphinic acid

> <ALOGPS_LOGP>
1.30

> <JCHEM_LOGP>
-0.24399170122373512

> <ALOGPS_LOGS>
-5.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.172461063244366

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8297435476134112

> <JCHEM_PKA_STRONGEST_BASIC>
9.679422059619888

> <JCHEM_POLAR_SURFACE_AREA>
102.01

> <JCHEM_REFRACTIVITY>
141.17989999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
21

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.42e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lysosphingomyelin

> <JCHEM_VEBER_RULE>
0

$$$$

https://cactus.nci.nih.gov/chemical/structure/CCCCCCCCCCCCC%5CC=C%5C%5BC@@H%5...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:80})
 81 80  0  0  0  0  0  0  0  0999 V2000
   15.2944   -2.8520   -0.1664 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9250   -2.7222   -0.8364 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0122   -1.8548    0.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6429   -1.7250   -0.6373 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7301   -0.8575    0.2318 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3607   -0.7278   -0.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4479    0.1397    0.4310 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0785    0.2695   -0.2391 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1657    1.1369    0.6300 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7963    1.2667   -0.0400 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8836    2.1341    0.8291 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5142    2.2639    0.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6014    3.1313    1.0282 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2527    3.2591    0.3683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8318    2.9280    1.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1805    3.0557    0.3647 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7698    3.8104    0.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0084    3.4438   -0.9999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9071    1.7106    0.4245 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3179    0.9559   -0.0963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0841    1.3116    1.8272 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2766    1.8404   -0.2455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9066    0.5588   -0.2936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3646    0.3220   -0.9342 P   0  0  1  0  0  0  0  0  0  0  0  0
   -7.3408    1.2263   -0.2866 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3133    0.6300   -2.5137 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8119   -1.2069   -0.6998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1018   -1.7045   -1.0611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1944   -3.1891   -0.7029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1474   -3.3443    0.7572 N   0  3  0  0  0  0  0  0  0  0  0  0
   -9.1936   -2.5161    1.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3700   -4.7536    1.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8317   -2.9186    1.2528 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7369   -1.8627   -0.0494 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.1772   -3.3157    0.8131 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.9447   -3.4699   -0.7855 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.0422   -2.2584   -1.8158 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.4826   -3.7114   -0.9534 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.8951   -2.3185    1.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.4547   -0.8655    0.1497 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7601   -1.2612   -1.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2004   -2.7142   -0.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6129   -1.3213    1.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1725    0.1317    0.3488 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4779   -0.2640   -1.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9182   -1.7170   -0.5552 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3307   -0.3241    1.4103 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8904    1.1289    0.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1957    0.7332   -1.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6360   -0.7198   -0.3561 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0485    0.6731    1.6094 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6082    2.1261    0.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9135    1.7304   -1.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3539    0.2774   -0.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7665    1.6703    1.8085 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3260    3.1234    0.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6314    2.7276   -0.8203 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0717    1.2746    0.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4842    2.6676    2.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0438    4.1206    1.1452 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1799    3.6239   -0.6456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7590    2.5632    2.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4921    2.8170   -1.5249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6276    1.9956    2.3319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5038    0.3964    1.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8974    2.5292    0.3274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1505    2.2216   -1.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6927    0.0729   -3.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8693   -1.1515   -0.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2522   -1.5794   -2.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1318   -3.5964   -1.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3578   -3.7241   -1.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1698   -2.8319    1.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1587   -2.6313    2.4549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0284   -1.4704    1.1119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5938   -5.3681    0.6512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3352   -4.8688    2.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3463   -5.0694    0.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7457   -1.8351    1.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7238   -3.2136    2.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0494   -3.3913    0.6590 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  2  3  1  0  0  0  0
  2 37  1  0  0  0  0
  2 38  1  0  0  0  0
  3  4  1  0  0  0  0
  3 39  1  0  0  0  0
  3 40  1  0  0  0  0
  4  5  1  0  0  0  0
  4 41  1  0  0  0  0
  4 42  1  0  0  0  0
  5  6  1  0  0  0  0
  5 43  1  0  0  0  0
  5 44  1  0  0  0  0
  6  7  1  0  0  0  0
  6 45  1  0  0  0  0
  6 46  1  0  0  0  0
  7  8  1  0  0  0  0
  7 47  1  0  0  0  0
  7 48  1  0  0  0  0
  8  9  1  0  0  0  0
  8 49  1  0  0  0  0
  8 50  1  0  0  0  0
  9 10  1  0  0  0  0
  9 51  1  0  0  0  0
  9 52  1  0  0  0  0
 10 11  1  0  0  0  0
 10 53  1  0  0  0  0
 10 54  1  0  0  0  0
 11 12  1  0  0  0  0
 11 55  1  0  0  0  0
 11 56  1  0  0  0  0
 12 13  1  0  0  0  0
 12 57  1  0  0  0  0
 12 58  1  0  0  0  0
 13 14  1  0  0  0  0
 13 59  1  0  0  0  0
 13 60  1  0  0  0  0
 14 15  2  0  0  0  0
 14 61  1  0  0  0  0
 15 16  1  0  0  0  0
 15 62  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 18 63  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 21 64  1  0  0  0  0
 21 65  1  0  0  0  0
 22 23  1  0  0  0  0
 22 66  1  0  0  0  0
 22 67  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  1  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 26 68  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 69  1  0  0  0  0
 28 70  1  0  0  0  0
 29 30  1  0  0  0  0
 29 71  1  0  0  0  0
 29 72  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 31 73  1  0  0  0  0
 31 74  1  0  0  0  0
 31 75  1  0  0  0  0
 32 76  1  0  0  0  0
 32 77  1  0  0  0  0
 32 78  1  0  0  0  0
 33 79  1  0  0  0  0
 33 80  1  0  0  0  0
 33 81  1  0  0  0  0
M  CHG  1  30   1
M  END
$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       7.135 -18.608   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.471 -17.843   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.803 -18.617   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.139 -17.851   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.470 -18.626   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.806 -17.860   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.137 -18.634   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.474 -17.869   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.805 -18.643   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      19.141 -17.877   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      20.472 -18.652   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.808 -17.886   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.139 -18.660   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      24.476 -17.895   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      25.807 -18.669   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      27.143 -17.903   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      28.474 -18.678   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      29.810 -17.912   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      27.148 -16.363   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0      28.469 -20.218   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0      31.141 -18.686   0.000  0.00  0.00           O+0
HETATM   22  P   UNK     0      32.478 -17.921   0.000  0.00  0.00           P+0
HETATM   23  O   UNK     0      33.809 -18.695   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      32.483 -16.381   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      32.494 -19.661   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      35.145 -17.930   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      36.476 -18.704   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0      37.812 -17.938   0.000  0.00  0.00           N+1
HETATM   29  C   UNK     0      36.481 -17.164   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      39.143 -18.713   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      37.817 -16.398   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    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   19                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   21                                                       
CONECT   19   16                                                            
CONECT   20   17                                                            
CONECT   21   18   22                                                       
CONECT   22   21   23   24   25                                             
CONECT   23   22   26                                                       
CONECT   24   22                                                            
CONECT   25   22                                                            
CONECT   26   23   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   30   31   29                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   60    0
END

COMPND    https://cactus.nci.nih.gov/chemical/structure/CCCCCCCCCCCCC%5CC=C%5C%5BC@@H%5... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  C   UNL     1      15.294  -2.852  -0.166  1.00  0.00           C  
HETATM    2  C   UNL     1      13.925  -2.722  -0.836  1.00  0.00           C  
HETATM    3  C   UNL     1      13.012  -1.855   0.033  1.00  0.00           C  
HETATM    4  C   UNL     1      11.643  -1.725  -0.637  1.00  0.00           C  
HETATM    5  C   UNL     1      10.730  -0.858   0.232  1.00  0.00           C  
HETATM    6  C   UNL     1       9.361  -0.728  -0.438  1.00  0.00           C  
HETATM    7  C   UNL     1       8.448   0.140   0.431  1.00  0.00           C  
HETATM    8  C   UNL     1       7.079   0.270  -0.239  1.00  0.00           C  
HETATM    9  C   UNL     1       6.166   1.137   0.630  1.00  0.00           C  
HETATM   10  C   UNL     1       4.796   1.267  -0.040  1.00  0.00           C  
HETATM   11  C   UNL     1       3.884   2.134   0.829  1.00  0.00           C  
HETATM   12  C   UNL     1       2.514   2.264   0.159  1.00  0.00           C  
HETATM   13  C   UNL     1       1.601   3.131   1.028  1.00  0.00           C  
HETATM   14  C   UNL     1       0.253   3.259   0.368  1.00  0.00           C  
HETATM   15  C   UNL     1      -0.832   2.928   1.025  1.00  0.00           C  
HETATM   16  C   UNL     1      -2.180   3.056   0.365  1.00  0.00           C  
HETATM   17  H   UNL     1      -2.770   3.810   0.885  1.00  0.00           H  
HETATM   18  O   UNL     1      -2.008   3.444  -1.000  1.00  0.00           O  
HETATM   19  C   UNL     1      -2.907   1.711   0.424  1.00  0.00           C  
HETATM   20  H   UNL     1      -2.318   0.956  -0.096  1.00  0.00           H  
HETATM   21  N   UNL     1      -3.084   1.312   1.827  1.00  0.00           N  
HETATM   22  C   UNL     1      -4.277   1.840  -0.245  1.00  0.00           C  
HETATM   23  O   UNL     1      -4.907   0.559  -0.294  1.00  0.00           O  
HETATM   24  P   UNL     1      -6.365   0.322  -0.934  1.00  0.00           P  
HETATM   25  O   UNL     1      -7.341   1.226  -0.287  1.00  0.00           O  
HETATM   26  O   UNL     1      -6.313   0.630  -2.514  1.00  0.00           O  
HETATM   27  O   UNL     1      -6.812  -1.207  -0.700  1.00  0.00           O  
HETATM   28  C   UNL     1      -8.102  -1.704  -1.061  1.00  0.00           C  
HETATM   29  C   UNL     1      -8.194  -3.189  -0.703  1.00  0.00           C  
HETATM   30  N   UNL     1      -8.147  -3.344   0.757  1.00  0.00           N1+
HETATM   31  C   UNL     1      -9.194  -2.516   1.372  1.00  0.00           C  
HETATM   32  C   UNL     1      -8.370  -4.754   1.107  1.00  0.00           C  
HETATM   33  C   UNL     1      -6.832  -2.919   1.253  1.00  0.00           C  
HETATM   34  H   UNL     1      15.737  -1.863  -0.049  1.00  0.00           H  
HETATM   35  H   UNL     1      15.177  -3.316   0.813  1.00  0.00           H  
HETATM   36  H   UNL     1      15.945  -3.470  -0.785  1.00  0.00           H  
HETATM   37  H   UNL     1      14.042  -2.258  -1.816  1.00  0.00           H  
HETATM   38  H   UNL     1      13.483  -3.711  -0.953  1.00  0.00           H  
HETATM   39  H   UNL     1      12.895  -2.318   1.012  1.00  0.00           H  
HETATM   40  H   UNL     1      13.455  -0.866   0.150  1.00  0.00           H  
HETATM   41  H   UNL     1      11.760  -1.261  -1.617  1.00  0.00           H  
HETATM   42  H   UNL     1      11.200  -2.714  -0.754  1.00  0.00           H  
HETATM   43  H   UNL     1      10.613  -1.321   1.211  1.00  0.00           H  
HETATM   44  H   UNL     1      11.172   0.132   0.349  1.00  0.00           H  
HETATM   45  H   UNL     1       9.478  -0.264  -1.418  1.00  0.00           H  
HETATM   46  H   UNL     1       8.918  -1.717  -0.555  1.00  0.00           H  
HETATM   47  H   UNL     1       8.331  -0.324   1.410  1.00  0.00           H  
HETATM   48  H   UNL     1       8.890   1.129   0.548  1.00  0.00           H  
HETATM   49  H   UNL     1       7.196   0.733  -1.218  1.00  0.00           H  
HETATM   50  H   UNL     1       6.636  -0.720  -0.356  1.00  0.00           H  
HETATM   51  H   UNL     1       6.048   0.673   1.609  1.00  0.00           H  
HETATM   52  H   UNL     1       6.608   2.126   0.747  1.00  0.00           H  
HETATM   53  H   UNL     1       4.913   1.730  -1.019  1.00  0.00           H  
HETATM   54  H   UNL     1       4.354   0.277  -0.157  1.00  0.00           H  
HETATM   55  H   UNL     1       3.767   1.670   1.808  1.00  0.00           H  
HETATM   56  H   UNL     1       4.326   3.123   0.946  1.00  0.00           H  
HETATM   57  H   UNL     1       2.631   2.728  -0.820  1.00  0.00           H  
HETATM   58  H   UNL     1       2.072   1.275   0.042  1.00  0.00           H  
HETATM   59  H   UNL     1       1.484   2.668   2.008  1.00  0.00           H  
HETATM   60  H   UNL     1       2.044   4.121   1.145  1.00  0.00           H  
HETATM   61  H   UNL     1       0.180   3.624  -0.646  1.00  0.00           H  
HETATM   62  H   UNL     1      -0.759   2.563   2.038  1.00  0.00           H  
HETATM   63  H   UNL     1      -1.492   2.817  -1.525  1.00  0.00           H  
HETATM   64  H   UNL     1      -3.628   1.996   2.332  1.00  0.00           H  
HETATM   65  H   UNL     1      -3.504   0.396   1.893  1.00  0.00           H  
HETATM   66  H   UNL     1      -4.897   2.529   0.327  1.00  0.00           H  
HETATM   67  H   UNL     1      -4.151   2.222  -1.259  1.00  0.00           H  
HETATM   68  H   UNL     1      -5.693   0.073  -3.003  1.00  0.00           H  
HETATM   69  H   UNL     1      -8.869  -1.151  -0.520  1.00  0.00           H  
HETATM   70  H   UNL     1      -8.252  -1.579  -2.133  1.00  0.00           H  
HETATM   71  H   UNL     1      -9.132  -3.596  -1.082  1.00  0.00           H  
HETATM   72  H   UNL     1      -7.358  -3.724  -1.152  1.00  0.00           H  
HETATM   73  H   UNL     1     -10.170  -2.832   1.004  1.00  0.00           H  
HETATM   74  H   UNL     1      -9.159  -2.631   2.455  1.00  0.00           H  
HETATM   75  H   UNL     1      -9.028  -1.470   1.112  1.00  0.00           H  
HETATM   76  H   UNL     1      -7.594  -5.368   0.651  1.00  0.00           H  
HETATM   77  H   UNL     1      -8.335  -4.869   2.191  1.00  0.00           H  
HETATM   78  H   UNL     1      -9.346  -5.069   0.740  1.00  0.00           H  
HETATM   79  H   UNL     1      -6.746  -1.835   1.171  1.00  0.00           H  
HETATM   80  H   UNL     1      -6.724  -3.214   2.297  1.00  0.00           H  
HETATM   81  H   UNL     1      -6.049  -3.391   0.659  1.00  0.00           H  
CONECT    1    2   34   35   36                                       
CONECT    2    1    3   37   38                                       
CONECT    3    2    4   39   40                                       
CONECT    4    3    5   41   42                                       
CONECT    5    4    6   43   44                                       
CONECT    6    5    7   45   46                                       
CONECT    7    6    8   47   48                                       
CONECT    8    7    9   49   50                                       
CONECT    9    8   10   51   52                                       
CONECT   10    9   11   53   54                                       
CONECT   11   10   12   55   56                                       
CONECT   12   11   13   57   58                                       
CONECT   13   12   14   59   60                                       
CONECT   14   13   15   15   61                                       
CONECT   15   14   14   16   62                                       
CONECT   16   15   17   18   19                                       
CONECT   17   16                                                      
CONECT   18   16   63                                                 
CONECT   19   16   20   21   22                                       
CONECT   20   19                                                      
CONECT   21   19   64   65                                            
CONECT   22   19   23   66   67                                       
CONECT   23   22   24                                                 
CONECT   24   23   25   25   26                                       
CONECT   24   27                                                      
CONECT   25   24   24                                                 
CONECT   26   24   68                                                 
CONECT   27   24   28                                                 
CONECT   28   27   29   69   70                                       
CONECT   29   28   30   71   72                                       
CONECT   30   29   31   32   33                                       
CONECT   31   30   73   74   75                                       
CONECT   32   30   76   77   78                                       
CONECT   33   30   79   80   81                                       
CONECT   34    1                                                      
CONECT   35    1                                                      
CONECT   36    1                                                      
CONECT   37    2                                                      
CONECT   38    2                                                      
CONECT   39    3                                                      
CONECT   40    3                                                      
CONECT   41    4                                                      
CONECT   42    4                                                      
CONECT   43    5                                                      
CONECT   44    5                                                      
CONECT   45    6                                                      
CONECT   46    6                                                      
CONECT   47    7                                                      
CONECT   48    7                                                      
CONECT   49    8                                                      
CONECT   50    8                                                      
CONECT   51    9                                                      
CONECT   52    9                                                      
CONECT   53   10                                                      
CONECT   54   10                                                      
CONECT   55   11                                                      
CONECT   56   11                                                      
CONECT   57   12                                                      
CONECT   58   12                                                      
CONECT   59   13                                                      
CONECT   60   13                                                      
CONECT   61   14                                                      
CONECT   62   15                                                      
CONECT   63   18                                                      
CONECT   64   21                                                      
CONECT   65   21                                                      
CONECT   66   22                                                      
CONECT   67   22                                                      
CONECT   68   26                                                      
CONECT   69   28                                                      
CONECT   70   28                                                      
CONECT   71   29                                                      
CONECT   72   29                                                      
CONECT   73   31                                                      
CONECT   74   31                                                      
CONECT   75   31                                                      
CONECT   76   32                                                      
CONECT   77   32                                                      
CONECT   78   32                                                      
CONECT   79   33                                                      
CONECT   80   33                                                      
CONECT   81   33                                                      
MASTER        0    0    0    0    0    0    0    0   81    0   81    0
END

https://cactus.nci.nih.gov/chemical/structure/CCCCCCCCCCCCC%5CC=C%5C%5BC@@H%5...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:80})
 81 80  0  0  0  0  0  0  0  0999 V2000
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   13.9250   -2.7222   -0.8364 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0122   -1.8548    0.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6429   -1.7250   -0.6373 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7301   -0.8575    0.2318 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3607   -0.7278   -0.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1657    1.1369    0.6300 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7963    1.2667   -0.0400 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8836    2.1341    0.8291 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6014    3.1313    1.0282 C   0  0  0  0  0  0  0  0  0  0  0  0
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 18 63  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
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 22 23  1  0  0  0  0
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 23 24  1  0  0  0  0
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 29 71  1  0  0  0  0
 29 72  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 31 73  1  0  0  0  0
 31 74  1  0  0  0  0
 31 75  1  0  0  0  0
 32 76  1  0  0  0  0
 32 77  1  0  0  0  0
 32 78  1  0  0  0  0
 33 79  1  0  0  0  0
 33 80  1  0  0  0  0
 33 81  1  0  0  0  0
M  CHG  1  30   1
M  END
$$$$

View in JSmol View Stereo Labels

Synonyms

Value	Source
Sphing-4-enine-1-phosphocholine	ChEBI
Sphingosyl-phosphocholine	ChEBI
Sphingosylphosphocholine	ChEBI
Lysosphingomyelin	MeSH
Sphingosine phosphorylcholine	MeSH
C18-Sphingosine phosphocholine	HMDB
D-erythro-Sphingosylphosphorylcholine	HMDB
SM(D18:1/0:0)	HMDB
Sphingenyl-1-phosphorylcholine	HMDB
Sphingomyelin(D18:1/0:0)	HMDB
Sphingosylphosphorylcholine	MeSH, HMDB

Chemical Formula

C₂₃H₅₀N₂O₅P

Average Molecular Weight

465.6273

Monoisotopic Molecular Weight

465.345734232

IUPAC Name

{[(2S,3R,4E)-2-amino-3-hydroxyoctadec-4-en-1-yl]oxy}[2-(trimethylazaniumyl)ethoxy]phosphinic acid

Traditional Name

lysosphingomyelin

CAS Registry Number

1670-26-4

SMILES

CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)COP(=O)(O)OCC[N+](C)(C)C

InChI Identifier

InChI=1S/C23H49N2O5P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(26)22(24)21-30-31(27,28)29-20-19-25(2,3)4/h17-18,22-23,26H,5-16,19-21,24H2,1-4H3/p+1/b18-17+/t22-,23+/m0/s1

InChI Key

JLVSPVFPBBFMBE-HXSWCURESA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sphingosylphosphorylcholines. These are sphingolipids containing a sphingosine attached to the phosphate group of a phosphocholine.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Sphingolipids

Sub Class

Phosphosphingolipids

Direct Parent

Sphingosylphosphorylcholines

Alternative Parents

Substituents

Sphingosylphosphorylcholine
Phosphocholine
Phosphoethanolamine
Dialkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Tetraalkylammonium salt
Quaternary ammonium salt
Secondary alcohol
Alcohol
Amine
Organic salt
Hydrocarbon derivative
Primary amine
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Primary aliphatic amine
Organic cation
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

quaternary ammonium ion (CHEBI:52897 )
phosphocholines (CHEBI:52897 )
phosphosphingolipid (CHEBI:52897 )
Lysosphingomyelins and lysoglycosphingolipids (C03640 )

Ontology

Physiological effect

Organoleptic effect:

Touch:

Smooth

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Cell and elements:

Extracellular

Subcellular:

Process

Naturally occurring process:

Biological process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Biochemical process:

Cellular process:

Cell signaling

Role

Industrial application:

Food and nutrition:

Biological role:

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

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00084 g/L	ALOGPS
logP	1.3	ALOGPS
logP	-0.24	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	1.83	ChemAxon
pKa (Strongest Basic)	9.68	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	102.01 Å²	ChemAxon
Rotatable Bond Count	21	ChemAxon
Refractivity	141.18 m³·mol⁻¹	ChemAxon
Polarizability	55.37 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 Spectral Properties

Collision Cross Sections

Name	Adduct	Type	Data Source	Value	Reference
DarkChem	[M+H]+	Predicted	Not Available	218.408	31661259
DarkChem	[M-H]-	Predicted	Not Available	216.575	31661259

Retention Indices

Underivatized

Not Available

Derivatized

Derivative	Value	Reference
LysoSM(d18:1),1TMS,#1	3281.2925	https://arxiv.org/abs/1905.12712
LysoSM(d18:1),1TMS,#2	3229.9478	https://arxiv.org/abs/1905.12712
LysoSM(d18:1),1TMS,#3	3308.1174	https://arxiv.org/abs/1905.12712
LysoSM(d18:1),1TBDMS,#1	3510.0195	https://arxiv.org/abs/1905.12712
LysoSM(d18:1),1TBDMS,#2	3441.9836	https://arxiv.org/abs/1905.12712
LysoSM(d18:1),1TBDMS,#3	3533.4692	https://arxiv.org/abs/1905.12712

Spectra

GC-MS

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00ej-9782140000-24f3d9fcbb4a3475e571	2017-10-06	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-004j-1591100000-77d79a2d77af68899edd	2021-09-05	View Spectrum

LC-MS/MS

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-0104900000-a7aeccafba8588e15456	2021-09-07	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001r-0900200000-b7b9a408b9290c492481	2021-09-07	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9800000000-f089839fe08ca8c6e6f6	2021-09-07	View Spectrum

NMR

Spectrum Type	Description	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023932

KNApSAcK ID

Not Available

Chemspider ID

4444221

KEGG Compound ID

C03640

BioCyc ID

Not Available

BiGG ID

2704995

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5280613

PDB ID

SPU

ChEBI ID

52897

Food Biomarker Ontology

Not Available

VMH ID

SPC_HS

MarkerDB ID

Not Available

References

Synthesis Reference

Sphingomyelin, intermediates thereof and methods for preparation of same. Rochlin, Elimelech; Hildesheim, Jean; Berlin, Alisa. (Biolab Ltd., Israel). PCT Int. Appl. (2005), 39 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Morita SY, Soda K, Teraoka R, Kitagawa S, Terada T: Specific and sensitive enzymatic measurement of sphingomyelin in cultured cells. Chem Phys Lipids. 2012 Jul;165(5):571-6. doi: 10.1016/j.chemphyslip.2012.06.003. Epub 2012 Jun 19. [PubMed:22727956 ]

Enzymes

Enzyme Details

1. Sphingomyelin phosphodiesterase

General function:: Involved in hydrolase activity
Specific function:: Converts sphingomyelin to ceramide. Also has phospholipase C activities toward 1,2-diacylglycerolphosphocholine and 1,2-diacylglycerolphosphoglycerol. Isoform 2 and isoform 3 have lost catalytic activity.
Gene Name:: SMPD1
Uniprot ID:: P17405
Molecular weight:: 69935.53

Enzyme Details

2. Galactosylgalactosylxylosylprotein 3-beta-glucuronosyltransferase 1

General function:: Involved in galactosylgalactosylxylosylprotein 3-beta-glucuronosyltransferase activity
Specific function:: Involved in the biosynthesis of L2/HNK-1 carbohydrate epitope on glycoproteins. Can also play a role in glycosaminoglycan biosynthesis. Substrates include asialo-orosomucoid (ASOR), asialo-fetuin, and asialo-neural cell adhesion molecule. Requires sphingomyelin for activity: stearoyl-sphingomyelin was the most effective, followed by palmitoyl-sphingomyelin and lignoceroyl-sphingomyelin. Activity was demonstrated only for sphingomyelin with a saturated fatty acid and not for that with an unsaturated fatty acid, regardless of the length of the acyl group (By similarity).
Gene Name:: B3GAT1
Uniprot ID:: Q9P2W7
Molecular weight:: 38255.675

Enzyme Details

3. Ectonucleotide pyrophosphatase/phosphodiesterase family member 7

General function:: Involved in catalytic activity
Specific function:: Converts sphingomyelin to ceramide. Also has phospholipase C activity toward palmitoyl lyso-phosphocholine. Does not appear to have nucleotide pyrophosphatase activity.
Gene Name:: ENPP7
Uniprot ID:: Q6UWV6
Molecular weight:: 51493.415

Enzyme Details

4. Sphingomyelin phosphodiesterase 2

General function:: Involved in metal ion binding
Specific function:: Converts sphingomyelin to ceramide. Hydrolyze 1-acyl-2-lyso-sn-glycero-3-phosphocholine (lyso-PC) and 1-O-alkyl-2-lyso-sn-glycero-3-phosphocholine (lyso-platelet-activating factor). The physiological substrate seems to be Lyso-PAF.
Gene Name:: SMPD2
Uniprot ID:: O60906
Molecular weight:: 47645.29

Enzyme Details

5. Proactivator polypeptide

General function:: Involved in lipid metabolic process
Specific function:: Saposin-D is a specific sphingomyelin phosphodiesterase activator (EC 3.1.4.12)
Gene Name:: PSAP
Uniprot ID:: P07602
Molecular weight:: 58112.1

Enzyme Details

6. 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase delta-3

General function:: Involved in calcium ion binding
Specific function:: Hydrolyzes the phosphatidylinositol 4,5-bisphosphate (PIP2) to generate 2 second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3). DAG mediates the activation of protein kinase C (PKC), while IP3 releases Ca(2+) from intracellular stores. Essential for trophoblast and placental development. May participate in cytokinesis by hydrolyzing PIP2 at the cleavage furrow.
Gene Name:: PLCD3
Uniprot ID:: Q8N3E9
Molecular weight:: 89257.54

Enzyme Details

7. Sphingomyelin phosphodiesterase 3

General function:: Involved in metal ion binding
Specific function:: Catalyzes the hydrolysis of sphingomyelin to form ceramide and phosphocholine. Ceramide mediates numerous cellular functions, such as apoptosis and growth arrest, and is capable of regulating these 2 cellular events independently. Also hydrolyzes sphingosylphosphocholine. Regulates the cell cycle by acting as a growth suppressor in confluent cells. Probably acts as a regulator of postnatal development and participates in bone and dentin mineralization.
Gene Name:: SMPD3
Uniprot ID:: Q9NY59
Molecular weight:: 71080.1

Enzyme Details

8. Sphingomyelin phosphodiesterase 4

General function:: Involved in metal ion binding
Specific function:: Catalyzes the hydrolysis of membrane sphingomyelin to form phosphorylcholine and ceramide.
Gene Name:: SMPD4
Uniprot ID:: Q9NXE4
Molecular weight:: 86192.575

Enzyme Details

9. Non-lysosomal glucosylceramidase

General function:: Involved in catalytic activity
Specific function:: Non-lysosomal glucosylceramidase that catalyzes the conversion of glucosylceramide to free glucose and ceramide. Involved in sphingomyelin generation and prevention of glycolipid accumulation. May also catalyze the hydrolysis of bile acid 3-O-glucosides, however, the relevance of such activity is unclear in vivo.
Gene Name:: GBA2
Uniprot ID:: Q9HCG7
Molecular weight:: 104648.13

Enzyme Details

10. Sphingomyelin synthase-related protein 1

General function:: Involved in sphingomyelin biosynthetic process
Specific function:: Not Available
Gene Name:: SAMD8
Uniprot ID:: Q96LT4
Molecular weight:: 48320.2

Showing metabocard for LysoSM(d18:1) (HMDB0006482)

MOL for HMDB0006482 (LysoSM(d18:1))

3D MOL for HMDB0006482 (LysoSM(d18:1))

3D SDF for HMDB0006482 (LysoSM(d18:1))

3D-SDF for HMDB0006482 (LysoSM(d18:1))

PDB for HMDB0006482 (LysoSM(d18:1))

3D PDB for HMDB0006482 (LysoSM(d18:1))

SMILES for HMDB0006482 (LysoSM(d18:1))

INCHI for HMDB0006482 (LysoSM(d18:1))

Structure for HMDB0006482 (LysoSM(d18:1))

3D Structure for HMDB0006482 (LysoSM(d18:1))

Collision Cross Sections

Retention Indices

Underivatized

Derivatized

GC-MS

LC-MS/MS

NMR

Enzymes