NP-MRD: Showing NP-Card for (2-{[(2s,3r,4e)-3-hydroxy-2-{[(9z)-1-hydroxyoctadec-9-en-1-ylidene]amino}octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium (NP0154905)

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Record Information

Version

2.0

Created at

2022-09-02 11:53:17 UTC

Updated at

2022-09-02 11:53:17 UTC

NP-MRD ID

NP0154905

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2-{[(2s,3r,4e)-3-hydroxy-2-{[(9z)-1-hydroxyoctadec-9-en-1-ylidene]amino}octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium

Description

SM(d18:1/18:1(9Z)), also known as sphingomyelin or SM D18:1/18:1(9Z), belongs to the class of organic compounds known as phosphosphingolipids. These are sphingolipids with a structure based on a sphingoid base that is attached to a phosphate head group. They differ from phosphonospingolipids which have a phosphonate head group. Thus, SM(D18:1/18:1(9Z)) is considered to be a phosphosphingolipid lipid molecule. (2-{[(2s,3r,4e)-3-hydroxy-2-{[(9z)-1-hydroxyoctadec-9-en-1-ylidene]amino}octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium is found in Trypanosoma brucei. (2-{[(2s,3r,4e)-3-hydroxy-2-{[(9z)-1-hydroxyoctadec-9-en-1-ylidene]amino}octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium was first documented in 1994 (PMID: 8106344). SM(d18:1/18:1(9Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 9034165).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241203392D          

 50 49  0  0  1  0            999 V2000
    4.0975   -3.3466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9503   -2.3516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1139   -3.7741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2433   -3.4810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8152   -2.9397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5264   -3.3579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2441   -2.9510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0884   -4.6233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9553   -3.3691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8061   -4.2164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6729   -2.9622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5174   -4.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3838   -3.3798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1014   -2.9730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8127   -3.3911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5303   -2.9843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2352   -4.2276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2415   -3.4024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9592   -2.9956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9464   -4.6457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6704   -3.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6641   -4.2387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3881   -3.0069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3752   -4.6570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0993   -3.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0928   -4.2501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8209   -2.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1032   -3.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2458   -3.0295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5281   -3.4364    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.8169   -3.0182    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.8038   -4.6678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5214   -4.2608    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.5322   -3.0629    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
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   16.9567   -3.4471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6744   -3.0403    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    8.4125   -4.6233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7863   -4.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.6237   -4.5134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0507   -4.5895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9322   -4.0634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1968   -4.4373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5052   -3.9872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7698   -4.3611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2 34  1  0  0  0  0
  3 34  1  0  0  0  0
  4 34  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 17  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 18  1  0  0  0  0
 17 20  1  0  0  0  0
 18 19  1  0  0  0  0
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
 23 25  2  0  0  0  0
 24 26  1  0  0  0  0
 25 31  1  0  0  0  0
 26 32  1  0  0  0  0
 27 28  1  0  0  0  0
 27 34  1  0  0  0  0
 28 39  1  0  0  0  0
 29 30  1  0  0  0  0
 29 40  1  0  0  0  0
 30 31  1  0  0  0  0
 30 33  1  6  0  0  0
 31 35  1  1  0  0  0
 32 33  1  0  0  0  0
 32 36  2  0  0  0  0
 37 41  1  0  0  0  0
 38 41  2  0  0  0  0
 39 41  1  0  0  0  0
 40 41  1  0  0  0  0
 42  8  2  0  0  0  0
 43 42  1  0  0  0  0
 44 45  1  0  0  0  0
 46 44  1  0  0  0  0
 43 46  1  0  0  0  0
 47 45  1  0  0  0  0
 48 47  1  0  0  0  0
 49 48  1  0  0  0  0
 50 49  1  0  0  0  0
M  CHG  2  34   1  37  -1
M  END

     RDKit          3D

131130  0  0  0  0  0  0  0  0999 V2000
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   -4.0499   -3.9482   -2.6368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8276   -3.3480   -1.2451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1510   -3.0690   -0.5791 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1754    1.7814    4.7641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7143    3.1929    5.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6942    3.5064    4.7179 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9984    3.3474    3.2677 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4091    3.7673    2.9385 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6501    3.5762    1.4447 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8680    2.7436    0.9439 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6157    4.2606    0.7347 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9706    4.3020   -0.6280 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4554    4.3121   -0.8472 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8381    4.3426   -2.1960 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5223    4.2975   -2.3333 P   0  0  2  0  0  5  0  0  0  0  0  0
    8.1542    3.9808   -0.9799 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0371    5.7970   -2.9257 O   0  0  0  0  0  1  0  0  0  0  0  0
    7.9528    3.1080   -3.4302 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9976    2.0979   -3.5893 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5154    1.0437   -4.5617 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5613   -0.0010   -4.7273 N   0  0  0  0  0  4  0  0  0  0  0  0
    5.9717   -0.3545   -3.4472 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5252    0.3212   -5.6814 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3903    3.3103   -1.5781 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -1.6537   -4.5607    1.9274 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2389    3.0912   -3.0804 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4531    1.2068   -0.7695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0443    0.7387   -2.4303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8614   -0.2654    0.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7128   -0.7776   -1.1789 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3707   -0.7642   -0.7333 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4077   -3.1461   -1.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3844   -3.2521   -1.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
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 33 99  1  0
 33100  1  0
 20 84  1  0
 17 82  1  0
 17 83  1  0
 16 80  1  0
 16 81  1  0
 15 78  1  0
 15 79  1  0
 14 76  1  0
 14 77  1  0
 13 74  1  0
 13 75  1  0
 12 72  1  0
 12 73  1  0
 11 70  1  0
 11 71  1  0
 10 69  1  0
  9 68  1  0
  8 66  1  0
  8 67  1  0
  7 64  1  0
  7 65  1  0
  6 62  1  0
  6 63  1  0
  5 60  1  0
  5 61  1  0
  4 58  1  0
  4 59  1  0
  3 56  1  0
  3 57  1  0
  2 54  1  0
  2 55  1  0
  1 51  1  0
  1 52  1  0
  1 53  1  0
M  CHG  2  26  -1  30   1
M  END


  Mrv0541 02241203392D          

 50 49  0  0  1  0            999 V2000
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   10.5174   -4.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.3752   -4.6570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.7974   -5.4927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2675   -2.3226    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   18.0812   -3.7579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3920   -2.6334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9567   -3.4471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6744   -3.0403    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    8.4125   -4.6233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7863   -4.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3593   -4.1396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6237   -4.5134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0507   -4.5895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9322   -4.0634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1968   -4.4373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5052   -3.9872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7698   -4.3611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2 34  1  0  0  0  0
  3 34  1  0  0  0  0
  4 34  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 17  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 18  1  0  0  0  0
 17 20  1  0  0  0  0
 18 19  1  0  0  0  0
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
 23 25  2  0  0  0  0
 24 26  1  0  0  0  0
 25 31  1  0  0  0  0
 26 32  1  0  0  0  0
 27 28  1  0  0  0  0
 27 34  1  0  0  0  0
 28 39  1  0  0  0  0
 29 30  1  0  0  0  0
 29 40  1  0  0  0  0
 30 31  1  0  0  0  0
 30 33  1  6  0  0  0
 31 35  1  1  0  0  0
 32 33  1  0  0  0  0
 32 36  2  0  0  0  0
 37 41  1  0  0  0  0
 38 41  2  0  0  0  0
 39 41  1  0  0  0  0
 40 41  1  0  0  0  0
 42  8  2  0  0  0  0
 43 42  1  0  0  0  0
 44 45  1  0  0  0  0
 46 44  1  0  0  0  0
 43 46  1  0  0  0  0
 47 45  1  0  0  0  0
 48 47  1  0  0  0  0
 49 48  1  0  0  0  0
 50 49  1  0  0  0  0
M  CHG  2  34   1  37  -1
M  END
> <DATABASE_ID>
NP0154905

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](COP([O-])(=O)OCC[N+](C)(C)C)NC(=O)CCCCCCC\C=C/CCCCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C41H81N2O6P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-41(45)42-39(38-49-50(46,47)48-37-36-43(3,4)5)40(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h20-21,32,34,39-40,44H,6-19,22-31,33,35-38H2,1-5H3,(H-,42,45,46,47)/b21-20-,34-32+/t39-,40+/m0/s1

> <INCHI_KEY>
NBEADXWAAWCCDG-QDDWGVBQSA-N

> <FORMULA>
C41H81N2O6P

> <MOLECULAR_WEIGHT>
729.0654

> <EXACT_MASS>
728.583224846

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
91.62697423150185

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-{[(2S,3R,4E)-3-hydroxy-2-[(9Z)-octadec-9-enamido]octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium

> <ALOGPS_LOGP>
5.41

> <JCHEM_LOGP>
8.592617509546525

> <ALOGPS_LOGS>
-7.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.507093903444801

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.870915028856634

> <JCHEM_PKA_STRONGEST_BASIC>
0.011796153755674221

> <JCHEM_POLAR_SURFACE_AREA>
107.92000000000002

> <JCHEM_REFRACTIVITY>
224.26050000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
37

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.23e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
C18:1 sphingomyelin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       7.649  -6.247   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      39.107  -4.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      37.546  -7.045   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      39.654  -6.498   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.988  -5.487   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.316  -6.268   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.656  -5.509   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.965  -8.630   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.983  -6.289   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.305  -7.871   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.323  -5.529   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      19.632  -8.651   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.650  -6.309   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.989  -5.550   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      18.317  -6.330   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      19.657  -5.571   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      20.972  -7.892   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      20.984  -6.351   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      22.324  -5.592   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      22.300  -8.672   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      23.651  -6.372   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      23.640  -7.912   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      24.991  -5.613   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      24.967  -8.693   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      26.319  -6.393   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      26.307  -7.934   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      36.999  -4.937   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      35.659  -5.696   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      30.325  -5.655   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      28.986  -6.415   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      27.658  -5.634   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      27.634  -8.713   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0      28.973  -7.953   0.000  0.00  0.00           N+0
HETATM   34  N   UNK     0      38.327  -5.717   0.000  0.00  0.00           N+1
HETATM   35  O   UNK     0      27.670  -4.094   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      27.622 -10.253   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      32.233  -4.336   0.000  0.00  0.00           O-1
HETATM   38  O   UNK     0      33.752  -7.015   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      34.332  -4.916   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      31.653  -6.435   0.000  0.00  0.00           O+0
HETATM   41  P   UNK     0      32.992  -5.675   0.000  0.00  0.00           P+0
HETATM   42  C   UNK     0      15.703  -8.630   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      14.534  -7.869   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      11.871  -7.727   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      10.498  -8.425   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      13.161  -8.567   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       9.207  -7.585   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       7.834  -8.283   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       6.543  -7.443   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       5.170  -8.141   0.000  0.00  0.00           C+0
CONECT    1    5                                                            
CONECT    2   34                                                            
CONECT    3   34                                                            
CONECT    4   34                                                            
CONECT    5    1    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    9                                                       
CONECT    8   10   42                                                       
CONECT    9    7   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   17                                                       
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   18                                                       
CONECT   17   12   20                                                       
CONECT   18   16   19                                                       
CONECT   19   18   21                                                       
CONECT   20   17   22                                                       
CONECT   21   19   23                                                       
CONECT   22   20   24                                                       
CONECT   23   21   25                                                       
CONECT   24   22   26                                                       
CONECT   25   23   31                                                       
CONECT   26   24   32                                                       
CONECT   27   28   34                                                       
CONECT   28   27   39                                                       
CONECT   29   30   40                                                       
CONECT   30   29   31   33                                                  
CONECT   31   25   30   35                                                  
CONECT   32   26   33   36                                                  
CONECT   33   30   32                                                       
CONECT   34    2    3    4   27                                             
CONECT   35   31                                                            
CONECT   36   32                                                            
CONECT   37   41                                                            
CONECT   38   41                                                            
CONECT   39   28   41                                                       
CONECT   40   29   41                                                       
CONECT   41   37   38   39   40                                             
CONECT   42    8   43                                                       
CONECT   43   42   46                                                       
CONECT   44   45   46                                                       
CONECT   45   44   47                                                       
CONECT   46   44   43                                                       
CONECT   47   45   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49                                                            
MASTER        0    0    0    0    0    0    0    0   50    0   98    0
END

View in JSmol

Synonyms

Value	Source
N-(9Z-Octadecenoyl)-sphing-4-enine-1-phosphocholine	ChEBI
N-(9Z-Octadecenoyl)-sphingosine-1-phosphocholine	ChEBI
C18:1 Sphingomyelin	HMDB
Sphingomyelin	HMDB
N-Oleoyl-sphingomyelin	HMDB
N-Oleoylsphingomyelin	HMDB
N-(9Z-Octadecenoyl)-1-phosphocholine-sphing-4-enine	HMDB
Sphingomyelin(D18:1/18:1(9Z))	HMDB
N-(9Z-Octadecenoyl)-1-phosphocholine-sphingosine	HMDB
N-(9Z-Octadecenoyl)-1-phosphocholine-D-erythro-sphingosine	HMDB
N-(9Z-Octadecenoyl)-1-phosphocholine-4-sphingenine	HMDB
N-(9Z-Octadecenoyl)-1-phosphocholine-D-sphingosine	HMDB
N-(9Z-Octadecenoyl)-1-phosphocholine-sphingenine	HMDB
N-(9Z-Octadecenoyl)-1-phosphocholine-erythro-4-sphingenine	HMDB
N-Oleyl sphingomyelin	HMDB
N-Oleylsphingomyelin	HMDB
SM D18:1/18:1(9Z)	HMDB
Sphingomyelin (D18:1,C18:1(9Z))	HMDB
Sphingomyelin (D18:1/18:1(9Z))	HMDB
SM(D18:1/18:1(9Z))	ChEBI

Chemical Formula

C₄₁H₈₁N₂O₆P

Average Mass

729.0654 Da

Monoisotopic Mass

728.58322 Da

IUPAC Name

(2-{[(2S,3R,4E)-3-hydroxy-2-[(9Z)-octadec-9-enamido]octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

C18:1 sphingomyelin

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](COP([O-])(=O)OCC[N+](C)(C)C)NC(=O)CCCCCCC\C=C/CCCCCCCC

InChI Identifier

InChI=1S/C41H81N2O6P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-41(45)42-39(38-49-50(46,47)48-37-36-43(3,4)5)40(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h20-21,32,34,39-40,44H,6-19,22-31,33,35-38H2,1-5H3,(H-,42,45,46,47)/b21-20-,34-32+/t39-,40+/m0/s1

InChI Key

NBEADXWAAWCCDG-QDDWGVBQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Trypanosoma brucei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phosphosphingolipids. These are sphingolipids with a structure based on a sphingoid base that is attached to a phosphate head group. They differ from phosphonospingolipids which have a phosphonate head group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Sphingolipids

Sub Class

Phosphosphingolipids

Direct Parent

Phosphosphingolipids

Alternative Parents

Substituents

Sphingoid-1-phosphate or derivatives
Phosphocholine
Phosphoethanolamine
Dialkyl phosphate
Fatty amide
N-acyl-amine
Organic phosphoric acid derivative
Phosphoric acid ester
Fatty acyl
Alkyl phosphate
Tetraalkylammonium salt
Quaternary ammonium salt
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Carboxylic acid derivative
Organic zwitterion
Alcohol
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Amine
Organic salt
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

N-octadecenoylsphingosine-1-phosphocholine (CHEBI:84487 )
Ceramide phosphocholines (sphingomyelins) (LMSP03010029 )

Physical Properties

State

Not Available

Experimental 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 Properties

Property	Value	Source
logP	5.41	ALOGPS
logP	8.59	ChemAxon
logS	-7.4	ALOGPS
pKa (Strongest Acidic)	1.87	ChemAxon
pKa (Strongest Basic)	0.012	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	107.92 Å²	ChemAxon
Rotatable Bond Count	37	ChemAxon
Refractivity	224.26 m³·mol⁻¹	ChemAxon
Polarizability	91.63 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0012101

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB028766

KNApSAcK ID

Not Available

Chemspider ID

4947837

KEGG Compound ID

C00550

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6443882

PDB ID

Not Available

ChEBI ID

84487

Good Scents ID

Not Available

References

General References

Ghosh S, Strum JC, Bell RM: Lipid biochemistry: functions of glycerolipids and sphingolipids in cellular signaling. FASEB J. 1997 Jan;11(1):45-50. [PubMed:9034165 ]
Hannun YA: The sphingomyelin cycle and the second messenger function of ceramide. J Biol Chem. 1994 Feb 4;269(5):3125-8. [PubMed:8106344 ]
LOTUS database [Link]

Showing NP-Card for (2-{[(2s,3r,4e)-3-hydroxy-2-{[(9z)-1-hydroxyoctadec-9-en-1-ylidene]amino}octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium (NP0154905)

MOL for NP0154905 ((2-{[(2s,3r,4e)-3-hydroxy-2-{[(9z)-1-hydroxyoctadec-9-en-1-ylidene]amino}octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium)

3D MOL for NP0154905 ((2-{[(2s,3r,4e)-3-hydroxy-2-{[(9z)-1-hydroxyoctadec-9-en-1-ylidene]amino}octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium)

3D SDF for NP0154905 ((2-{[(2s,3r,4e)-3-hydroxy-2-{[(9z)-1-hydroxyoctadec-9-en-1-ylidene]amino}octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium)

3D-SDF for NP0154905 ((2-{[(2s,3r,4e)-3-hydroxy-2-{[(9z)-1-hydroxyoctadec-9-en-1-ylidene]amino}octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium)

PDB for NP0154905 ((2-{[(2s,3r,4e)-3-hydroxy-2-{[(9z)-1-hydroxyoctadec-9-en-1-ylidene]amino}octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium)

3D PDB for NP0154905 ((2-{[(2s,3r,4e)-3-hydroxy-2-{[(9z)-1-hydroxyoctadec-9-en-1-ylidene]amino}octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium)

SMILES for NP0154905 ((2-{[(2s,3r,4e)-3-hydroxy-2-{[(9z)-1-hydroxyoctadec-9-en-1-ylidene]amino}octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium)

INCHI for NP0154905 ((2-{[(2s,3r,4e)-3-hydroxy-2-{[(9z)-1-hydroxyoctadec-9-en-1-ylidene]amino}octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium)

Structure for NP0154905 ((2-{[(2s,3r,4e)-3-hydroxy-2-{[(9z)-1-hydroxyoctadec-9-en-1-ylidene]amino}octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium)

3D Structure for NP0154905 ((2-{[(2s,3r,4e)-3-hydroxy-2-{[(9z)-1-hydroxyoctadec-9-en-1-ylidene]amino}octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium)