NP-MRD: Showing NP-Card for (2-{[(2s,3r,4e)-3-hydroxy-2-{[(13z)-1-hydroxydocos-13-en-1-ylidene]amino}octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium (NP0296824)

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Record Information

Version

2.0

Created at

2022-09-10 06:39:29 UTC

Updated at

2022-09-10 06:39:29 UTC

NP-MRD ID

NP0296824

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2-{[(2s,3r,4e)-3-hydroxy-2-{[(13z)-1-hydroxydocos-13-en-1-ylidene]amino}octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium

Description

SM(d18:1/22:1(13Z)), also known as C22:1 Sphingomyelin, 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(D18:1/22:1(13Z)) is considered to be a phosphosphingolipid lipid molecule. (2-{[(2s,3r,4e)-3-hydroxy-2-{[(13z)-1-hydroxydocos-13-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-{[(13z)-1-hydroxydocos-13-en-1-ylidene]amino}octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium was first documented in 1994 (PMID: 8106344). SM(d18:1/22:1(13Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 9034165).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241203392D          

 54 53  0  0  1  0            999 V2000
    6.5327   -4.1219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3854   -3.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5491   -4.5493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6784   -4.2562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2504   -3.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9616   -4.1332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8120   -4.9822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6793   -3.7263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5235   -5.4001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3905   -4.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2410   -4.9930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1081   -3.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9524   -5.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8190   -4.1551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5366   -3.7483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2479   -4.1664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9655   -3.7596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6700   -5.0038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6768   -4.1777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3944   -3.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3814   -5.4217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1056   -4.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0990   -5.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8232   -3.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8104   -5.4325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5345   -4.2003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5280   -5.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2560   -3.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5384   -3.8269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6810   -3.8048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9633   -4.2116    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.2520   -3.7935    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.2389   -5.4431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9566   -5.0361    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9673   -3.8382    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   17.2585   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2326   -6.2680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7027   -3.0979    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   20.5164   -4.5331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8271   -3.4087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3919   -4.2224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1096   -3.8156    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   10.0945   -5.3893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3831   -4.9714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6654   -5.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9896   -5.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3634   -4.9710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9364   -4.8948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2008   -5.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6278   -5.3449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5093   -4.8187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7738   -5.1925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0823   -4.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3467   -5.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2 35  1  0  0  0  0
  3 35  1  0  0  0  0
  4 35  1  0  0  0  0
  5  6  1  0  0  0  0
  6  8  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 14  1  0  0  0  0
 13 18  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 19  1  0  0  0  0
 18 21  1  0  0  0  0
 19 20  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  1  0  0  0  0
 24 26  2  0  0  0  0
 25 27  1  0  0  0  0
 26 32  1  0  0  0  0
 27 33  1  0  0  0  0
 28 29  1  0  0  0  0
 28 35  1  0  0  0  0
 29 40  1  0  0  0  0
 30 31  1  0  0  0  0
 30 41  1  0  0  0  0
 31 32  1  0  0  0  0
 31 34  1  6  0  0  0
 32 36  1  1  0  0  0
 33 34  1  0  0  0  0
 33 37  2  0  0  0  0
 38 42  1  0  0  0  0
 39 42  2  0  0  0  0
 40 42  1  0  0  0  0
 41 42  1  0  0  0  0
 43  7  1  0  0  0  0
 44 43  1  0  0  0  0
 45 44  1  0  0  0  0
 46 45  2  0  0  0  0
 47 46  1  0  0  0  0
 48 49  1  0  0  0  0
 50 48  1  0  0  0  0
 47 50  1  0  0  0  0
 51 49  1  0  0  0  0
 52 51  1  0  0  0  0
 53 52  1  0  0  0  0
 54 53  1  0  0  0  0
M  CHG  2  35   1  38  -1
M  END


  Mrv0541 02241203392D          

 54 53  0  0  1  0            999 V2000
    6.5327   -4.1219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3854   -3.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5491   -4.5493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6784   -4.2562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2504   -3.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9616   -4.1332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8120   -4.9822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6793   -3.7263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5235   -5.4001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3905   -4.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2410   -4.9930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1081   -3.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9524   -5.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8190   -4.1551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5366   -3.7483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2479   -4.1664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9655   -3.7596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6700   -5.0038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6768   -4.1777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3944   -3.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3814   -5.4217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1056   -4.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0990   -5.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8232   -3.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8104   -5.4325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5345   -4.2003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5280   -5.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2560   -3.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5384   -3.8269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6810   -3.8048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9633   -4.2116    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.2520   -3.7935    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.2389   -5.4431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9566   -5.0361    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9673   -3.8382    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   17.2585   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2326   -6.2680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7027   -3.0979    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   20.5164   -4.5331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8271   -3.4087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3919   -4.2224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1096   -3.8156    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   10.0945   -5.3893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3831   -4.9714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6654   -5.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9896   -5.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3634   -4.9710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9364   -4.8948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2008   -5.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6278   -5.3449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5093   -4.8187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7738   -5.1925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0823   -4.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3467   -5.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2 35  1  0  0  0  0
  3 35  1  0  0  0  0
  4 35  1  0  0  0  0
  5  6  1  0  0  0  0
  6  8  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 14  1  0  0  0  0
 13 18  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 19  1  0  0  0  0
 18 21  1  0  0  0  0
 19 20  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  1  0  0  0  0
 24 26  2  0  0  0  0
 25 27  1  0  0  0  0
 26 32  1  0  0  0  0
 27 33  1  0  0  0  0
 28 29  1  0  0  0  0
 28 35  1  0  0  0  0
 29 40  1  0  0  0  0
 30 31  1  0  0  0  0
 30 41  1  0  0  0  0
 31 32  1  0  0  0  0
 31 34  1  6  0  0  0
 32 36  1  1  0  0  0
 33 34  1  0  0  0  0
 33 37  2  0  0  0  0
 38 42  1  0  0  0  0
 39 42  2  0  0  0  0
 40 42  1  0  0  0  0
 41 42  1  0  0  0  0
 43  7  1  0  0  0  0
 44 43  1  0  0  0  0
 45 44  1  0  0  0  0
 46 45  2  0  0  0  0
 47 46  1  0  0  0  0
 48 49  1  0  0  0  0
 50 48  1  0  0  0  0
 47 50  1  0  0  0  0
 51 49  1  0  0  0  0
 52 51  1  0  0  0  0
 53 52  1  0  0  0  0
 54 53  1  0  0  0  0
M  CHG  2  35   1  38  -1
M  END
> <DATABASE_ID>
NP0296824

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C45H89N2O6P/c1-6-8-10-12-14-16-18-20-21-22-23-24-25-27-29-31-33-35-37-39-45(49)46-43(42-53-54(50,51)52-41-40-47(3,4)5)44(48)38-36-34-32-30-28-26-19-17-15-13-11-9-7-2/h20-21,36,38,43-44,48H,6-19,22-35,37,39-42H2,1-5H3,(H-,46,49,50,51)/b21-20-,38-36+/t43-,44+/m0/s1

> <INCHI_KEY>
VBFKEZGCUWHGSK-ADSSWVSQSA-N

> <FORMULA>
C45H89N2O6P

> <MOLECULAR_WEIGHT>
785.1717

> <EXACT_MASS>
784.645825102

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
99.50323798249225

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-{[(2S,3R,4E)-2-[(13Z)-docos-13-enamido]-3-hydroxyoctadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium

> <ALOGPS_LOGP>
6.06

> <JCHEM_LOGP>
10.370892169528412

> <ALOGPS_LOGS>
-7.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.499201320641198

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8709150288593719

> <JCHEM_PKA_STRONGEST_BASIC>
0.011796153944252485

> <JCHEM_POLAR_SURFACE_AREA>
107.92000000000002

> <JCHEM_REFRACTIVITY>
242.66450000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
41

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.78e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-{[(2S,3R,4E)-2-[(13Z)-docos-13-enamido]-3-hydroxyoctadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium

> <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      12.194  -7.694   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      43.653  -5.837   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      42.092  -8.492   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      44.200  -7.945   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.534  -6.935   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.862  -7.715   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.182  -9.300   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.201  -6.956   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.511 -10.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.529  -7.736   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.850  -9.320   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      18.868  -6.977   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      24.178 -10.100   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.195  -7.756   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.535  -6.997   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      22.863  -7.777   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      24.202  -7.018   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      25.517  -9.340   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      25.530  -7.798   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      26.870  -7.039   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      26.845 -10.121   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      28.197  -7.819   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      28.185  -9.361   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      29.537  -7.060   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      29.513 -10.141   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      30.864  -7.841   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      30.852  -9.381   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      41.545  -6.384   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      40.205  -7.144   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      34.871  -7.102   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      33.531  -7.862   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      32.204  -7.081   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      32.179 -10.160   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0      33.519  -9.401   0.000  0.00  0.00           N+0
HETATM   35  N   UNK     0      42.872  -7.165   0.000  0.00  0.00           N+1
HETATM   36  O   UNK     0      32.216  -5.541   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      32.168 -11.700   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      36.778  -5.783   0.000  0.00  0.00           O-1
HETATM   39  O   UNK     0      38.297  -8.462   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      38.877  -6.363   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      36.198  -7.882   0.000  0.00  0.00           O+0
HETATM   42  P   UNK     0      37.538  -7.122   0.000  0.00  0.00           P+0
HETATM   43  C   UNK     0      18.843 -10.060   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      17.515  -9.280   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      16.175 -10.040   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      14.914 -10.040   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      13.745  -9.279   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      11.081  -9.137   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       9.708  -9.835   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      12.372  -9.977   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       8.417  -8.995   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       7.044  -9.693   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       5.754  -8.853   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       4.381  -9.550   0.000  0.00  0.00           C+0
CONECT    1    5                                                            
CONECT    2   35                                                            
CONECT    3   35                                                            
CONECT    4   35                                                            
CONECT    5    1    6                                                       
CONECT    6    5    8                                                       
CONECT    7    9   43                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   14                                                       
CONECT   13   11   18                                                       
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   19                                                       
CONECT   18   13   21                                                       
CONECT   19   17   20                                                       
CONECT   20   19   22                                                       
CONECT   21   18   23                                                       
CONECT   22   20   24                                                       
CONECT   23   21   25                                                       
CONECT   24   22   26                                                       
CONECT   25   23   27                                                       
CONECT   26   24   32                                                       
CONECT   27   25   33                                                       
CONECT   28   29   35                                                       
CONECT   29   28   40                                                       
CONECT   30   31   41                                                       
CONECT   31   30   32   34                                                  
CONECT   32   26   31   36                                                  
CONECT   33   27   34   37                                                  
CONECT   34   31   33                                                       
CONECT   35    2    3    4   28                                             
CONECT   36   32                                                            
CONECT   37   33                                                            
CONECT   38   42                                                            
CONECT   39   42                                                            
CONECT   40   29   42                                                       
CONECT   41   30   42                                                       
CONECT   42   38   39   40   41                                             
CONECT   43    7   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   50                                                       
CONECT   48   49   50                                                       
CONECT   49   48   51                                                       
CONECT   50   48   47                                                       
CONECT   51   49   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  106    0
END

View in JSmol

Synonyms

Value	Source
C22:1 Sphingomyelin	ChEBI
N-(13Z-Docosenoyl)-sphing-4-enine-1-phosphocholine	ChEBI
SPH(D18:1/22:1(13Z))	ChEBI
Sphingomyelin (D18:1/22:1(13Z))	ChEBI
N-(13Z-Docosenoyl)-sphing-4-enine-1-phosphocholin	HMDB
Sphingomyelin	HMDB
Sphingomyelin (D18:1/11:1(13Z))	HMDB
N-(13Z-Docosenoyl)-1-phosphocholine-sphing-4-enine	HMDB
Sphingomyelin(D18:1/22:1(13Z))	HMDB
N-(13Z-Docosenoyl)-1-phosphocholine-sphingosine	HMDB
N-(13Z-Docosenoyl)-1-phosphocholine-D-erythro-sphingosine	HMDB
N-(13Z-Docosenoyl)-1-phosphocholine-4-sphingenine	HMDB
N-(13Z-Docosenoyl)-1-phosphocholine-D-sphingosine	HMDB
N-(13Z-Docosenoyl)-1-phosphocholine-sphingenine	HMDB
N-(13Z-Docosenoyl)-1-phosphocholine-erythro-4-sphingenine	HMDB
SM D18:1/22:1(13Z)	HMDB
Sphingomyelin (D18:1,C22:1(13Z))	HMDB
SM(D18:1/22:1(13Z))	ChEBI

Chemical Formula

C₄₅H₈₉N₂O₆P

Average Mass

785.1717 Da

Monoisotopic Mass

784.64583 Da

IUPAC Name

(2-{[(2S,3R,4E)-2-[(13Z)-docos-13-enamido]-3-hydroxyoctadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2S,3R,4E)-2-[(13Z)-docos-13-enamido]-3-hydroxyoctadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C45H89N2O6P/c1-6-8-10-12-14-16-18-20-21-22-23-24-25-27-29-31-33-35-37-39-45(49)46-43(42-53-54(50,51)52-41-40-47(3,4)5)44(48)38-36-34-32-30-28-26-19-17-15-13-11-9-7-2/h20-21,36,38,43-44,48H,6-19,22-35,37,39-42H2,1-5H3,(H-,46,49,50,51)/b21-20-,38-36+/t43-,44+/m0/s1

InChI Key

VBFKEZGCUWHGSK-ADSSWVSQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

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-docosenoylsphingosine-1-phosphocholine (CHEBI:74533 )
Ceramide phosphocholines (sphingomyelins) (LMSP03010072 )

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	6.06	ALOGPS
logP	10.37	ChemAxon
logS	-7.5	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	41	ChemAxon
Refractivity	242.66 m³·mol⁻¹	ChemAxon
Polarizability	99.5 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

HMDB0012104

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB028769

KNApSAcK ID

Not Available

Chemspider ID

29368329

KEGG Compound ID

C00550

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

52931203

PDB ID

Not Available

ChEBI ID

74533

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-{[(13z)-1-hydroxydocos-13-en-1-ylidene]amino}octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium (NP0296824)

MOL for NP0296824 ((2-{[(2s,3r,4e)-3-hydroxy-2-{[(13z)-1-hydroxydocos-13-en-1-ylidene]amino}octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium)

3D MOL for NP0296824 ((2-{[(2s,3r,4e)-3-hydroxy-2-{[(13z)-1-hydroxydocos-13-en-1-ylidene]amino}octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium)

3D SDF for NP0296824 ((2-{[(2s,3r,4e)-3-hydroxy-2-{[(13z)-1-hydroxydocos-13-en-1-ylidene]amino}octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium)

3D-SDF for NP0296824 ((2-{[(2s,3r,4e)-3-hydroxy-2-{[(13z)-1-hydroxydocos-13-en-1-ylidene]amino}octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium)

PDB for NP0296824 ((2-{[(2s,3r,4e)-3-hydroxy-2-{[(13z)-1-hydroxydocos-13-en-1-ylidene]amino}octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium)

3D PDB for NP0296824 ((2-{[(2s,3r,4e)-3-hydroxy-2-{[(13z)-1-hydroxydocos-13-en-1-ylidene]amino}octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium)

SMILES for NP0296824 ((2-{[(2s,3r,4e)-3-hydroxy-2-{[(13z)-1-hydroxydocos-13-en-1-ylidene]amino}octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium)

INCHI for NP0296824 ((2-{[(2s,3r,4e)-3-hydroxy-2-{[(13z)-1-hydroxydocos-13-en-1-ylidene]amino}octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium)

Structure for NP0296824 ((2-{[(2s,3r,4e)-3-hydroxy-2-{[(13z)-1-hydroxydocos-13-en-1-ylidene]amino}octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium)

3D Structure for NP0296824 ((2-{[(2s,3r,4e)-3-hydroxy-2-{[(13z)-1-hydroxydocos-13-en-1-ylidene]amino}octadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium)