MiMeDB: Showing metabocard for Cer 20:0;3/26:0;1 (MMDBc0033221)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:39:39 UTC

Update Date

2022-08-31 22:29:58 UTC

Metabolite ID

MMDBc0033221

Metabolite Identification

Common Name

Cer 20:0;3/26:0;1

Description

Cer 20:0;3/26:0;1 is a ceramide. Ceramides are composed of a sphingosine and a fatty acid. Ceramides are found in high concentrations within the cell membrane of cells. Caramides are known to promote transport of secretory vesicles from the ER to the Golgi apparatus. Sphingolipids like ceramide play import roles in lipid rafts which in yeast are responsible for delivering and sorting membrane bound proteins. Lipid rafts also play roles in membrane fusion during mating.[PMID: 16730802 ]

‚Üµ‚Üµ

There are three major pathways of ceramide generation. The sphingomyelinase pathway uses an enzyme to breakdown IPC, MIPC and M(IP)2C in the cell membrane and release ceramide. The de novo pathway creates ceramide from less complex molecules. Ceramide generation can also occur through breakdown of complex sphingolipids that are ultimately broken down into sphingosine, which is then reused by reacylation to form ceramide. This latter pathway is termed the Salvage pathway.[Wikipedia, PMID: 16730802 ]

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241222552D          

 52 51  0  0  1  0            999 V2000
   36.7046   15.4164    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   36.7046   16.2414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.9901   15.0039    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   35.9901   14.1789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.2756   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5612   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8467   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1322   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4177   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7033   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9888   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2743   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5599   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8454   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1309   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4164   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7020   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9875   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2730   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5586   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4190   15.0039    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   37.4190   14.1789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1335   13.7664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.1335   15.4164    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.8480   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8480   14.1789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.5624   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2769   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9914   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7059   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4203   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.1348   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.8493   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.5637   15.0039    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   44.5637   14.1789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   45.2782   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.9927   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.7072   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   47.4216   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   48.1361   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   48.8506   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   49.5650   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   50.2795   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   50.9940   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   51.7085   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   52.4229   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   53.1374   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   53.8519   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   54.5663   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   55.2808   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   55.9953   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   56.7098   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  1  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  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 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  1 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
M  END


  Mrv0541 02241222552D          

 52 51  0  0  1  0            999 V2000
   36.7046   15.4164    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   36.7046   16.2414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.9901   15.0039    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   35.9901   14.1789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.2756   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5612   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8467   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1322   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4177   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7033   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9888   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2743   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5599   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8454   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1309   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4164   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7020   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9875   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2730   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5586   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4190   15.0039    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   37.4190   14.1789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1335   13.7664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.1335   15.4164    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.8480   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8480   14.1789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.5624   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2769   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9914   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7059   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4203   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.1348   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.8493   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.5637   15.0039    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   44.5637   14.1789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   45.2782   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.9927   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.7072   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   47.4216   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   48.1361   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   48.8506   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   49.5650   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   50.2795   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   50.9940   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   51.7085   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   52.4229   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   53.1374   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   53.8519   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   54.5663   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   55.2808   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   55.9953   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   56.7098   15.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  1  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  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 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  1 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033221

> <DATABASE_NAME>
MIME

> <SMILES>
CCCCCCCCCCCCCCCCC[C@@H](O)CCCCCCCC(=O)N[C@@H](CO)[C@H](O)[C@H](O)CCCCCCCCCCCCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C46H93NO5/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-29-33-37-42(49)38-34-30-28-32-36-40-45(51)47-43(41-48)46(52)44(50)39-35-31-27-25-23-21-18-16-14-12-10-8-6-4-2/h42-44,46,48-50,52H,3-41H2,1-2H3,(H,47,51)/t42-,43+,44-,46+/m1/s1

> <INCHI_KEY>
PHSFNVKCRVZOMR-DEVDZBFCSA-N

> <FORMULA>
C46H93NO5

> <MOLECULAR_WEIGHT>
740.2343

> <EXACT_MASS>
739.705375091

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
100.58337103906975

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9R)-9-hydroxy-N-[(2S,3S,4R)-1,3,4-trihydroxyicosan-2-yl]hexacosanamide

> <ALOGPS_LOGP>
9.58

> <JCHEM_LOGP>
13.944571186333338

> <ALOGPS_LOGS>
-7.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.385631960970802

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.209740656153702

> <JCHEM_PKA_STRONGEST_BASIC>
0.050485364092658136

> <JCHEM_POLAR_SURFACE_AREA>
110.02

> <JCHEM_REFRACTIVITY>
223.0561

> <JCHEM_ROTATABLE_BOND_COUNT>
43

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.31e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9R)-9-hydroxy-N-[(2S,3S,4R)-1,3,4-trihydroxyicosan-2-yl]hexacosanamide

> <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      68.515  28.777   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      68.515  30.317   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      67.182  28.007   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      67.182  26.467   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      65.848  28.777   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      64.514  28.007   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      63.181  28.777   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      61.847  28.007   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      60.513  28.777   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      59.179  28.007   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      57.846  28.777   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      56.512  28.007   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      55.178  28.777   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      53.845  28.007   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      52.511  28.777   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      51.177  28.007   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      49.844  28.777   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      48.510  28.007   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      47.176  28.777   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      45.843  28.007   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      69.849  28.007   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      69.849  26.467   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      71.183  25.697   0.000  0.00  0.00           O+0
HETATM   24  N   UNK     0      71.183  28.777   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0      72.516  28.007   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      72.516  26.467   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      73.850  28.777   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      75.184  28.007   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      76.517  28.777   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      77.851  28.007   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      79.185  28.777   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      80.518  28.007   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      81.852  28.777   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      83.186  28.007   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      83.186  26.467   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      84.519  28.777   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      85.853  28.007   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      87.187  28.777   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      88.520  28.007   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      89.854  28.777   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      91.188  28.007   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      92.521  28.777   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      93.855  28.007   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      95.189  28.777   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      96.523  28.007   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      97.856  28.777   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      99.190  28.007   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0     100.524  28.777   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0     101.857  28.007   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0     103.191  28.777   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0     104.525  28.007   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0     105.858  28.777   0.000  0.00  0.00           C+0
CONECT    1    2    3   21                                                  
CONECT    2    1                                                            
CONECT    3    1    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21    1   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  102    0
END

Synonyms

Not Available

Molecular Formula

C₄₆H₉₃NO₅

Average Mass

740.2343

Monoisotopic Mass

739.705375091

IUPAC Name

(9R)-9-hydroxy-N-[(2S,3S,4R)-1,3,4-trihydroxyicosan-2-yl]hexacosanamide

Traditional Name

(9R)-9-hydroxy-N-[(2S,3S,4R)-1,3,4-trihydroxyicosan-2-yl]hexacosanamide

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCCC[C@@H](O)CCCCCCCC(=O)N[C@@H](CO)[C@H](O)[C@H](O)CCCCCCCCCCCCCCCC

InChI Identifier

InChI=1S/C46H93NO5/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-29-33-37-42(49)38-34-30-28-32-36-40-45(51)47-43(41-48)46(52)44(50)39-35-31-27-25-23-21-18-16-14-12-10-8-6-4-2/h42-44,46,48-50,52H,3-41H2,1-2H3,(H,47,51)/t42-,43+,44-,46+/m1/s1

InChI Key

PHSFNVKCRVZOMR-DEVDZBFCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phytoceramides. These are n-acylated 4-hydroxysphinganine.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Sphingolipids

Sub Class

Ceramides

Direct Parent

Phytoceramides

Alternative Parents

Substituents

N-acyl-4-hydroxysphinganine
Fatty acyl
N-acyl-amine
Fatty amide
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Polyol
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	6.3e-05 g/L	ALOGPS
logP	9.58	ALOGPS
logP	13.94	ChemAxon
logS	-7.1	ALOGPS
pKa (Strongest Acidic)	13.21	ChemAxon
pKa (Strongest Basic)	0.05	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	110.02 Å²	ChemAxon
Rotatable Bond Count	43	ChemAxon
Refractivity	223.06 m³·mol⁻¹	ChemAxon
Polarizability	100.58 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006x-0005000900-13ea3a30292890f3bd0a	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ly9-7136900300-836c7d73d90130e790a1	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000b-6396143000-83cb27fe5f6def6ef5e5	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0021301900-8f7004077328eb0f186e	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f79-1043900300-d4e2090fb7ad05ae2123	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9133200000-e41c22e8b69a7ca8bf22	2016-09-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Dickson RC: Thematic review series: sphingolipids. New insights into sphingolipid metabolism and function in budding yeast. J Lipid Res. 2008 May;49(5):909-21. doi: 10.1194/jlr.R800003-JLR200. Epub 2008 Feb 23. [PubMed:18296751 ]
Ejsing CS, Sampaio JL, Surendranath V, Duchoslav E, Ekroos K, Klemm RW, Simons K, Shevchenko A: Global analysis of the yeast lipidome by quantitative shotgun mass spectrometry. Proc Natl Acad Sci U S A. 2009 Feb 17;106(7):2136-41. doi: 10.1073/pnas.0811700106. Epub 2009 Jan 27. [PubMed:19174513 ]

Showing metabocard for Cer 20:0;3/26:0;1 (MMDBc0033221)

MOL for #<Metabolite:0x00007f46d95cd650>

3D MOL for #<Metabolite:0x00007f46d95cd650>

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Structure for #<Metabolite:0x00007f46d95cd650>

3D Structure for #<Metabolite:0x00007f46d95cd650>