MiMeDB: Showing metabocard for N-(26-hydroxyhexacosanoyl)sphinganine (MMDBc0033063)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:33:07 UTC

Update Date

2022-08-31 22:25:32 UTC

Metabolite ID

MMDBc0033063

Metabolite Identification

Common Name

N-(26-hydroxyhexacosanoyl)sphinganine

Description

N-(26-Hydroxyhexacosanoyl)sphinganine is a ceramide (a sphingolipid). Ceramides are found in high concentrations within the cell membrane of cells. 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

‚ÜµThere 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 ]‚Üµ

Structure

MOL SDF PDB SMILES InChI

Structure #1
  Mrv0541 02241222282D          

 49 48  0  0  0  0            999 V2000
   27.7135  -17.9180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4280  -17.5055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5701  -17.5055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1438  -17.5055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4293  -17.9180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7148  -17.5055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0004  -17.9180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2859  -17.5055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5714  -17.9180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8570  -17.5055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1425  -17.9180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9991  -17.5055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2846  -17.9180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8583  -17.9180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5727  -17.5055    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   36.2872  -17.9180    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   37.0017  -17.5055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8556  -17.9179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5727  -16.6806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.2871  -18.7432    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.7161  -17.9182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.5726  -19.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8582  -18.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1399  -18.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8543  -19.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5688  -18.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2833  -19.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9977  -18.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7122  -19.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4267  -18.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1412  -19.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8556  -18.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5701  -19.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2846  -18.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9990  -19.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7135  -18.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4280  -19.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1425  -18.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8569  -19.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5714  -18.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2859  -19.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0003  -18.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7148  -19.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4293  -18.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1437  -19.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5726  -19.9807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4254  -19.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7109  -18.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9964  -19.1557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3 18  1  0  0  0  0
  4  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  2  1  0  0  0  0
  1 12  1  0  0  0  0
 13  3  1  0  0  0  0
 12 13  1  0  0  0  0
 14  4  1  0  0  0  0
 15 14  1  0  0  0  0
 15 19  1  1  0  0  0
 15 16  1  0  0  0  0
 16 20  1  6  0  0  0
 16 17  1  0  0  0  0
 17 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 45 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 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  0  0  0  0
 35 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
 22 46  2  0  0  0  0
 24 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
M  END

Structure #1
  Mrv0541 02241222282D          

 49 48  0  0  0  0            999 V2000
   27.7135  -17.9180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4280  -17.5055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5701  -17.5055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1438  -17.5055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4293  -17.9180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7148  -17.5055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0004  -17.9180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2859  -17.5055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5714  -17.9180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8570  -17.5055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1425  -17.9180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9991  -17.5055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2846  -17.9180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8583  -17.9180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5727  -17.5055    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   36.2872  -17.9180    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   37.0017  -17.5055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8556  -17.9179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5727  -16.6806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.2871  -18.7432    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.7161  -17.9182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.5726  -19.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8582  -18.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1399  -18.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8543  -19.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5688  -18.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2833  -19.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9977  -18.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7122  -19.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4267  -18.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1412  -19.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8556  -18.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5701  -19.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2846  -18.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9990  -19.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7135  -18.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4280  -19.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1425  -18.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8569  -19.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5714  -18.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2859  -19.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0003  -18.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7148  -19.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4293  -18.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1437  -19.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5726  -19.9807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4254  -19.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7109  -18.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9964  -19.1557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3 18  1  0  0  0  0
  4  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  2  1  0  0  0  0
  1 12  1  0  0  0  0
 13  3  1  0  0  0  0
 12 13  1  0  0  0  0
 14  4  1  0  0  0  0
 15 14  1  0  0  0  0
 15 19  1  1  0  0  0
 15 16  1  0  0  0  0
 16 20  1  6  0  0  0
 16 17  1  0  0  0  0
 17 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 45 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 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  0  0  0  0
 35 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
 22 46  2  0  0  0  0
 24 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033063

> <DATABASE_NAME>
MIME

> <SMILES>
CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(=O)CCCCCCCCCCCCCCCCCCCCCCCCCO

> <INCHI_IDENTIFIER>
InChI=1S/C44H89NO4/c1-2-3-4-5-6-7-8-20-23-26-29-32-35-38-43(48)42(41-47)45-44(49)39-36-33-30-27-24-21-18-16-14-12-10-9-11-13-15-17-19-22-25-28-31-34-37-40-46/h42-43,46-48H,2-41H2,1H3,(H,45,49)/t42-,43+/m0/s1

> <INCHI_KEY>
XZMFWWLYDZUCKQ-WZYYJWNZSA-N

> <FORMULA>
C44H89NO4

> <MOLECULAR_WEIGHT>
696.1818

> <EXACT_MASS>
695.679160341

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
96.1141747812356

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]-26-hydroxyhexacosanamide

> <ALOGPS_LOGP>
9.94

> <JCHEM_LOGP>
14.08037737366667

> <ALOGPS_LOGS>
-7.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.492196702047824

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.831978572939391

> <JCHEM_PKA_STRONGEST_BASIC>
0.037754875836708

> <JCHEM_POLAR_SURFACE_AREA>
89.79

> <JCHEM_REFRACTIVITY>
212.75179999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
42

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.46e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]-26-hydroxyhexacosanamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      51.732 -33.447   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      53.066 -32.677   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      47.731 -32.677   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      63.735 -32.677   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      62.401 -33.447   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      61.068 -32.677   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      59.734 -33.447   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      58.400 -32.677   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      57.067 -33.447   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      55.733 -32.677   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      54.399 -33.447   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      50.398 -32.677   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      49.065 -33.447   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      65.069 -33.447   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      66.402 -32.677   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      67.736 -33.447   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      69.070 -32.677   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      46.397 -33.447   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      66.402 -31.137   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0      67.736 -34.987   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0      70.403 -33.447   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      66.402 -35.757   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      65.069 -34.987   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      35.728 -34.987   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      37.061 -35.757   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      38.395 -34.987   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      39.729 -35.757   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      41.062 -34.987   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      42.396 -35.757   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      43.730 -34.987   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      45.064 -35.757   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      46.397 -34.987   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      47.731 -35.757   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      49.065 -34.987   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      50.398 -35.757   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      51.732 -34.987   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      53.066 -35.757   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      54.399 -34.987   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      55.733 -35.757   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      57.067 -34.987   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      58.400 -35.757   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      59.734 -34.987   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      61.068 -35.757   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      62.401 -34.987   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      63.735 -35.757   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      66.402 -37.297   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      34.394 -35.757   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      33.060 -34.987   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      31.727 -35.757   0.000  0.00  0.00           O+0
CONECT    1    2   12                                                       
CONECT    2    1   11                                                       
CONECT    3   18   13                                                       
CONECT    4    5   14                                                       
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    2                                                       
CONECT   12    1   13                                                       
CONECT   13    3   12                                                       
CONECT   14    4   15                                                       
CONECT   15   14   19   16                                                  
CONECT   16   15   20   17                                                  
CONECT   17   16   21                                                       
CONECT   18    3                                                            
CONECT   19   15                                                            
CONECT   20   16   22                                                       
CONECT   21   17                                                            
CONECT   22   20   23   46                                                  
CONECT   23   22   45                                                       
CONECT   24   25   47                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   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                                                       
CONECT   35   34   36                                                       
CONECT   36   35   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   23   44                                                       
CONECT   46   22                                                            
CONECT   47   24   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48                                                            
MASTER        0    0    0    0    0    0    0    0   49    0   96    0
END

Synonyms

Not Available

Molecular Formula

C₄₄H₈₉NO₄

Average Mass

696.1818

Monoisotopic Mass

695.679160341

IUPAC Name

N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]-26-hydroxyhexacosanamide

Traditional Name

N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]-26-hydroxyhexacosanamide

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(=O)CCCCCCCCCCCCCCCCCCCCCCCCCO

InChI Identifier

InChI=1S/C44H89NO4/c1-2-3-4-5-6-7-8-20-23-26-29-32-35-38-43(48)42(41-47)45-44(49)39-36-33-30-27-24-21-18-16-14-12-10-9-11-13-15-17-19-22-25-28-31-34-37-40-46/h42-43,46-48H,2-41H2,1H3,(H,45,49)/t42-,43+/m0/s1

InChI Key

XZMFWWLYDZUCKQ-WZYYJWNZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ceramides. These are lipid molecules containing a sphingosine in which the amine group is linked to a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Sphingolipids

Sub Class

Ceramides

Direct Parent

Ceramides

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

N-acylsphinganines (dihydroceramides) (LMSP02020018 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	3.5e-05 g/L	ALOGPS
logP	9.94	ALOGPS
logP	14.08	ChemAxon
logS	-7.3	ALOGPS
pKa (Strongest Acidic)	13.83	ChemAxon
pKa (Strongest Basic)	0.038	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	89.79 Å²	ChemAxon
Rotatable Bond Count	42	ChemAxon
Refractivity	212.75 m³·mol⁻¹	ChemAxon
Polarizability	96.11 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	splash10-01t9-0012009000-e49cd78eb9cd64850c34	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0in9-1155109000-604003ba99ba813ab373	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uxs-4759000000-fca41f9d679bc9ccf331	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002f-0001109000-b4b547a746bd139aeffe	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fba-0024409000-1a3cd22e13972138da19	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9044100000-2d076da374d8c5df8814	2016-09-12	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-24	106.8
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	83.0
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-24	1082.3
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	1443.5
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	1686.8
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-24	693.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (retained)	2025-10-24	5673.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-24	246.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	233.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	1358.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	587.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	275.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	418.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	9.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (void)	2025-10-24	783.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	1075.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	798.7
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	3297.5
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	3875.8

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	N-(26-hydroxyhexacosanoyl)sphinganine_TMS_1	CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C)[C@H](CO)NC(=O)CCCCCCCCCCCCCCCCCCCCCCCCCO	standard non polar	2025-10-24	2838.36
Gas Chromatography	N-(26-hydroxyhexacosanoyl)sphinganine_TMS_2	CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO[Si](C)(C)C)NC(=O)CCCCCCCCCCCCCCCCCCCCCCCCCO	standard non polar	2025-10-24	3114.78
Gas Chromatography	N-(26-hydroxyhexacosanoyl)sphinganine_TMS_3	CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(=O)CCCCCCCCCCCCCCCCCCCCCCCCCO[Si](C)(C)C	standard non polar	2025-10-24	1998.26
Gas Chromatography	N-(26-hydroxyhexacosanoyl)sphinganine_TMS_4	CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)N(C(=O)CCCCCCCCCCCCCCCCCCCCCCCCCO)[Si](C)(C)C	standard non polar	2025-10-24	235.556
Gas Chromatography	N-(26-hydroxyhexacosanoyl)sphinganine_TMS_5	CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)NC(=O)CCCCCCCCCCCCCCCCCCCCCCCCCO	standard non polar	2025-10-24	1009.72
Gas Chromatography	N-(26-hydroxyhexacosanoyl)sphinganine_TMS_6	CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C)[C@H](CO)NC(=O)CCCCCCCCCCCCCCCCCCCCCCCCCO[Si](C)(C)C	standard non polar	2025-10-24	2097.26
Gas Chromatography	N-(26-hydroxyhexacosanoyl)sphinganine_TMS_7	CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C)[C@H](CO)N(C(=O)CCCCCCCCCCCCCCCCCCCCCCCCCO)[Si](C)(C)C	standard non polar	2025-10-24	2938.55
Gas Chromatography	N-(26-hydroxyhexacosanoyl)sphinganine_TMS_8	CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO[Si](C)(C)C)NC(=O)CCCCCCCCCCCCCCCCCCCCCCCCCO[Si](C)(C)C	standard non polar	2025-10-24	1410.95
Gas Chromatography	N-(26-hydroxyhexacosanoyl)sphinganine_TMS_9	CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO[Si](C)(C)C)N(C(=O)CCCCCCCCCCCCCCCCCCCCCCCCCO)[Si](C)(C)C	standard non polar	2025-10-24	2180.73
Gas Chromatography	N-(26-hydroxyhexacosanoyl)sphinganine_TMS_10	CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)N(C(=O)CCCCCCCCCCCCCCCCCCCCCCCCCO[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2291.32
Gas Chromatography	N-(26-hydroxyhexacosanoyl)sphinganine_TMS_1	CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C)[C@H](CO)NC(=O)CCCCCCCCCCCCCCCCCCCCCCCCCO	standard polar	2025-10-24	1813.99
Gas Chromatography	N-(26-hydroxyhexacosanoyl)sphinganine_TMS_2	CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO[Si](C)(C)C)NC(=O)CCCCCCCCCCCCCCCCCCCCCCCCCO	standard polar	2025-10-24	2431.39
Gas Chromatography	N-(26-hydroxyhexacosanoyl)sphinganine_TMS_3	CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(=O)CCCCCCCCCCCCCCCCCCCCCCCCCO[Si](C)(C)C	standard polar	2025-10-24	2977.11
Gas Chromatography	N-(26-hydroxyhexacosanoyl)sphinganine_TMS_4	CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)N(C(=O)CCCCCCCCCCCCCCCCCCCCCCCCCO)[Si](C)(C)C	standard polar	2025-10-24	216.273
Gas Chromatography	N-(26-hydroxyhexacosanoyl)sphinganine_TMS_5	CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)NC(=O)CCCCCCCCCCCCCCCCCCCCCCCCCO	standard polar	2025-10-24	2480.68
Gas Chromatography	N-(26-hydroxyhexacosanoyl)sphinganine_TMS_6	CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C)[C@H](CO)NC(=O)CCCCCCCCCCCCCCCCCCCCCCCCCO[Si](C)(C)C	standard polar	2025-10-24	1944.9
Gas Chromatography	N-(26-hydroxyhexacosanoyl)sphinganine_TMS_7	CCCCCCCCCCCCCCC[C@@H](O[Si](C)(C)C)[C@H](CO)N(C(=O)CCCCCCCCCCCCCCCCCCCCCCCCCO)[Si](C)(C)C	standard polar	2025-10-24	1944.45
Gas Chromatography	N-(26-hydroxyhexacosanoyl)sphinganine_TMS_8	CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO[Si](C)(C)C)NC(=O)CCCCCCCCCCCCCCCCCCCCCCCCCO[Si](C)(C)C	standard polar	2025-10-24	2315.89
Gas Chromatography	N-(26-hydroxyhexacosanoyl)sphinganine_TMS_9	CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO[Si](C)(C)C)N(C(=O)CCCCCCCCCCCCCCCCCCCCCCCCCO)[Si](C)(C)C	standard polar	2025-10-24	2480.71
Gas Chromatography	N-(26-hydroxyhexacosanoyl)sphinganine_TMS_10	CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)N(C(=O)CCCCCCCCCCCCCCCCCCCCCCCCCO[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2945.8

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

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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

Other Exposures

Source Type	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

25271604

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Reggiori F, Conzelmann A: Biosynthesis of inositol phosphoceramides and remodeling of glycosylphosphatidylinositol anchors in Saccharomyces cerevisiae are mediated by different enzymes. J Biol Chem. 1998 Nov 13;273(46):30550-9. doi: 10.1074/jbc.273.46.30550. [PubMed:9804825 ]
Funato K, Vallee B, Riezman H: Biosynthesis and trafficking of sphingolipids in the yeast Saccharomyces cerevisiae. Biochemistry. 2002 Dec 24;41(51):15105-14. doi: 10.1021/bi026616d. [PubMed:12484746 ]
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 ]
Herrgard MJ, Swainston N, Dobson P, Dunn WB, Arga KY, Arvas M, Bluthgen N, Borger S, Costenoble R, Heinemann M, Hucka M, Le Novere N, Li P, Liebermeister W, Mo ML, Oliveira AP, Petranovic D, Pettifer S, Simeonidis E, Smallbone K, Spasic I, Weichart D, Brent R, Broomhead DS, Westerhoff HV, Kirdar B, Penttila M, Klipp E, Palsson BO, Sauer U, Oliver SG, Mendes P, Nielsen J, Kell DB: A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology. Nat Biotechnol. 2008 Oct;26(10):1155-60. doi: 10.1038/nbt1492. [PubMed:18846089 ]

Showing metabocard for N-(26-hydroxyhexacosanoyl)sphinganine (MMDBc0033063)

MOL for #<Metabolite:0x00007f9ac44e36b0>

3D MOL for #<Metabolite:0x00007f9ac44e36b0>

3D SDF for #<Metabolite:0x00007f9ac44e36b0>

3D-SDF for #<Metabolite:0x00007f9ac44e36b0>

PDB for #<Metabolite:0x00007f9ac44e36b0>

3D PDB for #<Metabolite:0x00007f9ac44e36b0>

SMILES for #<Metabolite:0x00007f9ac44e36b0>

INCHI for #<Metabolite:0x00007f9ac44e36b0>

Structure for #<Metabolite:0x00007f9ac44e36b0>

3D Structure for #<Metabolite:0x00007f9ac44e36b0>