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Showing NP-Card for Cer(d18:0/20:1(11Z)) (NP0341434)

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Record Information
Version2.0
Created at2024-09-12 09:12:33 UTC
Updated at2024-09-12 09:12:33 UTC
NP-MRD IDNP0341434
Secondary Accession NumbersNone
Natural Product Identification
Common NameCer(d18:0/20:1(11Z))
DescriptionCer(d18:0/20:1(11Z)), also known as N-11Z-eicosenoyl-sphinganine, is a ceramide (Cer). Ceramides are members of the class of compounds known as sphingolipids (SPs), or glycosylceramides. SPs are lipids containing a backbone of sphingoid bases (e.G. Sphingosine or sphinganine) that are often covalently bound to a fatty acid derivative through N-acylation. SPs are found in cell membranes, particularly in peripheral nerve cells and the cells found in the central nervous system (including the brain and spinal cord). Sphingolipids are extremely versatile molecules that have functions controlling fundamental cellular processes such as cell division, differentiation, and cell death. Impairments associated with sphingolipid metabolism are associated with many common human diseases such as diabetes, various cancers, microbial infections, diseases of the cardiovascular and respiratory systems, Alzheimer’s disease and other neurological syndromes. The biosynthesis and catabolism of sphingolipids involves a large number of intermediate metabolites where many different enzymes are involved. Simple sphingolipids, which include the sphingoid bases and ceramides, make up the early products of the sphingolipid synthetic pathways, while complex sphingolipids may be formed by the addition of head groups to the ceramide template (Wikipedia). In humans, ceramides are phosphorylated to ceramide phosphates (CerPs) through the action of a specific ceramide kinase (CerK). Ceramide phosphates are important metabolites of ceramides as they act as a mediators of the inflammatory response. Ceramides are also one of the hydrolysis byproducts of sphingomyelins (SMs) through the action of the enzyme sphingomyelin phosphodiesterase, which has been identified in the subcellular fractions of human epidermis (PMID: 25935 ) And many other tissues. Ceramides can also be synthesized from serine and palmitate in a de novo pathway and are regarded as important cellular signals for inducing apoptosis (PMID: 14998372 ). Ceramides are key in the biosynthesis of glycosphingolipids and gangliosides. In terms of its appearance and structure, Cer(d18:0/20:1(11Z)) is a colorless solid that consists of a saturated 18-carbon sphingoid base with an attached unsaturated 11Z-eicosenoyl fatty acid side chain. Cer(d18:0/20:1(11Z)) was first documented in 1978 (PMID: 25935). In most mammalian SPs, the 18-carbon sphingoid bases are predominant (PMID: 9759481 ) (PMID: 14998372).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0341434 (Cer(d18:0/20:1(11Z)))

Cer(d18:0/20:1(11Z))
  Mrv1652304032007422D          

 42 41  0  0  1  0            999 V2000
   11.5317    9.5814    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.2462    9.9939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9607    9.5814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5317    8.6485    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8172    9.9939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8172   10.7654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1031    9.5808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3889    9.9939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6748    9.5808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9607    9.9939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2466    9.5808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5324    9.9939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8183    9.5808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1041    9.9939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3900    9.5808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6758    9.9939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9617    9.5808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2476    9.9939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5334    9.5808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8193    9.9939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1052    9.5808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8268    8.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8268    7.3553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1127    8.5399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3986    8.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6845    8.5399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9703    8.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2562    8.5399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5420    8.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8279    8.5399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1137    8.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3996    8.5399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6855    8.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8605    8.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1463    8.5399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4322    8.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7180    8.5399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0039    8.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7102    8.5399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4244    8.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1385    8.5399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8526    8.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6  0  0  0
  1  4  1  0  0  0  0
  2  3  1  0  0  0  0
  4 22  1  0  0  0  0
  5  1  1  0  0  0  0
  5  6  1  0  0  0  0
  5  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
 20 21  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  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  2  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
M  END
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3D MOL for NP0341434 (Cer(d18:0/20:1(11Z)))

Download
3D SDF for NP0341434 (Cer(d18:0/20:1(11Z)))
Cer(d18:0/20:1(11Z))
  Mrv1652304032007422D          

 42 41  0  0  1  0            999 V2000
   11.5317    9.5814    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.2462    9.9939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9607    9.5814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5317    8.6485    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8172    9.9939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8172   10.7654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1031    9.5808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3889    9.9939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6748    9.5808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9607    9.9939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2466    9.5808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5324    9.9939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8183    9.5808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1041    9.9939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3900    9.5808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6758    9.9939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9617    9.5808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2476    9.9939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5334    9.5808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8193    9.9939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1052    9.5808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8268    8.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8268    7.3553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1127    8.5399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3986    8.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6845    8.5399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9703    8.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2562    8.5399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5420    8.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8279    8.5399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1137    8.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3996    8.5399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6855    8.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8605    8.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1463    8.5399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4322    8.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7180    8.5399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0039    8.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7102    8.5399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4244    8.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1385    8.5399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8526    8.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6  0  0  0
  1  4  1  0  0  0  0
  2  3  1  0  0  0  0
  4 22  1  0  0  0  0
  5  1  1  0  0  0  0
  5  6  1  0  0  0  0
  5  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
 20 21  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  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  2  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
M  END
> <DATABASE_ID>
NP0341434

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCC(O)[C@H](CO)NC(=O)CCCCCCCCC\C=C/CCCCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C38H75NO3/c1-3-5-7-9-11-13-15-17-18-19-20-22-24-26-28-30-32-34-38(42)39-36(35-40)37(41)33-31-29-27-25-23-21-16-14-12-10-8-6-4-2/h17-18,36-37,40-41H,3-16,19-35H2,1-2H3,(H,39,42)/b18-17-/t36-,37?/m0/s1

> <INCHI_KEY>
PULBITQLTXYVQX-VQNGLQQLSA-N

> <FORMULA>
C38H75NO3

> <MOLECULAR_WEIGHT>
594.022

> <EXACT_MASS>
593.574695279

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
117

> <JCHEM_AVERAGE_POLARIZABILITY>
80.49174794041633

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(11Z)-N-[(2S)-1,3-dihydroxyoctadecan-2-yl]icos-11-enamide

> <ALOGPS_LOGP>
10.04

> <JCHEM_LOGP>
12.487722343666665

> <ALOGPS_LOGS>
-7.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.49219670204754

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.831978572938922

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0432563251212463

> <JCHEM_POLAR_SURFACE_AREA>
69.56

> <JCHEM_REFRACTIVITY>
184.3337

> <JCHEM_ROTATABLE_BOND_COUNT>
34

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.64e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(11Z)-N-[(2S)-1,3-dihydroxyoctadecan-2-yl]icos-11-enamide

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0341434 (Cer(d18:0/20:1(11Z)))
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PDB for NP0341434 (Cer(d18:0/20:1(11Z)))
HEADER    PROTEIN                                 03-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Cer(d18:0/20:1(11Z))                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-APR-20         0                                  
HETATM    1  C   UNK     0      21.526  17.885   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      22.860  18.655   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      24.193  17.885   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      21.526  16.144   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      20.192  18.655   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      20.192  20.095   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      18.859  17.884   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.526  18.655   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.193  17.884   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.860  18.655   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.527  17.884   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.194  18.655   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.861  17.884   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.528  18.655   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.195  17.884   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.861  18.655   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.529  17.884   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.196  18.655   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.862  17.884   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.529  18.655   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.196  17.884   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      20.210  15.170   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      20.210  13.730   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      18.877  15.941   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.544  15.170   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      16.211  15.941   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.878  15.170   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.545  15.941   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.212  15.170   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.879  15.941   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.546  15.170   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.213  15.941   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.880  15.170   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.340  15.170   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.006  15.941   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.673  15.170   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.340  15.941   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.007  15.170   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -1.326  15.941   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -2.659  15.170   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -3.992  15.941   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -5.325  15.170   0.000  0.00  0.00           C+0
CONECT    1    2    4    5                                                  
CONECT    2    1    3                                                       
CONECT    3    2                                                            
CONECT    4    1   22                                                       
CONECT    5    1    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    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   21                                                       
CONECT   21   20                                                            
CONECT   22    4   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
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                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   82    0
END

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3D PDB for NP0341434 (Cer(d18:0/20:1(11Z)))
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SMILES for NP0341434 (Cer(d18:0/20:1(11Z)))
CCCCCCCCCCCCCCCC(O)[C@H](CO)NC(=O)CCCCCCCCC\C=C/CCCCCCCC
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INCHI for NP0341434 (Cer(d18:0/20:1(11Z)))
InChI=1S/C38H75NO3/c1-3-5-7-9-11-13-15-17-18-19-20-22-24-26-28-30-32-34-38(42)39-36(35-40)37(41)33-31-29-27-25-23-21-16-14-12-10-8-6-4-2/h17-18,36-37,40-41H,3-16,19-35H2,1-2H3,(H,39,42)/b18-17-/t36-,37?/m0/s1
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View in JSmol
Synonyms
ValueSource
CeramideMetBuilder
N-(11Z-Eicosenoyl)-sphinganineMetBuilder
Ceramide(D18:0/20:1(11Z))MetBuilder
N-(11Z-Eicosenoyl)-dihydrosphingosineMetBuilder
N-(11Z-Eicosenoyl)-D-erythro-sphinganineMetBuilder
Chemical FormulaC38H75NO3
Average Mass594.0220 Da
Monoisotopic Mass593.57470 Da
IUPAC Name(11Z)-N-[(2S)-1,3-dihydroxyoctadecan-2-yl]icos-11-enamide
Traditional Name(11Z)-N-[(2S)-1,3-dihydroxyoctadecan-2-yl]icos-11-enamide
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCC(O)[C@H](CO)NC(=O)CCCCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C38H75NO3/c1-3-5-7-9-11-13-15-17-18-19-20-22-24-26-28-30-32-34-38(42)39-36(35-40)37(41)33-31-29-27-25-23-21-16-14-12-10-8-6-4-2/h17-18,36-37,40-41H,3-16,19-35H2,1-2H3,(H,39,42)/b18-17-/t36-,37?/m0/s1
InChI KeyPULBITQLTXYVQX-VQNGLQQLSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as long-chain ceramides. These are ceramides bearing a long chain fatty acid.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassSphingolipids  
Sub ClassCeramides  
Direct ParentLong-chain ceramides  
Alternative Parents
Substituents
  • Long-chain ceramide
    • 

  • Fatty amide
    • 

  • N-acyl-amine
    • 

  • Fatty acyl
    • 

  • Carboxamide group
    • 

  • Secondary carboxylic acid amide
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid derivative
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Alcohol
    • 

  • Organic nitrogen compound
    • 

  • Carbonyl group
    • 

  • Primary alcohol
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP10.04ALOGPS
logP12.49ChemAxon
logS-7.4ALOGPS
pKa (Strongest Acidic)13.83ChemAxon
pKa (Strongest Basic)-1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area69.56 ŲChemAxon
Rotatable Bond Count34ChemAxon
Refractivity184.33 m³·mol⁻¹ChemAxon
Polarizability80.49 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound89054488  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Bowser PA, Gray GM: Sphingomyelinase in pig and human epidermis. J Invest Dermatol. 1978 Jun;70(6):331-5. [PubMed:25935  ] 
  2. Tserng KY, Griffin RL: Ceramide metabolite, not intact ceramide molecule, may be responsible for cellular toxicity. Biochem J. 2004 Jun 15;380(Pt 3):715-22. doi: 10.1042/BJ20031733. [PubMed:14998372  ]