NP-MRD: Showing NP-Card for (2r)-n-[(2s,3s,4r,6e)-3,4-dihydroxy-1-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octadec-6-en-2-yl]-2-hydroxydocosanimidic acid (NP0260223)

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Record Information

Version

2.0

Created at

2022-09-08 02:19:26 UTC

Updated at

2022-09-08 02:19:26 UTC

NP-MRD ID

NP0260223

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r)-n-[(2s,3s,4r,6e)-3,4-dihydroxy-1-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octadec-6-en-2-yl]-2-hydroxydocosanimidic acid

Description

Amphimelibioside C belongs to the class of organic compounds known as glycosphingolipids. These are sphingolipids containing a saccharide moiety glycosidically attached to the sphingoid base. Although saccharide moieties are mostly O-glycosidically linked to the ceramide moiety, other sphingolipids with glycosidic bonds of other types (e.G. S-,C-, or N-type) has been reported. (2r)-n-[(2s,3s,4r,6e)-3,4-dihydroxy-1-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octadec-6-en-2-yl]-2-hydroxydocosanimidic acid is found in Amphimedon compressa. Based on a literature review very few articles have been published on Amphimelibioside C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082204192D          

 68 69  0  0  1  0            999 V2000
  -16.4328   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.7184   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.0039   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2894   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5749   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8605   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -6.6000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2868   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7158   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7158   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  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 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 27 26  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 29 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
 27 36  1  0  0  0  0
 36 37  1  1  0  0  0
 24 38  1  0  0  0  0
 38 39  1  1  0  0  0
 38 40  1  0  0  0  0
 40 41  1  6  0  0  0
 40 42  1  0  0  0  0
 22 42  1  0  0  0  0
 42 43  1  1  0  0  0
 19 44  1  1  0  0  0
 44 45  2  0  0  0  0
 45 46  1  4  0  0  0
 45 47  1  0  0  0  0
 47 48  1  6  0  0  0
 47 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
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  1  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
 61 62  1  0  0  0  0
 62 63  1  0  0  0  0
 63 64  1  0  0  0  0
 64 65  1  0  0  0  0
 65 66  1  0  0  0  0
 66 67  1  0  0  0  0
 67 68  1  0  0  0  0
M  END

     RDKit          3D

167168  0  0  0  0  0  0  0  0999 V2000
    4.3021   -4.5754   -7.7653 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3939   -4.0130   -6.8696 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8680   -3.5708   -5.5461 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.6111   -1.8007   -5.2582 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6910   -1.2635   -4.3140 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3654   -0.0628   -4.8878 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4416    1.0630   -5.1686 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7085    1.6367   -3.9959 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6867    2.1954   -2.9946 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1136    2.8277   -1.7966 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309082204192D          

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  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  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 27 26  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 29 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
 27 36  1  0  0  0  0
 36 37  1  1  0  0  0
 24 38  1  0  0  0  0
 38 39  1  1  0  0  0
 38 40  1  0  0  0  0
 40 41  1  6  0  0  0
 40 42  1  0  0  0  0
 22 42  1  0  0  0  0
 42 43  1  1  0  0  0
 19 44  1  1  0  0  0
 44 45  2  0  0  0  0
 45 46  1  4  0  0  0
 45 47  1  0  0  0  0
 47 48  1  6  0  0  0
 47 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
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  1  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
 61 62  1  0  0  0  0
 62 63  1  0  0  0  0
 63 64  1  0  0  0  0
 64 65  1  0  0  0  0
 65 66  1  0  0  0  0
 66 67  1  0  0  0  0
 67 68  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0260223

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCCCCCC[C@@H](O)C(O)=N[C@@H](CO[C@@H]1O[C@H](CO[C@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O)[C@H](O)[C@H](O)C\C=C\CCCCCCCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C52H99NO15/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-26-28-30-32-34-40(56)50(64)53-38(43(57)39(55)33-31-29-27-25-23-16-14-12-10-8-6-4-2)36-65-51-49(63)47(61)45(59)42(68-51)37-66-52-48(62)46(60)44(58)41(35-54)67-52/h29,31,38-49,51-52,54-63H,3-28,30,32-37H2,1-2H3,(H,53,64)/b31-29+/t38-,39+,40+,41+,42+,43-,44-,45+,46-,47-,48+,49+,51+,52-/m0/s1

> <INCHI_KEY>
KFCVBGVYKUTMSK-PYZNSCESSA-N

> <FORMULA>
C52H99NO15

> <MOLECULAR_WEIGHT>
978.356

> <EXACT_MASS>
977.701471492

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
167

> <JCHEM_AVERAGE_POLARIZABILITY>
118.4695548621444

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-N-[(2S,3S,4R,6E)-3,4-dihydroxy-1-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octadec-6-en-2-yl]-2-hydroxydocosanimidic acid

> <JCHEM_LOGP>
8.708822981666664

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.91167229632797

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9101147717758447

> <JCHEM_PKA_STRONGEST_BASIC>
1.623609308752868

> <JCHEM_POLAR_SURFACE_AREA>
271.80999999999995

> <JCHEM_REFRACTIVITY>
261.7377000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
42

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-N-[(2S,3S,4R,6E)-3,4-dihydroxy-1-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octadec-6-en-2-yl]-2-hydroxydocosanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0     -30.675  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -29.341  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -28.007  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -26.674  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -25.340  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -24.006  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -22.673  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -21.339  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -20.005  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -18.672  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -17.338  -5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -16.004  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0     -12.003  -6.930   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0     -10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0     -10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.667 -12.320   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -1.334 -16.170   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -4.001 -14.630   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -8.002 -13.860   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0     -10.669 -12.320   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0     -10.669  -9.240   0.000  0.00  0.00           O+0
HETATM   44  N   UNK     0      -8.002  -4.620   0.000  0.00  0.00           N+0
HETATM   45  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      -6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      16.004  -4.620   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      17.338  -5.390   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      18.672  -4.620   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      20.005  -5.390   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0      21.339  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
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   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   44                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   42                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   38                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   36                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   29   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   27   37                                                  
CONECT   37   36                                                            
CONECT   38   24   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   22   43                                                  
CONECT   43   42                                                            
CONECT   44   19   45                                                       
CONECT   45   44   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   59                                                       
CONECT   59   58   60                                                       
CONECT   60   59   61                                                       
CONECT   61   60   62                                                       
CONECT   62   61   63                                                       
CONECT   63   62   64                                                       
CONECT   64   63   65                                                       
CONECT   65   64   66                                                       
CONECT   66   65   67                                                       
CONECT   67   66   68                                                       
CONECT   68   67                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  138    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₅₂H₉₉NO₁₅

Average Mass

978.3560 Da

Monoisotopic Mass

977.70147 Da

IUPAC Name

(2R)-N-[(2S,3S,4R,6E)-3,4-dihydroxy-1-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octadec-6-en-2-yl]-2-hydroxydocosanimidic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCCCCCC[C@@H](O)C(O)=N[C@@H](CO[C@@H]1O[C@H](CO[C@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O)[C@H](O)[C@H](O)C\C=C\CCCCCCCCCCC

InChI Identifier

InChI=1S/C52H99NO15/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-26-28-30-32-34-40(56)50(64)53-38(43(57)39(55)33-31-29-27-25-23-16-14-12-10-8-6-4-2)36-65-51-49(63)47(61)45(59)42(68-51)37-66-52-48(62)46(60)44(58)41(35-54)67-52/h29,31,38-49,51-52,54-63H,3-28,30,32-37H2,1-2H3,(H,53,64)/b31-29+/t38-,39+,40+,41+,42+,43-,44-,45+,46-,47-,48+,49+,51+,52-/m0/s1

InChI Key

KFCVBGVYKUTMSK-PYZNSCESSA-N

Experimental Spectra

Not Available

Predicted Spectra

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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Amphimedon compressa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glycosphingolipids. These are sphingolipids containing a saccharide moiety glycosidically attached to the sphingoid base. Although saccharide moieties are mostly O-glycosidically linked to the ceramide moiety, other sphingolipids with glycosidic bonds of other types (e.G. S-,C-, or N-type) has been reported.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Sphingolipids

Sub Class

Glycosphingolipids

Direct Parent

Glycosphingolipids

Alternative Parents

Substituents

Glycosphingolipid
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Disaccharide
Glycosyl compound
O-glycosyl compound
Fatty amide
Fatty acyl
N-acyl-amine
Oxane
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Alcohol
Organic oxygen compound
Organic nitrogen compound
Primary alcohol
Carbonyl group
Organonitrogen compound
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

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	8.71	ChemAxon
pKa (Strongest Acidic)	3.91	ChemAxon
pKa (Strongest Basic)	1.62	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	271.81 Å²	ChemAxon
Rotatable Bond Count	42	ChemAxon
Refractivity	261.74 m³·mol⁻¹	ChemAxon
Polarizability	118.47 Å³	ChemAxon
Number of Rings	2	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9553034

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

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METLIN ID

Not Available

PubChem Compound

11378119

PDB ID

Not Available

ChEBI ID

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Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r)-n-[(2s,3s,4r,6e)-3,4-dihydroxy-1-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octadec-6-en-2-yl]-2-hydroxydocosanimidic acid (NP0260223)

MOL for NP0260223 ((2r)-n-[(2s,3s,4r,6e)-3,4-dihydroxy-1-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octadec-6-en-2-yl]-2-hydroxydocosanimidic acid)

3D MOL for NP0260223 ((2r)-n-[(2s,3s,4r,6e)-3,4-dihydroxy-1-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octadec-6-en-2-yl]-2-hydroxydocosanimidic acid)

3D SDF for NP0260223 ((2r)-n-[(2s,3s,4r,6e)-3,4-dihydroxy-1-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octadec-6-en-2-yl]-2-hydroxydocosanimidic acid)

3D-SDF for NP0260223 ((2r)-n-[(2s,3s,4r,6e)-3,4-dihydroxy-1-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octadec-6-en-2-yl]-2-hydroxydocosanimidic acid)

PDB for NP0260223 ((2r)-n-[(2s,3s,4r,6e)-3,4-dihydroxy-1-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octadec-6-en-2-yl]-2-hydroxydocosanimidic acid)

3D PDB for NP0260223 ((2r)-n-[(2s,3s,4r,6e)-3,4-dihydroxy-1-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octadec-6-en-2-yl]-2-hydroxydocosanimidic acid)

SMILES for NP0260223 ((2r)-n-[(2s,3s,4r,6e)-3,4-dihydroxy-1-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octadec-6-en-2-yl]-2-hydroxydocosanimidic acid)

INCHI for NP0260223 ((2r)-n-[(2s,3s,4r,6e)-3,4-dihydroxy-1-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octadec-6-en-2-yl]-2-hydroxydocosanimidic acid)

Structure for NP0260223 ((2r)-n-[(2s,3s,4r,6e)-3,4-dihydroxy-1-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octadec-6-en-2-yl]-2-hydroxydocosanimidic acid)

3D Structure for NP0260223 ((2r)-n-[(2s,3s,4r,6e)-3,4-dihydroxy-1-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octadec-6-en-2-yl]-2-hydroxydocosanimidic acid)