NP-MRD: Showing NP-Card for (1s,3r,4s,5r,6r,8r,10s,16s,23r,24r,25r,26r)-5,16-bis(acetyloxy)-4,26-dihydroxy-6-methyl-17,20-dioxo-24-{[(2e)-3-phenylprop-2-enoyl]oxy}-10-propyl-2,7,9,21,27-pentaoxatricyclo[21.3.1.0³,⁸]heptacosan-25-yl (2e)-2-methylbut-2-enoate (NP0198751)

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Record Information

Version

2.0

Created at

2022-09-04 17:15:24 UTC

Updated at

2022-09-04 17:15:25 UTC

NP-MRD ID

NP0198751

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3r,4s,5r,6r,8r,10s,16s,23r,24r,25r,26r)-5,16-bis(acetyloxy)-4,26-dihydroxy-6-methyl-17,20-dioxo-24-{[(2e)-3-phenylprop-2-enoyl]oxy}-10-propyl-2,7,9,21,27-pentaoxatricyclo[21.3.1.0³,⁸]heptacosan-25-yl (2e)-2-methylbut-2-enoate

Description

Ipomoeassin D belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety. (1s,3r,4s,5r,6r,8r,10s,16s,23r,24r,25r,26r)-5,16-bis(acetyloxy)-4,26-dihydroxy-6-methyl-17,20-dioxo-24-{[(2e)-3-phenylprop-2-enoyl]oxy}-10-propyl-2,7,9,21,27-pentaoxatricyclo[21.3.1.0³,⁸]heptacosan-25-yl (2e)-2-methylbut-2-enoate is found in Ipomoea squamosa. Based on a literature review very few articles have been published on ipomoeassin D.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042219152D          

 61 64  0  0  1  0            999 V2000
    9.7868    1.0154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9916    0.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7842   -0.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3719   -0.5816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9889   -0.2222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7815   -1.0207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4011    0.3567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6059    0.1371    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0181    0.7160    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2256    1.5145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2229    0.4964    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0154   -0.3021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6032   -0.8810    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3957   -1.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6005   -1.8991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0127   -1.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2202   -0.5217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2175   -1.5397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6297   -0.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8344   -1.1804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6270   -1.9789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2467   -0.6015    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0392   -1.4000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2440   -1.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0365   -2.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3438   -1.0407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4514   -0.8211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1364   -0.2422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0711    0.5563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8663    0.7759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0738    1.5744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8690    1.7940    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0765    2.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4887    3.1714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6961    3.9698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4568    1.2150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2520    1.4346    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4595    2.2331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2547    2.4527    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4622    3.2512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8425    1.8738    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6378    2.0934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8452    2.8919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2574    3.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6405    3.1115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8124    0.7735    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4509    0.9525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8398    0.8557    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6351    1.0753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3984   -0.6614    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9862   -1.2403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7788   -2.0388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3666   -2.6177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9835   -2.2584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7761   -3.0569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9808   -3.2765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7734   -4.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9781   -4.2945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3903   -3.7156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5978   -2.9171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3930   -2.6976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 13 12  1  1  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  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 22 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  6  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 32 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  6  0  0  0
 38 39  1  0  0  0  0
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 46 47  1  6  0  0  0
 46 48  1  0  0  0  0
 37 48  1  0  0  0  0
 48 49  1  1  0  0  0
 11 49  1  0  0  0  0
 13 50  1  0  0  0  0
  8 50  1  0  0  0  0
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 59 60  1  0  0  0  0
 60 61  2  0  0  0  0
 56 61  1  0  0  0  0
M  END

     RDKit          3D

121124  0  0  0  0  0  0  0  0999 V2000
    7.0561   -4.3021   -0.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8929   -3.4834   -0.0561 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8876   -2.7585    1.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0300   -2.7177    1.9664 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6822   -1.9596    1.3527 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6325   -1.2537    2.3938 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5837   -1.9552    0.5286 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4578   -1.1878    0.8522 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2194   -2.0191    1.0275 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2180   -2.4649    2.3716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0629   -1.4121    0.6517 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.6992    1.8917   -0.4668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4032    2.5254    0.1775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3980    3.7848    0.7145 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1101    5.1808   -1.2242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2720    5.9185   -0.6779 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.6602   -1.6454   -1.4620 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8818   -5.4270   -0.6313 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9278   -6.2013    0.0736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5347   -7.4677   -0.2556 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.8973    5.1189   -0.3501 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1570    4.8439    0.7780 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0922    3.9820    0.6916 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309042219152D          

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M  END
> <DATABASE_ID>
NP0198751

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC[C@H]1CCCCC[C@H](OC(C)=O)C(=O)CCC(=O)OC[C@H]2O[C@@H](O[C@@H]3[C@@H](O)[C@@H](OC(C)=O)[C@@H](C)O[C@H]3O1)[C@H](O)[C@@H](OC(=O)C(\C)=C\C)[C@@H]2OC(=O)\C=C\C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C44H60O17/c1-7-15-30-18-13-10-14-19-32(55-27(5)45)31(47)21-23-34(48)53-24-33-39(59-35(49)22-20-29-16-11-9-12-17-29)40(60-42(52)25(3)8-2)37(51)43(58-33)61-41-36(50)38(56-28(6)46)26(4)54-44(41)57-30/h8-9,11-12,16-17,20,22,26,30,32-33,36-41,43-44,50-51H,7,10,13-15,18-19,21,23-24H2,1-6H3/b22-20+,25-8+/t26-,30+,32+,33-,36+,37-,38+,39-,40-,41-,43+,44+/m1/s1

> <INCHI_KEY>
RGCFRCYTLQGODZ-JRKLWBHCSA-N

> <FORMULA>
C44H60O17

> <MOLECULAR_WEIGHT>
860.947

> <EXACT_MASS>
860.383050472

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
121

> <JCHEM_AVERAGE_POLARIZABILITY>
88.66126645188427

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R,4S,5R,6R,8R,10S,16S,23R,24R,25R,26R)-5,16-bis(acetyloxy)-4,26-dihydroxy-6-methyl-17,20-dioxo-24-{[(2E)-3-phenylprop-2-enoyl]oxy}-10-propyl-2,7,9,21,27-pentaoxatricyclo[21.3.1.0^{3,8}]heptacosan-25-yl (2E)-2-methylbut-2-enoate

> <JCHEM_LOGP>
6.229231847999998

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.039396185490464

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.240991738072077

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6981710854657592

> <JCHEM_POLAR_SURFACE_AREA>
225.94999999999993

> <JCHEM_REFRACTIVITY>
213.17589999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,4S,5R,6R,8R,10S,16S,23R,24R,25R,26R)-5,16-bis(acetyloxy)-4,26-dihydroxy-6-methyl-17,20-dioxo-24-{[(2E)-3-phenylprop-2-enoyl]oxy}-10-propyl-2,7,9,21,27-pentaoxatricyclo[21.3.1.0^{3,8}]heptacosan-25-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      18.269   1.895   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.784   1.486   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.397  -0.005   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      17.494  -1.086   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.913  -0.415   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      14.525  -1.905   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      13.815   0.666   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      12.331   0.256   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.234   1.337   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      11.621   2.827   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.749   0.927   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.362  -0.564   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      10.459  -1.645   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.072  -3.135   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.588  -3.545   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       7.490  -2.464   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.878  -0.974   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.006  -2.874   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.909  -1.794   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.424  -2.203   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.037  -3.694   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.327  -1.123   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.940  -2.613   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.455  -3.023   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.068  -4.514   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.642  -1.943   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.843  -1.533   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.255  -0.452   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.133   1.038   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.617   1.448   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.004   2.939   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.489   3.349   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.876   4.839   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.779   5.920   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.166   7.410   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.586   2.268   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       6.070   2.678   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       6.458   4.168   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       7.942   4.578   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       8.329   6.069   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       9.039   3.498   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      10.524   3.908   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      10.911   5.398   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       9.814   6.479   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      12.396   5.808   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       8.983   1.444   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      10.175   1.778   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0       7.168   1.597   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0       8.652   2.007   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      11.944  -1.235   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      13.041  -2.315   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      12.654  -3.806   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      13.751  -4.886   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      11.169  -4.216   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      10.782  -5.706   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       9.298  -6.116   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       8.910  -7.607   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       7.426  -8.016   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       6.329  -6.936   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       6.716  -5.445   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       8.200  -5.035   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   50                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   49                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   50                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   22   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   36                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   32   37                                                       
CONECT   37   36   38   48                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42   46                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43                                                            
CONECT   46   41   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   37   49                                                  
CONECT   49   48   11                                                       
CONECT   50   13    8   51                                                  
CONECT   51   50   52                                                       
CONECT   52   51   53   54                                                  
CONECT   53   52                                                            
CONECT   54   52   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   57   61                                                  
CONECT   57   56   58                                                       
CONECT   58   57   59                                                       
CONECT   59   58   60                                                       
CONECT   60   59   61                                                       
CONECT   61   60   56                                                       
MASTER        0    0    0    0    0    0    0    0   61    0  128    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₄H₆₀O₁₇

Average Mass

860.9470 Da

Monoisotopic Mass

860.38305 Da

IUPAC Name

(1S,3R,4S,5R,6R,8R,10S,16S,23R,24R,25R,26R)-5,16-bis(acetyloxy)-4,26-dihydroxy-6-methyl-17,20-dioxo-24-{[(2E)-3-phenylprop-2-enoyl]oxy}-10-propyl-2,7,9,21,27-pentaoxatricyclo[21.3.1.0^{3,8}]heptacosan-25-yl (2E)-2-methylbut-2-enoate

Traditional Name

CAS Registry Number

Not Available

SMILES

CCC[C@H]1CCCCC[C@H](OC(C)=O)C(=O)CCC(=O)OC[C@H]2O[C@@H](O[C@@H]3[C@@H](O)[C@@H](OC(C)=O)[C@@H](C)O[C@H]3O1)[C@H](O)[C@@H](OC(=O)C(\C)=C\C)[C@@H]2OC(=O)\C=C\C1=CC=CC=C1

InChI Identifier

InChI=1S/C44H60O17/c1-7-15-30-18-13-10-14-19-32(55-27(5)45)31(47)21-23-34(48)53-24-33-39(59-35(49)22-20-29-16-11-9-12-17-29)40(60-42(52)25(3)8-2)37(51)43(58-33)61-41-36(50)38(56-28(6)46)26(4)54-44(41)57-30/h8-9,11-12,16-17,20,22,26,30,32-33,36-41,43-44,50-51H,7,10,13-15,18-19,21,23-24H2,1-6H3/b22-20+,25-8+/t26-,30+,32+,33-,36+,37-,38+,39-,40-,41-,43+,44+/m1/s1

InChI Key

RGCFRCYTLQGODZ-JRKLWBHCSA-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
Ipomoea squamosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Saccharolipids

Sub Class

Not Available

Direct Parent

Saccharolipids

Alternative Parents

Substituents

Saccharolipid
Pentacarboxylic acid or derivatives
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Macrolide
Alkyl glycoside
Cinnamic acid or derivatives
Cinnamic acid ester
Disaccharide
Styrene
Fatty acid ester
Alpha-acyloxy ketone
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Oxane
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Cyclic ketone
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Organoheterocyclic compound
Acetal
Carboxylic acid derivative
Oxacycle
Organic oxygen compound
Carbonyl group
Organooxygen compound
Alcohol
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	6.23	ChemAxon
pKa (Strongest Acidic)	12.24	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	225.95 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	213.18 m³·mol⁻¹	ChemAxon
Polarizability	88.66 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00042624

Chemspider ID

9380266

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11205204

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3r,4s,5r,6r,8r,10s,16s,23r,24r,25r,26r)-5,16-bis(acetyloxy)-4,26-dihydroxy-6-methyl-17,20-dioxo-24-{[(2e)-3-phenylprop-2-enoyl]oxy}-10-propyl-2,7,9,21,27-pentaoxatricyclo[21.3.1.0³,⁸]heptacosan-25-yl (2e)-2-methylbut-2-enoate (NP0198751)

MOL for NP0198751 ((1s,3r,4s,5r,6r,8r,10s,16s,23r,24r,25r,26r)-5,16-bis(acetyloxy)-4,26-dihydroxy-6-methyl-17,20-dioxo-24-{[(2e)-3-phenylprop-2-enoyl]oxy}-10-propyl-2,7,9,21,27-pentaoxatricyclo[21.3.1.0³,⁸]heptacosan-25-yl (2e)-2-methylbut-2-enoate)

3D MOL for NP0198751 ((1s,3r,4s,5r,6r,8r,10s,16s,23r,24r,25r,26r)-5,16-bis(acetyloxy)-4,26-dihydroxy-6-methyl-17,20-dioxo-24-{[(2e)-3-phenylprop-2-enoyl]oxy}-10-propyl-2,7,9,21,27-pentaoxatricyclo[21.3.1.0³,⁸]heptacosan-25-yl (2e)-2-methylbut-2-enoate)

3D SDF for NP0198751 ((1s,3r,4s,5r,6r,8r,10s,16s,23r,24r,25r,26r)-5,16-bis(acetyloxy)-4,26-dihydroxy-6-methyl-17,20-dioxo-24-{[(2e)-3-phenylprop-2-enoyl]oxy}-10-propyl-2,7,9,21,27-pentaoxatricyclo[21.3.1.0³,⁸]heptacosan-25-yl (2e)-2-methylbut-2-enoate)

3D-SDF for NP0198751 ((1s,3r,4s,5r,6r,8r,10s,16s,23r,24r,25r,26r)-5,16-bis(acetyloxy)-4,26-dihydroxy-6-methyl-17,20-dioxo-24-{[(2e)-3-phenylprop-2-enoyl]oxy}-10-propyl-2,7,9,21,27-pentaoxatricyclo[21.3.1.0³,⁸]heptacosan-25-yl (2e)-2-methylbut-2-enoate)

PDB for NP0198751 ((1s,3r,4s,5r,6r,8r,10s,16s,23r,24r,25r,26r)-5,16-bis(acetyloxy)-4,26-dihydroxy-6-methyl-17,20-dioxo-24-{[(2e)-3-phenylprop-2-enoyl]oxy}-10-propyl-2,7,9,21,27-pentaoxatricyclo[21.3.1.0³,⁸]heptacosan-25-yl (2e)-2-methylbut-2-enoate)

3D PDB for NP0198751 ((1s,3r,4s,5r,6r,8r,10s,16s,23r,24r,25r,26r)-5,16-bis(acetyloxy)-4,26-dihydroxy-6-methyl-17,20-dioxo-24-{[(2e)-3-phenylprop-2-enoyl]oxy}-10-propyl-2,7,9,21,27-pentaoxatricyclo[21.3.1.0³,⁸]heptacosan-25-yl (2e)-2-methylbut-2-enoate)

SMILES for NP0198751 ((1s,3r,4s,5r,6r,8r,10s,16s,23r,24r,25r,26r)-5,16-bis(acetyloxy)-4,26-dihydroxy-6-methyl-17,20-dioxo-24-{[(2e)-3-phenylprop-2-enoyl]oxy}-10-propyl-2,7,9,21,27-pentaoxatricyclo[21.3.1.0³,⁸]heptacosan-25-yl (2e)-2-methylbut-2-enoate)

INCHI for NP0198751 ((1s,3r,4s,5r,6r,8r,10s,16s,23r,24r,25r,26r)-5,16-bis(acetyloxy)-4,26-dihydroxy-6-methyl-17,20-dioxo-24-{[(2e)-3-phenylprop-2-enoyl]oxy}-10-propyl-2,7,9,21,27-pentaoxatricyclo[21.3.1.0³,⁸]heptacosan-25-yl (2e)-2-methylbut-2-enoate)

Structure for NP0198751 ((1s,3r,4s,5r,6r,8r,10s,16s,23r,24r,25r,26r)-5,16-bis(acetyloxy)-4,26-dihydroxy-6-methyl-17,20-dioxo-24-{[(2e)-3-phenylprop-2-enoyl]oxy}-10-propyl-2,7,9,21,27-pentaoxatricyclo[21.3.1.0³,⁸]heptacosan-25-yl (2e)-2-methylbut-2-enoate)

3D Structure for NP0198751 ((1s,3r,4s,5r,6r,8r,10s,16s,23r,24r,25r,26r)-5,16-bis(acetyloxy)-4,26-dihydroxy-6-methyl-17,20-dioxo-24-{[(2e)-3-phenylprop-2-enoyl]oxy}-10-propyl-2,7,9,21,27-pentaoxatricyclo[21.3.1.0³,⁸]heptacosan-25-yl (2e)-2-methylbut-2-enoate)