NP-MRD: Showing NP-Card for (-)-Ardisimamilloside E (NP0072717)

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Record Information

Version

2.0

Created at

2022-04-28 18:01:19 UTC

Updated at

2022-04-28 18:01:20 UTC

NP-MRD ID

NP0072717

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Ardisimamilloside E

Description

(2S,3R,4R,5R,6S)-2-{[(2S,3R,4S,5R,6R)-4,5-dihydroxy-2-{[(3S,4S,5R,6S)-4-hydroxy-6-{[(1S,2R,4S,5R,8R,10S,13S,14R,17S,18R,20R)-2-hydroxy-20-(hydroxymethyl)-4,5,9,9,13,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]Tetracosan-10-yl]oxy}-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (-)-Ardisimamilloside E is found in Ardisia mamillata and Ardisia mamillata HANCE.. Based on a literature review very few articles have been published on (2S,3R,4R,5R,6S)-2-{[(2S,3R,4S,5R,6R)-4,5-dihydroxy-2-{[(3S,4S,5R,6S)-4-hydroxy-6-{[(1S,2R,4S,5R,8R,10S,13S,14R,17S,18R,20R)-2-hydroxy-20-(hydroxymethyl)-4,5,9,9,13,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]Tetracosan-10-yl]oxy}-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282220012D          

 75 84  0  0  1  0            999 V2000
    4.5860    0.5313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0077    1.2404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6045    1.9601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7796    1.9708    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3579    1.2618    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7611    0.5420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5329    1.2725    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1297    1.9922    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5515    2.7013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3764    2.6906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2848    2.0233    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.2571    1.6865    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   10.7266   -3.1210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7452   -1.6922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9388   -0.2527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2889   -0.2313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7107    0.4778    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.5356    0.4671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9573    1.1762    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.5541    1.8959    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7292    1.9066    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3075    1.1976    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4825    1.2083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.9759    2.6050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7822    1.1655    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
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  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
  4 10  1  1  0  0  0
  8 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
  7 14  1  1  0  0  0
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 15 16  1  0  0  0  0
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 17 18  1  0  0  0  0
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 17 19  1  6  0  0  0
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 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
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 22 25  1  6  0  0  0
 25 26  1  0  0  0  0
 16 27  1  1  0  0  0
 27 28  1  0  0  0  0
 12 28  1  1  0  0  0
 11 29  1  6  0  0  0
  8 30  1  1  0  0  0
  5 31  1  6  0  0  0
  3 32  1  0  0  0  0
  3 33  1  0  0  0  0
  2 34  1  1  0  0  0
 35 34  1  6  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
 35 40  1  0  0  0  0
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 42 47  1  0  0  0  0
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 48 49  1  0  0  0  0
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 55 54  1  1  0  0  0
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 56 57  1  0  0  0  0
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 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
 55 60  1  0  0  0  0
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 61 62  1  0  0  0  0
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 66 71  1  0  0  0  0
 71 72  1  6  0  0  0
 70 73  1  6  0  0  0
 69 74  1  1  0  0  0
 68 75  1  6  0  0  0
M  END

     RDKit          3D

163172  0  0  0  0  0  0  0  0999 V2000
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    7.6847    4.8258   -0.3826 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.3779    0.4886   -1.4094 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1593    0.0405    0.7820 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7711   -1.3523    0.6729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2899   -1.2947    0.6760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8221   -0.4084   -0.3944 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -6.3274    0.6721    1.2603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6884   -0.0508    1.0392 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.3461    1.0346    2.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0841   -2.0706    0.1882 C   0  0  2  0  0  0  0  0  0  0  0  0
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    7.2340   -1.3907   -3.0155 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304282220012D          

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    9.9388   -0.2527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2889   -0.2313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7107    0.4778    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.5356    0.4671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9573    1.1762    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.5541    1.8959    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7292    1.9066    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3075    1.1976    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4825    1.2083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3260    2.6264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9759    2.6050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7822    1.1655    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
  1  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
  4 10  1  1  0  0  0
  8 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
  7 14  1  1  0  0  0
 12 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
 11 18  1  0  0  0  0
 17 19  1  6  0  0  0
 16 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 15 23  1  1  0  0  0
 22 24  1  1  0  0  0
 22 25  1  6  0  0  0
 25 26  1  0  0  0  0
 16 27  1  1  0  0  0
 27 28  1  0  0  0  0
 12 28  1  1  0  0  0
 11 29  1  6  0  0  0
  8 30  1  1  0  0  0
  5 31  1  6  0  0  0
  3 32  1  0  0  0  0
  3 33  1  0  0  0  0
  2 34  1  1  0  0  0
 35 34  1  6  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
 35 40  1  0  0  0  0
 40 41  1  1  0  0  0
 42 41  1  6  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 42 47  1  0  0  0  0
 46 48  1  6  0  0  0
 48 49  1  0  0  0  0
 45 50  1  6  0  0  0
 44 51  1  6  0  0  0
 43 52  1  1  0  0  0
 39 53  1  6  0  0  0
 38 54  1  6  0  0  0
 55 54  1  1  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
 55 60  1  0  0  0  0
 59 61  1  1  0  0  0
 61 62  1  0  0  0  0
 58 63  1  1  0  0  0
 57 64  1  1  0  0  0
 56 65  1  6  0  0  0
 66 65  1  1  0  0  0
 66 67  1  0  0  0  0
 67 68  1  0  0  0  0
 68 69  1  0  0  0  0
 69 70  1  0  0  0  0
 70 71  1  0  0  0  0
 66 71  1  0  0  0  0
 71 72  1  6  0  0  0
 70 73  1  6  0  0  0
 69 74  1  1  0  0  0
 68 75  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0072717

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]2O[C@H]2CO[C@@H](O[C@H]3CC[C@]4(C)[C@@H](CC[C@]5(C)[C@@H]4CC[C@]46OC[C@@]7(CC[C@@](C)(CO)C[C@@H]47)[C@H](O)C[C@@]56C)C3(C)C)[C@H](O[C@@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)[C@H]2O)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C53H88O22/c1-23-32(58)36(62)39(65)43(69-23)75-42-38(64)34(60)25(19-55)71-46(42)72-26-20-67-45(41(35(26)61)74-44-40(66)37(63)33(59)24(18-54)70-44)73-31-10-11-49(5)27(47(31,2)3)8-12-50(6)28(49)9-13-53-29-16-48(4,21-56)14-15-52(29,22-68-53)30(57)17-51(50,53)7/h23-46,54-66H,8-22H2,1-7H3/t23-,24+,25+,26-,27-,28+,29+,30+,31-,32-,33-,34-,35-,36+,37-,38-,39+,40+,41+,42+,43-,44-,45-,46-,48+,49+,50+,51-,52+,53-/m0/s1

> <INCHI_KEY>
LTTSWSWZQNISIB-CTHKGNACSA-N

> <FORMULA>
C53H88O22

> <MOLECULAR_WEIGHT>
1077.265

> <EXACT_MASS>
1076.576724474

> <JCHEM_ACCEPTOR_COUNT>
22

> <JCHEM_ATOM_COUNT>
163

> <JCHEM_AVERAGE_POLARIZABILITY>
113.19096232545283

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
13

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5R,6R)-2-{[(2S,3R,4S,5S)-5-{[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-2-{[(1S,2R,4S,5R,8R,10S,13S,14R,17S,18R,20R)-2-hydroxy-20-(hydroxymethyl)-4,5,9,9,13,20-hexamethyl-24-oxahexacyclo[15.5.2.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tetracosan-10-yl]oxy}oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
0.13

> <JCHEM_LOGP>
-1.3093732013333308

> <ALOGPS_LOGS>
-3.10

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
10

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.294451198262657

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.841768424913083

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6483775957536375

> <JCHEM_POLAR_SURFACE_AREA>
346.06000000000006

> <JCHEM_REFRACTIVITY>
256.21020000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.57e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5R,6R)-2-{[(2S,3R,4S,5S)-5-{[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-2-{[(1S,2R,4S,5R,8R,10S,13S,14R,17S,18R,20R)-2-hydroxy-20-(hydroxymethyl)-4,5,9,9,13,20-hexamethyl-24-oxahexacyclo[15.5.2.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tetracosan-10-yl]oxy}oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       8.561   0.992   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.348   2.315   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.595   3.659   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.055   3.679   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.268   2.355   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.021   1.012   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.728   2.375   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.976   3.719   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.763   5.042   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.303   5.022   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.398   3.777   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.551   2.354   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.407   1.032   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.950   1.034   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.480   3.148   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.890   3.853   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.024   5.198   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.630   5.228   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.710   6.552   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.184   3.019   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.110   1.481   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.740   0.776   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.733   1.735   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.048  -0.547   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.396  -0.617   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.931  -0.745   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.153   2.221   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.216   1.348   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.217   5.081   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.175   5.246   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.481   1.032   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.912   4.458   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.669   5.197   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      10.888   2.295   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      11.640   0.952   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      13.180   0.932   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      13.933  -0.412   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      13.146  -1.735   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      11.606  -1.715   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      10.853  -0.372   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       9.313  -0.352   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       8.526  -1.675   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       6.986  -1.655   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       6.199  -2.979   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       6.951  -4.323   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       8.491  -4.342   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       9.279  -3.019   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0       9.244  -5.686   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0       8.457  -7.010   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0       6.164  -5.646   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0       4.659  -2.959   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0       6.233  -0.312   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      10.818  -3.039   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0      13.898  -3.079   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      15.438  -3.099   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      16.225  -1.775   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      17.765  -1.795   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      18.518  -3.139   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      17.731  -4.462   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0      16.191  -4.442   0.000  0.00  0.00           O+0
HETATM   61  C   UNK     0      18.483  -5.806   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0      20.023  -5.826   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0      20.058  -3.159   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0      18.552  -0.472   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0      15.473  -0.432   0.000  0.00  0.00           O+0
HETATM   66  C   UNK     0      16.260   0.892   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0      17.800   0.872   0.000  0.00  0.00           O+0
HETATM   68  C   UNK     0      18.587   2.196   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0      17.834   3.539   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      16.294   3.559   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0      15.507   2.235   0.000  0.00  0.00           C+0
HETATM   72  O   UNK     0      13.967   2.255   0.000  0.00  0.00           O+0
HETATM   73  O   UNK     0      15.542   4.903   0.000  0.00  0.00           O+0
HETATM   74  O   UNK     0      18.622   4.863   0.000  0.00  0.00           O+0
HETATM   75  C   UNK     0      20.127   2.176   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   34                                                  
CONECT    3    2    4   32   33                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   31                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   14                                                  
CONECT    8    7    9   11   30                                             
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12   18   29                                             
CONECT   12   11   13   15   28                                             
CONECT   13   12   14                                                       
CONECT   14   13    7                                                       
CONECT   15   12   16   23                                                  
CONECT   16   15   17   20   27                                             
CONECT   17   16   18   19                                                  
CONECT   18   17   11                                                       
CONECT   19   17                                                            
CONECT   20   16   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24   25                                             
CONECT   23   22   15                                                       
CONECT   24   22                                                            
CONECT   25   22   26                                                       
CONECT   26   25                                                            
CONECT   27   16   28                                                       
CONECT   28   27   12                                                       
CONECT   29   11                                                            
CONECT   30    8                                                            
CONECT   31    5                                                            
CONECT   32    3                                                            
CONECT   33    3                                                            
CONECT   34    2   35                                                       
CONECT   35   34   36   40                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   54                                                  
CONECT   39   38   40   53                                                  
CONECT   40   39   35   41                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43   47                                                  
CONECT   43   42   44   52                                                  
CONECT   44   43   45   51                                                  
CONECT   45   44   46   50                                                  
CONECT   46   45   47   48                                                  
CONECT   47   46   42                                                       
CONECT   48   46   49                                                       
CONECT   49   48                                                            
CONECT   50   45                                                            
CONECT   51   44                                                            
CONECT   52   43                                                            
CONECT   53   39                                                            
CONECT   54   38   55                                                       
CONECT   55   54   56   60                                                  
CONECT   56   55   57   65                                                  
CONECT   57   56   58   64                                                  
CONECT   58   57   59   63                                                  
CONECT   59   58   60   61                                                  
CONECT   60   59   55                                                       
CONECT   61   59   62                                                       
CONECT   62   61                                                            
CONECT   63   58                                                            
CONECT   64   57                                                            
CONECT   65   56   66                                                       
CONECT   66   65   67   71                                                  
CONECT   67   66   68                                                       
CONECT   68   67   69   75                                                  
CONECT   69   68   70   74                                                  
CONECT   70   69   71   73                                                  
CONECT   71   70   66   72                                                  
CONECT   72   71                                                            
CONECT   73   70                                                            
CONECT   74   69                                                            
CONECT   75   68                                                            
MASTER        0    0    0    0    0    0    0    0   75    0  168    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₅₃H₈₈O₂₂

Average Mass

1077.2650 Da

Monoisotopic Mass

1076.57672 Da

IUPAC Name

(2S,3R,4S,5R,6R)-2-{[(2S,3R,4S,5S)-5-{[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-2-{[(1S,2R,4S,5R,8R,10S,13S,14R,17S,18R,20R)-2-hydroxy-20-(hydroxymethyl)-4,5,9,9,13,20-hexamethyl-24-oxahexacyclo[15.5.2.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tetracosan-10-yl]oxy}oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]2O[C@H]2CO[C@@H](O[C@H]3CC[C@]4(C)[C@@H](CC[C@]5(C)[C@@H]4CC[C@]46OC[C@@]7(CC[C@@](C)(CO)C[C@@H]47)[C@H](O)C[C@@]56C)C3(C)C)[C@H](O[C@@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)[C@H]2O)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C53H88O22/c1-23-32(58)36(62)39(65)43(69-23)75-42-38(64)34(60)25(19-55)71-46(42)72-26-20-67-45(41(35(26)61)74-44-40(66)37(63)33(59)24(18-54)70-44)73-31-10-11-49(5)27(47(31,2)3)8-12-50(6)28(49)9-13-53-29-16-48(4,21-56)14-15-52(29,22-68-53)30(57)17-51(50,53)7/h23-46,54-66H,8-22H2,1-7H3/t23-,24+,25+,26-,27-,28+,29+,30+,31-,32-,33-,34-,35-,36+,37-,38-,39+,40+,41+,42+,43-,44-,45-,46-,48+,49+,50+,51-,52+,53-/m0/s1

InChI Key

LTTSWSWZQNISIB-CTHKGNACSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Ardisia mamillata HANCE	LOTUS Database	35616633
Ardisia mamillata HANCE.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Oligosaccharide
O-glycosyl compound
Glycosyl compound
Oxepane
Oxane
Tetrahydrofuran
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Dialkyl ether
Acetal
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	0.13	ALOGPS
logP	-1.3	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	11.84	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	22	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	346.06 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	256.21 m³·mol⁻¹	ChemAxon
Polarizability	113.19 Å³	ChemAxon
Number of Rings	10	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

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

163018770

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Ardisimamilloside E (NP0072717)

MOL for NP0072717 ((-)-Ardisimamilloside E)

3D MOL for NP0072717 ((-)-Ardisimamilloside E)

3D SDF for NP0072717 ((-)-Ardisimamilloside E)

3D-SDF for NP0072717 ((-)-Ardisimamilloside E)

PDB for NP0072717 ((-)-Ardisimamilloside E)

3D PDB for NP0072717 ((-)-Ardisimamilloside E)

SMILES for NP0072717 ((-)-Ardisimamilloside E)

INCHI for NP0072717 ((-)-Ardisimamilloside E)

Structure for NP0072717 ((-)-Ardisimamilloside E)

3D Structure for NP0072717 ((-)-Ardisimamilloside E)