NP-MRD: Showing NP-Card for (-)-Saprosmoside E (NP0080297)

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Record Information

Version

2.0

Created at

2022-04-29 01:20:24 UTC

Updated at

2022-04-29 01:20:24 UTC

NP-MRD ID

NP0080297

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Saprosmoside E

Description

(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(4R,7S,8S,11S)-6-({[(methylsulfanyl)carbonyl]oxy}methyl)-2-oxo-3,9-dioxatricyclo[5.3.1.0⁴,¹¹]Undeca-1(10),5-dien-8-yl]oxy}oxan-3-yl (1S,4aS,5R,7aS)-5-hydroxy-7-({[(methylsulfanyl)carbonyl]oxy}methyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylate belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton. (-)-Saprosmoside E is found in Saprosma scortechinii. Based on a literature review very few articles have been published on (2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(4R,7S,8S,11S)-6-({[(methylsulfanyl)carbonyl]oxy}methyl)-2-oxo-3,9-dioxatricyclo[5.3.1.0⁴,¹¹]Undeca-1(10),5-dien-8-yl]oxy}oxan-3-yl (1S,4aS,5R,7aS)-5-hydroxy-7-({[(methylsulfanyl)carbonyl]oxy}methyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292203202D          

 60 66  0  0  1  0            999 V2000
    7.1467   -0.2691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3680   -0.5416    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2146   -1.3522    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8400   -1.8903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4359   -1.6247    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8106   -1.0866    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9639   -0.2760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7426   -0.0034    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8960    0.8072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6747    1.0797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0319   -1.3591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4065   -0.8210    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5599   -0.0103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9345    0.5278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1559    0.2553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0025   -0.5554    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6278   -1.0935    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3093   -1.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4871   -1.7867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2975   -0.9838    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6721   -0.4457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9907    0.3153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5514    1.0137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7378   -2.5595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3414   -3.2831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7699   -3.9881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5947   -3.9696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3735   -4.7117    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8020   -5.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2826   -2.4353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.6866   -2.7009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7546   -3.7841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9759   -4.0566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8225   -4.8672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4479   -5.4053    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2266   -5.1328    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3799   -4.3222    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1982   -4.2175    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5507   -4.9635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9501   -5.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0548   -6.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3984   -6.8473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5031   -7.6656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2641   -7.9841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8467   -8.1654    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.9513   -8.9837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5946   -3.4940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2945   -6.2159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5158   -6.4884    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3625   -7.2990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5838   -7.5716    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9584   -7.0334    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1118   -6.2228    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8905   -5.9503    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0438   -5.1397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4864   -5.6847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1797   -7.3059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4304   -8.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6517   -8.6547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  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
  2  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
  6 11  1  6  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 16 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 15 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
  5 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 33  1  1  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 37 41  1  1  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 44 46  1  0  0  0  0
 46 47  1  0  0  0  0
 39 48  1  6  0  0  0
 36 49  1  6  0  0  0
 50 49  1  6  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
 50 55  1  0  0  0  0
 55 56  1  1  0  0  0
 54 57  1  6  0  0  0
 53 58  1  1  0  0  0
 52 59  1  6  0  0  0
 59 60  1  0  0  0  0
M  END

     RDKit          3D

104110  0  0  0  0  0  0  0  0999 V2000
   -6.3099    1.0837   -5.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7459    0.1590   -5.2409 S   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.0130   -1.4938   -1.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7687   -1.0717   -0.8069 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6286   -1.0238    0.1269 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4239   -1.5667   -0.3385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9193    0.3209   -0.4647 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3265    1.4759    0.1644 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0057    1.9327   -0.2563 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5131    2.9693    0.2740 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7513    1.2946   -1.2086 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1015    0.7675   -1.1790 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -6.9126    0.9334   -5.9549 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.9276   -1.4000   -0.8815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6595   -2.8869   -0.7269 H   0  0  0  0  0  0  0  0  0  0  0  0
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 35 81  1  6
 36 82  1  6
M  END


  Mrv1652304292203202D          

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  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  6  0  0  0
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 12 11  1  1  0  0  0
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 12 17  1  0  0  0  0
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 28 29  1  0  0  0  0
  5 30  1  1  0  0  0
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 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 33  1  1  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 37 41  1  1  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 44 46  1  0  0  0  0
 46 47  1  0  0  0  0
 39 48  1  6  0  0  0
 36 49  1  6  0  0  0
 50 49  1  6  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
 50 55  1  0  0  0  0
 55 56  1  1  0  0  0
 54 57  1  6  0  0  0
 53 58  1  1  0  0  0
 52 59  1  6  0  0  0
 59 60  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0080297

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CSC(=O)OCC1=C[C@H]2OC(=O)C3=CO[C@@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4OC(=O)C4=CO[C@@H](O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)[C@H]5[C@@H]4[C@H](O)C=C5COC(=O)SC)[C@H]1[C@H]23

> <INCHI_IDENTIFIER>
InChI=1S/C36H44O22S2/c1-59-35(47)51-7-11-3-15(39)21-13(9-49-31(19(11)21)57-33-27(44)25(42)23(40)17(5-37)54-33)30(46)56-28-26(43)24(41)18(6-38)55-34(28)58-32-20-12(8-52-36(48)60-2)4-16-22(20)14(10-50-32)29(45)53-16/h3-4,9-10,15-28,31-34,37-44H,5-8H2,1-2H3/t15-,16-,17-,18-,19-,20-,21+,22+,23-,24-,25+,26+,27-,28-,31+,32+,33+,34+/m1/s1

> <INCHI_KEY>
YUOFAUXZZZPWPA-SLZDHSGSSA-N

> <FORMULA>
C36H44O22S2

> <MOLECULAR_WEIGHT>
892.85

> <EXACT_MASS>
892.176565405

> <JCHEM_ACCEPTOR_COUNT>
20

> <JCHEM_ATOM_COUNT>
104

> <JCHEM_AVERAGE_POLARIZABILITY>
84.83484909669576

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(4R,7S,8S,11S)-6-({[(methylsulfanyl)carbonyl]oxy}methyl)-2-oxo-3,9-dioxatricyclo[5.3.1.0^{4,11}]undeca-1(10),5-dien-8-yl]oxy}oxan-3-yl (1S,4aS,5R,7aS)-5-hydroxy-7-({[(methylsulfanyl)carbonyl]oxy}methyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylate

> <ALOGPS_LOGP>
-0.27

> <JCHEM_LOGP>
-2.0679310406666653

> <ALOGPS_LOGS>
-1.99

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.688011768731105

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.082904641945849

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810847615636256

> <JCHEM_POLAR_SURFACE_AREA>
322.42

> <JCHEM_REFRACTIVITY>
197.50920000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.17e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(4R,7S,8S,11S)-6-({[(methylsulfanyl)carbonyl]oxy}methyl)-2-oxo-3,9-dioxatricyclo[5.3.1.0^{4,11}]undeca-1(10),5-dien-8-yl]oxy}oxan-3-yl (1S,4aS,5R,7aS)-5-hydroxy-7-({[(methylsulfanyl)carbonyl]oxy}methyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0      13.340  -0.502   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      11.887  -1.011   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.601  -2.524   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      12.768  -3.529   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.147  -3.033   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.980  -2.028   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.266  -0.515   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      10.720  -0.006   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.006   1.507   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      12.459   2.015   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       7.526  -2.537   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.359  -1.532   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.645  -0.019   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.478   0.985   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.024   0.477   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.738  -1.037   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.905  -2.041   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.311  -3.462   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.776  -3.335   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.422  -1.836   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.255  -0.832   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.849   0.589   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.029   1.892   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.110  -4.778   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.371  -6.128   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.170  -7.444   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.710  -7.410   0.000  0.00  0.00           O+0
HETATM   28  S   UNK     0       4.431  -8.795   0.000  0.00  0.00           S+0
HETATM   29  C   UNK     0       5.230 -10.111   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       9.861  -4.546   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      11.028  -5.550   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      12.482  -5.042   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      10.742  -7.064   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.288  -7.572   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       9.002  -9.085   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      10.169 -10.090   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      11.623  -9.581   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      11.909  -8.068   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      13.437  -7.873   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      14.095  -9.265   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      12.974 -10.321   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      13.169 -11.849   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      11.944 -12.782   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      12.139 -14.309   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      13.560 -14.904   0.000  0.00  0.00           O+0
HETATM   46  S   UNK     0      10.914 -15.242   0.000  0.00  0.00           S+0
HETATM   47  C   UNK     0      11.109 -16.770   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      14.177  -6.522   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0       9.883 -11.603   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0       8.430 -12.112   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       8.143 -13.625   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0       6.690 -14.134   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       5.522 -13.129   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       5.809 -11.616   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       7.262 -11.107   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0       7.548  -9.594   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0       4.641 -10.611   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0       4.069 -13.638   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0       6.403 -15.647   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0       4.950 -16.155   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   30                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    2    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    6   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   15   17   20                                                  
CONECT   17   16   12   18                                                  
CONECT   18   17   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   16   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   15   23                                                  
CONECT   23   22                                                            
CONECT   24   18   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28                                                            
CONECT   30    5   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   49                                                  
CONECT   37   36   38   41                                                  
CONECT   38   37   33   39                                                  
CONECT   39   38   40   48                                                  
CONECT   40   39   41                                                       
CONECT   41   40   37   42                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47                                                       
CONECT   47   46                                                            
CONECT   48   39                                                            
CONECT   49   36   50                                                       
CONECT   50   49   51   55                                                  
CONECT   51   50   52                                                       
CONECT   52   51   53   59                                                  
CONECT   53   52   54   58                                                  
CONECT   54   53   55   57                                                  
CONECT   55   54   50   56                                                  
CONECT   56   55                                                            
CONECT   57   54                                                            
CONECT   58   53                                                            
CONECT   59   52   60                                                       
CONECT   60   59                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  132    0
END

View in JSmol

Synonyms

Value	Source
(2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-2-{[(4R,7S,8S,11S)-6-({[(methylsulfanyl)carbonyl]oxy}methyl)-2-oxo-3,9-dioxatricyclo[5.3.1.0,]undeca-1(10),5-dien-8-yl]oxy}oxan-3-yl (1S,4as,5R,7as)-5-hydroxy-7-({[(methylsulfanyl)carbonyl]oxy}methyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4ah,5H,7ah-cyclopenta[c]pyran-4-carboxylic acid	Generator
(2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-2-{[(4R,7S,8S,11S)-6-({[(methylsulphanyl)carbonyl]oxy}methyl)-2-oxo-3,9-dioxatricyclo[5.3.1.0,]undeca-1(10),5-dien-8-yl]oxy}oxan-3-yl (1S,4as,5R,7as)-5-hydroxy-7-({[(methylsulphanyl)carbonyl]oxy}methyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4ah,5H,7ah-cyclopenta[c]pyran-4-carboxylate	Generator
(2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-2-{[(4R,7S,8S,11S)-6-({[(methylsulphanyl)carbonyl]oxy}methyl)-2-oxo-3,9-dioxatricyclo[5.3.1.0,]undeca-1(10),5-dien-8-yl]oxy}oxan-3-yl (1S,4as,5R,7as)-5-hydroxy-7-({[(methylsulphanyl)carbonyl]oxy}methyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4ah,5H,7ah-cyclopenta[c]pyran-4-carboxylic acid	Generator

Chemical Formula

C₃₆H₄₄O₂₂S₂

Average Mass

892.8500 Da

Monoisotopic Mass

892.17657 Da

IUPAC Name

(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(4R,7S,8S,11S)-6-({[(methylsulfanyl)carbonyl]oxy}methyl)-2-oxo-3,9-dioxatricyclo[5.3.1.0^{4,11}]undeca-1(10),5-dien-8-yl]oxy}oxan-3-yl (1S,4aS,5R,7aS)-5-hydroxy-7-({[(methylsulfanyl)carbonyl]oxy}methyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylate

Traditional Name

CAS Registry Number

Not Available

SMILES

CSC(=O)OCC1=C[C@H]2OC(=O)C3=CO[C@@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4OC(=O)C4=CO[C@@H](O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)[C@H]5[C@@H]4[C@H](O)C=C5COC(=O)SC)[C@H]1[C@H]23

InChI Identifier

InChI=1S/C36H44O22S2/c1-59-35(47)51-7-11-3-15(39)21-13(9-49-31(19(11)21)57-33-27(44)25(42)23(40)17(5-37)54-33)30(46)56-28-26(43)24(41)18(6-38)55-34(28)58-32-20-12(8-52-36(48)60-2)4-16-22(20)14(10-50-32)29(45)53-16/h3-4,9-10,15-28,31-34,37-44H,5-8H2,1-2H3/t15-,16-,17-,18-,19-,20-,21+,22+,23-,24-,25+,26+,27-,28-,31+,32+,33+,34+/m1/s1

InChI Key

YUOFAUXZZZPWPA-SLZDHSGSSA-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
Saprosma scortechinii	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Iridoid O-glycosides

Alternative Parents

Substituents

Iridoid o-glycoside
Saccharolipid
Terpene lactone
O-glycosyl compound
Iridoid-skeleton
Glycosyl compound
Monoterpenoid
Furopyran
Pyran
Oxane
Monosaccharide
Gamma butyrolactone
Dicarboxylic acid or derivatives
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Monothioacetal
Furan
Secondary alcohol
Thiocarbonic acid derivative
Carbonic acid derivative
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Sulfenyl compound
Polyol
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organosulfur compound
Organooxygen compound
Carbonyl group
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	-0.27	ALOGPS
logP	-2.1	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	12.08	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	322.42 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	197.51 m³·mol⁻¹	ChemAxon
Polarizability	84.83 Å³	ChemAxon
Number of Rings	7	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

162928863

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (-)-Saprosmoside E (NP0080297)

MOL for NP0080297 ((-)-Saprosmoside E)

3D MOL for NP0080297 ((-)-Saprosmoside E)

3D SDF for NP0080297 ((-)-Saprosmoside E)

3D-SDF for NP0080297 ((-)-Saprosmoside E)

PDB for NP0080297 ((-)-Saprosmoside E)

3D PDB for NP0080297 ((-)-Saprosmoside E)

SMILES for NP0080297 ((-)-Saprosmoside E)

INCHI for NP0080297 ((-)-Saprosmoside E)

Structure for NP0080297 ((-)-Saprosmoside E)

3D Structure for NP0080297 ((-)-Saprosmoside E)