NP-MRD: Showing NP-Card for β-escin (NP0280805)

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Record Information

Version

1.0

Created at

2022-09-09 06:47:55 UTC

Updated at

2022-09-09 06:47:55 UTC

NP-MRD ID

NP0280805

Secondary Accession Numbers

None

Natural Product Identification

Common Name

β-escin

Description

Escin Ib, also known as reparil, belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton. β-escin is found in Aesculus chinensis, Aesculus hippocastanum and Aesculus turbinata. It was first documented in 2010 (PMID: 20662111). Based on a literature review a significant number of articles have been published on escin Ib (PMID: 24334163) (PMID: 34324856) (PMID: 32158393) (PMID: 26819933).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092208472D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309092208472D          

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   10.2020   -5.2520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.7895   -5.9664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -5.2520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9337   -6.0644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8522   -5.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9955   -6.3466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -5.2520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8395   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -5.2520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1895   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -5.2520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6907   -6.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -5.9664    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6257   -6.7869    0.0000 O   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  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 25 24  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
 32 31  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  6  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 34 38  1  0  0  0  0
 38 39  1  1  0  0  0
 40 39  1  1  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  1  0  0  0
 43 44  1  0  0  0  0
 42 45  1  0  0  0  0
 45 46  1  6  0  0  0
 45 47  1  0  0  0  0
 47 48  1  1  0  0  0
 47 49  1  0  0  0  0
 40 49  1  0  0  0  0
 49 50  1  6  0  0  0
 38 51  1  0  0  0  0
 51 52  1  6  0  0  0
 51 53  1  0  0  0  0
 32 53  1  0  0  0  0
 53 54  1  1  0  0  0
 55 54  1  6  0  0  0
 55 56  1  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  6  0  0  0
 58 59  1  0  0  0  0
 57 60  1  0  0  0  0
 60 61  1  1  0  0  0
 60 62  1  0  0  0  0
 62 63  1  6  0  0  0
 62 64  1  0  0  0  0
 55 64  1  0  0  0  0
 64 65  1  1  0  0  0
 30 66  1  0  0  0  0
 66 67  1  1  0  0  0
 66 68  1  6  0  0  0
 68 69  1  0  0  0  0
 66 70  1  0  0  0  0
 26 70  1  0  0  0  0
 70 71  1  6  0  0  0
 71 72  1  0  0  0  0
 72 73  1  0  0  0  0
 25 73  1  0  0  0  0
 73 74  1  6  0  0  0
 73 75  1  0  0  0  0
 22 75  1  0  0  0  0
 75 76  1  1  0  0  0
 75 77  1  0  0  0  0
 77 78  1  0  0  0  0
 14 78  1  0  0  0  0
 78 79  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0280805

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(\C)C(=O)O[C@H]1[C@H](OC(C)=O)[C@]2(CO)[C@H](O)C[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O[C@@H]6O[C@@H]([C@@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H](O)[C@H]6O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)C(O)=O)[C@](C)(CO)[C@@H]5CC[C@@]34C)[C@@H]2CC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C55H86O24/c1-10-23(2)46(71)79-43-44(72-24(3)60)55(22-59)26(17-50(43,4)5)25-11-12-30-51(6)15-14-32(52(7,21-58)29(51)13-16-53(30,8)54(25,9)18-31(55)61)75-49-41(77-48-38(67)36(65)34(63)28(20-57)74-48)39(68)40(42(78-49)45(69)70)76-47-37(66)35(64)33(62)27(19-56)73-47/h10-11,26-44,47-49,56-59,61-68H,12-22H2,1-9H3,(H,69,70)/b23-10-/t26-,27+,28+,29+,30+,31+,32-,33+,34+,35-,36-,37+,38+,39-,40-,41+,42-,43-,44-,47-,48-,49+,51-,52+,53+,54+,55-/m0/s1

> <INCHI_KEY>
AXNVHPCVMSNXNP-OXPBSUTMSA-N

> <FORMULA>
C55H86O24

> <MOLECULAR_WEIGHT>
1131.269

> <EXACT_MASS>
1130.550903649

> <JCHEM_ACCEPTOR_COUNT>
22

> <JCHEM_ATOM_COUNT>
165

> <JCHEM_AVERAGE_POLARIZABILITY>
119.1176602495174

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
13

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6R)-6-{[(3S,4S,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-9-(acetyloxy)-8-hydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-{[(2Z)-2-methylbut-2-enoyl]oxy}-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-4-hydroxy-3,5-bis({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})oxane-2-carboxylic acid

> <JCHEM_LOGP>
-0.8771895139999987

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.904149483257452

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3492294373675984

> <JCHEM_PKA_STRONGEST_BASIC>
-3.648377595753688

> <JCHEM_POLAR_SURFACE_AREA>
388.0400000000001

> <JCHEM_REFRACTIVITY>
269.7838000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
opino

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.056  -4.469   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.826  -5.803   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.056  -7.136   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.826  -8.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.516  -7.136   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.746  -5.803   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -1.746  -8.470   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.206  -8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.564  -9.804   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.206 -11.137   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.746 -11.137   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.516  -9.804   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.516 -12.471   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.104  -9.804   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334 -11.137   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.104 -12.471   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.874  -8.470   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.104  -7.136   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.564  -7.136   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.742  -6.320   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.510  -5.597   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.414  -8.470   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.184  -7.136   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.724  -7.136   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.494  -8.470   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.034  -8.470   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.264  -7.136   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.804  -7.136   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.344  -7.136   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.114  -8.470   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      13.654  -8.470   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      14.424  -7.136   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      13.654  -5.803   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      14.424  -4.469   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      13.654  -3.135   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      14.424  -1.802   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      12.114  -3.135   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      15.964  -4.469   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      16.734  -3.135   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      18.274  -3.135   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      19.044  -4.469   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      20.584  -4.469   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      21.816  -5.341   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      23.356  -5.341   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      21.354  -3.135   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      22.894  -3.135   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      20.584  -1.802   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      21.354  -0.468   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      19.044  -1.802   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      18.274  -0.468   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      16.734  -5.803   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      18.274  -5.803   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      15.964  -7.136   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      16.734  -8.470   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      18.274  -8.470   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      19.044  -7.136   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0      20.584  -7.136   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      21.354  -5.803   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0      22.894  -5.803   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0      21.354  -8.470   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0      22.894  -8.470   0.000  0.00  0.00           O+0
HETATM   62  C   UNK     0      20.584  -9.804   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0      21.354 -11.137   0.000  0.00  0.00           O+0
HETATM   64  C   UNK     0      19.044  -9.804   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0      18.274 -11.137   0.000  0.00  0.00           O+0
HETATM   66  C   UNK     0      11.344  -9.804   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      11.076 -11.320   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0      12.791 -10.330   0.000  0.00  0.00           C+0
HETATM   69  O   UNK     0      13.058 -11.847   0.000  0.00  0.00           O+0
HETATM   70  C   UNK     0       9.804  -9.804   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0       9.034 -11.137   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0       7.494 -11.137   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0       6.724  -9.804   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0       5.954 -11.137   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0       5.184  -9.804   0.000  0.00  0.00           C+0
HETATM   76  C   UNK     0       5.023 -11.335   0.000  0.00  0.00           C+0
HETATM   77  C   UNK     0       4.414 -11.137   0.000  0.00  0.00           C+0
HETATM   78  C   UNK     0       2.874 -11.137   0.000  0.00  0.00           C+0
HETATM   79  O   UNK     0       3.035 -12.669   0.000  0.00  0.00           O+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   19                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    9   15   17   78                                             
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18    8   20   21                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   17   23   75                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   73                                                  
CONECT   26   25   27   28   70                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   66                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   53                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   38                                                  
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   34   39   51                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41   49                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43   45                                                  
CONECT   43   42   44                                                       
CONECT   44   43                                                            
CONECT   45   42   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47   40   50                                                  
CONECT   50   49                                                            
CONECT   51   38   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51   32   54                                                  
CONECT   54   53   55                                                       
CONECT   55   54   56   64                                                  
CONECT   56   55   57                                                       
CONECT   57   56   58   60                                                  
CONECT   58   57   59                                                       
CONECT   59   58                                                            
CONECT   60   57   61   62                                                  
CONECT   61   60                                                            
CONECT   62   60   63   64                                                  
CONECT   63   62                                                            
CONECT   64   62   55   65                                                  
CONECT   65   64                                                            
CONECT   66   30   67   68   70                                             
CONECT   67   66                                                            
CONECT   68   66   69                                                       
CONECT   69   68                                                            
CONECT   70   66   26   71                                                  
CONECT   71   70   72                                                       
CONECT   72   71   73                                                       
CONECT   73   72   25   74   75                                             
CONECT   74   73                                                            
CONECT   75   73   22   76   77                                             
CONECT   76   75                                                            
CONECT   77   75   78                                                       
CONECT   78   77   14   79                                                  
CONECT   79   78                                                            
MASTER        0    0    0    0    0    0    0    0   79    0  172    0
END

View in JSmol

Synonyms

Value	Source
Escin	Kegg
Reparil	Kegg
Escin-iib	MeSH

Chemical Formula

C₅₅H₈₆O₂₄

Average Mass

1131.2690 Da

Monoisotopic Mass

1130.55090 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C\C=C(\C)C(=O)O[C@H]1[C@H](OC(C)=O)[C@]2(CO)[C@H](O)C[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O[C@@H]6O[C@@H]([C@@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H](O)[C@H]6O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)C(O)=O)[C@](C)(CO)[C@@H]5CC[C@@]34C)[C@@H]2CC1(C)C

InChI Identifier

InChI=1S/C55H86O24/c1-10-23(2)46(71)79-43-44(72-24(3)60)55(22-59)26(17-50(43,4)5)25-11-12-30-51(6)15-14-32(52(7,21-58)29(51)13-16-53(30,8)54(25,9)18-31(55)61)75-49-41(77-48-38(67)36(65)34(63)28(20-57)74-48)39(68)40(42(78-49)45(69)70)76-47-37(66)35(64)33(62)27(19-56)73-47/h10-11,26-44,47-49,56-59,61-68H,12-22H2,1-9H3,(H,69,70)/b23-10-/t26-,27+,28+,29+,30+,31+,32-,33+,34+,35-,36-,37+,38+,39-,40-,41+,42-,43-,44-,47-,48-,49+,51-,52+,53+,54+,55-/m0/s1

InChI Key

AXNVHPCVMSNXNP-OXPBSUTMSA-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
Aesculus chinensis	LOTUS Database	35616633
Aesculus hippocastanum	LOTUS Database	35616633
Aesculus turbinata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Triterpene saponins

Alternative Parents

Substituents

Triterpene saponin
Triterpenoid
Oligosaccharide
Hydroxysteroid
16-oxosteroid
Oxosteroid
7-alpha-hydroxysteroid
7-hydroxysteroid
Steroid
Fatty acyl glycoside
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Glycosyl compound
O-glycosyl compound
Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Pyran
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Polyol
Acetal
Organoheterocyclic compound
Carboxylic acid
Carboxylic acid derivative
Oxacycle
Primary alcohol
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organooxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

triterpenoid saponin (CHEBI:2500 )
Triterpenoids (C30) (C08921 )

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00003497

Chemspider ID

4977652

KEGG Compound ID

C08921

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6476031

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

rw1364331

References

General References

Wu XJ, Zhang ML, Cui XY, Paul Fawcett J, Gu JK: Comparative pharmacokinetics and the bioavailability of escin Ib and isoescin Ib following the administration of escin, pure escin Ib and isoescin Ib in rats. J Ethnopharmacol. 2014 Feb 3;151(2):839-45. doi: 10.1016/j.jep.2013.11.039. Epub 2013 Dec 12. [PubMed:24334163 ]
Sun Y, Zhang X, Shen X, Wang S, Wang Q, Yang X: Computational and experimental characterization of isomers of escin-induced renal cytotoxicity by inhibiting heat shock proteins. Eur J Pharmacol. 2021 Oct 5;908:174372. doi: 10.1016/j.ejphar.2021.174372. Epub 2021 Jul 27. [PubMed:34324856 ]
Sun Y, Jiang X, Pan R, Zhou X, Qin D, Xiong R, Wang Y, Qiu W, Wu A, Wu J: Escins Isolated from Aesculus chinensis Bge. Promote the Autophagic Degradation of Mutant Huntingtin and Inhibit its Induced Apoptosis in HT22 cells. Front Pharmacol. 2020 Feb 25;11:116. doi: 10.3389/fphar.2020.00116. eCollection 2020. [PubMed:32158393 ]
Abudayeh ZH, Al Azzam KM, Naddaf A, Karpiuk UV, Kislichenko VS: Determination of Four Major Saponins in Skin and Endosperm of Seeds of Horse Chestnut (Aesculus Hippocastanum L.) Using High Performance Liquid Chromatography with Positive Confirmation by Thin Layer Chromatography. Adv Pharm Bull. 2015 Nov;5(4):587-91. doi: 10.15171/apb.2015.079. Epub 2015 Nov 30. [PubMed:26819933 ]
Liu L, Wu X, Wu D, Wang Y, Li P, Sun Y, Yang Y, Gu J, Cui Y: A liquid chromatography-tandem mass spectrometry method for the simultaneous quantification of escin Ia and escin Ib in human plasma: application to a pharmacokinetic study after intravenous administration. Biomed Chromatogr. 2010 Dec;24(12):1309-15. doi: 10.1002/bmc.1441. [PubMed:20662111 ]
LOTUS database [Link]

Showing NP-Card for β-escin (NP0280805)

MOL for NP0280805 (β-escin)

3D MOL for NP0280805 (β-escin)

3D SDF for NP0280805 (β-escin)

3D-SDF for NP0280805 (β-escin)

PDB for NP0280805 (β-escin)

3D PDB for NP0280805 (β-escin)

SMILES for NP0280805 (β-escin)

INCHI for NP0280805 (β-escin)

Structure for NP0280805 (β-escin)

3D Structure for NP0280805 (β-escin)