NP-MRD: Showing NP-Card for 4,8a-bis[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2s,3r,4s,4ar,6ar,6bs,8as,12as,14ar,14br)-2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylate (NP0146053)

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Record Information

Version

2.0

Created at

2022-09-02 01:22:39 UTC

Updated at

2022-09-02 01:22:39 UTC

NP-MRD ID

NP0146053

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,8a-bis[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2s,3r,4s,4ar,6ar,6bs,8as,12as,14ar,14br)-2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylate

Description

4,8A-bis[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2S,3R,4S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4,8a-dicarboxylate belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. 4,8a-bis[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2s,3r,4s,4ar,6ar,6bs,8as,12as,14ar,14br)-2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylate is found in Amaranthus caudatus. Based on a literature review very few articles have been published on 4,8a-bis[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2S,3R,4S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4,8a-dicarboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022203222D          

 57 63  0  0  1  0            999 V2000
   -0.1105   -3.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -5.2520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -6.6809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -5.9664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230   -6.6809    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3480   -6.6809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7605   -7.3954    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5855   -7.3954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9980   -8.1099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -8.1099    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7605   -8.8243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.8522   -5.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.8099   -5.8503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6667   -5.0379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3212   -7.1931    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0965   -7.4753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6892   -7.7234    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.8325   -8.5359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9140   -7.4412    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2820   -7.9715    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
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    3.6882   -6.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1270   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  6  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  6  0  0  0
  5 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 27 26  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
 35 36  1  6  0  0  0
 35 37  1  1  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 40 39  1  6  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  6  0  0  0
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 35 51  1  0  0  0  0
 28 51  1  0  0  0  0
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 56 24  1  1  0  0  0
  5 56  1  0  0  0  0
 56 57  1  0  0  0  0
  2 57  1  0  0  0  0
M  END

     RDKit          3D

119125  0  0  0  0  0  0  0  0999 V2000
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   -6.3235    0.7608   -0.1763 O   0  0  0  0  0  0  0  0  0  0  0  0
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 50108  1  0
M  END


  Mrv1652309022203222D          

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 27 54  1  0  0  0  0
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 56 57  1  0  0  0  0
  2 57  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0146053

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12C[C@H](O)[C@H](O)[C@](C)([C@@H]1CC[C@]1(C)[C@@H]2CC=C2[C@@H]3CC(=C)CC[C@@]3(CC[C@@]12C)C(=O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(=O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C41H62O16/c1-18-8-11-41(36(53)57-34-31(50)29(48)27(46)23(17-43)55-34)13-12-38(3)19(20(41)14-18)6-7-24-37(2)15-21(44)32(51)40(5,25(37)9-10-39(24,38)4)35(52)56-33-30(49)28(47)26(45)22(16-42)54-33/h6,20-34,42-51H,1,7-17H2,2-5H3/t20-,21-,22+,23+,24+,25+,26+,27+,28-,29-,30+,31+,32-,33-,34-,37+,38+,39+,40-,41-/m0/s1

> <INCHI_KEY>
HFXIXQIJWYYSGD-QCXNNXLKSA-N

> <FORMULA>
C41H62O16

> <MOLECULAR_WEIGHT>
810.931

> <EXACT_MASS>
810.403785916

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
119

> <JCHEM_AVERAGE_POLARIZABILITY>
86.04952370898127

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,8a-bis[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2S,3R,4S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4,8a-dicarboxylate

> <ALOGPS_LOGP>
0.78

> <JCHEM_LOGP>
-0.4722066923333341

> <ALOGPS_LOGS>
-3.00

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.393261296212952

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.884161788647047

> <JCHEM_PKA_STRONGEST_BASIC>
-3.169406055656494

> <JCHEM_POLAR_SURFACE_AREA>
273.35999999999996

> <JCHEM_REFRACTIVITY>
196.86800000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.20e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,8a-bis[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2S,3R,4S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.206  -5.803   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.564  -7.136   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.206  -8.470   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.564  -9.804   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.104  -9.804   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334 -11.137   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.104 -12.471   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -0.206 -11.137   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.976 -12.471   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.516 -12.471   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -3.286 -13.805   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.826 -13.805   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -5.596 -15.138   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.516 -15.138   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -3.286 -16.472   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.976 -15.138   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.206 -16.472   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.206 -13.805   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.334 -13.805   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.874 -11.137   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.414 -11.137   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.184  -9.804   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.954 -11.137   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.414  -8.470   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.184  -7.136   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.724  -7.136   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.494  -8.470   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.034  -8.470   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.264  -7.136   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.804  -7.136   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.344  -7.136   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      12.114  -5.803   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      12.114  -8.470   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      13.654  -8.470   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      11.344  -9.804   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      11.076 -11.320   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      12.791 -10.330   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      13.971  -9.340   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      13.058 -11.847   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      14.505 -12.374   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      15.685 -11.384   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      17.132 -11.911   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      18.312 -10.921   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      18.044  -9.404   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      17.400 -13.427   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      18.847 -13.954   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      16.220 -14.417   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      16.487 -15.934   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      14.773 -13.890   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      13.593 -14.880   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0       9.804  -9.804   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       9.034 -11.137   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       7.494 -11.137   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       6.724  -9.804   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       6.885 -11.335   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       2.874  -8.470   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       2.104  -7.136   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   57                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   20   56                                             
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    9   19                                                  
CONECT   19   18                                                            
CONECT   20    5   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24   54                                             
CONECT   23   22                                                            
CONECT   24   22   25   56                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   54                                                  
CONECT   28   27   29   30   51                                             
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37   51                                             
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   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   35   28   52                                                  
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   27   22   55                                             
CONECT   55   54                                                            
CONECT   56   24    5   57                                                  
CONECT   57   56    2                                                       
MASTER        0    0    0    0    0    0    0    0   57    0  126    0
END

View in JSmol

Synonyms

Value	Source
4,8a-Bis[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2S,3R,4S,4ar,6ar,6BS,8as,12as,14ar,14BR)-2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4,8a-dicarboxylic acid	Generator

Chemical Formula

C₄₁H₆₂O₁₆

Average Mass

810.9310 Da

Monoisotopic Mass

810.40379 Da

IUPAC Name

4,8a-bis[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2S,3R,4S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4,8a-dicarboxylate

Traditional Name

4,8a-bis[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2S,3R,4S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylate

CAS Registry Number

Not Available

SMILES

C[C@]12C[C@H](O)[C@H](O)[C@](C)([C@@H]1CC[C@]1(C)[C@@H]2CC=C2[C@@H]3CC(=C)CC[C@@]3(CC[C@@]12C)C(=O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(=O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C41H62O16/c1-18-8-11-41(36(53)57-34-31(50)29(48)27(46)23(17-43)55-34)13-12-38(3)19(20(41)14-18)6-7-24-37(2)15-21(44)32(51)40(5,25(37)9-10-39(24,38)4)35(52)56-33-30(49)28(47)26(45)22(16-42)54-33/h6,20-34,42-51H,1,7-17H2,2-5H3/t20-,21-,22+,23+,24+,25+,26+,27+,28-,29-,30+,31+,32-,33-,34-,37+,38+,39+,40-,41-/m0/s1

InChI Key

HFXIXQIJWYYSGD-QCXNNXLKSA-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
Amaranthus caudatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Diterpene glycosides

Alternative Parents

Substituents

Diterpene glycoside
Diterpenoid
12-hydroxysteroid
Hydroxysteroid
12-alpha-hydroxysteroid
Steroid
Hexose monosaccharide
Beta-hydroxy acid
Oxane
Dicarboxylic acid or derivatives
Monosaccharide
Hydroxy acid
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Acetal
Carboxylic acid derivative
Polyol
Oxacycle
Alcohol
Primary alcohol
Organooxygen compound
Organic oxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
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	0.78	ALOGPS
logP	-0.47	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	11.88	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	273.36 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	196.87 m³·mol⁻¹	ChemAxon
Polarizability	86.05 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

101918550

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4,8a-bis[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2s,3r,4s,4ar,6ar,6bs,8as,12as,14ar,14br)-2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylate (NP0146053)

MOL for NP0146053 (4,8a-bis[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2s,3r,4s,4ar,6ar,6bs,8as,12as,14ar,14br)-2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylate)

3D MOL for NP0146053 (4,8a-bis[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2s,3r,4s,4ar,6ar,6bs,8as,12as,14ar,14br)-2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylate)

3D SDF for NP0146053 (4,8a-bis[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2s,3r,4s,4ar,6ar,6bs,8as,12as,14ar,14br)-2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylate)

3D-SDF for NP0146053 (4,8a-bis[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2s,3r,4s,4ar,6ar,6bs,8as,12as,14ar,14br)-2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylate)

PDB for NP0146053 (4,8a-bis[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2s,3r,4s,4ar,6ar,6bs,8as,12as,14ar,14br)-2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylate)

3D PDB for NP0146053 (4,8a-bis[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2s,3r,4s,4ar,6ar,6bs,8as,12as,14ar,14br)-2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylate)

SMILES for NP0146053 (4,8a-bis[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2s,3r,4s,4ar,6ar,6bs,8as,12as,14ar,14br)-2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylate)

INCHI for NP0146053 (4,8a-bis[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2s,3r,4s,4ar,6ar,6bs,8as,12as,14ar,14br)-2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylate)

Structure for NP0146053 (4,8a-bis[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2s,3r,4s,4ar,6ar,6bs,8as,12as,14ar,14br)-2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylate)

3D Structure for NP0146053 (4,8a-bis[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2s,3r,4s,4ar,6ar,6bs,8as,12as,14ar,14br)-2,3-dihydroxy-4,6a,6b,14b-tetramethyl-11-methylidene-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylate)