NP-MRD: Showing NP-Card for (1s,4as,7s,7as)-4-({[(2r,3r,4r,5s,6r)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate (NP0272768)

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Record Information

Version

2.0

Created at

2022-09-08 19:32:34 UTC

Updated at

2022-09-08 19:32:34 UTC

NP-MRD ID

NP0272768

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4as,7s,7as)-4-({[(2r,3r,4r,5s,6r)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate

Description

(1S,4aS,7S,7aS)-4-({[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-1-yl 3-methylbutanoate belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. (1s,4as,7s,7as)-4-({[(2r,3r,4r,5s,6r)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate is found in Penstemon confertus. Based on a literature review very few articles have been published on (1S,4aS,7S,7aS)-4-({[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-1-yl 3-methylbutanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082221322D          

 42 45  0  0  1  0            999 V2000
    6.1368    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7079   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.5645    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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 42 39  1  1  0  0  0
  8 42  1  0  0  0  0
 36 42  1  0  0  0  0
M  END

     RDKit          3D

 86 89  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652309082221322D          

 42 45  0  0  1  0            999 V2000
    6.1368    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4223    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8513   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5658   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5658   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2802   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2802   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5658   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9947   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.7092   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9947   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.7092   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2802   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2802    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8513   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4223   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0769    2.4777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  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  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  1  0  0  0
 21 20  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 21 30  1  0  0  0  0
 30 31  1  6  0  0  0
 19 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  0  0  0  0
 14 34  1  0  0  0  0
 34 35  1  1  0  0  0
 11 36  1  0  0  0  0
 36 37  1  1  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  6  0  0  0
 40 41  1  0  0  0  0
 42 39  1  1  0  0  0
  8 42  1  0  0  0  0
 36 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0272768

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O15/c1-11(2)5-17(31)41-25-18-12(6-28)3-4-14(18)13(9-37-25)10-38-26-23(36)21(34)24(16(8-30)40-26)42-27-22(35)20(33)19(32)15(7-29)39-27/h9,11-12,14-16,18-30,32-36H,3-8,10H2,1-2H3/t12-,14-,15-,16-,18-,19-,20-,21-,22-,23-,24-,25+,26-,27+/m1/s1

> <INCHI_KEY>
BQSALWKNICBNHF-OHYFXBBNSA-N

> <FORMULA>
C27H44O15

> <MOLECULAR_WEIGHT>
608.634

> <EXACT_MASS>
608.268020717

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
86

> <JCHEM_AVERAGE_POLARIZABILITY>
61.54082504701546

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4aS,7S,7aS)-4-({[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-1-yl 3-methylbutanoate

> <JCHEM_LOGP>
-2.636383325999999

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.485625060969554

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.939585970685185

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6007264027621195

> <JCHEM_POLAR_SURFACE_AREA>
234.28999999999996

> <JCHEM_REFRACTIVITY>
138.36330000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4aS,7S,7aS)-4-({[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-1-yl 3-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      11.455   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.122   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.122   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.788   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.454   4.620   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       7.454   6.160   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       6.121   3.850   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       7.454   1.540   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.121  -2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       7.454  -3.080   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.788  -2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.788  -0.770   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.122   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.122   1.540   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      11.455   2.310   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      11.455  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      12.789  -0.000   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      14.123  -0.770   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      14.123  -2.310   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      15.456  -3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.456  -4.620   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      14.123  -5.390   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      16.790  -2.310   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      18.124  -3.080   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      16.790  -0.770   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      18.124  -0.000   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      15.456  -0.000   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      15.456   1.540   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      11.455  -2.310   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      12.789  -3.080   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      10.122  -3.080   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      10.122  -4.620   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       2.846   3.481   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       3.877   4.625   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   42                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   36                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   34                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20   32                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   30                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   21   31                                                  
CONECT   31   30                                                            
CONECT   32   19   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   14   35                                                  
CONECT   35   34                                                            
CONECT   36   11   37   42                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40   42                                                  
CONECT   40   39   41                                                       
CONECT   41   40                                                            
CONECT   42   39    8   36                                                  
MASTER        0    0    0    0    0    0    0    0   42    0   90    0
END

View in JSmol

Synonyms

Value	Source
(1S,4AS,7S,7as)-4-({[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1H,4ah,5H,6H,7H,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoic acid	Generator

Chemical Formula

C₂₇H₄₄O₁₅

Average Mass

608.6340 Da

Monoisotopic Mass

608.26802 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C27H44O15/c1-11(2)5-17(31)41-25-18-12(6-28)3-4-14(18)13(9-37-25)10-38-26-23(36)21(34)24(16(8-30)40-26)42-27-22(35)20(33)19(32)15(7-29)39-27/h9,11-12,14-16,18-30,32-36H,3-8,10H2,1-2H3/t12-,14-,15-,16-,18-,19-,20-,21-,22-,23-,24-,25+,26-,27+/m1/s1

InChI Key

BQSALWKNICBNHF-OHYFXBBNSA-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
Penstemon confertus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Disaccharide
Glycosyl compound
Iridoid-skeleton
O-glycosyl compound
Monoterpenoid
Bicyclic monoterpenoid
Fatty acid ester
Fatty acyl
Oxane
Carboxylic acid ester
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
Monocarboxylic acid or derivatives
Polyol
Hydrocarbon derivative
Organic oxygen compound
Primary alcohol
Alcohol
Carbonyl group
Organic oxide
Organooxygen compound
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	-2.6	ChemAxon
pKa (Strongest Acidic)	11.94	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	234.29 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	138.36 m³·mol⁻¹	ChemAxon
Polarizability	61.54 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

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

162965654

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,4as,7s,7as)-4-({[(2r,3r,4r,5s,6r)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate (NP0272768)

MOL for NP0272768 ((1s,4as,7s,7as)-4-({[(2r,3r,4r,5s,6r)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate)

3D MOL for NP0272768 ((1s,4as,7s,7as)-4-({[(2r,3r,4r,5s,6r)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate)

3D SDF for NP0272768 ((1s,4as,7s,7as)-4-({[(2r,3r,4r,5s,6r)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate)

3D-SDF for NP0272768 ((1s,4as,7s,7as)-4-({[(2r,3r,4r,5s,6r)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate)

PDB for NP0272768 ((1s,4as,7s,7as)-4-({[(2r,3r,4r,5s,6r)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate)

3D PDB for NP0272768 ((1s,4as,7s,7as)-4-({[(2r,3r,4r,5s,6r)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate)

SMILES for NP0272768 ((1s,4as,7s,7as)-4-({[(2r,3r,4r,5s,6r)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate)

INCHI for NP0272768 ((1s,4as,7s,7as)-4-({[(2r,3r,4r,5s,6r)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate)

Structure for NP0272768 ((1s,4as,7s,7as)-4-({[(2r,3r,4r,5s,6r)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate)

3D Structure for NP0272768 ((1s,4as,7s,7as)-4-({[(2r,3r,4r,5s,6r)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-7-(hydroxymethyl)-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-1-yl 3-methylbutanoate)