NP-MRD: Showing NP-Card for Quinoasaponin 8 (NP0073697)

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Record Information

Version

2.0

Created at

2022-04-28 18:55:17 UTC

Updated at

2022-04-28 18:55:17 UTC

NP-MRD ID

NP0073697

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Quinoasaponin 8

Description

(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2S,4aR,6aS,6bR,8aR,9R,10S,12aS,12bR,14bS)-2-(acetyloxy)-10-{[(2R,3R,4S,5R)-4-{[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxyoxan-2-yl]oxy}-9-(hydroxymethyl)-2,6a,6b,9,12a-pentamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Quinoasaponin 8 is found in Chenopodium quinoa and Chenopodium quinoa Wild. . Based on a literature review very few articles have been published on (2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2S,4aR,6aS,6bR,8aR,9R,10S,12aS,12bR,14bS)-2-(acetyloxy)-10-{[(2R,3R,4S,5R)-4-{[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxyoxan-2-yl]oxy}-9-(hydroxymethyl)-2,6a,6b,9,12a-pentamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282220552D          

 79 87  0  0  1  0            999 V2000
    6.0770   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
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  7 12  1  0  0  0  0
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  4 14  1  0  0  0  0
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 22 23  1  0  0  0  0
 18 23  1  0  0  0  0
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 22 27  1  6  0  0  0
 28 27  1  1  0  0  0
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M  END

     RDKit          3D

165173  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652304282220552D          

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   -5.8855   -2.4454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0605   -3.8743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4105   -3.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855   -3.8743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855   -2.4454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6907    1.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9020    2.5559    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7270    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1395    3.2704    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7270    3.9849    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9020    3.9849    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4895    3.2704    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6645    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    4.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1395    4.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9645    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3770    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7766   -0.7392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5050   -0.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5338    0.4727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2047   -0.7890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1058   -1.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  4 14  1  0  0  0  0
 12 15  1  1  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  1  0  0  0
 25 26  1  0  0  0  0
 22 27  1  6  0  0  0
 28 27  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 28 33  1  0  0  0  0
 33 34  1  1  0  0  0
 32 35  1  6  0  0  0
 36 35  1  6  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 36 41  1  0  0  0  0
 41 42  1  1  0  0  0
 43 42  1  6  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 43 48  1  0  0  0  0
 47 49  1  6  0  0  0
 49 50  1  0  0  0  0
 46 51  1  1  0  0  0
 45 52  1  6  0  0  0
 44 53  1  1  0  0  0
 40 54  1  6  0  0  0
 39 55  1  6  0  0  0
 38 56  1  6  0  0  0
 56 57  1  0  0  0  0
 31 58  1  1  0  0  0
 19 59  1  1  0  0  0
 11 60  1  6  0  0  0
  4 61  1  6  0  0  0
 61 62  2  0  0  0  0
 61 63  1  0  0  0  0
 64 63  1  6  0  0  0
 64 65  1  0  0  0  0
 65 66  1  0  0  0  0
 66 67  1  0  0  0  0
 67 68  1  0  0  0  0
 68 69  1  0  0  0  0
 64 69  1  0  0  0  0
 69 70  1  6  0  0  0
 68 71  1  1  0  0  0
 67 72  1  6  0  0  0
 66 73  1  1  0  0  0
 73 74  1  0  0  0  0
  1 75  1  6  0  0  0
 75 76  1  0  0  0  0
 76 77  2  0  0  0  0
 76 78  1  0  0  0  0
  1 79  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0073697

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@]1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@]5(C)CC[C@H](O[C@H]6OC[C@@H](O)[C@H](O[C@@H]7O[C@H](CO)[C@H](O)[C@H](O)[C@H]7O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H]6O)[C@@](C)(CO)[C@@H]5CC[C@@]34C)[C@@H]2C1)C(=O)O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C54H86O25/c1-23(59)79-49(2)13-15-54(48(70)78-46-40(68)37(65)34(62)28(19-56)73-46)16-14-52(5)24(25(54)17-49)7-8-31-50(3)11-10-32(51(4,22-58)30(50)9-12-53(31,52)6)75-44-41(69)42(26(60)21-71-44)76-47-43(38(66)35(63)29(20-57)74-47)77-45-39(67)36(64)33(61)27(18-55)72-45/h7,25-47,55-58,60-69H,8-22H2,1-6H3/t25-,26+,27+,28+,29+,30+,31+,32-,33+,34+,35-,36-,37-,38-,39+,40+,41+,42-,43+,44+,45-,46+,47-,49-,50+,51-,52+,53+,54-/m0/s1

> <INCHI_KEY>
ODDHORHEPJPDSC-VEVFAQNVSA-N

> <FORMULA>
C54H86O25

> <MOLECULAR_WEIGHT>
1135.257

> <EXACT_MASS>
1134.545818269

> <JCHEM_ACCEPTOR_COUNT>
23

> <JCHEM_ATOM_COUNT>
165

> <JCHEM_AVERAGE_POLARIZABILITY>
117.03718148825806

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
14

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2S,4aR,6aS,6bR,8aR,9R,10S,12aS,12bR,14bS)-2-(acetyloxy)-10-{[(2R,3R,4S,5R)-4-{[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxyoxan-2-yl]oxy}-9-(hydroxymethyl)-2,6a,6b,9,12a-pentamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate

> <ALOGPS_LOGP>
-0.31

> <JCHEM_LOGP>
-2.8882604763333304

> <ALOGPS_LOGS>
-2.81

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.174826794863254

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.746813367013774

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6483977515465424

> <JCHEM_POLAR_SURFACE_AREA>
400.43000000000006

> <JCHEM_REFRACTIVITY>
265.5433000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.74e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2S,4aR,6aS,6bR,8aR,9R,10S,12aS,12bR,14bS)-2-(acetyloxy)-10-{[(2R,3R,4S,5R)-4-{[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxyoxan-2-yl]oxy}-9-(hydroxymethyl)-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      11.344  -0.564   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.114   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.344   2.104   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.804   2.104   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.804  -0.564   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.494   3.437   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.034   3.437   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.742   2.920   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.510   3.643   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.850   4.366   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -1.746   0.770   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -2.516  -0.564   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.746  -1.897   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -2.516  -3.231   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -4.056  -3.231   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.826  -1.897   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -4.056  -0.564   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -4.826   0.770   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -6.366  -1.897   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -7.136  -3.231   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -6.366  -4.565   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -7.136  -5.898   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -8.676  -5.898   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -9.446  -4.565   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -8.676  -3.231   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -9.446  -1.897   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0     -10.986  -1.897   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0     -11.756  -0.564   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0     -13.296  -0.564   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0     -14.066  -1.897   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0     -13.296  -3.231   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0     -11.756  -3.231   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0     -14.066  -4.565   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0     -15.606  -4.565   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0     -15.606  -1.897   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0     -14.066   0.770   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0     -10.986   0.770   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0     -10.986  -4.565   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      -9.446  -7.232   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      -6.366  -7.232   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      -4.826  -7.232   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0      -4.826  -4.565   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       5.023   3.635   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      10.574   3.437   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0       9.804   4.771   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0      12.114   3.437   0.000  0.00  0.00           O+0
HETATM   64  C   UNK     0      12.884   4.771   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0      14.424   4.771   0.000  0.00  0.00           O+0
HETATM   66  C   UNK     0      15.194   6.105   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      14.424   7.438   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0      12.884   7.438   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0      12.114   6.105   0.000  0.00  0.00           C+0
HETATM   70  O   UNK     0      10.574   6.105   0.000  0.00  0.00           O+0
HETATM   71  O   UNK     0      12.114   8.772   0.000  0.00  0.00           O+0
HETATM   72  O   UNK     0      15.194   8.772   0.000  0.00  0.00           O+0
HETATM   73  C   UNK     0      16.734   6.105   0.000  0.00  0.00           C+0
HETATM   74  O   UNK     0      17.504   7.438   0.000  0.00  0.00           O+0
HETATM   75  O   UNK     0      12.650  -1.380   0.000  0.00  0.00           O+0
HETATM   76  C   UNK     0      14.009  -0.657   0.000  0.00  0.00           C+0
HETATM   77  O   UNK     0      14.063   0.882   0.000  0.00  0.00           O+0
HETATM   78  C   UNK     0      15.315  -1.473   0.000  0.00  0.00           C+0
HETATM   79  C   UNK     0      11.397  -2.103   0.000  0.00  0.00           C+0
CONECT    1    2    6   75   79                                             
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   14   61                                             
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10   12   16   60                                             
CONECT   12   11    7   13   15                                             
CONECT   13   12   14                                                       
CONECT   14   13    4                                                       
CONECT   15   12                                                            
CONECT   16   11   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   10   20   59                                             
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   18   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25                                                            
CONECT   27   22   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   58                                                  
CONECT   32   31   33   35                                                  
CONECT   33   32   28   34                                                  
CONECT   34   33                                                            
CONECT   35   32   36                                                       
CONECT   36   35   37   41                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   56                                                  
CONECT   39   38   40   55                                                  
CONECT   40   39   41   54                                                  
CONECT   41   40   36   42                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44   48                                                  
CONECT   44   43   45   53                                                  
CONECT   45   44   46   52                                                  
CONECT   46   45   47   51                                                  
CONECT   47   46   48   49                                                  
CONECT   48   47   43                                                       
CONECT   49   47   50                                                       
CONECT   50   49                                                            
CONECT   51   46                                                            
CONECT   52   45                                                            
CONECT   53   44                                                            
CONECT   54   40                                                            
CONECT   55   39                                                            
CONECT   56   38   57                                                       
CONECT   57   56                                                            
CONECT   58   31                                                            
CONECT   59   19                                                            
CONECT   60   11                                                            
CONECT   61    4   62   63                                                  
CONECT   62   61                                                            
CONECT   63   61   64                                                       
CONECT   64   63   65   69                                                  
CONECT   65   64   66                                                       
CONECT   66   65   67   73                                                  
CONECT   67   66   68   72                                                  
CONECT   68   67   69   71                                                  
CONECT   69   68   64   70                                                  
CONECT   70   69                                                            
CONECT   71   68                                                            
CONECT   72   67                                                            
CONECT   73   66   74                                                       
CONECT   74   73                                                            
CONECT   75    1   76                                                       
CONECT   76   75   77   78                                                  
CONECT   77   76                                                            
CONECT   78   76                                                            
CONECT   79    1                                                            
MASTER        0    0    0    0    0    0    0    0   79    0  174    0
END

View in JSmol

Synonyms

Value

Source

(2R,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl (2S,4ar,6as,6BR,8ar,9R,10S,12as,12BR,14BS)-2-(acetyloxy)-10-{[(2R,3R,4S,5R)-4-{[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxyoxan-2-yl]oxy}-9-(hydroxymethyl)-2,6a,6b,9,12a-pentamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

Generator

Chemical Formula

C₅₄H₈₆O₂₅

Average Mass

1135.2570 Da

Monoisotopic Mass

1134.54582 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@]1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@]5(C)CC[C@H](O[C@H]6OC[C@@H](O)[C@H](O[C@@H]7O[C@H](CO)[C@H](O)[C@H](O)[C@H]7O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H]6O)[C@@](C)(CO)[C@@H]5CC[C@@]34C)[C@@H]2C1)C(=O)O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C54H86O25/c1-23(59)79-49(2)13-15-54(48(70)78-46-40(68)37(65)34(62)28(19-56)73-46)16-14-52(5)24(25(54)17-49)7-8-31-50(3)11-10-32(51(4,22-58)30(50)9-12-53(31,52)6)75-44-41(69)42(26(60)21-71-44)76-47-43(38(66)35(63)29(20-57)74-47)77-45-39(67)36(64)33(61)27(18-55)72-45/h7,25-47,55-58,60-69H,8-22H2,1-6H3/t25-,26+,27+,28+,29+,30+,31+,32-,33+,34+,35-,36-,37-,38-,39+,40+,41+,42-,43+,44+,45-,46+,47-,49-,50+,51-,52+,53+,54-/m0/s1

InChI Key

ODDHORHEPJPDSC-VEVFAQNVSA-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
Chenopodium quinoa	LOTUS Database	35616633
Chenopodium quinoa Wild.	Plant	KNApSAcK

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Oligosaccharide
Steroid
O-glycosyl compound
Glycosyl compound
Oxane
Dicarboxylic acid or derivatives
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
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	-0.31	ALOGPS
logP	-2.9	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	11.75	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	23	ChemAxon
Hydrogen Donor Count	14	ChemAxon
Polar Surface Area	400.43 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	265.54 m³·mol⁻¹	ChemAxon
Polarizability	117.04 Å³	ChemAxon
Number of Rings	9	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

163105335

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Quinoasaponin 8 (NP0073697)

MOL for NP0073697 (Quinoasaponin 8)

3D MOL for NP0073697 (Quinoasaponin 8)

3D SDF for NP0073697 (Quinoasaponin 8)

3D-SDF for NP0073697 (Quinoasaponin 8)

PDB for NP0073697 (Quinoasaponin 8)

3D PDB for NP0073697 (Quinoasaponin 8)

SMILES for NP0073697 (Quinoasaponin 8)

INCHI for NP0073697 (Quinoasaponin 8)

Structure for NP0073697 (Quinoasaponin 8)

3D Structure for NP0073697 (Quinoasaponin 8)