NP-MRD: Showing NP-Card for Giganteoside M (NP0071278)

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Record Information

Version

1.0

Created at

2022-04-28 16:40:02 UTC

Updated at

2022-04-28 16:40:02 UTC

NP-MRD ID

NP0071278

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Giganteoside M

Description

Macranthoidin A 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. Giganteoside M is found in Cephalaria gigantea, Lonicera macranthoides and Nigella damascena. It was first documented in 2011 (PMID: 22007545). Based on a literature review a significant number of articles have been published on Macranthoidin A (PMID: 34923253) (PMID: 29484987) (PMID: 27455548) (PMID: 22734414).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282218402D          

 86 95  0  0  1  0            999 V2000
    4.8395    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2520    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    4.0145    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3480   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730   -1.7309    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    9.3770    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2020    3.9849    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.6145    3.2704    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
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  4  5  1  0  0  0  0
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  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
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M  END

     RDKit          3D

182191  0  0  0  0  0  0  0  0999 V2000
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   -8.4481    1.9702    1.5625 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304282218402D          

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   -3.8230   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0605   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8855    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0605    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8855    1.8414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.2980    2.5559    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.1230    2.5559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.5355    1.8414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.1230    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2980    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.3605    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3605    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5355    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8855    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4105    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4105   -1.0164    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
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6882    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  2  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
   10.2020    3.9849    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.6145    3.2704    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.4395    3.2704    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.8520    3.9849    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.4395    4.6993    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.6145    4.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8520    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6770    5.4138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6770    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8520    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2020    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7766   -0.7392    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  0  0  0  0
  1  6  1  1  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  1  0  0  0
 20 21  1  0  0  0  0
 17 22  1  6  0  0  0
 23 22  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  1  0  0  0
 30 29  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
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 34 36  1  1  0  0  0
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 39 38  1  6  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 39 44  1  0  0  0  0
 43 45  1  6  0  0  0
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 42 47  1  1  0  0  0
 41 48  1  6  0  0  0
 40 49  1  1  0  0  0
 31 50  1  1  0  0  0
 27 51  1  6  0  0  0
 26 52  1  6  0  0  0
 14 53  1  6  0  0  0
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  5 55  1  1  0  0  0
  2 56  1  6  0  0  0
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 76 77  1  0  0  0  0
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 72 79  1  6  0  0  0
 71 80  1  1  0  0  0
  2 81  1  0  0  0  0
 81 82  1  0  0  0  0
 82 83  1  0  0  0  0
 83 84  1  0  0  0  0
  1 84  1  0  0  0  0
 83 85  1  0  0  0  0
 83 86  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0071278

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@@H](O)CO[C@H]2O[C@H]2CC[C@@]3(C)[C@@H](CC[C@]4(C)[C@@H]3CC=C3[C@@H]5CC(C)(C)CC[C@@]5(CC[C@@]43C)C(=O)O[C@@H]3O[C@H](CO[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)[C@]2(C)CO)[C@H](O)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C59H96O27/c1-24-34(64)46(84-49-43(73)40(70)37(67)29(20-61)81-49)45(75)51(79-24)85-47-35(65)27(63)21-77-52(47)83-33-11-12-55(4)31(56(33,5)23-62)10-13-58(7)32(55)9-8-25-26-18-54(2,3)14-16-59(26,17-15-57(25,58)6)53(76)86-50-44(74)41(71)38(68)30(82-50)22-78-48-42(72)39(69)36(66)28(19-60)80-48/h8,24,26-52,60-75H,9-23H2,1-7H3/t24-,26-,27-,28+,29+,30+,31+,32+,33-,34-,35-,36+,37+,38+,39-,40-,41-,42+,43+,44+,45+,46+,47+,48+,49-,50-,51-,52-,55-,56-,57+,58+,59-/m0/s1

> <INCHI_KEY>
VUEGHZSQVJADCO-UGZFTLGKSA-N

> <FORMULA>
C59H96O27

> <MOLECULAR_WEIGHT>
1237.39

> <EXACT_MASS>
1236.613897831

> <JCHEM_ACCEPTOR_COUNT>
26

> <JCHEM_ATOM_COUNT>
182

> <JCHEM_AVERAGE_POLARIZABILITY>
130.4122609461521

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
16

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl (4aS,6aS,6bR,8aR,9R,10S,12aR,12bR,14bS)-10-{[(2S,3R,4S,5S)-3-{[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-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>
0.00

> <JCHEM_LOGP>
-2.360103490666669

> <ALOGPS_LOGS>
-2.85

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
10

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.079554916996333

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.66968862241793

> <JCHEM_PKA_STRONGEST_BASIC>
-3.678613072130494

> <JCHEM_POLAR_SURFACE_AREA>
433.0500000000001

> <JCHEM_REFRACTIVITY>
289.97740000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.75e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl (4aS,6aS,6bR,8aR,9R,10S,12aR,12bR,14bS)-10-{[(2S,3R,4S,5S)-3-{[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-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       9.034   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.804   2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.034   3.437   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.494   3.437   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.742   2.920   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.510   3.643   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.850   4.366   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.746   0.770   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.516  -0.564   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.746  -1.897   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.516  -3.231   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.056  -3.231   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.826  -1.897   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.056  -0.564   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -4.826   0.770   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -6.366   0.770   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -7.136   2.104   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -8.676   2.104   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -9.446   0.770   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -8.676  -0.564   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -7.136  -0.564   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -9.446  -1.897   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0     -10.986   0.770   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -9.446   3.437   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0     -10.986   3.437   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0     -11.756   4.771   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0     -13.296   4.771   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0     -14.066   3.437   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0     -13.296   2.104   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0     -11.756   2.104   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0     -14.066   0.770   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0     -15.606   0.770   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0     -15.606   3.437   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0     -14.066   6.105   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0     -10.986   6.105   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      -6.366   3.437   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      -6.366  -1.897   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      -4.826  -4.565   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       6.885   3.635   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      10.574   3.437   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0       9.804   4.771   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0      12.114   3.437   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0      12.884   4.771   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0      14.424   4.771   0.000  0.00  0.00           O+0
HETATM   61  C   UNK     0      15.194   6.105   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      14.424   7.438   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      12.884   7.438   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      12.114   6.105   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0      10.574   6.105   0.000  0.00  0.00           O+0
HETATM   66  O   UNK     0      12.114   8.772   0.000  0.00  0.00           O+0
HETATM   67  O   UNK     0      15.194   8.772   0.000  0.00  0.00           O+0
HETATM   68  C   UNK     0      16.734   6.105   0.000  0.00  0.00           C+0
HETATM   69  O   UNK     0      17.504   7.438   0.000  0.00  0.00           O+0
HETATM   70  C   UNK     0      19.044   7.438   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0      19.814   6.105   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0      21.354   6.105   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0      22.124   7.438   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0      21.354   8.772   0.000  0.00  0.00           C+0
HETATM   75  O   UNK     0      19.814   8.772   0.000  0.00  0.00           O+0
HETATM   76  C   UNK     0      22.124  10.106   0.000  0.00  0.00           C+0
HETATM   77  O   UNK     0      23.664  10.106   0.000  0.00  0.00           O+0
HETATM   78  O   UNK     0      23.664   7.438   0.000  0.00  0.00           O+0
HETATM   79  O   UNK     0      22.124   4.771   0.000  0.00  0.00           O+0
HETATM   80  O   UNK     0      19.044   4.771   0.000  0.00  0.00           O+0
HETATM   81  C   UNK     0      11.344   2.104   0.000  0.00  0.00           C+0
HETATM   82  C   UNK     0      12.114   0.770   0.000  0.00  0.00           C+0
HETATM   83  C   UNK     0      11.344  -0.564   0.000  0.00  0.00           C+0
HETATM   84  C   UNK     0       9.804  -0.564   0.000  0.00  0.00           C+0
HETATM   85  C   UNK     0      12.650  -1.380   0.000  0.00  0.00           C+0
HETATM   86  C   UNK     0      11.397  -2.103   0.000  0.00  0.00           C+0
CONECT    1    2    6   84                                                  
CONECT    2    1    3   56   81                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10   55                                             
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9    5   11   54                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13    9   15   53                                             
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   13   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20                                                            
CONECT   22   17   23                                                       
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   52                                                  
CONECT   27   26   28   51                                                  
CONECT   28   27   23   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   35                                                  
CONECT   31   30   32   50                                                  
CONECT   32   31   33   38                                                  
CONECT   33   32   34   37                                                  
CONECT   34   33   35   36                                                  
CONECT   35   34   30                                                       
CONECT   36   34                                                            
CONECT   37   33                                                            
CONECT   38   32   39                                                       
CONECT   39   38   40   44                                                  
CONECT   40   39   41   49                                                  
CONECT   41   40   42   48                                                  
CONECT   42   41   43   47                                                  
CONECT   43   42   44   45                                                  
CONECT   44   43   39                                                       
CONECT   45   43   46                                                       
CONECT   46   45                                                            
CONECT   47   42                                                            
CONECT   48   41                                                            
CONECT   49   40                                                            
CONECT   50   31                                                            
CONECT   51   27                                                            
CONECT   52   26                                                            
CONECT   53   14                                                            
CONECT   54   10                                                            
CONECT   55    5                                                            
CONECT   56    2   57   58                                                  
CONECT   57   56                                                            
CONECT   58   56   59                                                       
CONECT   59   58   60   64                                                  
CONECT   60   59   61                                                       
CONECT   61   60   62   68                                                  
CONECT   62   61   63   67                                                  
CONECT   63   62   64   66                                                  
CONECT   64   63   59   65                                                  
CONECT   65   64                                                            
CONECT   66   63                                                            
CONECT   67   62                                                            
CONECT   68   61   69                                                       
CONECT   69   68   70                                                       
CONECT   70   69   71   75                                                  
CONECT   71   70   72   80                                                  
CONECT   72   71   73   79                                                  
CONECT   73   72   74   78                                                  
CONECT   74   73   75   76                                                  
CONECT   75   74   70                                                       
CONECT   76   74   77                                                       
CONECT   77   76                                                            
CONECT   78   73                                                            
CONECT   79   72                                                            
CONECT   80   71                                                            
CONECT   81    2   82                                                       
CONECT   82   81   83                                                       
CONECT   83   82   84   85   86                                             
CONECT   84   83    1                                                       
CONECT   85   83                                                            
CONECT   86   83                                                            
MASTER        0    0    0    0    0    0    0    0   86    0  190    0
END

View in JSmol

Synonyms

Value	Source
3-O-beta-D-Glucopyranosyl-(1-3)-alpha-L-rhamnopyranosyl-(1-2)-alpha-L-arabinopyranosyl-3 beta,23-dihydroxyolean-12-en-28-O-beta-D-glucopyranosyl-(1-6)-beta-D-glucopyranoside	MeSH

Chemical Formula

C₅₉H₉₆O₂₇

Average Mass

1237.3900 Da

Monoisotopic Mass

1236.61390 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@@H](O)CO[C@H]2O[C@H]2CC[C@@]3(C)[C@@H](CC[C@]4(C)[C@@H]3CC=C3[C@@H]5CC(C)(C)CC[C@@]5(CC[C@@]43C)C(=O)O[C@@H]3O[C@H](CO[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)[C@]2(C)CO)[C@H](O)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]1O

InChI Identifier

InChI=1S/C59H96O27/c1-24-34(64)46(84-49-43(73)40(70)37(67)29(20-61)81-49)45(75)51(79-24)85-47-35(65)27(63)21-77-52(47)83-33-11-12-55(4)31(56(33,5)23-62)10-13-58(7)32(55)9-8-25-26-18-54(2,3)14-16-59(26,17-15-57(25,58)6)53(76)86-50-44(74)41(71)38(68)30(82-50)22-78-48-42(72)39(69)36(66)28(19-60)80-48/h8,24,26-52,60-75H,9-23H2,1-7H3/t24-,26-,27-,28+,29+,30+,31+,32+,33-,34-,35-,36+,37+,38+,39-,40-,41-,42+,43+,44+,45+,46+,47+,48+,49-,50-,51-,52-,55-,56-,57+,58+,59-/m0/s1

InChI Key

VUEGHZSQVJADCO-UGZFTLGKSA-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
Cephalaria gigantea	Plant	KNApSAcK
Lonicera macranthoides	LOTUS Database	35616633
Nigella damascena	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
Steroid
Glycosyl compound
O-glycosyl compound
Oxane
Secondary alcohol
Carboxylic acid ester
Oxacycle
Polyol
Acetal
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Primary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen 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	ALOGPS
logP	-2.4	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	11.67	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	26	ChemAxon
Hydrogen Donor Count	16	ChemAxon
Polar Surface Area	433.05 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	289.98 m³·mol⁻¹	ChemAxon
Polarizability	130.41 Å³	ChemAxon
Number of Rings	10	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

C00051393

Chemspider ID

10259073

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14564503

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yang R, Min K, Wang Y, Chen S, Ma M, Li M, Yan J, Chen B, Yao S: Rapid semi-quantitative analysis of hemolytic triterpenoid saponins in Lonicerae Flos crude drugs and preparations by paper spray mass spectrometry. Talanta. 2022 Mar 1;239:123148. doi: 10.1016/j.talanta.2021.123148. Epub 2021 Dec 13. [PubMed:34923253 ]
Liu X, Zhou R, Shen B, Chen L, Zhou Q, Wan D, Huang L, Zhang S: Determination and Isolation of Four Anti-tumour Saponins from Lonicera macranthoides by HPLC-ESI-QTOF/MS and HSCCC. Curr Pharm Biotechnol. 2017;18(13):1106-1114. doi: 10.2174/1389201019666180226145427. [PubMed:29484987 ]
Wang Y, He Y, Dai Z, Ma S: Simultaneous determination of five triterpenoid saponins in different parts of Lonicera macranthoides by RRLC-MS/MS method. Pharmazie. 2016 Jun;71(6):306-10. [PubMed:27455548 ]
Hu YF, Wu CC: [Chemical constituents from stems of Lonicera macranthoides]. Zhong Yao Cai. 2012 Jan;35(1):66-9. [PubMed:22734414 ]
Wang N, Yang X: [Chemical constitutents from pre-formulation of lonicerae japonicae flos in shuanghuanglian lyophilized powder for injection]. Zhongguo Zhong Yao Za Zhi. 2011 Jun;36(12):1613-9. [PubMed:22007545 ]

Showing NP-Card for Giganteoside M (NP0071278)

MOL for NP0071278 (Giganteoside M)

3D MOL for NP0071278 (Giganteoside M)

3D SDF for NP0071278 (Giganteoside M)

3D-SDF for NP0071278 (Giganteoside M)

PDB for NP0071278 (Giganteoside M)

3D PDB for NP0071278 (Giganteoside M)

SMILES for NP0071278 (Giganteoside M)

INCHI for NP0071278 (Giganteoside M)

Structure for NP0071278 (Giganteoside M)

3D Structure for NP0071278 (Giganteoside M)