NP-MRD: Showing NP-Card for (+)-Calenduloside F 6'-O-n-butyl ester (NP0077907)

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Record Information

Version

1.0

Created at

2022-04-28 23:02:54 UTC

Updated at

2022-04-28 23:02:54 UTC

NP-MRD ID

NP0077907

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Calenduloside F 6'-O-n-butyl ester

Description

Chikusetsusaponin-IVa butyl ester 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. (+)-Calenduloside F 6'-O-n-butyl ester is found in Achyranthes bidentata, Aralia armata, Aralia taibaiensis, Calendula officinalis and Panax japonicus. It was first documented in 2007 (PMID: 17631105). Based on a literature review a small amount of articles have been published on Chikusetsusaponin-IVa butyl ester (PMID: 33637959) (PMID: 26929249) (PMID: 28861969) (PMID: 22796399).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292201022D          

 60 66  0  0  1  0            999 V2000
    5.2520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 C   0  0  1  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
    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  2  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
    7.3145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7270   -0.3020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5520   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9645   -1.0164    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.5520   -1.7309    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7270   -1.7309    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3145   -1.0164    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4895   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145   -2.4454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9645   -2.4454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7895   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   12.6770   -3.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1058    1.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7766    1.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5395    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2732   -1.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3977   -0.7392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1270    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230    2.5559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -1.7605    3.2704    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    4.4270   -0.3020    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  0  0  0  0
  5  7  1  1  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  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  1  0  0  0
 12 15  1  6  0  0  0
 11 16  1  1  0  0  0
 10 17  1  6  0  0  0
 17 18  2  0  0  0  0
 17 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
  4 24  1  0  0  0  0
  4 25  1  0  0  0  0
  3 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  2 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 28 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
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 37 32  1  6  0  0  0
 37 38  1  0  0  0  0
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 49 56  1  6  0  0  0
 56 57  1  0  0  0  0
 33 58  1  6  0  0  0
 28 59  1  1  0  0  0
  2 60  1  1  0  0  0
M  END

     RDKit          3D

134140  0  0  0  0  0  0  0  0999 V2000
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   -4.4370   -5.4563   -0.7675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0852   -4.7276   -1.8017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7981   -3.3012   -0.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8991   -3.6744   -2.4830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5407   -4.9563   -1.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1033   -3.4239   -3.6999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4828   -2.8808   -3.0591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6584   -0.9131   -3.7311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2233   -1.5528   -3.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8088    0.1482   -0.4918 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3362    1.5041   -0.5201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9454    4.3372    0.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3998    3.6235   -0.1106 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1178    3.2744   -2.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6615    2.8387    2.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4651    0.4000    2.2917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8016    0.7089    3.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0212    1.8544    3.8030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5052    0.1300    2.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5835   -1.1150    2.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9790    1.4598   -1.2197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0746    0.9727   -2.9189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8524    0.6491   -3.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8539    1.9128   -1.9685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1914   -1.8976   -1.7124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9604   -1.0678   -3.0864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4420   -0.3953   -2.5187 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9089    3.7028   -0.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3725    3.5212    0.5563 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8378    2.7667    1.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1421    3.0351   -2.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0623    1.2249   -2.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5847    1.9446   -1.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4746    2.5260    1.9207 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8660    3.6656   -0.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7414    1.8144    0.0311 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7954    3.0365    2.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6505    0.9414    2.9409 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6714    0.2653    2.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
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 30100  1  0
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 57131  1  6
 58132  1  0
 59133  1  1
 60134  1  0
M  END


  Mrv1652304292201022D          

 60 66  0  0  1  0            999 V2000
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    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2732   -1.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3977   -0.7392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1270    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3480    3.9849    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    4.4270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  1  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
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 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  1  0  0  0
 12 15  1  6  0  0  0
 11 16  1  1  0  0  0
 10 17  1  6  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
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 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  4 24  1  0  0  0  0
  4 25  1  0  0  0  0
  3 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  2 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 28 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 32  1  6  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
 39 42  1  0  0  0  0
 39 43  1  0  0  0  0
 36 44  1  1  0  0  0
 44 45  2  0  0  0  0
 44 46  1  0  0  0  0
 47 46  1  6  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 47 52  1  0  0  0  0
 52 53  1  1  0  0  0
 51 54  1  6  0  0  0
 50 55  1  1  0  0  0
 49 56  1  6  0  0  0
 56 57  1  0  0  0  0
 33 58  1  6  0  0  0
 28 59  1  1  0  0  0
  2 60  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0077907

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCOC(=O)[C@H]1O[C@@H](O[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](O)[C@H](O)[C@H]3O)C2(C)C)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C46H74O14/c1-9-10-21-56-37(54)36-33(51)32(50)35(53)39(59-36)58-29-14-15-43(6)27(42(29,4)5)13-16-45(8)28(43)12-11-24-25-22-41(2,3)17-19-46(25,20-18-44(24,45)7)40(55)60-38-34(52)31(49)30(48)26(23-47)57-38/h11,25-36,38-39,47-53H,9-10,12-23H2,1-8H3/t25-,26+,27-,28+,29-,30+,31-,32-,33-,34+,35+,36-,38-,39+,43-,44+,45+,46-/m0/s1

> <INCHI_KEY>
UMELIPOCPCVHGJ-GUQBEPFPSA-N

> <FORMULA>
C46H74O14

> <MOLECULAR_WEIGHT>
851.084

> <EXACT_MASS>
850.507857063

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
134

> <JCHEM_AVERAGE_POLARIZABILITY>
94.19737281657024

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
butyl (2S,3S,4S,5R,6R)-6-{[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-4,4,6a,6b,11,11,14b-heptamethyl-8a-({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate

> <ALOGPS_LOGP>
4.41

> <JCHEM_LOGP>
4.345997303

> <ALOGPS_LOGS>
-4.63

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.398802706289828

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.884592361724522

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981093680175836

> <JCHEM_POLAR_SURFACE_AREA>
221.89999999999995

> <JCHEM_REFRACTIVITY>
216.9791000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.98e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
butyl (2S,3S,4S,5R,6R)-6-{[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-4,4,6a,6b,11,11,14b-heptamethyl-8a-({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       9.804  -0.564   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.804   2.104   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.344   2.104   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.114   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.344  -0.564   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      13.654   0.770   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      14.424  -0.564   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      15.964  -0.564   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      16.734  -1.897   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.964  -3.231   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.424  -3.231   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.654  -1.897   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      12.114  -1.897   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      13.654  -4.565   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      16.734  -4.565   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      18.274  -1.897   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      19.044  -0.564   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      19.044  -3.231   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      20.584  -3.231   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      21.354  -4.565   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      22.894  -4.565   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      23.664  -5.898   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.397   3.643   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.650   2.920   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.034   3.437   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.494   3.437   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       0.510  -2.103   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -0.742  -1.380   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       1.334   3.437   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       2.104   4.771   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      -0.206   3.437   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      -0.976   4.771   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      -2.516   4.771   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      -3.286   6.105   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      -2.516   7.438   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      -0.976   7.438   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      -0.206   6.105   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0       1.334   6.105   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0      -0.206   8.772   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      -3.286   8.772   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      -4.826   6.105   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      -5.596   7.438   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       6.885   3.635   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       8.264  -0.564   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   29   60                                             
CONECT    3    2    4   26                                                  
CONECT    4    3    5   24   25                                             
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12    8   14                                                  
CONECT   14   13                                                            
CONECT   15   12                                                            
CONECT   16   11                                                            
CONECT   17   10   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24    4                                                            
CONECT   25    4                                                            
CONECT   26    3   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   33   59                                             
CONECT   29   28    2   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   37                                                  
CONECT   33   32   28   34   58                                             
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   41   44                                             
CONECT   37   36   32   38                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   42   43                                             
CONECT   40   39   41                                                       
CONECT   41   40   36                                                       
CONECT   42   39                                                            
CONECT   43   39                                                            
CONECT   44   36   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47                                                       
CONECT   47   46   48   52                                                  
CONECT   48   47   49                                                       
CONECT   49   48   50   56                                                  
CONECT   50   49   51   55                                                  
CONECT   51   50   52   54                                                  
CONECT   52   51   47   53                                                  
CONECT   53   52                                                            
CONECT   54   51                                                            
CONECT   55   50                                                            
CONECT   56   49   57                                                       
CONECT   57   56                                                            
CONECT   58   33                                                            
CONECT   59   28                                                            
CONECT   60    2                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  132    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₆H₇₄O₁₄

Average Mass

851.0840 Da

Monoisotopic Mass

850.50786 Da

IUPAC Name

butyl (2S,3S,4S,5R,6R)-6-{[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-4,4,6a,6b,11,11,14b-heptamethyl-8a-({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate

Traditional Name

butyl (2S,3S,4S,5R,6R)-6-{[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-4,4,6a,6b,11,11,14b-heptamethyl-8a-({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate

CAS Registry Number

Not Available

SMILES

CCCCOC(=O)[C@H]1O[C@@H](O[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](O)[C@H](O)[C@H]3O)C2(C)C)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C46H74O14/c1-9-10-21-56-37(54)36-33(51)32(50)35(53)39(59-36)58-29-14-15-43(6)27(42(29,4)5)13-16-45(8)28(43)12-11-24-25-22-41(2,3)17-19-46(25,20-18-44(24,45)7)40(55)60-38-34(52)31(49)30(48)26(23-47)57-38/h11,25-36,38-39,47-53H,9-10,12-23H2,1-8H3/t25-,26+,27-,28+,29-,30+,31-,32-,33-,34+,35+,36-,38-,39+,43-,44+,45+,46-/m0/s1

InChI Key

UMELIPOCPCVHGJ-GUQBEPFPSA-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
Achyranthes bidentata	LOTUS Database	35616633
Aralia armata	LOTUS Database	35616633
Aralia taibaiensis	Plant	KNApSAcK
Calendula officinalis	Plant	KNApSAcK
Panax Japonicus	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
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Glycosyl compound
O-glycosyl compound
Beta-hydroxy acid
Pyran
Oxane
Dicarboxylic acid or derivatives
Hydroxy acid
Monosaccharide
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Polyol
Acetal
Organooxygen compound
Primary alcohol
Organic oxygen compound
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

triterpenoid saponin (CHEBI:67979 )

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	4.41	ALOGPS
logP	4.35	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	11.88	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	221.9 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	216.98 m³·mol⁻¹	ChemAxon
Polarizability	94.2 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

23339216

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44566502

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yang J, Ling Y, Hua D, Zhao C, Sun X, Cai X, Chen J, Hu C, Cao P: IL-6R blockade by chikusetsusaponin IVa butyl ester inhibits Th17 cell differentiation and ameliorates collagen-induced arthritis. Cell Mol Immunol. 2021 Jun;18(6):1584-1586. doi: 10.1038/s41423-021-00651-6. Epub 2021 Feb 26. [PubMed:33637959 ]
Yang J, Qian S, Cai X, Lu W, Hu C, Sun X, Yang Y, Yu Q, Gao SP, Cao P: Chikusetsusaponin IVa Butyl Ester (CS-IVa-Be), a Novel IL6R Antagonist, Inhibits IL6/STAT3 Signaling Pathway and Induces Cancer Cell Apoptosis. Mol Cancer Ther. 2016 Jun;15(6):1190-200. doi: 10.1158/1535-7163.MCT-15-0551. Epub 2016 Feb 29. [PubMed:26929249 ]
Zhou QL, Xu W, Yang XW: [Chemical constituents of Chinese red ginseng]. Zhongguo Zhong Yao Za Zhi. 2016 Jan;41(2):233-249. doi: 10.4268/cjcmm20160214. [PubMed:28861969 ]
Wang J, Lu J, Lv C, Xu T, Jia L: Three new triterpenoid saponins from root of Gardenia jasminoides Ellis. Fitoterapia. 2012 Dec;83(8):1396-401. doi: 10.1016/j.fitote.2012.07.004. Epub 2012 Jul 14. [PubMed:22796399 ]
Li J, Qi H, Qi LW, Yi L, Li P: Simultaneous determination of main phytoecdysones and triterpenoids in radix achyranthis bidentatae by high-performance liquid chromatography with diode array-evaporative light scattering detectors and mass spectrometry. Anal Chim Acta. 2007 Jul 23;596(2):264-72. doi: 10.1016/j.aca.2007.05.016. Epub 2007 May 21. [PubMed:17631105 ]

Showing NP-Card for (+)-Calenduloside F 6'-O-n-butyl ester (NP0077907)

MOL for NP0077907 ((+)-Calenduloside F 6'-O-n-butyl ester)

3D MOL for NP0077907 ((+)-Calenduloside F 6'-O-n-butyl ester)

3D SDF for NP0077907 ((+)-Calenduloside F 6'-O-n-butyl ester)

3D-SDF for NP0077907 ((+)-Calenduloside F 6'-O-n-butyl ester)

PDB for NP0077907 ((+)-Calenduloside F 6'-O-n-butyl ester)

3D PDB for NP0077907 ((+)-Calenduloside F 6'-O-n-butyl ester)

SMILES for NP0077907 ((+)-Calenduloside F 6'-O-n-butyl ester)

INCHI for NP0077907 ((+)-Calenduloside F 6'-O-n-butyl ester)

Structure for NP0077907 ((+)-Calenduloside F 6'-O-n-butyl ester)

3D Structure for NP0077907 ((+)-Calenduloside F 6'-O-n-butyl ester)