NP-MRD: Showing NP-Card for (+)-Beesioside H (NP0080194)

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Record Information

Version

2.0

Created at

2022-04-29 01:14:50 UTC

Updated at

2022-04-29 01:14:50 UTC

NP-MRD ID

NP0080194

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Beesioside H

Description

(2R,3R,4S,5R,6R)-2-(hydroxymethyl)-6-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,3R,6S,8R,11S,12S,14S,15R,16S)-14-hydroxy-16-(hydroxymethyl)-15-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]Octadecan-6-yl]oxy}oxan-2-yl]methoxy}oxane-3,4,5-triol belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus. (+)-Beesioside H is found in Beesia calthifolia. Based on a literature review very few articles have been published on (2R,3R,4S,5R,6R)-2-(hydroxymethyl)-6-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,3R,6S,8R,11S,12S,14S,15R,16S)-14-hydroxy-16-(hydroxymethyl)-15-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]Octadecan-6-yl]oxy}oxan-2-yl]methoxy}oxane-3,4,5-triol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292203142D          

 57 64  0  0  1  0            999 V2000
   -2.4651    1.7932    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9970    1.1625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7167    0.3866    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9045    0.2414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3727    0.8721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6530    1.6480    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1212    2.2787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4015    3.0546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8697    3.6853    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1500    4.4612    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6182    5.0920    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1940    4.9467    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4743    4.1708    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0576    3.5401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2864    4.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8182    4.6563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7258    5.5774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8985    5.8679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9621    4.6065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6242   -0.5346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8121   -0.6798    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5318   -1.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2803   -1.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8121   -0.9702    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5318   -0.1943    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2803   -0.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1635    0.7676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8921    0.5044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0636    0.4364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8758    0.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1561   -0.4847    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6242   -1.1154    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9045   -1.8914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7167   -2.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2485   -1.4059    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9682   -0.6299    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6195   -0.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3024   -0.5866    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0730   -1.3791    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5794   -2.0304    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2101   -2.5622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8992   -3.3264    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0764   -3.2669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8787   -2.4659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3347   -4.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7702   -4.7278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6340   -4.4626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0354   -3.5916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1742   -1.4587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0783   -0.3063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7705    0.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6083   -2.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1454   -2.8311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0924   -1.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2485   -0.2441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8091    1.3077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7454    2.5691    0.0000 O   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
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 13 15  1  1  0  0  0
 15 16  1  0  0  0  0
 12 17  1  1  0  0  0
 11 18  1  1  0  0  0
 10 19  1  6  0  0  0
  4 20  1  1  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 25 29  1  6  0  0  0
 29 30  1  0  0  0  0
 31 30  1  1  0  0  0
 31 32  1  0  0  0  0
 24 32  1  0  0  0  0
 32 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
 31 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 35 39  1  0  0  0  0
 39 40  1  6  0  0  0
 40 41  1  1  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 40 44  1  0  0  0  0
 42 45  1  1  0  0  0
 45 46  1  0  0  0  0
 45 47  1  0  0  0  0
 45 48  1  0  0  0  0
 40 49  1  6  0  0  0
 38 50  1  6  0  0  0
 36 51  1  1  0  0  0
 35 52  1  6  0  0  0
 52 53  1  0  0  0  0
 32 54  1  6  0  0  0
 24 54  1  6  0  0  0
  3 55  1  6  0  0  0
  2 56  1  1  0  0  0
  1 57  1  1  0  0  0
M  END

     RDKit          3D

127134  0  0  0  0  0  0  0  0999 V2000
  -10.3026    0.5575    1.6853 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4331    0.6992    0.1840 C   0  0  1  0  0  0  0  0  0  0  0  0
  -11.8128    0.3031   -0.2925 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2178    2.0292   -0.1634 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3949   -0.2055   -0.4369 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.3906    0.0740   -1.9323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9102    0.0790   -2.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2482   -0.4620   -0.9526 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.3714   -1.9403   -1.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8738    0.0814   -0.9479 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9292    1.5956   -0.9240 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.1526    2.0297   -0.4292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8069    2.0717   -0.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9567    0.8626    0.0686 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0839    0.8120   -1.1615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0776    0.7637    1.2671 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3999    2.1143    1.3916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1262    2.0311    2.2255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2139    1.1815    1.3678 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1844    1.1790    1.9390 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2692    0.5539    3.2965 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5335    2.6629    2.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1389    0.5287    1.0041 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9026   -0.4832    1.5603 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2519   -0.2878    1.4366 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8282   -1.1812    0.4947 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1700   -0.7669    0.4265 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7632   -0.9388   -0.9440 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0883   -0.4956   -0.8924 O   0  0  0  0  0  0  0  0  0  0  0  0
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   11.4298   -3.5886   -2.1287 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7655   -0.4168   -3.8892 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.0778   -0.4650   -4.3723 O   0  0  0  0  0  0  0  0  0  0  0  0
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   11.4058    0.9479   -1.9980 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1227    0.7783   -2.5463 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2684    1.1857   -3.5721 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8930   -1.4832    1.5146 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1016   -2.8455    1.2402 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1108   -1.3265    2.7890 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5390   -2.5421    3.1660 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0409   -0.2356    2.6982 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7109    1.0062    2.8414 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3579   -0.1448   -0.1373 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3000   -1.0085    0.5056 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.1903   -2.1994   -1.7528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4659   -2.3752   -1.4444 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3712    0.7126    0.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1938   -0.3952   -1.7112 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304292203142D          

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    3.8787   -2.4659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  3 55  1  6  0  0  0
  2 56  1  1  0  0  0
  1 57  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0080194

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)[C@H]1CC[C@](C)(O1)[C@H]1[C@@H](O)C[C@@]2(C)[C@@H]3CC[C@@H]4[C@]5(C[C@@]35CC[C@]12CO)CC[C@H](O[C@@H]1O[C@H](CO[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H](O)[C@H]1O)C4(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C42H70O15/c1-36(2)23-7-8-24-38(5)15-20(45)33(39(6)11-9-26(57-39)37(3,4)52)42(38,19-44)14-13-41(24)18-40(23,41)12-10-25(36)56-35-32(51)30(49)28(47)22(55-35)17-53-34-31(50)29(48)27(46)21(16-43)54-34/h20-35,43-52H,7-19H2,1-6H3/t20-,21+,22+,23-,24-,25-,26+,27-,28-,29-,30-,31+,32+,33+,34+,35-,38-,39-,40+,41-,42-/m0/s1

> <INCHI_KEY>
CPPPESTUUSAHJH-UVELPHSASA-N

> <FORMULA>
C42H70O15

> <MOLECULAR_WEIGHT>
815.007

> <EXACT_MASS>
814.471471554

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
127

> <JCHEM_AVERAGE_POLARIZABILITY>
87.81926833579976

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S,5R,6R)-2-{[(1S,3R,6S,8R,11S,12S,14S,15R,16S)-14-hydroxy-16-(hydroxymethyl)-15-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12-trimethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-6-yl]oxy}-6-({[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
0.36

> <JCHEM_LOGP>
-0.9138843319999974

> <ALOGPS_LOGS>
-3.50

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.428927197139092

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.908878015858278

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083422322401

> <JCHEM_POLAR_SURFACE_AREA>
248.44999999999996

> <JCHEM_REFRACTIVITY>
200.72480000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.59e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S,5R,6R)-2-{[(1S,3R,6S,8R,11S,12S,14S,15R,16S)-14-hydroxy-16-(hydroxymethyl)-15-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12-trimethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-6-yl]oxy}-6-({[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-3,4,5-triol

> <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      -4.602   3.347   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.594   2.170   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.071   0.722   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.555   0.451   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.562   1.628   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -3.086   3.076   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.093   4.254   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.616   5.702   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.623   6.879   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.147   8.328   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.154   9.505   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.362   9.234   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.885   7.786   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.107   6.608   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.401   7.514   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.394   8.692   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.355  10.411   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.677  10.953   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -3.663   8.599   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -3.032  -0.998   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.516  -1.269   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.993  -2.717   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.523  -2.988   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.516  -1.811   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.993  -0.363   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.523  -0.092   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.305   1.433   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.665   0.942   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.985   0.815   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.501   0.544   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.025  -0.905   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.032  -2.082   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.555  -3.531   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.071  -3.802   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.064  -2.624   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.541  -1.176   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.756  -0.231   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.031  -1.095   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       7.603  -2.574   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       8.548  -3.790   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       9.726  -4.783   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       9.145  -6.209   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       7.609  -6.098   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       7.240  -4.603   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       9.958  -7.517   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      10.771  -8.825   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0       8.650  -8.330   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      11.266  -6.704   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       9.659  -2.723   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       9.479  -0.572   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0       5.172   0.319   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       6.736  -4.010   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0       5.871  -5.285   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0       2.039  -3.259   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      -6.064  -0.456   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      -7.110   2.441   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      -5.125   4.796   0.000  0.00  0.00           O+0
CONECT    1    2    6   57                                                  
CONECT    2    1    3   56                                                  
CONECT    3    2    4   55                                                  
CONECT    4    3    5   20                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11   19                                                  
CONECT   11   10   12   18                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13    9                                                       
CONECT   15   13   16                                                       
CONECT   16   15                                                            
CONECT   17   12                                                            
CONECT   18   11                                                            
CONECT   19   10                                                            
CONECT   20    4   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   32   54                                             
CONECT   25   24   26   29                                                  
CONECT   26   25   21   27   28                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   25   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   24   33   54                                             
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   39   52                                             
CONECT   36   35   31   37   51                                             
CONECT   37   36   38                                                       
CONECT   38   37   39   50                                                  
CONECT   39   38   35   40                                                  
CONECT   40   39   41   44   49                                             
CONECT   41   40   42                                                       
CONECT   42   41   43   45                                                  
CONECT   43   42   44                                                       
CONECT   44   43   40                                                       
CONECT   45   42   46   47   48                                             
CONECT   46   45                                                            
CONECT   47   45                                                            
CONECT   48   45                                                            
CONECT   49   40                                                            
CONECT   50   38                                                            
CONECT   51   36                                                            
CONECT   52   35   53                                                       
CONECT   53   52                                                            
CONECT   54   32   24                                                       
CONECT   55    3                                                            
CONECT   56    2                                                            
CONECT   57    1                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  128    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₂H₇₀O₁₅

Average Mass

815.0070 Da

Monoisotopic Mass

814.47147 Da

IUPAC Name

(2R,3R,4S,5R,6R)-2-{[(1S,3R,6S,8R,11S,12S,14S,15R,16S)-14-hydroxy-16-(hydroxymethyl)-15-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12-trimethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-6-yl]oxy}-6-({[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-3,4,5-triol

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(C)(O)[C@H]1CC[C@](C)(O1)[C@H]1[C@@H](O)C[C@@]2(C)[C@@H]3CC[C@@H]4[C@]5(C[C@@]35CC[C@]12CO)CC[C@H](O[C@@H]1O[C@H](CO[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H](O)[C@H]1O)C4(C)C

InChI Identifier

InChI=1S/C42H70O15/c1-36(2)23-7-8-24-38(5)15-20(45)33(39(6)11-9-26(57-39)37(3,4)52)42(38,19-44)14-13-41(24)18-40(23,41)12-10-25(36)56-35-32(51)30(49)28(47)22(55-35)17-53-34-31(50)29(48)27(46)21(16-43)54-34/h20-35,43-52H,7-19H2,1-6H3/t20-,21+,22+,23-,24-,25-,26+,27-,28-,29-,30-,31+,32+,33+,34+,35-,38-,39-,40+,41-,42-/m0/s1

InChI Key

CPPPESTUUSAHJH-UVELPHSASA-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
Beesia calthifolia	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Cucurbitacin glycosides

Alternative Parents

Substituents

Cucurbitacin glycoside skeleton
Triterpene saponin
Triterpene glycoside
Cycloartanol-skeleton
Triterpenoid
Cycloartane-skeleton
9b,19-cyclo-lanostane-skeleton
18-hydroxysteroid
16-hydroxysteroid
16-beta-hydroxysteroid
Hydroxysteroid
O-glycosyl compound
Glycosyl compound
Disaccharide
Oxane
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Dialkyl ether
Acetal
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
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	0.36	ALOGPS
logP	-0.91	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	11.91	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	248.45 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	200.72 m³·mol⁻¹	ChemAxon
Polarizability	87.82 Å³	ChemAxon
Number of Rings	8	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

162969068

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (+)-Beesioside H (NP0080194)

MOL for NP0080194 ((+)-Beesioside H)

3D MOL for NP0080194 ((+)-Beesioside H)

3D SDF for NP0080194 ((+)-Beesioside H)

3D-SDF for NP0080194 ((+)-Beesioside H)

PDB for NP0080194 ((+)-Beesioside H)

3D PDB for NP0080194 ((+)-Beesioside H)

SMILES for NP0080194 ((+)-Beesioside H)

INCHI for NP0080194 ((+)-Beesioside H)

Structure for NP0080194 ((+)-Beesioside H)

3D Structure for NP0080194 ((+)-Beesioside H)