NP-MRD: Showing NP-Card for (-)-Bacobitacin C (NP0073837)

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Record Information

Version

2.0

Created at

2022-04-28 19:03:38 UTC

Updated at

2022-04-28 19:03:38 UTC

NP-MRD ID

NP0073837

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Bacobitacin C

Description

(3E,6R)-6-hydroxy-6-[(1R,2R,10S,11S,13R,14R,15R)-13-hydroxy-4-{[(2R,3S,4S,5S)-4-hydroxy-5-{[(2S,3R,4S,5S)-4-hydroxy-5-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxolan-2-yl]oxy}-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,7-dien-14-yl]-2-methyl-5-oxohept-3-en-2-yl acetate 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. (-)-Bacobitacin C is found in Bacopa monnieri . Based on a literature review very few articles have been published on (3E,6R)-6-hydroxy-6-[(1R,2R,10S,11S,13R,14R,15R)-13-hydroxy-4-{[(2R,3S,4S,5S)-4-hydroxy-5-{[(2S,3R,4S,5S)-4-hydroxy-5-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxolan-2-yl]oxy}-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,7-dien-14-yl]-2-methyl-5-oxohept-3-en-2-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282221032D          

 78 85  0  0  1  0            999 V2000
    6.1708   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1072    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4830    0.7528    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0148    0.1221    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7345   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2663   -1.2846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
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  8 34  1  1  0  0  0
  4 35  1  0  0  0  0
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M  END

     RDKit          3D

158165  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652304282221032D          

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    9.3905   -1.8199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7663   -2.1103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2981   -2.7410    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.0178   -3.5170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5496   -4.1477    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.3617   -4.0025    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.6420   -3.2265    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.1102   -2.5958    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.7931   -2.1328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4542   -3.0813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8936   -4.6332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2693   -4.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  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  2  0  0  0  0
 24 26  1  0  0  0  0
 22 27  1  0  0  0  0
 22 28  1  0  0  0  0
 17 29  1  1  0  0  0
 17 30  1  1  0  0  0
 15 31  1  6  0  0  0
 13 32  1  6  0  0  0
 12 33  1  1  0  0  0
  8 34  1  1  0  0  0
  4 35  1  0  0  0  0
 35 36  1  0  0  0  0
  1 36  1  0  0  0  0
 36 37  2  0  0  0  0
 35 38  1  0  0  0  0
 35 39  1  0  0  0  0
  1 40  1  0  0  0  0
 41 40  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
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 41 46  1  0  0  0  0
 44 47  1  6  0  0  0
 48 47  1  6  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
 48 52  1  0  0  0  0
 51 53  1  1  0  0  0
 53 54  1  0  0  0  0
 50 55  1  6  0  0  0
 49 56  1  1  0  0  0
 57 56  1  6  0  0  0
 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
 61 62  1  0  0  0  0
 57 62  1  0  0  0  0
 61 63  1  1  0  0  0
 60 64  1  6  0  0  0
 59 65  1  1  0  0  0
 58 66  1  1  0  0  0
 43 67  1  6  0  0  0
 42 68  1  6  0  0  0
 69 68  1  1  0  0  0
 69 70  1  0  0  0  0
 70 71  1  0  0  0  0
 71 72  1  0  0  0  0
 72 73  1  0  0  0  0
 73 74  1  0  0  0  0
 69 74  1  0  0  0  0
 74 75  1  6  0  0  0
 73 76  1  6  0  0  0
 72 77  1  1  0  0  0
 71 78  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0073837

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](CO)O[C@H]2O[C@H]2CO[C@H](OC3=C[C@@H]4C(=CC[C@H]5[C@]6(C)C[C@@H](O)[C@H]([C@@](C)(O)C(=O)\C=C\C(C)(C)OC(C)=O)[C@@]6(C)CC(=O)[C@@]45C)C(C)(C)C3=O)[C@@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)[C@H]2O)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C54H80O24/c1-21-33(60)37(64)39(66)45(71-21)76-41-36(63)29(75-48-42(35(62)28(19-55)74-48)77-46-40(67)38(65)34(61)22(2)72-46)20-70-47(41)73-27-16-25-24(50(6,7)44(27)68)12-13-30-51(8)17-26(57)43(52(51,9)18-32(59)53(25,30)10)54(11,69)31(58)14-15-49(4,5)78-23(3)56/h12,14-16,21-22,25-26,28-30,33-43,45-48,55,57,60-67,69H,13,17-20H2,1-11H3/b15-14+/t21-,22-,25+,26+,28-,29-,30-,33-,34-,35-,36-,37+,38+,39+,40+,41-,42+,43-,45-,46-,47+,48-,51-,52+,53-,54-/m0/s1

> <INCHI_KEY>
GEYQRPFTIAUWJM-NXVRWHDUSA-N

> <FORMULA>
C54H80O24

> <MOLECULAR_WEIGHT>
1113.21

> <EXACT_MASS>
1112.503953456

> <JCHEM_ACCEPTOR_COUNT>
23

> <JCHEM_ATOM_COUNT>
158

> <JCHEM_AVERAGE_POLARIZABILITY>
113.51526996376725

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3E,6R)-6-hydroxy-6-[(1R,2R,10S,11S,13R,14R,15R)-13-hydroxy-4-{[(2R,3S,4S,5S)-4-hydroxy-5-{[(2S,3R,4S,5S)-4-hydroxy-5-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxolan-2-yl]oxy}-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,7-dien-14-yl]-2-methyl-5-oxohept-3-en-2-yl acetate

> <ALOGPS_LOGP>
1.15

> <JCHEM_LOGP>
-0.7758351513333307

> <ALOGPS_LOGS>
-3.42

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.283855570527363

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.839154408812975

> <JCHEM_PKA_STRONGEST_BASIC>
-3.612182629449056

> <JCHEM_POLAR_SURFACE_AREA>
373.88000000000005

> <JCHEM_REFRACTIVITY>
267.25260000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.19e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3E,6R)-6-hydroxy-6-[(1R,2R,10S,11S,13R,14R,15R)-13-hydroxy-4-{[(2R,3S,4S,5S)-4-hydroxy-5-{[(2S,3R,4S,5S)-4-hydroxy-5-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxolan-2-yl]oxy}-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,7-dien-14-yl]-2-methyl-5-oxohept-3-en-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      11.519  -0.407   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.003  -0.678   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.010   0.499   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.533   1.947   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.541   3.125   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.025   2.854   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.502   1.405   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.494   0.228   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.971  -1.221   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.964  -2.398   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.455  -1.492   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.462  -0.314   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.986   1.134   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.770   2.079   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.495   1.215   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.923  -0.264   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.978  -1.480   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.033  -2.696   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.613  -4.122   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.493  -2.485   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.438  -3.701   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.963  -3.490   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -4.489  -3.280   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -5.434  -4.496   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -4.854  -5.922   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -6.960  -4.285   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.174  -5.016   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.753  -1.965   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.194  -2.425   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.762  -0.535   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       1.047   1.738   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.355   2.629   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.791  -1.700   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.487  -0.949   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.049   2.218   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      12.042   1.041   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      13.558   1.312   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      10.831   3.743   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      12.191   3.252   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      12.512  -1.585   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      14.028  -1.314   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      15.020  -2.491   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      16.536  -2.220   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      17.059  -0.771   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      16.067   0.406   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      14.551   0.135   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      18.575  -0.500   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      19.099   0.948   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      20.578   1.376   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      20.628   2.915   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      19.180   3.438   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      18.234   2.223   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      18.752   4.918   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      17.256   5.287   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      21.903   3.779   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      21.794   0.431   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0      23.220   1.011   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      24.436   0.066   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      25.863   0.646   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      26.073   2.172   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      24.857   3.117   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0      23.431   2.537   0.000  0.00  0.00           O+0
HETATM   63  C   UNK     0      25.068   4.643   0.000  0.00  0.00           C+0
HETATM   64  O   UNK     0      27.500   2.752   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0      27.078  -0.299   0.000  0.00  0.00           O+0
HETATM   66  O   UNK     0      24.225  -1.460   0.000  0.00  0.00           O+0
HETATM   67  O   UNK     0      17.529  -3.397   0.000  0.00  0.00           O+0
HETATM   68  O   UNK     0      14.497  -3.939   0.000  0.00  0.00           O+0
HETATM   69  C   UNK     0      15.490  -5.117   0.000  0.00  0.00           C+0
HETATM   70  O   UNK     0      14.967  -6.565   0.000  0.00  0.00           O+0
HETATM   71  C   UNK     0      15.959  -7.742   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0      17.475  -7.471   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0      17.998  -6.023   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0      17.006  -4.846   0.000  0.00  0.00           C+0
HETATM   75  O   UNK     0      18.280  -3.981   0.000  0.00  0.00           O+0
HETATM   76  O   UNK     0      19.514  -5.752   0.000  0.00  0.00           O+0
HETATM   77  O   UNK     0      18.468  -8.649   0.000  0.00  0.00           O+0
HETATM   78  C   UNK     0      15.436  -9.191   0.000  0.00  0.00           C+0
CONECT    1    2   36   40                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5   35                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    3    9   34                                             
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   16   33                                             
CONECT   13   12    7   14   32                                             
CONECT   14   13   15                                                       
CONECT   15   14   16   31                                                  
CONECT   16   15   12   17                                                  
CONECT   17   16   18   29   30                                             
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   27   28                                             
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   22                                                            
CONECT   28   22                                                            
CONECT   29   17                                                            
CONECT   30   17                                                            
CONECT   31   15                                                            
CONECT   32   13                                                            
CONECT   33   12                                                            
CONECT   34    8                                                            
CONECT   35    4   36   38   39                                             
CONECT   36   35    1   37                                                  
CONECT   37   36                                                            
CONECT   38   35                                                            
CONECT   39   35                                                            
CONECT   40    1   41                                                       
CONECT   41   40   42   46                                                  
CONECT   42   41   43   68                                                  
CONECT   43   42   44   67                                                  
CONECT   44   43   45   47                                                  
CONECT   45   44   46                                                       
CONECT   46   45   41                                                       
CONECT   47   44   48                                                       
CONECT   48   47   49   52                                                  
CONECT   49   48   50   56                                                  
CONECT   50   49   51   55                                                  
CONECT   51   50   52   53                                                  
CONECT   52   51   48                                                       
CONECT   53   51   54                                                       
CONECT   54   53                                                            
CONECT   55   50                                                            
CONECT   56   49   57                                                       
CONECT   57   56   58   62                                                  
CONECT   58   57   59   66                                                  
CONECT   59   58   60   65                                                  
CONECT   60   59   61   64                                                  
CONECT   61   60   62   63                                                  
CONECT   62   61   57                                                       
CONECT   63   61                                                            
CONECT   64   60                                                            
CONECT   65   59                                                            
CONECT   66   58                                                            
CONECT   67   43                                                            
CONECT   68   42   69                                                       
CONECT   69   68   70   74                                                  
CONECT   70   69   71                                                       
CONECT   71   70   72   78                                                  
CONECT   72   71   73   77                                                  
CONECT   73   72   74   76                                                  
CONECT   74   73   69   75                                                  
CONECT   75   74                                                            
CONECT   76   73                                                            
CONECT   77   72                                                            
CONECT   78   71                                                            
MASTER        0    0    0    0    0    0    0    0   78    0  170    0
END

View in JSmol

Synonyms

Value

Source

(3E,6R)-6-Hydroxy-6-[(1R,2R,10S,11S,13R,14R,15R)-13-hydroxy-4-{[(2R,3S,4S,5S)-4-hydroxy-5-{[(2S,3R,4S,5S)-4-hydroxy-5-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxolan-2-yl]oxy}-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0,.0,]heptadeca-3,7-dien-14-yl]-2-methyl-5-oxohept-3-en-2-yl acetic acid

Generator

Chemical Formula

C₅₄H₈₀O₂₄

Average Mass

1113.2100 Da

Monoisotopic Mass

1112.50395 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](CO)O[C@H]2O[C@H]2CO[C@H](OC3=C[C@@H]4C(=CC[C@H]5[C@]6(C)C[C@@H](O)[C@H]([C@@](C)(O)C(=O)\C=C\C(C)(C)OC(C)=O)[C@@]6(C)CC(=O)[C@@]45C)C(C)(C)C3=O)[C@@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)[C@H]2O)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C54H80O24/c1-21-33(60)37(64)39(66)45(71-21)76-41-36(63)29(75-48-42(35(62)28(19-55)74-48)77-46-40(67)38(65)34(61)22(2)72-46)20-70-47(41)73-27-16-25-24(50(6,7)44(27)68)12-13-30-51(8)17-26(57)43(52(51,9)18-32(59)53(25,30)10)54(11,69)31(58)14-15-49(4,5)78-23(3)56/h12,14-16,21-22,25-26,28-30,33-43,45-48,55,57,60-67,69H,13,17-20H2,1-11H3/b15-14+/t21-,22-,25+,26+,28-,29-,30-,33-,34-,35-,36-,37+,38+,39+,40+,41-,42+,43-,45-,46-,47+,48-,51-,52+,53-,54-/m0/s1

InChI Key

GEYQRPFTIAUWJM-NXVRWHDUSA-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
Bacopa monnieri	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
Triterpenoid
Cucurbitacin skeleton
Oligosaccharide
22-oxosteroid
21-oxosteroid
Steroid ester
20-hydroxysteroid
14-alpha-methylsteroid
16-hydroxysteroid
16-alpha-hydroxysteroid
Oxosteroid
11-oxosteroid
Hydroxysteroid
3-oxosteroid
3-oxo-delta-1-steroid
Delta-1-steroid
O-glycosyl compound
Glycosyl compound
Cyclohexenone
Oxane
Acyloin
Alpha,beta-unsaturated ketone
Tetrahydrofuran
Tertiary alcohol
Enone
Cyclic alcohol
Alpha-hydroxy ketone
Acryloyl-group
Cyclic ketone
Secondary alcohol
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.15	ALOGPS
logP	-0.78	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	11.84	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	23	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	373.88 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	267.25 m³·mol⁻¹	ChemAxon
Polarizability	113.52 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

162916187

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Bacobitacin C (NP0073837)

MOL for NP0073837 ((-)-Bacobitacin C)

3D MOL for NP0073837 ((-)-Bacobitacin C)

3D SDF for NP0073837 ((-)-Bacobitacin C)

3D-SDF for NP0073837 ((-)-Bacobitacin C)

PDB for NP0073837 ((-)-Bacobitacin C)

3D PDB for NP0073837 ((-)-Bacobitacin C)

SMILES for NP0073837 ((-)-Bacobitacin C)

INCHI for NP0073837 ((-)-Bacobitacin C)

Structure for NP0073837 ((-)-Bacobitacin C)

3D Structure for NP0073837 ((-)-Bacobitacin C)