NP-MRD: Showing NP-Card for 6-(6-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl)-n-(4,5-dimethyl-2-oxooxolan-3-yl)-2-methylhepta-2,4-dienimidic acid (NP0143258)

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Record Information

Version

2.0

Created at

2022-09-01 21:57:51 UTC

Updated at

2022-09-01 21:57:51 UTC

NP-MRD ID

NP0143258

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-(6-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl)-n-(4,5-dimethyl-2-oxooxolan-3-yl)-2-methylhepta-2,4-dienimidic acid

Description

6-(6-{[4,5-Dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]Octadecan-15-yl)-N-(4,5-dimethyl-2-oxooxolan-3-yl)-2-methylhepta-2,4-dienimidic acid 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. 6-(6-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl)-n-(4,5-dimethyl-2-oxooxolan-3-yl)-2-methylhepta-2,4-dienimidic acid is found in Mussaenda pubescens. 6-(6-{[4,5-Dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]Octadecan-15-yl)-N-(4,5-dimethyl-2-oxooxolan-3-yl)-2-methylhepta-2,4-dienimidic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161507502D          

 63 70  0  0  0  0            999 V2000
    5.6974    3.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0083    2.8554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8256    2.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1365    1.9784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9537    1.8655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2646    1.1013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7583    0.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0819    0.9885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5882    1.6398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3927    0.2243    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2100    0.1114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7817    0.7063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6364    1.5184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5240    0.3464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2515    0.7355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4112   -0.4708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5991   -0.6161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2392   -1.3584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5020    2.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7313    1.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0484    0.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3971    1.4549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1995    0.6540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5850    1.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3047    0.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4926    0.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9608    1.0193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1486    0.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4327    0.0995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4352    0.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6168    1.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8971    2.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7092    2.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2411    1.7952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5214    2.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0532    1.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3335    2.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1456    2.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6774    2.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0373    2.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1953    1.3596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4756    0.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0562   -0.0471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2241   -0.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3077   -1.4537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1199   -1.3085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0362   -0.9682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3165   -1.7441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5680   -0.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3801   -0.4827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2877    0.4384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8195    1.0691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5392    1.8451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7271    1.9903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4468    2.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3653    2.9114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6456    3.6873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9786    3.3969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6983    4.1728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7908    3.2517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3226    3.8824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0711    2.4758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8832    2.3306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  4  0  0  0
  3  4  2  0  0  0  0
  5  4  1  4  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 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
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  2  0  0  0  0
  2 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
 22 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
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 27 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 24 36  1  0  0  0  0
 34 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
 19 39  1  0  0  0  0
 22 39  1  0  0  0  0
 39 40  1  0  0  0  0
 31 41  1  0  0  0  0
 41 42  1  0  0  0  0
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 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 44 47  1  0  0  0  0
 47 48  1  0  0  0  0
 47 49  1  0  0  0  0
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 49 51  1  0  0  0  0
 42 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  1  0  0  0  0
 56 57  1  0  0  0  0
 55 58  1  0  0  0  0
 58 59  1  0  0  0  0
 58 60  1  0  0  0  0
 60 61  1  0  0  0  0
 60 62  1  0  0  0  0
 53 62  1  0  0  0  0
 62 63  1  0  0  0  0
M  END

     RDKit          3D

138145  0  0  0  0  0  0  0  0999 V2000
   10.5359   -1.7455    2.1194 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5360   -1.3711    1.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2705   -1.5948    1.2712 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1635   -1.3159    0.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9019   -1.5849    0.7430 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7151   -1.3348   -0.1007 C   0  0  2  0  0  0  0  0  0  0  0  0
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    3.8431   -0.3734    0.6341 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4912   -1.0028    1.9683 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0917   -0.5689    2.2722 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7465    0.4123    1.2121 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2476    1.8113    1.5038 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004161507502D          

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M  END
> <DATABASE_ID>
NP0143258

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C=CC=C(C)C(=O)NC1C(C)C(C)OC1=O)C1CCC2(C)C3CCC4C5(CC35CCC12C)CCC(OC1OC(CO)C(O)C(O)C1OC1OC(CO)C(O)C(O)C1O)C4(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C48H75NO14/c1-23(10-9-11-24(2)40(57)49-33-25(3)26(4)59-41(33)58)27-14-16-46(8)31-13-12-30-44(5,6)32(15-17-47(30)22-48(31,47)19-18-45(27,46)7)62-43-39(37(55)35(53)29(21-51)61-43)63-42-38(56)36(54)34(52)28(20-50)60-42/h9-11,23,25-39,42-43,50-56H,12-22H2,1-8H3,(H,49,57)

> <INCHI_KEY>
SMLUUCVJPGLTPV-UHFFFAOYSA-N

> <FORMULA>
C48H75NO14

> <MOLECULAR_WEIGHT>
890.121

> <EXACT_MASS>
889.518756099

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
138

> <JCHEM_AVERAGE_POLARIZABILITY>
97.7581109530702

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-(6-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl)-N-(4,5-dimethyl-2-oxooxolan-3-yl)-2-methylhepta-2,4-dienamide

> <ALOGPS_LOGP>
3.56

> <JCHEM_LOGP>
2.8726625139999995

> <ALOGPS_LOGS>
-4.78

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.540351571505347

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.021888023445827

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810835766873476

> <JCHEM_POLAR_SURFACE_AREA>
233.92999999999995

> <JCHEM_REFRACTIVITY>
228.7431

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.49e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-(6-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl)-N-(4,5-dimethyl-2-oxooxolan-3-yl)-2-methylhepta-2,4-dienamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      10.635   6.757   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.216   5.330   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.741   5.119   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.321   3.693   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.847   3.482   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.427   2.056   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.482   0.840   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.953   1.845   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      17.898   3.061   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0      17.533   0.419   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      19.059   0.208   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      20.126   1.318   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.855   2.834   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      21.512   0.647   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      22.870   1.373   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      21.301  -0.879   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      19.785  -1.150   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      19.113  -2.536   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      10.270   4.114   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.698   2.635   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.424   1.771   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.208   2.716   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.839   1.221   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.692   2.445   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.169   0.996   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.653   0.725   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.660   1.903   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.144   1.632   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.674   0.186   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.812   0.858   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.151   2.809   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.675   4.257   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.191   4.528   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.183   3.351   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.707   4.799   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.699   3.622   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.222   5.071   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       7.738   5.342   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       8.731   4.164   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       9.403   5.550   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -0.365   2.538   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -0.888   1.089   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       0.105  -0.088   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      -0.418  -1.536   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       0.574  -2.714   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       2.090  -2.442   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      -1.934  -1.807   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      -2.457  -3.256   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      -2.927  -0.630   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      -4.443  -0.901   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      -2.404   0.818   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      -3.396   1.996   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      -2.873   3.444   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      -1.357   3.715   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      -0.834   5.164   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       0.682   5.435   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0       1.205   6.883   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0      -1.827   6.341   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0      -1.304   7.789   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0      -3.343   6.070   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0      -4.335   7.247   0.000  0.00  0.00           O+0
HETATM   62  C   UNK     0      -3.866   4.621   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0      -5.382   4.350   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   11   18                                                  
CONECT   18   17                                                            
CONECT   19    2   20   39                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24   39                                             
CONECT   23   22                                                            
CONECT   24   22   25   36                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   34                                                  
CONECT   28   27   29   30   31                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28   32   41                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   27   35   36                                             
CONECT   35   34   36                                                       
CONECT   36   35   24   34   37                                             
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   19   22   40                                             
CONECT   40   39                                                            
CONECT   41   31   42                                                       
CONECT   42   41   43   51                                                  
CONECT   43   42   44                                                       
CONECT   44   43   45   47                                                  
CONECT   45   44   46                                                       
CONECT   46   45                                                            
CONECT   47   44   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49   42   52                                                  
CONECT   52   51   53                                                       
CONECT   53   52   54   62                                                  
CONECT   54   53   55                                                       
CONECT   55   54   56   58                                                  
CONECT   56   55   57                                                       
CONECT   57   56                                                            
CONECT   58   55   59   60                                                  
CONECT   59   58                                                            
CONECT   60   58   61   62                                                  
CONECT   61   60                                                            
CONECT   62   60   53   63                                                  
CONECT   63   62                                                            
MASTER        0    0    0    0    0    0    0    0   63    0  140    0
END

View in JSmol

Synonyms

Value	Source
6-(6-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-7,7,12,16-tetramethylpentacyclo[9.7.0.0,.0,.0,]octadecan-15-yl)-N-(4,5-dimethyl-2-oxooxolan-3-yl)-2-methylhepta-2,4-dienimidate	Generator
6-(6-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl)-N-(4,5-dimethyl-2-oxooxolan-3-yl)-2-methylhepta-2,4-dienimidate	Generator

Chemical Formula

C₄₈H₇₅NO₁₄

Average Mass

890.1210 Da

Monoisotopic Mass

889.51876 Da

IUPAC Name

6-(6-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl)-N-(4,5-dimethyl-2-oxooxolan-3-yl)-2-methylhepta-2,4-dienamide

Traditional Name

6-(6-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl)-N-(4,5-dimethyl-2-oxooxolan-3-yl)-2-methylhepta-2,4-dienamide

CAS Registry Number

Not Available

SMILES

CC(C=CC=C(C)C(=O)NC1C(C)C(C)OC1=O)C1CCC2(C)C3CCC4C5(CC35CCC12C)CCC(OC1OC(CO)C(O)C(O)C1OC1OC(CO)C(O)C(O)C1O)C4(C)C

InChI Identifier

InChI=1S/C48H75NO14/c1-23(10-9-11-24(2)40(57)49-33-25(3)26(4)59-41(33)58)27-14-16-46(8)31-13-12-30-44(5,6)32(15-17-47(30)22-48(31,47)19-18-45(27,46)7)62-43-39(37(55)35(53)29(21-51)61-43)63-42-38(56)36(54)34(52)28(20-50)60-42/h9-11,23,25-39,42-43,50-56H,12-22H2,1-8H3,(H,49,57)

InChI Key

SMLUUCVJPGLTPV-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Mussaenda pubescens	LOTUS Database	35616633

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
9b,19-cyclo-lanostane-skeleton
Triterpenoid
Cycloartane-skeleton
Steroid lactone
Alpha-amino acid ester
N-acyl-alpha amino acid or derivatives
Disaccharide
Glycosyl compound
O-glycosyl compound
Alpha-amino acid or derivatives
Gamma butyrolactone
N-acyl-amine
Oxane
Tetrahydrofuran
Carboxamide group
Carboxylic acid ester
Secondary carboxylic acid amide
Secondary alcohol
Lactone
Oxacycle
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Organoheterocyclic compound
Organonitrogen compound
Organopnictogen compound
Organic nitrogen compound
Alcohol
Organic oxygen compound
Organic oxide
Carbonyl group
Primary alcohol
Hydrocarbon derivative
Organooxygen compound
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	3.56	ALOGPS
logP	2.87	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	12.02	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	233.93 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	228.74 m³·mol⁻¹	ChemAxon
Polarizability	97.76 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

85184951

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-(6-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl)-n-(4,5-dimethyl-2-oxooxolan-3-yl)-2-methylhepta-2,4-dienimidic acid (NP0143258)

MOL for NP0143258 (6-(6-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl)-n-(4,5-dimethyl-2-oxooxolan-3-yl)-2-methylhepta-2,4-dienimidic acid)

3D MOL for NP0143258 (6-(6-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl)-n-(4,5-dimethyl-2-oxooxolan-3-yl)-2-methylhepta-2,4-dienimidic acid)

3D SDF for NP0143258 (6-(6-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl)-n-(4,5-dimethyl-2-oxooxolan-3-yl)-2-methylhepta-2,4-dienimidic acid)

3D-SDF for NP0143258 (6-(6-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl)-n-(4,5-dimethyl-2-oxooxolan-3-yl)-2-methylhepta-2,4-dienimidic acid)

PDB for NP0143258 (6-(6-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl)-n-(4,5-dimethyl-2-oxooxolan-3-yl)-2-methylhepta-2,4-dienimidic acid)

3D PDB for NP0143258 (6-(6-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl)-n-(4,5-dimethyl-2-oxooxolan-3-yl)-2-methylhepta-2,4-dienimidic acid)

SMILES for NP0143258 (6-(6-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl)-n-(4,5-dimethyl-2-oxooxolan-3-yl)-2-methylhepta-2,4-dienimidic acid)

INCHI for NP0143258 (6-(6-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl)-n-(4,5-dimethyl-2-oxooxolan-3-yl)-2-methylhepta-2,4-dienimidic acid)

Structure for NP0143258 (6-(6-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl)-n-(4,5-dimethyl-2-oxooxolan-3-yl)-2-methylhepta-2,4-dienimidic acid)

3D Structure for NP0143258 (6-(6-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-15-yl)-n-(4,5-dimethyl-2-oxooxolan-3-yl)-2-methylhepta-2,4-dienimidic acid)