NP-MRD: Showing NP-Card for 16-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-8-hydroxy-6-(3-hydroxy-2-methylprop-1-en-1-yl)-2,8,10,13,18,18-hexamethyl-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-15,19-diene-12,17-dione (NP0263543)

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Record Information

Version

2.0

Created at

2022-09-08 06:45:30 UTC

Updated at

2022-09-08 06:45:31 UTC

NP-MRD ID

NP0263543

Secondary Accession Numbers

None

Natural Product Identification

Common Name

16-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-8-hydroxy-6-(3-hydroxy-2-methylprop-1-en-1-yl)-2,8,10,13,18,18-hexamethyl-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-15,19-diene-12,17-dione

Description

16-{[4,5-Dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-8-hydroxy-6-(3-hydroxy-2-methylprop-1-en-1-yl)-2,8,10,13,18,18-hexamethyl-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]Henicosa-15,19-diene-12,17-dione 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. 16-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-8-hydroxy-6-(3-hydroxy-2-methylprop-1-en-1-yl)-2,8,10,13,18,18-hexamethyl-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-15,19-diene-12,17-dione is found in Citrullus colocynthis. 16-{[4,5-Dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-8-hydroxy-6-(3-hydroxy-2-methylprop-1-en-1-yl)-2,8,10,13,18,18-hexamethyl-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]Henicosa-15,19-diene-12,17-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251505462D          

 57 63  0  0  0  0            999 V2000
    4.6540   -4.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1696   -5.3964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3491   -5.3108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8646   -5.9786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0441   -5.8930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7080   -5.1396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8874   -5.0540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4030   -5.7218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5513   -4.3006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2693   -4.2150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0357   -3.6328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6995   -2.8794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1839   -2.2116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8562   -3.7184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1924   -4.4718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0129   -4.5574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4973   -3.8896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3179   -3.9752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9505   -1.8862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7711   -1.9718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1072   -2.7252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9278   -2.8108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6722   -2.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.0481   -4.5373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.2639   -3.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7795   -4.2320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4746   -4.8142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1384   -4.0608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4376   -2.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0511   -3.2623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8802   -4.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8355   -3.0067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4491   -3.5583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6456   -2.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8724   -1.6752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9038   -2.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1612   -3.1362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3406   -3.0506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7164   -7.3999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3263   -6.2355    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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  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
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 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  1  0  0  0  0
 24 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
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
 27 34  1  0  0  0  0
 34 35  1  0  0  0  0
 24 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 19 40  1  0  0  0  0
 23 40  1  0  0  0  0
 40 41  1  0  0  0  0
 42 29  1  4  0  0  0
 42 43  2  0  0  0  0
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 17 50  1  0  0  0  0
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 54 56  1  0  0  0  0
  2 56  1  0  0  0  0
 56 57  1  0  0  0  0
M  END

     RDKit          3D

119125  0  0  0  0  0  0  0  0999 V2000
   10.5571    0.9149   -2.6858 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2564    1.6588   -1.3445 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9897    1.8222    0.1630 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4547    3.1586    0.4890 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2439   -0.4751   -0.4108 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7183   -1.5904    0.4545 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1448   -2.6525    2.2033 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8939   -2.3646    3.0130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1077   -1.7949    2.3267 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1371   -1.5340    0.8878 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9861   -0.8750    0.2025 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


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M  END
> <DATABASE_ID>
NP0263543

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(OC2C(O)C(O)C(CO)OC2OC2=CC3C(=CCC4C5(C)CC6OC(CC(C)(O)C6C5(C)CC(=O)C34C)C=C(C)CO)C(C)(C)C2=O)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C42H62O15/c1-18(16-43)11-20-13-41(7,52)34-24(54-20)14-39(5)26-10-9-21-22(42(26,8)27(45)15-40(34,39)6)12-23(35(51)38(21,3)4)55-37-33(31(49)29(47)25(17-44)56-37)57-36-32(50)30(48)28(46)19(2)53-36/h9,11-12,19-20,22,24-26,28-34,36-37,43-44,46-50,52H,10,13-17H2,1-8H3

> <INCHI_KEY>
BEQDSDZQSKPXIG-UHFFFAOYSA-N

> <FORMULA>
C42H62O15

> <MOLECULAR_WEIGHT>
806.943

> <EXACT_MASS>
806.408871296

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
119

> <JCHEM_AVERAGE_POLARIZABILITY>
85.86516607442333

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
16-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-8-hydroxy-6-(3-hydroxy-2-methylprop-1-en-1-yl)-2,8,10,13,18,18-hexamethyl-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-15,19-diene-12,17-dione

> <ALOGPS_LOGP>
1.53

> <JCHEM_LOGP>
0.01763837699999904

> <ALOGPS_LOGS>
-3.29

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.714354850946421

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.098389305730832

> <JCHEM_PKA_STRONGEST_BASIC>
-2.730962805656178

> <JCHEM_POLAR_SURFACE_AREA>
242.12999999999997

> <JCHEM_REFRACTIVITY>
204.01510000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.15e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-8-hydroxy-6-(3-hydroxy-2-methylprop-1-en-1-yl)-2,8,10,13,18,18-hexamethyl-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-15,19-diene-12,17-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       8.687  -8.827   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.783 -10.073   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.252  -9.914   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       5.347 -11.160   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.816 -11.000   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.188  -9.594   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.656  -9.434   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.752 -10.681   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.029  -8.028   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.503  -7.868   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.933  -6.781   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.306  -5.375   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.210  -4.128   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       3.465  -6.941   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.092  -8.347   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.624  -8.507   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.528  -7.261   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.060  -7.420   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.964  -6.174   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.337  -4.767   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.241  -3.521   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.773  -3.681   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.400  -5.087   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.932  -5.247   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.455  -3.783   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.075  -4.215   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.410  -4.984   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      16.874  -4.507   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      18.019  -5.537   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      17.700  -7.044   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.236  -7.521   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      16.960  -8.880   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      15.023  -8.470   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      15.091  -6.491   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      13.559  -6.653   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      14.330  -7.986   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      12.655  -7.900   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      11.123  -7.740   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      10.219  -8.987   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      10.496  -6.334   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       9.592  -7.580   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      19.484  -5.060   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      20.629  -6.090   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      20.310  -7.596   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      22.093  -5.613   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      23.238  -6.642   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0       6.805  -4.608   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       7.228  -3.127   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       5.420  -3.934   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       5.901  -5.854   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       4.369  -5.694   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0       5.975 -12.567   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0       5.071 -13.813   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0       7.506 -12.726   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0       8.134 -14.133   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0       8.411 -11.480   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0       9.942 -11.640   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   56                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   52                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15                                                       
CONECT   15   14    6   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   50                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   40                                                  
CONECT   20   19   21   47                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   40                                                  
CONECT   24   23   25   26   35                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   34                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   42                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33   34                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   31   27   35                                                  
CONECT   35   34   24   36   37                                             
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   19   23   41                                             
CONECT   41   40                                                            
CONECT   42   29   43                                                       
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   46                                                       
CONECT   46   45                                                            
CONECT   47   20   48   49   50                                             
CONECT   48   47                                                            
CONECT   49   47                                                            
CONECT   50   47   17   51                                                  
CONECT   51   50                                                            
CONECT   52    4   53   54                                                  
CONECT   53   52                                                            
CONECT   54   52   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54    2   57                                                  
CONECT   57   56                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  126    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₂H₆₂O₁₅

Average Mass

806.9430 Da

Monoisotopic Mass

806.40887 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CC1OC(OC2C(O)C(O)C(CO)OC2OC2=CC3C(=CCC4C5(C)CC6OC(CC(C)(O)C6C5(C)CC(=O)C34C)C=C(C)CO)C(C)(C)C2=O)C(O)C(O)C1O

InChI Identifier

InChI=1S/C42H62O15/c1-18(16-43)11-20-13-41(7,52)34-24(54-20)14-39(5)26-10-9-21-22(42(26,8)27(45)15-40(34,39)6)12-23(35(51)38(21,3)4)55-37-33(31(49)29(47)25(17-44)56-37)57-36-32(50)30(48)28(46)19(2)53-36/h9,11-12,19-20,22,24-26,28-34,36-37,43-44,46-50,52H,10,13-17H2,1-8H3

InChI Key

BEQDSDZQSKPXIG-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
Citrullus colocynthis	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
Diterpene glycoside
20-hydroxysteroid
Diterpenoid
3-oxo-delta-1-steroid
3-oxosteroid
Hydroxysteroid
11-oxosteroid
Oxosteroid
Delta-1-steroid
Terpene glycoside
Disaccharide
O-glycosyl compound
Glycosyl compound
Cyclohexenone
Oxane
Tertiary alcohol
Cyclic ketone
Secondary alcohol
Ketone
Ether
Organoheterocyclic compound
Dialkyl ether
Oxacycle
Polyol
Acetal
Primary alcohol
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Aldehyde
Alcohol
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	1.53	ALOGPS
logP	0.018	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	12.1	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	242.13 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	204.02 m³·mol⁻¹	ChemAxon
Polarizability	85.87 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

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

73000896

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 16-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-8-hydroxy-6-(3-hydroxy-2-methylprop-1-en-1-yl)-2,8,10,13,18,18-hexamethyl-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-15,19-diene-12,17-dione (NP0263543)

MOL for NP0263543 (16-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-8-hydroxy-6-(3-hydroxy-2-methylprop-1-en-1-yl)-2,8,10,13,18,18-hexamethyl-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-15,19-diene-12,17-dione)

3D MOL for NP0263543 (16-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-8-hydroxy-6-(3-hydroxy-2-methylprop-1-en-1-yl)-2,8,10,13,18,18-hexamethyl-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-15,19-diene-12,17-dione)

3D SDF for NP0263543 (16-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-8-hydroxy-6-(3-hydroxy-2-methylprop-1-en-1-yl)-2,8,10,13,18,18-hexamethyl-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-15,19-diene-12,17-dione)

3D-SDF for NP0263543 (16-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-8-hydroxy-6-(3-hydroxy-2-methylprop-1-en-1-yl)-2,8,10,13,18,18-hexamethyl-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-15,19-diene-12,17-dione)

PDB for NP0263543 (16-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-8-hydroxy-6-(3-hydroxy-2-methylprop-1-en-1-yl)-2,8,10,13,18,18-hexamethyl-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-15,19-diene-12,17-dione)

3D PDB for NP0263543 (16-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-8-hydroxy-6-(3-hydroxy-2-methylprop-1-en-1-yl)-2,8,10,13,18,18-hexamethyl-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-15,19-diene-12,17-dione)

SMILES for NP0263543 (16-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-8-hydroxy-6-(3-hydroxy-2-methylprop-1-en-1-yl)-2,8,10,13,18,18-hexamethyl-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-15,19-diene-12,17-dione)

INCHI for NP0263543 (16-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-8-hydroxy-6-(3-hydroxy-2-methylprop-1-en-1-yl)-2,8,10,13,18,18-hexamethyl-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-15,19-diene-12,17-dione)

Structure for NP0263543 (16-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-8-hydroxy-6-(3-hydroxy-2-methylprop-1-en-1-yl)-2,8,10,13,18,18-hexamethyl-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-15,19-diene-12,17-dione)

3D Structure for NP0263543 (16-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-8-hydroxy-6-(3-hydroxy-2-methylprop-1-en-1-yl)-2,8,10,13,18,18-hexamethyl-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-15,19-diene-12,17-dione)