NP-MRD: Showing NP-Card for 6,7-dihydroxy-4,8,18-trimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl benzoate (NP0186515)

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Record Information

Version

2.0

Created at

2022-09-04 02:23:53 UTC

Updated at

2022-09-04 02:23:54 UTC

NP-MRD ID

NP0186515

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6,7-dihydroxy-4,8,18-trimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl benzoate

Description

6,7-Dihydroxy-4,8,18-trimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]Nonadec-3-en-17-yl benzoate belongs to the class of organic compounds known as rhamnofolane and daphnane diterpenoids. These are diterpenoids with a structure based on one the rhamnofolane or daphnane skeleton. The rhamnofolane and daphnane skeletons are closely related, being formally derived from casbane by two cyclizations (6,10 and 5,14) followed by cleavage of the 1,15 (daphnane) or 2,15 (rhamnofolane) cyclopropane bonds. 6,7-dihydroxy-4,8,18-trimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl benzoate is found in Trigonostemon xyphophylloides. 6,7-Dihydroxy-4,8,18-trimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]Nonadec-3-en-17-yl benzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241506422D          

 43 50  0  0  0  0            999 V2000
    2.7814    0.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1275   -0.2488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5680   -1.4934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7194   -2.0528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3363   -1.9079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2061   -2.9309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0111   -3.1112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2574   -3.8986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6987   -4.5056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8937   -4.3252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6474   -3.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9523   -0.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0907   -0.0532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5286    1.3666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3149    1.0148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0620    0.9752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8776    0.8506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7026    0.8490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2887    0.1353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2266   -0.1024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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  5  6  2  0  0  0  0
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 27 33  1  0  0  0  0
  2 33  1  0  0  0  0
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 15 34  1  0  0  0  0
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 35 40  1  0  0  0  0
 13 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
M  END

     RDKit          3D

 77 84  0  0  0  0  0  0  0  0999 V2000
    1.4260    3.4026    1.7975 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9672    2.5936    0.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1 44  1  0
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M  END


  Mrv1533004241506422D          

 43 50  0  0  0  0            999 V2000
    2.7814    0.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5286    1.3666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3149    1.0148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0620    0.9752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8776    0.8506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7026    0.8490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2887    0.1353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2266   -0.1024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9858   -0.6321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8281   -0.9690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1970   -0.8737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9978   -1.3627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5162   -0.4076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8626   -0.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2404   -1.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6946   -2.5882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9641   -1.6651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3135   -2.5131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4562    0.4152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6113    0.3120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4425    1.4658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2674    1.4506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6930    2.1574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2937    2.8793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4689    2.8945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0433    2.1878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2986   -0.9543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5955   -1.2891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1696   -1.7723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
  3 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
 16 17  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 25 31  1  0  0  0  0
 31 32  2  0  0  0  0
 27 33  1  0  0  0  0
  2 33  1  0  0  0  0
 18 33  1  0  0  0  0
 33 34  1  0  0  0  0
 15 34  1  0  0  0  0
 15 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 35 40  1  0  0  0  0
 13 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0186515

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C(OC(=O)C2=CC=CC=C2)C2(OC3(OC2C2C4OC4(C)C(O)C4(O)C(C=C(C)C4=O)C12O3)C1=CC=CC=C1)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C34H34O9/c1-17(2)32-25(39-28(36)20-12-8-6-9-13-20)19(4)33-22-16-18(3)24(35)31(22,38)29(37)30(5)26(40-30)23(33)27(32)41-34(42-32,43-33)21-14-10-7-11-15-21/h6-16,19,22-23,25-27,29,37-38H,1H2,2-5H3

> <INCHI_KEY>
XVFFINDRMYVYJL-UHFFFAOYSA-N

> <FORMULA>
C34H34O9

> <MOLECULAR_WEIGHT>
586.637

> <EXACT_MASS>
586.220282675

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
60.33101472959771

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6,7-dihydroxy-4,8,18-trimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl benzoate

> <ALOGPS_LOGP>
3.34

> <JCHEM_LOGP>
4.844274171666666

> <ALOGPS_LOGS>
-4.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.458803760628939

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.660899371092832

> <JCHEM_PKA_STRONGEST_BASIC>
-3.828468305754636

> <JCHEM_POLAR_SURFACE_AREA>
124.05000000000003

> <JCHEM_REFRACTIVITY>
152.09889999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.20e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,7-dihydroxy-4,8,18-trimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       5.192   0.451   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.971  -0.464   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.604  -1.449   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.927  -2.788   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.343  -3.832   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.628  -3.561   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.251  -5.471   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.754  -5.808   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.214  -7.277   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.171  -8.410   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.668  -8.074   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.208  -6.604   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.778  -0.054   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.169  -0.099   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.032   1.417   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.987   2.551   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.454   1.894   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.849   1.820   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.371   1.588   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.911   1.585   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.139   0.253   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.890  -0.191   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.573  -1.180   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.146  -1.809   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.101  -1.631   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.596  -2.544   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.830  -0.761   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.610  -1.701   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.315  -3.260   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.297  -4.831   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.666  -3.108   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.319  -4.691   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.718   0.775   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.141   0.582   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -0.826   2.736   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.366   2.708   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -3.160   4.027   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -2.415   5.375   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -0.875   5.403   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -0.081   4.084   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       0.557  -1.781   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -1.112  -2.406   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       0.317  -3.308   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13    3   14   17   41                                             
CONECT   14   13   15                                                       
CONECT   15   14   16   34   35                                             
CONECT   16   15   17                                                       
CONECT   17   16   13   18                                                  
CONECT   18   17   19   33                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19   21                                                       
CONECT   21   20   19   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27   31                                             
CONECT   26   25                                                            
CONECT   27   25   28   33                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   25   32                                                  
CONECT   32   31                                                            
CONECT   33   27    2   18   34                                             
CONECT   34   33   15                                                       
CONECT   35   15   36   40                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   35                                                       
CONECT   41   13   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41                                                            
MASTER        0    0    0    0    0    0    0    0   43    0  100    0
END

View in JSmol

Synonyms

Value	Source
6,7-Dihydroxy-4,8,18-trimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0,.0,.0,.0,]nonadec-3-en-17-yl benzoic acid	Generator
6,7-Dihydroxy-4,8,18-trimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl benzoic acid	Generator

Chemical Formula

C₃₄H₃₄O₉

Average Mass

586.6370 Da

Monoisotopic Mass

586.22028 Da

IUPAC Name

6,7-dihydroxy-4,8,18-trimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl benzoate

Traditional Name

6,7-dihydroxy-4,8,18-trimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl benzoate

CAS Registry Number

Not Available

SMILES

CC1C(OC(=O)C2=CC=CC=C2)C2(OC3(OC2C2C4OC4(C)C(O)C4(O)C(C=C(C)C4=O)C12O3)C1=CC=CC=C1)C(C)=C

InChI Identifier

InChI=1S/C34H34O9/c1-17(2)32-25(39-28(36)20-12-8-6-9-13-20)19(4)33-22-16-18(3)24(35)31(22,38)29(37)30(5)26(40-30)23(33)27(32)41-34(42-32,43-33)21-14-10-7-11-15-21/h6-16,19,22-23,25-27,29,37-38H,1H2,2-5H3

InChI Key

XVFFINDRMYVYJL-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
Trigonostemon xyphophylloides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as rhamnofolane and daphnane diterpenoids. These are diterpenoids with a structure based on one the rhamnofolane or daphnane skeleton. The rhamnofolane and daphnane skeletons are closely related, being formally derived from casbane by two cyclizations (6,10 and 5,14) followed by cleavage of the 1,15 (daphnane) or 2,15 (rhamnofolane) cyclopropane bonds.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Rhamnofolane and daphnane diterpenoids

Alternative Parents

Substituents

Daphnane diterpenoid
Benzoate ester
Benzoic acid or derivatives
Benzoyl
1,3-dioxepane
Carboxylic acid orthoester
Dioxepane
Ortho ester
Benzenoid
Monocyclic benzene moiety
Meta-dioxane
Meta-dioxolane
Tertiary alcohol
Cyclic alcohol
Orthocarboxylic acid derivative
Secondary alcohol
Carboxylic acid ester
Ketone
1,2-diol
Organoheterocyclic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Oxacycle
Oxirane
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	3.34	ALOGPS
logP	4.84	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	11.66	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	124.05 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	152.1 m³·mol⁻¹	ChemAxon
Polarizability	60.33 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

46912659

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6,7-dihydroxy-4,8,18-trimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl benzoate (NP0186515)

MOL for NP0186515 (6,7-dihydroxy-4,8,18-trimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl benzoate)

3D MOL for NP0186515 (6,7-dihydroxy-4,8,18-trimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl benzoate)

3D SDF for NP0186515 (6,7-dihydroxy-4,8,18-trimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl benzoate)

3D-SDF for NP0186515 (6,7-dihydroxy-4,8,18-trimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl benzoate)

PDB for NP0186515 (6,7-dihydroxy-4,8,18-trimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl benzoate)

3D PDB for NP0186515 (6,7-dihydroxy-4,8,18-trimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl benzoate)

SMILES for NP0186515 (6,7-dihydroxy-4,8,18-trimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl benzoate)

INCHI for NP0186515 (6,7-dihydroxy-4,8,18-trimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl benzoate)

Structure for NP0186515 (6,7-dihydroxy-4,8,18-trimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl benzoate)

3D Structure for NP0186515 (6,7-dihydroxy-4,8,18-trimethyl-5-oxo-14-phenyl-16-(prop-1-en-2-yl)-9,13,15,19-tetraoxahexacyclo[12.4.1.0¹,¹¹.0²,⁶.0⁸,¹⁰.0¹²,¹⁶]nonadec-3-en-17-yl benzoate)