NP-MRD: Showing NP-Card for 2alpha,8-diangeloyloxy-3alpha,4alpha,10,11-diepoxy-1alpha-hydroxybisabol-+ (NP0032119)

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Record Information

Version

2.0

Created at

2021-06-19 23:00:23 UTC

Updated at

2021-06-30 00:01:07 UTC

NP-MRD ID

NP0032119

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2alpha,8-diangeloyloxy-3alpha,4alpha,10,11-diepoxy-1alpha-hydroxybisabol-+

Provided By

JEOL Database JEOL Logo

Description

2alpha,8-diangeloyloxy-3alpha,4alpha,10,11-diepoxy-1alpha-hydroxybisabol-+ is found in Ligularia cymbulifera. 2alpha,8-diangeloyloxy-3alpha,4alpha,10,11-diepoxy-1alpha-hydroxybisabol-+ was first documented in 2006 (Liu, C. -M., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202101003D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306202101003D          

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M  END
> <DATABASE_ID>
NP0032119

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])[C@]([H])(OC(=O)C(=C(\[H])C([H])([H])[H])\C([H])([H])[H])[C@]2(O[C@@]2([H])C([H])([H])[C@]1([H])C(=C([H])[H])[C@@]([H])(OC(=O)C(=C(\[H])C([H])([H])[H])\C([H])([H])[H])C([H])([H])[C@@]1([H])OC1(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H36O7/c1-9-13(3)22(27)29-17(12-18-24(6,7)31-18)15(5)16-11-19-25(8,32-19)21(20(16)26)30-23(28)14(4)10-2/h9-10,16-21,26H,5,11-12H2,1-4,6-8H3/b13-9-,14-10-/t16-,17+,18-,19+,20-,21+,25+/m1/s1

> <INCHI_KEY>
SOLKVQDUFSZHNA-OQPCPOJHSA-N

> <FORMULA>
C25H36O7

> <MOLECULAR_WEIGHT>
448.556

> <EXACT_MASS>
448.246103499

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
48.17501347598984

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-1-[(2R)-3,3-dimethyloxiran-2-yl]-3-[(1S,3R,4R,5S,6S)-4-hydroxy-6-methyl-5-{[(2Z)-2-methylbut-2-enoyl]oxy}-7-oxabicyclo[4.1.0]heptan-3-yl]but-3-en-2-yl (2Z)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
4.86

> <JCHEM_LOGP>
4.050426092333334

> <ALOGPS_LOGS>
-4.51

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.758124116058955

> <JCHEM_PKA_STRONGEST_BASIC>
-3.341996511635812

> <JCHEM_POLAR_SURFACE_AREA>
97.89

> <JCHEM_REFRACTIVITY>
119.65839999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.40e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-1-[(2R)-3,3-dimethyloxiran-2-yl]-3-[(1S,3R,4R,5S,6S)-4-hydroxy-6-methyl-5-{[(2Z)-2-methylbut-2-enoyl]oxy}-7-oxabicyclo[4.1.0]heptan-3-yl]but-3-en-2-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

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 29 63  1  0
 21 22  1  6
 25 26  2  0
 21 19  1  0
 13 14  1  0
  2  1  2  3
 15 16  1  0
 19 18  1  0
 27 28  1  0
  5  7  1  0
 29 30  1  0
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 19 55  1  6
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  3 35  1  1
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 28 61  1  0
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 30 64  1  0
 30 65  1  0
 30 66  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.652  -1.768  -0.854  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.700  -0.966  -0.334  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.644  -0.558   1.141  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.628  -1.293   2.077  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.337  -1.020   3.525  0.00  0.00           C+0
HETATM    6  O   UNK     0      -3.600  -2.124   4.404  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.230  -1.704   4.311  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.325  -2.720   3.687  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.715  -1.030   5.546  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.949   0.853   1.180  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.165   1.635   1.958  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.204   1.273   2.619  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.554   3.064   1.812  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.385   4.000   1.717  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.828   3.503   1.776  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.083   2.707   1.940  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.583  -0.453  -1.272  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.948   0.930  -1.833  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.933   1.447  -2.793  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.368   0.471  -3.670  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.515   1.041  -2.678  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.570   1.907  -3.303  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.960   0.044  -1.625  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.997   0.696  -0.840  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.817  -0.100  -0.118  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.758  -1.318  -0.060  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.866   0.707   0.551  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.255   0.171   0.374  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.600   1.811   1.277  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.259   2.390   1.606  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.163  -0.432  -0.655  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.116  -1.766  -0.189  0.00  0.00           O+0
HETATM   33  H   UNK     0      -4.468  -2.175  -0.268  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.644  -2.044  -1.905  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.634  -0.757   1.512  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.595  -2.373   1.894  0.00  0.00           H+0
HETATM   37  H   UNK     0      -4.654  -0.959   1.879  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.670  -0.040   3.841  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.822  -3.311   2.913  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.459  -2.225   3.233  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.957  -3.420   4.444  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.452  -0.342   5.974  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.464  -1.771   6.312  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.813  -0.455   5.314  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.792   3.973   2.637  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.699   5.036   1.555  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.739   3.717   0.879  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.999   4.571   1.644  0.00  0.00           H+0
HETATM   49  H   UNK     0      -5.561   2.551   0.968  0.00  0.00           H+0
HETATM   50  H   UNK     0      -4.919   1.739   2.419  0.00  0.00           H+0
HETATM   51  H   UNK     0      -5.782   3.259   2.577  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.535  -1.162  -2.112  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.920   0.885  -2.340  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.045   1.664  -1.028  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.189   2.415  -3.203  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.189   2.443  -4.178  0.00  0.00           H+0
HETATM   57  H   UNK     0       2.422   1.301  -3.628  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.926   2.654  -2.587  0.00  0.00           H+0
HETATM   59  H   UNK     0       1.409  -0.814  -2.143  0.00  0.00           H+0
HETATM   60  H   UNK     0       5.344  -0.824   0.822  0.00  0.00           H+0
HETATM   61  H   UNK     0       5.502   0.097  -0.690  0.00  0.00           H+0
HETATM   62  H   UNK     0       6.006   0.815   0.844  0.00  0.00           H+0
HETATM   63  H   UNK     0       4.436   2.347   1.724  0.00  0.00           H+0
HETATM   64  H   UNK     0       1.434   1.702   1.414  0.00  0.00           H+0
HETATM   65  H   UNK     0       2.096   3.308   1.034  0.00  0.00           H+0
HETATM   66  H   UNK     0       2.223   2.641   2.672  0.00  0.00           H+0
HETATM   67  H   UNK     0      -0.150   0.219   0.226  0.00  0.00           H+0
HETATM   68  H   UNK     0       1.075  -1.837   0.001  0.00  0.00           H+0
CONECT    1    2   33   34                                                  
CONECT    2   17    3    1                                                  
CONECT    3    4   10    2   35                                             
CONECT    4    5    3   36   37                                             
CONECT    5    6    4    7   38                                             
CONECT    6    5    7                                                       
CONECT    7    6    8    9    5                                             
CONECT    8    7   39   40   41                                             
CONECT    9    7   42   43   44                                             
CONECT   10    3   11                                                       
CONECT   11   10   13   12                                                  
CONECT   12   11                                                            
CONECT   13   11   15   14                                                  
CONECT   14   13   45   46   47                                             
CONECT   15   13   48   16                                                  
CONECT   16   15   49   50   51                                             
CONECT   17   31    2   18   52                                             
CONECT   18   17   19   53   54                                             
CONECT   19   20   21   18   55                                             
CONECT   20   21   19                                                       
CONECT   21   20   23   22   19                                             
CONECT   22   21   56   57   58                                             
CONECT   23   21   24   31   59                                             
CONECT   24   25   23                                                       
CONECT   25   24   27   26                                                  
CONECT   26   25                                                            
CONECT   27   25   29   28                                                  
CONECT   28   27   60   61   62                                             
CONECT   29   27   63   30                                                  
CONECT   30   29   64   65   66                                             
CONECT   31   17   32   23   67                                             
CONECT   32   31   68                                                       
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    3                                                            
CONECT   36    4                                                            
CONECT   37    4                                                            
CONECT   38    5                                                            
CONECT   39    8                                                            
CONECT   40    8                                                            
CONECT   41    8                                                            
CONECT   42    9                                                            
CONECT   43    9                                                            
CONECT   44    9                                                            
CONECT   45   14                                                            
CONECT   46   14                                                            
CONECT   47   14                                                            
CONECT   48   15                                                            
CONECT   49   16                                                            
CONECT   50   16                                                            
CONECT   51   16                                                            
CONECT   52   17                                                            
CONECT   53   18                                                            
CONECT   54   18                                                            
CONECT   55   19                                                            
CONECT   56   22                                                            
CONECT   57   22                                                            
CONECT   58   22                                                            
CONECT   59   23                                                            
CONECT   60   28                                                            
CONECT   61   28                                                            
CONECT   62   28                                                            
CONECT   63   29                                                            
CONECT   64   30                                                            
CONECT   65   30                                                            
CONECT   66   30                                                            
CONECT   67   31                                                            
CONECT   68   32                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  140    0
END

RDKit          3D

68 70  0  0  0  0  0  0  0  0999 V2000
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 30 66  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₆O₇

Average Mass

448.5560 Da

Monoisotopic Mass

448.24610 Da

IUPAC Name

(2S)-1-[(2R)-3,3-dimethyloxiran-2-yl]-3-[(1S,3R,4R,5S,6S)-4-hydroxy-6-methyl-5-{[(2Z)-2-methylbut-2-enoyl]oxy}-7-oxabicyclo[4.1.0]heptan-3-yl]but-3-en-2-yl (2Z)-2-methylbut-2-enoate

Traditional Name

(2S)-1-[(2R)-3,3-dimethyloxiran-2-yl]-3-[(1S,3R,4R,5S,6S)-4-hydroxy-6-methyl-5-{[(2Z)-2-methylbut-2-enoyl]oxy}-7-oxabicyclo[4.1.0]heptan-3-yl]but-3-en-2-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])[C@]([H])(OC(=O)C(=C(\[H])C([H])([H])[H])\C([H])([H])[H])[C@]2(O[C@@]2([H])C([H])([H])[C@]1([H])C(=C([H])[H])[C@@]([H])(OC(=O)C(=C(\[H])C([H])([H])[H])\C([H])([H])[H])C([H])([H])[C@@]1([H])OC1(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C25H36O7/c1-9-13(3)22(27)29-17(12-18-24(6,7)31-18)15(5)16-11-19-25(8,32-19)21(20(16)26)30-23(28)14(4)10-2/h9-10,16-21,26H,5,11-12H2,1-4,6-8H3/b13-9-,14-10-/t16-,17+,18-,19+,20-,21+,25+/m1/s1

InChI Key

SOLKVQDUFSZHNA-OQPCPOJHSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ligularia cymbulifera	JEOL database	Liu, C. -M., et al, J. Nat. Prod. 69, 695 (2006)

Chemical Taxonomy

Classification

Not classified

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	4.86	ALOGPS
logP	4.05	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	13.76	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	97.89 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	119.66 m³·mol⁻¹	ChemAxon
Polarizability	48.18 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

Not Available

References

General References

Liu, C. -M., et al. (2006). Liu, C. -M., et al, J. Nat. Prod. 69, 695 (2006) . J. Nat. Prod..

Showing NP-Card for 2alpha,8-diangeloyloxy-3alpha,4alpha,10,11-diepoxy-1alpha-hydroxybisabol-+ (NP0032119)

MOL for NP0032119 (2alpha,8-diangeloyloxy-3alpha,4alpha,10,11-diepoxy-1alpha-hydroxybisabol-+)

3D MOL for NP0032119 (2alpha,8-diangeloyloxy-3alpha,4alpha,10,11-diepoxy-1alpha-hydroxybisabol-+)

3D SDF for NP0032119 (2alpha,8-diangeloyloxy-3alpha,4alpha,10,11-diepoxy-1alpha-hydroxybisabol-+)

3D-SDF for NP0032119 (2alpha,8-diangeloyloxy-3alpha,4alpha,10,11-diepoxy-1alpha-hydroxybisabol-+)

PDB for NP0032119 (2alpha,8-diangeloyloxy-3alpha,4alpha,10,11-diepoxy-1alpha-hydroxybisabol-+)

3D PDB for NP0032119 (2alpha,8-diangeloyloxy-3alpha,4alpha,10,11-diepoxy-1alpha-hydroxybisabol-+)

SMILES for NP0032119 (2alpha,8-diangeloyloxy-3alpha,4alpha,10,11-diepoxy-1alpha-hydroxybisabol-+)

INCHI for NP0032119 (2alpha,8-diangeloyloxy-3alpha,4alpha,10,11-diepoxy-1alpha-hydroxybisabol-+)

Structure for NP0032119 (2alpha,8-diangeloyloxy-3alpha,4alpha,10,11-diepoxy-1alpha-hydroxybisabol-+)

3D Structure for NP0032119 (2alpha,8-diangeloyloxy-3alpha,4alpha,10,11-diepoxy-1alpha-hydroxybisabol-+)