NP-MRD: Showing NP-Card for ineupatolide A (NP0041706)

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Record Information

Version

2.0

Created at

2021-06-20 23:33:35 UTC

Updated at

2021-06-30 00:16:22 UTC

NP-MRD ID

NP0041706

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ineupatolide A

Provided By

JEOL Database JEOL Logo

Description

ineupatolide A is found in Inula cappa. ineupatolide A was first documented in 2012 (Wang,, F.-Y., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212101333D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306212101333D          

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M  END
> <DATABASE_ID>
NP0041706

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]12O[C@@]([H])(C([H])([H])[C@]1([H])C([H])([H])[H])C([H])([H])[C@](O[H])(C([H])([H])[H])[C@@]([H])(OC(=O)C(=C(\[H])C([H])([H])[H])\C([H])([H])[H])[C@]1([H])OC(=O)C(=C([H])[H])[C@@]1([H])[C@]2([H])OC(=O)C([H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H34O9/c1-8-12(4)21(26)32-19-17-16(14(6)22(27)30-17)18(31-20(25)11(2)3)24(29)13(5)9-15(33-24)10-23(19,7)28/h8,11,13,15-19,28-29H,6,9-10H2,1-5,7H3/b12-8-/t13-,15-,16+,17+,18-,19-,23+,24+/m0/s1

> <INCHI_KEY>
YOOURRKGHWQFKF-XFKAKOHKSA-N

> <FORMULA>
C24H34O9

> <MOLECULAR_WEIGHT>
466.527

> <EXACT_MASS>
466.220282675

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
48.17106569367013

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,3R,7R,8S,9R,11S,13S)-1,9-dihydroxy-9,13-dimethyl-4-methylidene-2-[(2-methylpropanoyl)oxy]-5-oxo-6,14-dioxatricyclo[9.2.1.0^{3,7}]tetradecan-8-yl (2Z)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
1.89

> <JCHEM_LOGP>
3.268797865333334

> <ALOGPS_LOGS>
-2.98

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.863119887329493

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.898601150932565

> <JCHEM_PKA_STRONGEST_BASIC>
-3.29638623308393

> <JCHEM_POLAR_SURFACE_AREA>
128.59

> <JCHEM_REFRACTIVITY>
115.8892

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.88e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3R,7R,8S,9R,11S,13S)-1,9-dihydroxy-9,13-dimethyl-4-methylidene-2-[(2-methylpropanoyl)oxy]-5-oxo-6,14-dioxatricyclo[9.2.1.0^{3,7}]tetradecan-8-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 67 69  0  0  0  0  0  0  0  0999 V2000
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 32 65  1  0
 32 66  1  0
 13 41  1  0
 12 38  1  0
 12 39  1  0
 12 40  1  0
 14 42  1  0
 14 43  1  0
 14 44  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       2.059   0.767   1.451  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.448   0.082   0.475  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.968  -1.231   0.051  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.012  -1.747   0.405  0.00  0.00           O+0
HETATM    5  O   UNK     0       1.059  -1.798  -0.774  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.011  -0.888  -1.090  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.396  -1.595  -0.982  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.261  -2.906  -0.361  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.113  -2.903   0.988  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.127  -1.916   1.705  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.912  -4.296   1.459  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.096  -5.108   0.702  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.559  -4.767   2.543  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.587  -4.062   3.372  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.092  -1.825  -2.372  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.541  -2.289  -2.159  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.412  -2.906  -3.042  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.055  -0.643  -3.374  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.548   0.721  -2.883  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.906   1.885  -3.631  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.776   2.936  -2.546  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.804   4.049  -2.890  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.468   2.090  -1.303  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.010   2.773  -0.176  0.00  0.00           O+0
HETATM   25  O   UNK     0      -2.236   0.901  -1.501  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.030   1.684  -1.048  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.661   2.788  -0.351  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.869   3.204  -0.834  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.424   2.727  -1.812  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.413   4.334   0.021  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.910   4.512  -0.213  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.658   5.624  -0.275  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.142   0.367  -0.197  0.00  0.00           C+0
HETATM   34  H   UNK     0       1.643   1.682   1.857  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.982   0.403   1.898  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.188  -0.610  -2.126  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.086  -1.016  -0.359  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.037  -4.556   0.602  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.324  -6.052   1.209  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.274  -5.351  -0.299  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.341  -5.782   2.872  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.169  -3.815   4.353  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.446  -4.724   3.525  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.966  -3.147   2.911  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.019  -2.527  -3.117  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.582  -3.208  -1.565  0.00  0.00           H+0
HETATM   47  H   UNK     0      -4.139  -1.523  -1.655  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.245  -3.591  -2.365  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.031  -0.552  -3.756  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.620  -0.911  -4.278  0.00  0.00           H+0
HETATM   51  H   UNK     0      -3.640   0.770  -2.967  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.917   1.619  -4.024  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.516   2.215  -4.478  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.763   3.401  -2.412  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.186   3.665  -3.150  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.701   4.747  -2.054  0.00  0.00           H+0
HETATM   57  H   UNK     0      -1.167   4.615  -3.754  0.00  0.00           H+0
HETATM   58  H   UNK     0      -1.460   2.560   0.595  0.00  0.00           H+0
HETATM   59  H   UNK     0       0.507   1.508  -2.019  0.00  0.00           H+0
HETATM   60  H   UNK     0       2.272   4.058   1.073  0.00  0.00           H+0
HETATM   61  H   UNK     0       4.449   3.579  -0.014  0.00  0.00           H+0
HETATM   62  H   UNK     0       4.122   4.803  -1.248  0.00  0.00           H+0
HETATM   63  H   UNK     0       4.318   5.285   0.447  0.00  0.00           H+0
HETATM   64  H   UNK     0       1.737   5.896  -1.333  0.00  0.00           H+0
HETATM   65  H   UNK     0       2.051   6.453   0.323  0.00  0.00           H+0
HETATM   66  H   UNK     0       0.594   5.518  -0.040  0.00  0.00           H+0
HETATM   67  H   UNK     0      -0.621   0.393   0.590  0.00  0.00           H+0
CONECT    1    2   34   35                                                  
CONECT    2   33    3    1                                                  
CONECT    3    2    5    4                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6   33    7    5   36                                             
CONECT    7    8   15    6   37                                             
CONECT    8    7    9                                                       
CONECT    9    8   11   10                                                  
CONECT   10    9                                                            
CONECT   11    9   13   12                                                  
CONECT   12   11   38   39   40                                             
CONECT   13   11   14   41                                                  
CONECT   14   13   42   43   44                                             
CONECT   15   17   16   18    7                                             
CONECT   16   15   45   46   47                                             
CONECT   17   15   48                                                       
CONECT   18   19   15   49   50                                             
CONECT   19   51   18   20   25                                             
CONECT   20   21   19   52   53                                             
CONECT   21   20   22   23   54                                             
CONECT   22   21   55   56   57                                             
CONECT   23   25   21   26   24                                             
CONECT   24   23   58                                                       
CONECT   25   23   19                                                       
CONECT   26   33   23   27   59                                             
CONECT   27   26   28                                                       
CONECT   28   27   30   29                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32   60                                             
CONECT   31   30   61   62   63                                             
CONECT   32   30   64   65   66                                             
CONECT   33    6   26    2   67                                             
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    6                                                            
CONECT   37    7                                                            
CONECT   38   12                                                            
CONECT   39   12                                                            
CONECT   40   12                                                            
CONECT   41   13                                                            
CONECT   42   14                                                            
CONECT   43   14                                                            
CONECT   44   14                                                            
CONECT   45   16                                                            
CONECT   46   16                                                            
CONECT   47   16                                                            
CONECT   48   17                                                            
CONECT   49   18                                                            
CONECT   50   18                                                            
CONECT   51   19                                                            
CONECT   52   20                                                            
CONECT   53   20                                                            
CONECT   54   21                                                            
CONECT   55   22                                                            
CONECT   56   22                                                            
CONECT   57   22                                                            
CONECT   58   24                                                            
CONECT   59   26                                                            
CONECT   60   30                                                            
CONECT   61   31                                                            
CONECT   62   31                                                            
CONECT   63   31                                                            
CONECT   64   32                                                            
CONECT   65   32                                                            
CONECT   66   32                                                            
CONECT   67   33                                                            
MASTER        0    0    0    0    0    0    0    0   67    0  138    0
END

RDKit          3D

67 69  0  0  0  0  0  0  0  0999 V2000
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 14 44  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₄O₉

Average Mass

466.5270 Da

Monoisotopic Mass

466.22028 Da

IUPAC Name

(1R,2S,3R,7R,8S,9R,11S,13S)-1,9-dihydroxy-9,13-dimethyl-4-methylidene-2-[(2-methylpropanoyl)oxy]-5-oxo-6,14-dioxatricyclo[9.2.1.0^{3,7}]tetradecan-8-yl (2Z)-2-methylbut-2-enoate

Traditional Name

(1R,2S,3R,7R,8S,9R,11S,13S)-1,9-dihydroxy-9,13-dimethyl-4-methylidene-2-[(2-methylpropanoyl)oxy]-5-oxo-6,14-dioxatricyclo[9.2.1.0^{3,7}]tetradecan-8-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

[H]O[C@@]12O[C@@]([H])(C([H])([H])[C@]1([H])C([H])([H])[H])C([H])([H])[C@](O[H])(C([H])([H])[H])[C@@]([H])(OC(=O)C(=C(\[H])C([H])([H])[H])\C([H])([H])[H])[C@]1([H])OC(=O)C(=C([H])[H])[C@@]1([H])[C@]2([H])OC(=O)C([H])(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C24H34O9/c1-8-12(4)21(26)32-19-17-16(14(6)22(27)30-17)18(31-20(25)11(2)3)24(29)13(5)9-15(33-24)10-23(19,7)28/h8,11,13,15-19,28-29H,6,9-10H2,1-5,7H3/b12-8-/t13-,15-,16+,17+,18-,19-,23+,24+/m0/s1

InChI Key

YOOURRKGHWQFKF-XFKAKOHKSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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, 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
Duhaldea cappa	JEOL database	Wang,, F.-Y., et al, Phytochem. Lett. 5, 639 (2012)

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	1.89	ALOGPS
logP	3.27	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	10.9	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	128.59 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	115.89 m³·mol⁻¹	ChemAxon
Polarizability	48.17 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

Wang,, F.-Y., et al. (2012). Wang,, F.-Y., et al, Phytochem. Lett. 5, 639 (2012). Phytochem..

Showing NP-Card for ineupatolide A (NP0041706)

MOL for NP0041706 (ineupatolide A)

3D MOL for NP0041706 (ineupatolide A)

3D SDF for NP0041706 (ineupatolide A)

3D-SDF for NP0041706 (ineupatolide A)

PDB for NP0041706 (ineupatolide A)

3D PDB for NP0041706 (ineupatolide A)

SMILES for NP0041706 (ineupatolide A)

INCHI for NP0041706 (ineupatolide A)

Structure for NP0041706 (ineupatolide A)

3D Structure for NP0041706 (ineupatolide A)