NP-MRD: Showing NP-Card for 2-epihelmanticine (NP0030223)

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Record Information

Version

2.0

Created at

2021-06-19 21:38:04 UTC

Updated at

2021-06-29 23:58:04 UTC

NP-MRD ID

NP0030223

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-epihelmanticine

Provided By

JEOL Database JEOL Logo

Description

2-epihelmanticine is found in Ferula szowitsiana. 2-epihelmanticine was first documented in 2007 (Iranshahi, M. et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192123383D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306192123383D          

 70 71  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0030223

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@](C(=O)O[C@@]([H])(C([H])([H])[H])[C@@]([H])(OC(=O)C(=C(/[H])C([H])([H])[H])\C([H])([H])[H])C1=C([H])C(OC([H])([H])[H])=C2OC([H])([H])OC2=C1[H])(C([H])([H])[H])[C@]([H])(OC(=O)C(=C(/[H])C([H])([H])[H])\C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O10/c1-9-14(3)23(27)35-17(6)26(7,30)25(29)34-16(5)21(36-24(28)15(4)10-2)18-11-19(31-8)22-20(12-18)32-13-33-22/h9-12,16-17,21,30H,13H2,1-8H3/b14-9+,15-10+/t16-,17+,21+,26-/m0/s1

> <INCHI_KEY>
GWGKUNRASDCVQT-PSWWWTRISA-N

> <FORMULA>
C26H34O10

> <MOLECULAR_WEIGHT>
506.548

> <EXACT_MASS>
506.215197295

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
53.26564318295301

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S)-3-hydroxy-4-{[(1S,2S)-1-(7-methoxy-2H-1,3-benzodioxol-5-yl)-1-{[(2E)-2-methylbut-2-enoyl]oxy}propan-2-yl]oxy}-3-methyl-4-oxobutan-2-yl (2E)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
3.97

> <JCHEM_LOGP>
4.878645353333334

> <ALOGPS_LOGS>
-4.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.639514888404669

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2686761878117965

> <JCHEM_POLAR_SURFACE_AREA>
126.82000000000002

> <JCHEM_REFRACTIVITY>
129.16830000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.30e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S)-3-hydroxy-4-{[(1S,2S)-1-(7-methoxy-2H-1,3-benzodioxol-5-yl)-1-{[(2E)-2-methylbut-2-enoyl]oxy}propan-2-yl]oxy}-3-methyl-4-oxobutan-2-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 70 71  0  0  0  0  0  0  0  0999 V2000
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    4.3341    1.1914    4.8598 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5827    0.3510    3.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3147   -0.5744    4.7238 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0
 28 30  1  0
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 13 46  1  0
 13 47  1  0
 13 48  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -4.646  -3.576   6.109  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.728  -2.908   5.137  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.929  -2.691   3.821  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.133  -3.114   3.033  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.834  -1.981   3.087  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.729  -1.741   3.549  0.00  0.00           O+0
HETATM    7  O   UNK     0      -3.259  -1.632   1.849  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.294  -0.954   1.020  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.674  -1.192  -0.439  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.643  -1.329  -1.406  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.929  -1.528  -2.762  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.013  -1.664  -3.764  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.356  -1.713  -3.382  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.264  -1.584  -3.121  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.272  -1.459  -2.192  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.014  -1.265  -0.852  0.00  0.00           C+0
HETATM   17  O   UNK     0      -5.511  -1.545  -2.748  0.00  0.00           O+0
HETATM   18  C   UNK     0      -5.172  -1.743  -4.135  0.00  0.00           C+0
HETATM   19  O   UNK     0      -3.755  -1.765  -4.381  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.189   0.551   1.394  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.519   1.303   1.323  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.242   1.204   0.518  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.507   2.215   1.050  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.574   2.599   2.213  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.465   2.812   0.016  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.330   3.336  -1.181  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.135   3.948   0.592  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.509   1.742  -0.382  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.589   2.263  -1.330  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.209   1.305   0.812  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.996   0.027   1.216  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.282  -0.782   0.641  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.701  -0.271   2.501  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.172  -1.491   3.199  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.705   0.517   2.939  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.519   0.351   4.183  0.00  0.00           C+0
HETATM   37  H   UNK     0      -4.815  -2.914   6.965  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.187  -4.498   6.479  0.00  0.00           H+0
HETATM   39  H   UNK     0      -5.624  -3.825   5.692  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.797  -2.562   5.590  0.00  0.00           H+0
HETATM   41  H   UNK     0      -4.831  -3.683   2.147  0.00  0.00           H+0
HETATM   42  H   UNK     0      -5.812  -3.758   3.597  0.00  0.00           H+0
HETATM   43  H   UNK     0      -5.703  -2.238   2.707  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.313  -1.427   1.165  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.613  -1.272  -1.063  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.549  -2.549  -2.701  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.676  -0.762  -2.944  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.949  -1.878  -4.287  0.00  0.00           H+0
HETATM   49  H   UNK     0      -4.834  -1.169  -0.149  0.00  0.00           H+0
HETATM   50  H   UNK     0      -5.619  -0.933  -4.723  0.00  0.00           H+0
HETATM   51  H   UNK     0      -5.602  -2.695  -4.468  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.837   0.605   2.431  0.00  0.00           H+0
HETATM   53  H   UNK     0      -4.295   0.813   1.918  0.00  0.00           H+0
HETATM   54  H   UNK     0      -3.868   1.403   0.290  0.00  0.00           H+0
HETATM   55  H   UNK     0      -3.397   2.324   1.700  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.140   3.994  -0.846  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.297   3.936  -1.848  0.00  0.00           H+0
HETATM   58  H   UNK     0      -0.779   2.522  -1.760  0.00  0.00           H+0
HETATM   59  H   UNK     0       1.375   3.687   1.503  0.00  0.00           H+0
HETATM   60  H   UNK     0       1.008   0.903  -0.879  0.00  0.00           H+0
HETATM   61  H   UNK     0       3.143   3.096  -0.887  0.00  0.00           H+0
HETATM   62  H   UNK     0       2.168   2.586  -2.286  0.00  0.00           H+0
HETATM   63  H   UNK     0       3.324   1.475  -1.531  0.00  0.00           H+0
HETATM   64  H   UNK     0       2.430  -2.393   2.635  0.00  0.00           H+0
HETATM   65  H   UNK     0       2.558  -1.610   4.214  0.00  0.00           H+0
HETATM   66  H   UNK     0       1.082  -1.437   3.285  0.00  0.00           H+0
HETATM   67  H   UNK     0       4.004   1.381   2.346  0.00  0.00           H+0
HETATM   68  H   UNK     0       4.334   1.191   4.860  0.00  0.00           H+0
HETATM   69  H   UNK     0       5.583   0.351   3.925  0.00  0.00           H+0
HETATM   70  H   UNK     0       4.315  -0.574   4.724  0.00  0.00           H+0
CONECT    1    2   37   38   39                                             
CONECT    2    3    1   40                                                  
CONECT    3    5    2    4                                                  
CONECT    4    3   41   42   43                                             
CONECT    5    7    3    6                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    9    7   20   44                                             
CONECT    9    8   10   16                                                  
CONECT   10    9   11   45                                                  
CONECT   11   14   10   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   46   47   48                                             
CONECT   14   19   11   15                                                  
CONECT   15   14   16   17                                                  
CONECT   16    9   15   49                                                  
CONECT   17   18   15                                                       
CONECT   18   17   19   50   51                                             
CONECT   19   18   14                                                       
CONECT   20    8   22   21   52                                             
CONECT   21   20   53   54   55                                             
CONECT   22   20   23                                                       
CONECT   23   22   25   24                                                  
CONECT   24   23                                                            
CONECT   25   26   27   23   28                                             
CONECT   26   25   56   57   58                                             
CONECT   27   25   59                                                       
CONECT   28   30   29   25   60                                             
CONECT   29   28   61   62   63                                             
CONECT   30   28   31                                                       
CONECT   31   30   33   32                                                  
CONECT   32   31                                                            
CONECT   33   31   35   34                                                  
CONECT   34   33   64   65   66                                             
CONECT   35   33   36   67                                                  
CONECT   36   35   68   69   70                                             
CONECT   37    1                                                            
CONECT   38    1                                                            
CONECT   39    1                                                            
CONECT   40    2                                                            
CONECT   41    4                                                            
CONECT   42    4                                                            
CONECT   43    4                                                            
CONECT   44    8                                                            
CONECT   45   10                                                            
CONECT   46   13                                                            
CONECT   47   13                                                            
CONECT   48   13                                                            
CONECT   49   16                                                            
CONECT   50   18                                                            
CONECT   51   18                                                            
CONECT   52   20                                                            
CONECT   53   21                                                            
CONECT   54   21                                                            
CONECT   55   21                                                            
CONECT   56   26                                                            
CONECT   57   26                                                            
CONECT   58   26                                                            
CONECT   59   27                                                            
CONECT   60   28                                                            
CONECT   61   29                                                            
CONECT   62   29                                                            
CONECT   63   29                                                            
CONECT   64   34                                                            
CONECT   65   34                                                            
CONECT   66   34                                                            
CONECT   67   35                                                            
CONECT   68   36                                                            
CONECT   69   36                                                            
CONECT   70   36                                                            
MASTER        0    0    0    0    0    0    0    0   70    0  142    0
END

RDKit          3D

70 71  0  0  0  0  0  0  0  0999 V2000
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  4 41  1  0
  4 42  1  0
  4 43  1  0
 26 56  1  0
 26 57  1  0
 26 58  1  0
 29 61  1  0
 29 62  1  0
 29 63  1  0
 27 59  1  0
 34 64  1  0
 34 65  1  0
 34 66  1  0
 13 46  1  0
 13 47  1  0
 13 48  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₄O₁₀

Average Mass

506.5480 Da

Monoisotopic Mass

506.21520 Da

IUPAC Name

(2R,3S)-3-hydroxy-4-{[(1S,2S)-1-(7-methoxy-2H-1,3-benzodioxol-5-yl)-1-{[(2E)-2-methylbut-2-enoyl]oxy}propan-2-yl]oxy}-3-methyl-4-oxobutan-2-yl (2E)-2-methylbut-2-enoate

Traditional Name

(2R,3S)-3-hydroxy-4-{[(1S,2S)-1-(7-methoxy-2H-1,3-benzodioxol-5-yl)-1-{[(2E)-2-methylbut-2-enoyl]oxy}propan-2-yl]oxy}-3-methyl-4-oxobutan-2-yl (2E)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

[H]O[C@@](C(=O)O[C@@]([H])(C([H])([H])[H])[C@@]([H])(OC(=O)C(=C(/[H])C([H])([H])[H])\C([H])([H])[H])C1=C([H])C(OC([H])([H])[H])=C2OC([H])([H])OC2=C1[H])(C([H])([H])[H])[C@]([H])(OC(=O)C(=C(/[H])C([H])([H])[H])\C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C26H34O10/c1-9-14(3)23(27)35-17(6)26(7,30)25(29)34-16(5)21(36-24(28)15(4)10-2)18-11-19(31-8)22-20(12-18)32-13-33-22/h9-12,16-17,21,30H,13H2,1-8H3/b14-9+,15-10+/t16-,17+,21+,26-/m0/s1

InChI Key

GWGKUNRASDCVQT-PSWWWTRISA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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
Ferula szowitziana	JEOL database	Iranshahi, M. et al, Phytochemistry 68, 554 (2007)

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	3.97	ALOGPS
logP	4.88	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	11.64	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	126.82 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	129.17 m³·mol⁻¹	ChemAxon
Polarizability	53.27 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

Not Available

References

General References

Iranshahi, M. et al. (2007). Iranshahi, M. et al, Phytochemistry 68, 554 (2007). Phytochem..

Showing NP-Card for 2-epihelmanticine (NP0030223)

MOL for NP0030223 (2-epihelmanticine)

3D MOL for NP0030223 (2-epihelmanticine)

3D SDF for NP0030223 (2-epihelmanticine)

3D-SDF for NP0030223 (2-epihelmanticine)

PDB for NP0030223 (2-epihelmanticine)

3D PDB for NP0030223 (2-epihelmanticine)

SMILES for NP0030223 (2-epihelmanticine)

INCHI for NP0030223 (2-epihelmanticine)

Structure for NP0030223 (2-epihelmanticine)

3D Structure for NP0030223 (2-epihelmanticine)