NP-MRD: Showing NP-Card for Deoxyelephantopin (NP0051864)

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Record Information

Version

2.0

Created at

2022-04-27 23:04:12 UTC

Updated at

2022-04-27 23:04:12 UTC

NP-MRD ID

NP0051864

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Deoxyelephantopin

Description

Deoxyelephantopin is found in Elephantopus carolianus, Elephantopus carolinianus and Elephantopus scaber .

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 45 47  0  0  0  0  0  0  0  0999 V2000
    4.8155    0.6657    0.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1030   -0.0391   -0.7122 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8127   -0.6721   -1.8457 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6678   -0.2142   -0.5837 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0057   -0.8819   -1.3967 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9467    0.3670    0.4756 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5501    0.1733    0.5662 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2250   -0.4511    1.9299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0204   -1.2291    1.9000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1114   -1.2129    2.6106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1686   -1.7483    1.6520 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5869   -0.7076    0.6438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7527   -0.6090   -0.5442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9795   -1.5901   -1.6726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8075    0.2786   -0.7231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6084    1.3697    0.2102 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8938    2.5929   -0.4808 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7676    2.9033   -1.2537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7783    3.4334   -2.3934 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3694    2.4707   -0.4290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5910    2.9394   -0.6047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1370    1.5057    0.5304 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4677   -2.8494    1.0392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2013   -2.2966    0.8483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4025   -2.6599   -0.0476 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8822    0.7908    0.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3372    1.1480    0.9889 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5989   -0.0522   -2.7478 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4656   -1.7142   -2.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9104   -0.6753   -1.6888 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2017   -0.4393   -0.2603 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3767    0.3298    2.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0652   -1.1915    2.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4857   -0.9691    3.6006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0131   -2.2265    2.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6038   -1.0703    0.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8487    0.2541    1.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8498   -1.2401   -2.2726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1113   -1.6256   -2.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2000   -2.5992   -1.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1534    0.2157   -1.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1519    1.3502    1.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8250    3.6629   -1.3600 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3837    2.5915    0.0323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0324    1.9220    1.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  3
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  3
 20 22  1  0
 11 23  1  0
 23 24  1  0
 24 25  2  0
 22  7  1  0
 24  9  1  0
 22 16  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  1 26  1  0
  1 27  1  0
  7 31  1  6
  8 32  1  0
  8 33  1  0
 10 34  1  0
 11 35  1  1
 12 36  1  0
 12 37  1  0
 14 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 16 42  1  1
 21 43  1  0
 21 44  1  0
 22 45  1  1
M  END


  Mrv1652304282201042D          

 25 27  0  0  1  0            999 V2000
    1.2868   -0.8596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9602   -0.1020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7692    0.4533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5741    0.2722    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1188   -0.3474    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1953   -1.1689    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7744   -1.8784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0168   -2.2050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2119   -2.0239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6672   -1.4043    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0424   -0.9833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1387   -0.1784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4060    0.4412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0932   -3.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0002   -1.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4212   -0.6405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2426   -0.5640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8764   -0.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0575    0.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9951    0.9817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5911    1.7010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7661    1.7108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0120    2.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6081    3.1299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8370    2.4007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 14  1  0  0  0  0
  6 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  5 18  1  1  0  0  0
 18 19  2  0  0  0  0
  4 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051864

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)C(=O)O[C@H]1CC2=C[C@@H](C\C(C)=C/[C@@H]3OC(=O)C(=C)[C@H]13)OC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H20O6/c1-9(2)17(20)24-15-8-12-7-13(23-19(12)22)5-10(3)6-14-16(15)11(4)18(21)25-14/h6-7,13-16H,1,4-5,8H2,2-3H3/b10-6-/t13-,14+,15+,16+/m1/s1

> <INCHI_KEY>
JMUOPRSXUVOHFE-KPWKVVFQSA-N

> <FORMULA>
C19H20O6

> <MOLECULAR_WEIGHT>
344.363

> <EXACT_MASS>
344.125988364

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
33.93453945181757

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,4R,8S,9E,12R)-10-methyl-5-methylidene-6,14-dioxo-7,13-dioxatricyclo[10.2.1.0^{4,8}]pentadeca-1(15),9-dien-3-yl 2-methylprop-2-enoate

> <ALOGPS_LOGP>
1.50

> <JCHEM_LOGP>
3.155993076666666

> <ALOGPS_LOGS>
-3.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.566343787697537

> <JCHEM_PKA_STRONGEST_BASIC>
-6.39251525198143

> <JCHEM_POLAR_SURFACE_AREA>
78.9

> <JCHEM_REFRACTIVITY>
89.4139

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.49e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4R,8S,9E,12R)-10-methyl-5-methylidene-6,14-dioxo-7,13-dioxatricyclo[10.2.1.0^{4,8}]pentadeca-1(15),9-dien-3-yl 2-methylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       2.402  -1.605   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.792  -0.190   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.303   0.846   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.805   0.508   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.822  -0.649   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.965  -2.182   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.179  -3.506   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.765  -4.116   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.262  -3.778   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.245  -2.621   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.079  -1.836   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.259  -0.333   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.758   0.824   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.907  -5.649   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.467  -2.520   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.253  -1.196   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.786  -1.053   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.236  -0.039   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.574   1.464   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.591   1.833   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.837   3.175   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.297   3.194   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.622   4.500   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.868   5.842   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.162   4.481   0.000  0.00  0.00           C+0
CONECT    1    2   10                                                       
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   20                                                  
CONECT    5    4    6   18                                                  
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9    1   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11    2   13                                                  
CONECT   13   12                                                            
CONECT   14    8                                                            
CONECT   15    6   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    5   19                                                  
CONECT   19   18                                                            
CONECT   20    4   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₀O₆

Average Mass

344.3630 Da

Monoisotopic Mass

344.12599 Da

IUPAC Name

(3S,4R,8S,9E,12R)-10-methyl-5-methylidene-6,14-dioxo-7,13-dioxatricyclo[10.2.1.0^{4,8}]pentadeca-1(15),9-dien-3-yl 2-methylprop-2-enoate

Traditional Name

(3S,4R,8S,9E,12R)-10-methyl-5-methylidene-6,14-dioxo-7,13-dioxatricyclo[10.2.1.0^{4,8}]pentadeca-1(15),9-dien-3-yl 2-methylprop-2-enoate

CAS Registry Number

Not Available

SMILES

CC(=C)C(=O)O[C@H]1CC2=C[C@@H](C\C(C)=C/[C@@H]3OC(=O)C(=C)[C@H]13)OC2=O

InChI Identifier

InChI=1S/C19H20O6/c1-9(2)17(20)24-15-8-12-7-13(23-19(12)22)5-10(3)6-14-16(15)11(4)18(21)25-14/h6-7,13-16H,1,4-5,8H2,2-3H3/b10-6-/t13-,14+,15+,16+/m1/s1

InChI Key

JMUOPRSXUVOHFE-KPWKVVFQSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Elephantopus carolianus	Plant	KNApSAcK
Elephantopus carolinianus	Plant	KNApSAcK
Elephantopus scaber	Plant	KNApSAcK

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	1.5	ALOGPS
logP	3.16	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	13.57	ChemAxon
pKa (Strongest Basic)	-6.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	78.9 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	89.41 m³·mol⁻¹	ChemAxon
Polarizability	33.93 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	No	ChemAxon

External Links

Not Available

References

General References

Not Available

Showing NP-Card for Deoxyelephantopin (NP0051864)

MOL for NP0051864 (Deoxyelephantopin)

3D MOL for NP0051864 (Deoxyelephantopin)

3D SDF for NP0051864 (Deoxyelephantopin)

3D-SDF for NP0051864 (Deoxyelephantopin)

PDB for NP0051864 (Deoxyelephantopin)

3D PDB for NP0051864 (Deoxyelephantopin)

SMILES for NP0051864 (Deoxyelephantopin)

INCHI for NP0051864 (Deoxyelephantopin)

Structure for NP0051864 (Deoxyelephantopin)

3D Structure for NP0051864 (Deoxyelephantopin)