NP-MRD: Showing NP-Card for E-thesinine-O-4'-alpha-rhamnoside (NP0037230)

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Record Information

Version

2.0

Created at

2021-06-20 20:12:05 UTC

Updated at

2021-06-30 00:09:18 UTC

NP-MRD ID

NP0037230

Secondary Accession Numbers

None

Natural Product Identification

Common Name

E-thesinine-O-4'-alpha-rhamnoside

Provided By

JEOL Database JEOL Logo

Description

E-thesinine-O-4'-alpha-rhamnoside is found in grasses (Poaceae). E-thesinine-O-4'-alpha-rhamnoside was first documented in 2008 (Koulman, A., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202122123D          

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M  END

     RDKit          3D

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  Mrv1652306202122123D          

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M  END
> <DATABASE_ID>
NP0037230

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])[C@@]([H])(OC2=C([H])C([H])=C(\C([H])=C(/[H])C(=O)OC([H])([H])[C@]3([H])C([H])([H])C([H])([H])N4C([H])([H])C([H])([H])C([H])([H])[C@]34[H])C([H])=C2[H])O[C@]([H])(C([H])([H])[H])[C@@]([H])(O[H])[C@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H31NO7/c1-14-20(26)21(27)22(28)23(30-14)31-17-7-4-15(5-8-17)6-9-19(25)29-13-16-10-12-24-11-2-3-18(16)24/h4-9,14,16,18,20-23,26-28H,2-3,10-13H2,1H3/b9-6+/t14-,16+,18-,20-,21+,22+,23-/m1/s1

> <INCHI_KEY>
NZLSLVIWDCNZHH-XGDMJICBSA-N

> <FORMULA>
C23H31NO7

> <MOLECULAR_WEIGHT>
433.501

> <EXACT_MASS>
433.210052342

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
47.151513612135716

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1R,7aR)-hexahydro-1H-pyrrolizin-1-yl]methyl (2E)-3-(4-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}phenyl)prop-2-enoate

> <ALOGPS_LOGP>
1.61

> <JCHEM_LOGP>
1.5405496753333323

> <ALOGPS_LOGS>
-2.59

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.269060473942513

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.217745860535826

> <JCHEM_PKA_STRONGEST_BASIC>
10.229026501348775

> <JCHEM_POLAR_SURFACE_AREA>
108.69000000000001

> <JCHEM_REFRACTIVITY>
113.19109999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.12e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,7aR)-hexahydro-1H-pyrrolizin-1-ylmethyl (2E)-3-(4-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}phenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

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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      -1.103   5.415  -3.373  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.265   4.064  -4.063  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.165   3.280  -3.262  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.338   1.941  -3.759  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.123   1.196  -3.842  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.572   0.741  -2.678  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.940   1.121  -1.389  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.281   0.579  -0.277  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.750  -0.355  -0.438  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.484  -0.926   0.699  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.925  -1.222   1.882  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.749  -1.808   2.958  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.938  -2.065   2.880  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.948  -2.006   4.034  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.620  -2.573   5.167  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.605  -2.782   6.284  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.198  -3.402   7.548  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.111  -4.325   8.098  0.00  0.00           C+0
HETATM   19  N   UNK     0      -1.075  -4.092   7.260  0.00  0.00           N+0
HETATM   20  C   UNK     0      -1.858  -5.312   7.034  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.329  -5.953   5.753  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.264  -5.001   5.228  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.570  -3.687   5.936  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.131  -0.712  -1.735  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.473  -0.170  -2.844  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.983   2.014  -5.157  0.00  0.00           C+0
HETATM   27  O   UNK     0      -4.294   2.617  -5.101  0.00  0.00           O+0
HETATM   28  C   UNK     0      -2.113   2.853  -6.098  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.787   3.055  -7.353  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.806   4.227  -5.491  0.00  0.00           C+0
HETATM   31  O   UNK     0      -0.868   4.912  -6.324  0.00  0.00           O+0
HETATM   32  H   UNK     0      -2.066   5.933  -3.294  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.738   5.277  -2.349  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.400   6.060  -3.908  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.278   3.587  -4.081  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.051   1.438  -3.094  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.719   1.855  -1.208  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.577   0.916   0.714  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.541  -1.128   0.528  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.124  -1.065   2.095  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.400  -1.880   5.506  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.092  -3.520   4.881  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.189  -1.799   6.551  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.105  -3.978   7.331  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.462  -2.622   8.270  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.111  -4.099   9.145  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.465  -5.363   8.050  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.909  -5.032   6.889  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.834  -6.002   7.885  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.138  -6.064   5.022  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.904  -6.944   5.941  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.308  -4.902   4.139  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.729  -5.389   5.485  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.344  -3.135   5.388  0.00  0.00           H+0
HETATM   55  H   UNK     0       1.940  -1.420  -1.900  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.782  -0.463  -3.844  0.00  0.00           H+0
HETATM   57  H   UNK     0      -3.114   1.012  -5.581  0.00  0.00           H+0
HETATM   58  H   UNK     0      -4.291   3.246  -4.352  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.177   2.331  -6.327  0.00  0.00           H+0
HETATM   60  H   UNK     0      -3.743   3.070  -7.141  0.00  0.00           H+0
HETATM   61  H   UNK     0      -2.721   4.832  -5.481  0.00  0.00           H+0
HETATM   62  H   UNK     0      -1.186   4.780  -7.240  0.00  0.00           H+0
CONECT    1    2   32   33   34                                             
CONECT    2    3   30    1   35                                             
CONECT    3    4    2                                                       
CONECT    4    3    5   26   36                                             
CONECT    5    4    6                                                       
CONECT    6    7   25    5                                                  
CONECT    7    8    6   37                                                  
CONECT    8    9    7   38                                                  
CONECT    9   10    8   24                                                  
CONECT   10   11    9   39                                                  
CONECT   11   12   10   40                                                  
CONECT   12   14   11   13                                                  
CONECT   13   12                                                            
CONECT   14   15   12                                                       
CONECT   15   16   14   41   42                                             
CONECT   16   15   17   23   43                                             
CONECT   17   18   16   44   45                                             
CONECT   18   19   17   46   47                                             
CONECT   19   20   18   23                                                  
CONECT   20   21   19   48   49                                             
CONECT   21   22   20   50   51                                             
CONECT   22   23   21   52   53                                             
CONECT   23   22   16   19   54                                             
CONECT   24   25    9   55                                                  
CONECT   25    6   24   56                                                  
CONECT   26   28    4   27   57                                             
CONECT   27   26   58                                                       
CONECT   28   29   30   26   59                                             
CONECT   29   28   60                                                       
CONECT   30    2   28   31   61                                             
CONECT   31   30   62                                                       
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    2                                                            
CONECT   36    4                                                            
CONECT   37    7                                                            
CONECT   38    8                                                            
CONECT   39   10                                                            
CONECT   40   11                                                            
CONECT   41   15                                                            
CONECT   42   15                                                            
CONECT   43   16                                                            
CONECT   44   17                                                            
CONECT   45   17                                                            
CONECT   46   18                                                            
CONECT   47   18                                                            
CONECT   48   20                                                            
CONECT   49   20                                                            
CONECT   50   21                                                            
CONECT   51   21                                                            
CONECT   52   22                                                            
CONECT   53   22                                                            
CONECT   54   23                                                            
CONECT   55   24                                                            
CONECT   56   25                                                            
CONECT   57   26                                                            
CONECT   58   27                                                            
CONECT   59   28                                                            
CONECT   60   29                                                            
CONECT   61   30                                                            
CONECT   62   31                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  130    0
END

RDKit          3D

62 65  0  0  0  0  0  0  0  0999 V2000
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   -1.8055    4.2272   -5.4906 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8679    4.9124   -6.3242 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5409   -1.1279    0.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1243   -1.0646    2.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3998   -1.8800    5.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0923   -3.5199    4.8807 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1891   -1.7991    6.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1054   -3.9781    7.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4623   -2.6219    8.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1111   -4.0988    9.1454 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4651   -5.3630    8.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9086   -5.0323    6.8889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8341   -6.0018    7.8850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1379   -6.0644    5.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9041   -6.9439    5.9412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3083   -4.9024    4.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7288   -5.3890    5.4848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3440   -3.1355    5.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9404   -1.4200   -1.8998 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7820   -0.4632   -3.8444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1135    1.0125   -5.5814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2914    3.2457   -4.3518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1768    2.3312   -6.3270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7433    3.0695   -7.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7213    4.8316   -5.4814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1859    4.7799   -7.2400 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
  3  2  1  0
  2 30  1  0
  4  5  1  0
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 16 15  1  0
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 14 12  1  0
 28 29  1  0
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  9  8  1  0
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  7  6  1  0
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  6 25  2  0
 16 23  1  0
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  8 38  1  0
  7 37  1  0
 25 56  1  0
 24 55  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₁NO₇

Average Mass

433.5010 Da

Monoisotopic Mass

433.21005 Da

IUPAC Name

[(1R,7aR)-hexahydro-1H-pyrrolizin-1-yl]methyl (2E)-3-(4-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}phenyl)prop-2-enoate

Traditional Name

(1R,7aR)-hexahydro-1H-pyrrolizin-1-ylmethyl (2E)-3-(4-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}phenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])[C@@]([H])(OC2=C([H])C([H])=C(\C([H])=C(/[H])C(=O)OC([H])([H])[C@]3([H])C([H])([H])C([H])([H])N4C([H])([H])C([H])([H])C([H])([H])[C@]34[H])C([H])=C2[H])O[C@]([H])(C([H])([H])[H])[C@@]([H])(O[H])[C@]1([H])O[H]

InChI Identifier

InChI=1S/C23H31NO7/c1-14-20(26)21(27)22(28)23(30-14)31-17-7-4-15(5-8-17)6-9-19(25)29-13-16-10-12-24-11-2-3-18(16)24/h4-9,14,16,18,20-23,26-28H,2-3,10-13H2,1H3/b9-6+/t14-,16+,18-,20-,21+,22+,23-/m1/s1

InChI Key

NZLSLVIWDCNZHH-XGDMJICBSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, 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
grasses (Poaceae)	JEOL database	Koulman, A., et al, Phytochem. 69, 1927 (2008)

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	1.61	ALOGPS
logP	1.54	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	12.22	ChemAxon
pKa (Strongest Basic)	10.23	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	108.69 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	113.19 m³·mol⁻¹	ChemAxon
Polarizability	47.15 Å³	ChemAxon
Number of Rings	4	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

Koulman, A., et al. (2008). Koulman, A., et al, Phytochem. 69, 1927 (2008). Phytochem..

Showing NP-Card for E-thesinine-O-4'-alpha-rhamnoside (NP0037230)

MOL for NP0037230 (E-thesinine-O-4'-alpha-rhamnoside )

3D MOL for NP0037230 (E-thesinine-O-4'-alpha-rhamnoside )

3D SDF for NP0037230 (E-thesinine-O-4'-alpha-rhamnoside )

3D-SDF for NP0037230 (E-thesinine-O-4'-alpha-rhamnoside )

PDB for NP0037230 (E-thesinine-O-4'-alpha-rhamnoside )

3D PDB for NP0037230 (E-thesinine-O-4'-alpha-rhamnoside )

SMILES for NP0037230 (E-thesinine-O-4'-alpha-rhamnoside )

INCHI for NP0037230 (E-thesinine-O-4'-alpha-rhamnoside )

Structure for NP0037230 (E-thesinine-O-4'-alpha-rhamnoside )

3D Structure for NP0037230 (E-thesinine-O-4'-alpha-rhamnoside )