NP-MRD: Showing NP-Card for 2-(alpha-L-Rhamnopyranosyloxy)benzyl glucosinolate (NP0055237)

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Record Information

Version

2.0

Created at

2022-04-28 01:21:37 UTC

Updated at

2022-04-28 01:21:37 UTC

NP-MRD ID

NP0055237

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(alpha-L-Rhamnopyranosyloxy)benzyl glucosinolate

Description

{[(E)-(1-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}-2-(2-{[(2S,3R,4S,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}phenyl)ethylidene)amino]oxy}sulfonic acid belongs to the class of organic compounds known as alkylglucosinolates. These are organic compounds containing a glucosinolate moiety that carries an alkyl chain. 2-(alpha-L-Rhamnopyranosyloxy)benzyl glucosinolate is found in Reseda odorata. Based on a literature review very few articles have been published on {[(E)-(1-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}-2-(2-{[(2S,3R,4S,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}phenyl)ethylidene)amino]oxy}sulfonic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282203212D          

 37 39  0  0  1  0            999 V2000
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.5572   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1447   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7158    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
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  4  5  1  0  0  0  0
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 27 35  1  6  0  0  0
  4 36  1  1  0  0  0
  3 37  1  6  0  0  0
M  END

     RDKit          3D

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   -0.0591    1.6728    1.8477 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304282203212D          

 37 39  0  0  1  0            999 V2000
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 27 35  1  6  0  0  0
  4 36  1  1  0  0  0
  3 37  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0055237

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](OC2=CC=CC=C2C\C(S[C@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)=N/OS(O)(=O)=O)[C@H](O)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H29NO14S2/c1-8-13(23)15(25)17(27)19(32-8)33-10-5-3-2-4-9(10)6-12(21-35-37(29,30)31)36-20-18(28)16(26)14(24)11(7-22)34-20/h2-5,8,11,13-20,22-28H,6-7H2,1H3,(H,29,30,31)/b21-12+/t8-,11+,13-,14-,15-,16-,17+,18+,19-,20+/m0/s1

> <INCHI_KEY>
MNXOVJKRTWAMSF-MWRNYBTQSA-N

> <FORMULA>
C20H29NO14S2

> <MOLECULAR_WEIGHT>
571.57

> <EXACT_MASS>
571.102946966

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
52.78690338376346

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(E)-(1-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}-2-(2-{[(2S,3R,4S,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}phenyl)ethylidene)amino]oxy}sulfonic acid

> <ALOGPS_LOGP>
-1.36

> <JCHEM_LOGP>
-3.9985754835818454

> <ALOGPS_LOGS>
-1.68

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.013831720424829

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.14832066240243

> <JCHEM_PKA_STRONGEST_BASIC>
-2.979762897631196

> <JCHEM_POLAR_SURFACE_AREA>
245.25999999999993

> <JCHEM_REFRACTIVITY>
122.72859999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.19e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(E)-(1-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}-2-(2-{[(2S,3R,4S,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}phenyl)ethylidene)amino]oxysulfonic acid

> <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  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   10  S   UNK     0       8.002  -0.000   0.000  0.00  0.00           S+0
HETATM   11  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      10.669  -0.000   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   14  S   UNK     0      13.337  -0.000   0.000  0.00  0.00           S+0
HETATM   15  O   UNK     0      14.107  -1.334   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      12.567   1.334   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      14.670   0.770   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      10.669   1.540   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      10.669   4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   37                                                  
CONECT    4    3    5   36                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    5   11                                                       
CONECT   11   10   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14                                                            
CONECT   18   11   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   19   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   31                                                  
CONECT   27   26   28   35                                                  
CONECT   28   27   29   34                                                  
CONECT   29   28   30   33                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30   26                                                       
CONECT   32   30                                                            
CONECT   33   29                                                            
CONECT   34   28                                                            
CONECT   35   27                                                            
CONECT   36    4                                                            
CONECT   37    3                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

View in JSmol

Synonyms

Value	Source
{[(e)-(1-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}-2-(2-{[(2S,3R,4S,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}phenyl)ethylidene)amino]oxy}sulfonate	Generator
{[(e)-(1-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulphanyl}-2-(2-{[(2S,3R,4S,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}phenyl)ethylidene)amino]oxy}sulphonate	Generator
{[(e)-(1-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulphanyl}-2-(2-{[(2S,3R,4S,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}phenyl)ethylidene)amino]oxy}sulphonic acid	Generator

Chemical Formula

C₂₀H₂₉NO₁₄S₂

Average Mass

571.5700 Da

Monoisotopic Mass

571.10295 Da

IUPAC Name

{[(E)-(1-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}-2-(2-{[(2S,3R,4S,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}phenyl)ethylidene)amino]oxy}sulfonic acid

Traditional Name

[(E)-(1-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}-2-(2-{[(2S,3R,4S,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}phenyl)ethylidene)amino]oxysulfonic acid

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](OC2=CC=CC=C2C\C(S[C@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)=N/OS(O)(=O)=O)[C@H](O)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C20H29NO14S2/c1-8-13(23)15(25)17(27)19(32-8)33-10-5-3-2-4-9(10)6-12(21-35-37(29,30)31)36-20-18(28)16(26)14(24)11(7-22)34-20/h2-5,8,11,13-20,22-28H,6-7H2,1H3,(H,29,30,31)/b21-12+/t8-,11+,13-,14-,15-,16-,17+,18+,19-,20+/m0/s1

InChI Key

MNXOVJKRTWAMSF-MWRNYBTQSA-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
Reseda odorata	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkylglucosinolates. These are organic compounds containing a glucosinolate moiety that carries an alkyl chain.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Alkylglucosinolates

Alternative Parents

Substituents

Alkylglucosinolate
Phenolic glycoside
S-glycosyl compound
O-glycosyl compound
Glycosyl compound
Phenoxy compound
Phenol ether
Benzenoid
Oxane
Monocyclic benzene moiety
Organic sulfuric acid or derivatives
Monothioacetal
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Sulfenyl compound
Polyol
Acetal
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organosulfur compound
Organonitrogen compound
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

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	-1.4	ALOGPS
logP	-4	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	-2.1	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	245.26 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	122.73 m³·mol⁻¹	ChemAxon
Polarizability	52.79 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

154495978

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2-(alpha-L-Rhamnopyranosyloxy)benzyl glucosinolate (NP0055237)

MOL for NP0055237 (2-(alpha-L-Rhamnopyranosyloxy)benzyl glucosinolate)

3D MOL for NP0055237 (2-(alpha-L-Rhamnopyranosyloxy)benzyl glucosinolate)

3D SDF for NP0055237 (2-(alpha-L-Rhamnopyranosyloxy)benzyl glucosinolate)

3D-SDF for NP0055237 (2-(alpha-L-Rhamnopyranosyloxy)benzyl glucosinolate)

PDB for NP0055237 (2-(alpha-L-Rhamnopyranosyloxy)benzyl glucosinolate)

3D PDB for NP0055237 (2-(alpha-L-Rhamnopyranosyloxy)benzyl glucosinolate)

SMILES for NP0055237 (2-(alpha-L-Rhamnopyranosyloxy)benzyl glucosinolate)

INCHI for NP0055237 (2-(alpha-L-Rhamnopyranosyloxy)benzyl glucosinolate)

Structure for NP0055237 (2-(alpha-L-Rhamnopyranosyloxy)benzyl glucosinolate)

3D Structure for NP0055237 (2-(alpha-L-Rhamnopyranosyloxy)benzyl glucosinolate)