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Showing NP-Card for 1-O-Sinapoyl-beta-D-glucose (NP0046442)

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Record Information
Version2.0
Created at2022-03-17 20:01:08 UTC
Updated at2022-03-17 20:01:08 UTC
NP-MRD IDNP0046442
Secondary Accession NumbersNone
Natural Product Identification
Common Name1-O-Sinapoyl-beta-D-glucose
Description 1-O-Sinapoyl-beta-D-glucose is found in Arabidopsis thaliana, Brassica napus, Bunias orientalis, Paraburkholderia phymatum, Pseudo-nitzschia multistriata, Raphanus sativus, Rheum rhabarbarum, Rorippa indica and Swertia japonica. 1-O-Sinapoyl-beta-D-glucose was first documented in 1982 (PMID: 24271623).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0046442 (1-O-Sinapoyl-beta-D-glucose)

 
  Mrv0541 02241221412D          
 
 27 28  0  0  1  0            999 V2000
   14.7262  -13.5712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7262  -14.3962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4407  -14.8087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1552  -14.3962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1552  -13.5712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4407  -13.1587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8807  -13.1523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8807  -14.8152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4407  -15.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7163  -16.0520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8807  -12.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0118  -13.1587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3073  -13.5656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6076  -13.1616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9056  -13.5671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6075  -12.3339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1912  -13.9796    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.4693  -13.5627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7548  -13.9751    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.7547  -14.8001    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.4766  -15.2170    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.1911  -14.8046    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.0296  -13.5560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3115  -13.9700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0217  -15.2233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4764  -16.0462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8980  -15.2129    0.0000 O   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  4  8  1  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
  7 11  1  0  0  0  0
  1 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 17 15  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 17 22  1  0  0  0  0
 19 23  1  1  0  0  0
 23 24  1  0  0  0  0
 20 25  1  6  0  0  0
 21 26  1  1  0  0  0
 22 27  1  6  0  0  0
M  END
Download

3D MOL for NP0046442 (1-O-Sinapoyl-beta-D-glucose)

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3D SDF for NP0046442 (1-O-Sinapoyl-beta-D-glucose)
 
  Mrv0541 02241221412D          
 
 27 28  0  0  1  0            999 V2000
   14.7262  -13.5712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7262  -14.3962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4407  -14.8087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1552  -14.3962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1552  -13.5712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4407  -13.1587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8807  -13.1523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8807  -14.8152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4407  -15.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7163  -16.0520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8807  -12.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0118  -13.1587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3073  -13.5656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6076  -13.1616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9056  -13.5671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6075  -12.3339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1912  -13.9796    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.4693  -13.5627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7548  -13.9751    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.7547  -14.8001    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.4766  -15.2170    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.1911  -14.8046    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.0296  -13.5560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3115  -13.9700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0217  -15.2233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4764  -16.0462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8980  -15.2129    0.0000 O   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  4  8  1  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
  7 11  1  0  0  0  0
  1 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 17 15  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 17 22  1  0  0  0  0
 19 23  1  1  0  0  0
 23 24  1  0  0  0  0
 20 25  1  6  0  0  0
 21 26  1  1  0  0  0
 22 27  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0046442

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(\C=C\C(=O)O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)=CC(OC)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O10/c1-24-9-5-8(6-10(25-2)13(9)20)3-4-12(19)27-17-16(23)15(22)14(21)11(7-18)26-17/h3-6,11,14-18,20-23H,7H2,1-2H3/b4-3+/t11-,14-,15+,16-,17+/m1/s1

> <INCHI_KEY>
XRKBRPFTFKKHEF-DGDBGZAXSA-N

> <FORMULA>
C17H22O10

> <MOLECULAR_WEIGHT>
386.3506

> <EXACT_MASS>
386.121296924

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
38.14791333013246

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
-0.18

> <JCHEM_LOGP>
-0.517556353

> <ALOGPS_LOGS>
-2.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.19621617510204

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.287858926698199

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810938220288765

> <JCHEM_POLAR_SURFACE_AREA>
155.14000000000001

> <JCHEM_REFRACTIVITY>
90.39839999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.47e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-O-sinapoyl-β-D-glucose

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0046442 (1-O-Sinapoyl-beta-D-glucose)
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PDB for NP0046442 (1-O-Sinapoyl-beta-D-glucose)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      27.489 -25.333   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      27.489 -26.873   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      28.823 -27.643   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      30.156 -26.873   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      30.156 -25.333   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.823 -24.563   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      31.511 -24.551   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      31.511 -27.655   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      28.823 -29.183   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      27.470 -29.964   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      31.511 -23.011   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      26.155 -24.563   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      24.840 -25.322   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      23.534 -24.568   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      22.224 -25.325   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      23.534 -23.023   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      20.890 -26.095   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      19.543 -25.317   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      18.209 -26.087   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      18.209 -27.627   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      19.556 -28.405   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      20.890 -27.635   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      16.855 -25.305   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      15.515 -26.077   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      16.841 -28.417   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      19.556 -29.953   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      22.210 -28.397   0.000  0.00  0.00           O+0
CONECT    1    2    6   12                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5   11                                                       
CONECT    8    4                                                            
CONECT    9    3   10                                                       
CONECT   10    9                                                            
CONECT   11    7                                                            
CONECT   12    1   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14   17                                                       
CONECT   16   14                                                            
CONECT   17   15   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   23                                                  
CONECT   20   19   21   25                                                  
CONECT   21   20   22   26                                                  
CONECT   22   21   17   27                                                  
CONECT   23   19   24                                                       
CONECT   24   23                                                            
CONECT   25   20                                                            
CONECT   26   21                                                            
CONECT   27   22                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

Download
3D PDB for NP0046442 (1-O-Sinapoyl-beta-D-glucose)
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SMILES for NP0046442 (1-O-Sinapoyl-beta-D-glucose)
COC1=CC(\C=C\C(=O)O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)=CC(OC)=C1O
Download
INCHI for NP0046442 (1-O-Sinapoyl-beta-D-glucose)
InChI=1S/C17H22O10/c1-24-9-5-8(6-10(25-2)13(9)20)3-4-12(19)27-17-16(23)15(22)14(21)11(7-18)26-17/h3-6,11,14-18,20-23H,7H2,1-2H3/b4-3+/t11-,14-,15+,16-,17+/m1/s1
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View in JSmol
Synonyms
ValueSource
(e)-(2S,3R,4S,5S,6R)-TETRAHYDRO-3,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-2-yl 3-(4-hydroxy-3,5-dimethoxyphenyl)acrylATEChEBI
1-O-(trans-Sinapoyl)-beta-D-glucoseChEBI
1-O-[(2E)-Sinapoyl]-beta-D-glucopyranoseChEBI
1-O-[(2E)-Sinapoyl]-beta-D-glucoseChEBI
1-O-[(e)-Sinapoyl]-beta-D-glucopyranoseChEBI
1-O-Sinapoyl beta-D-glucosideChEBI
(e)-(2S,3R,4S,5S,6R)-TETRAHYDRO-3,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-2-yl 3-(4-hydroxy-3,5-dimethoxyphenyl)acrylic acidGenerator
1-O-(trans-Sinapoyl)-b-D-glucoseGenerator
1-O-(trans-Sinapoyl)-β-D-glucoseGenerator
1-O-[(2E)-Sinapoyl]-b-D-glucopyranoseGenerator
1-O-[(2E)-Sinapoyl]-β-D-glucopyranoseGenerator
1-O-[(2E)-Sinapoyl]-b-D-glucoseGenerator
1-O-[(2E)-Sinapoyl]-β-D-glucoseGenerator
1-O-[(e)-Sinapoyl]-b-D-glucopyranoseGenerator
1-O-[(e)-Sinapoyl]-β-D-glucopyranoseGenerator
1-O-Sinapoyl b-D-glucosideGenerator
1-O-Sinapoyl β-D-glucosideGenerator
1-O-Sinapoyl-b-D-glucoseGenerator
1-O-Sinapoyl-β-D-glucoseGenerator
Chemical FormulaC17H22O10
Average Mass386.3506 Da
Monoisotopic Mass386.12130 Da
IUPAC Name(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
Traditional Name1-O-sinapoyl-β-D-glucose
CAS Registry NumberNot Available
SMILES
COC1=CC(\C=C\C(=O)O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)=CC(OC)=C1O
InChI Identifier
InChI=1S/C17H22O10/c1-24-9-5-8(6-10(25-2)13(9)20)3-4-12(19)27-17-16(23)15(22)14(21)11(7-18)26-17/h3-6,11,14-18,20-23H,7H2,1-2H3/b4-3+/t11-,14-,15+,16-,17+/m1/s1
InChI KeyXRKBRPFTFKKHEF-DGDBGZAXSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Arabidopsis thalianaPlant
Brassica napusLOTUS Database
Brassica oleracea var. capitataFooDB
Brassica oleracea var. italicaFooDB
Bunias orientalisLOTUS Database
Paraburkholderia phymatum-
Pisum sativumFooDB
Pseudo-nitzschia multistriataLOTUS Database
Raphanus sativusLOTUS Database
Rheum rhabarbarumLOTUS Database
Rorippa indicaLOTUS Database
Swertia japonicaLOTUS Database
Zea mays L.FooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxycinnamic acid glycosides. These are glycosylated hydoxycinnamic acids derivatives.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassCinnamic acids and derivatives  
Sub ClassHydroxycinnamic acids and derivatives  
Direct ParentHydroxycinnamic acid glycosides  
Alternative Parents
Substituents
  • Hydroxycinnamic acid glycoside
    • 

  • O-cinnamoyl glycoside
    • 

  • Hexose monosaccharide
    • 

  • Cinnamic acid ester
    • 

  • Coumaric acid or derivatives
    • 

  • Methoxyphenol
    • 

  • Dimethoxybenzene
    • 

  • M-dimethoxybenzene
    • 

  • Methoxybenzene
    • 

  • Phenoxy compound
    • 

  • Anisole
    • 

  • Styrene
    • 

  • Phenol ether
    • 

  • Fatty acid ester
    • 

  • Alkyl aryl ether
    • 

  • Phenol
    • 

  • Fatty acyl
    • 

  • Benzenoid
    • 

  • Monosaccharide
    • 

  • Monocyclic benzene moiety
    • 

  • Oxane
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Carboxylic acid ester
    • 

  • Secondary alcohol
    • 

  • Acetal
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Ether
    • 

  • Polyol
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Alcohol
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Primary alcohol
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.18ALOGPS
logP-0.52ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)9.29ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area155.14 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity90.4 m³·mol⁻¹ChemAxon
Polarizability38.15 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB004337  
KNApSAcK IDC00013592  
Chemspider IDNot Available
KEGG Compound IDC01175  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5280406  
PDB IDNot Available
ChEBI ID16546  
Good Scents IDNot Available
References
General References
  1. Strack D, Reinecke J, Takeuchi S: Evidence for a relationship between malate metabolism and activity of 1-sinapoylglucose: L-malate sinapoyltransferase in radish (Raphanus sativus L.) cotyledons. Planta. 1986 Feb;167(2):212-7. doi: 10.1007/BF00391417. [PubMed:24241853  ] 
  2. Strack D: Development of 1-O-sinapoyl-beta-D-glucose: L-malate sinapoyltransferase activity in cotyledons of red radish (Raphanus sativus L. var. sativus). Planta. 1982 Jun;155(1):31-6. doi: 10.1007/BF00402928. [PubMed:24271623  ]