NP-MRD: Showing NP-Card for trans-p-Feruloyl-beta-D-glucopyranoside (NP0045707)

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Record Information

Version

2.0

Created at

2022-03-17 19:36:08 UTC

Updated at

2022-03-17 19:36:08 UTC

NP-MRD ID

NP0045707

Secondary Accession Numbers

None

Natural Product Identification

Common Name

trans-p-Feruloyl-beta-D-glucopyranoside

Description

trans-p-Feruloyl-beta-D-glucopyranoside is found in Ananas comosus, Aruncus dioicus, Baccharis dracunculifolia, Bacopa monnieri, Balanophora fungosa, Balanophora japonica, Beta vulgaris, Camellia sinensis , Coussarea hydrangeifolia, Daphnia pulex, Digitalis lanata, Ligustrum obtusifolium, Linaria japonica, Myoporum bontioides, Persicaria lapathifolia, Raphanus sativus, Rheum rhabarbarum, Salix cheilophila and Sinoadina racemosa. trans-p-Feruloyl-beta-D-glucopyranoside was first documented in 2003 (PMID: 12895536).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241212272D          

 25 26  0  0  0  0            999 V2000
   -3.2614    1.1049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9758    1.5174    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6903    1.1049    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6903    0.2799    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9759   -0.1326    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2614    0.2799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9759   -0.9576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9758    2.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4048    1.5174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4048   -0.1326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6903    2.7549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4035   -1.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3110   -0.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0255   -1.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0255   -2.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3110   -2.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4035   -2.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7400   -2.6076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1180   -0.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1180   -0.1326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8324    0.2799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5469   -0.1326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8324    1.1049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7400   -0.9576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4544   -1.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2  8  1  1  0  0  0
  4  3  1  0  0  0  0
  3  9  1  6  0  0  0
  4  5  1  0  0  0  0
  4 10  1  1  0  0  0
  5  6  1  0  0  0  0
  5  7  1  6  0  0  0
  6 22  1  1  0  0  0
  8 11  1  0  0  0  0
 12 13  2  0  0  0  0
 12 17  1  0  0  0  0
 12 19  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 18  1  0  0  0  0
 16 17  2  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 14 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045707

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(\C=C\C(=O)O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H20O9/c1-23-10-6-8(2-4-9(10)18)3-5-12(19)25-16-15(22)14(21)13(20)11(7-17)24-16/h2-6,11,13-18,20-22H,7H2,1H3/b5-3+/t11-,13-,14+,15-,16+/m1/s1

> <INCHI_KEY>
JWRQVQWBNRGGPK-PMQCXRHVSA-N

> <FORMULA>
C16H20O9

> <MOLECULAR_WEIGHT>
356.3246

> <EXACT_MASS>
356.110732238

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
34.31260695635697

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
-0.44

> <JCHEM_LOGP>
-0.35988508733333324

> <ALOGPS_LOGS>
-1.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.19756280671132

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.865378836097273

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810938220288765

> <JCHEM_POLAR_SURFACE_AREA>
145.91

> <JCHEM_REFRACTIVITY>
83.93520000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.98e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -6.088   2.062   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -7.421   2.832   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.755   2.062   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.755   0.522   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.422  -0.248   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.088   0.522   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -7.422  -1.788   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -7.421   4.372   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0     -10.089   2.832   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0     -10.089  -0.248   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -8.755   5.142   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.753  -2.558   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.581  -1.788   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.914  -2.558   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.914  -4.098   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.581  -4.868   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.753  -4.098   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.248  -4.868   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.087  -1.788   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.087  -0.248   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.420   0.522   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.754  -0.248   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -3.420   2.062   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       3.248  -1.788   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.582  -2.558   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3    8                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    1    5   22                                                  
CONECT    7    5                                                            
CONECT    8    2   11                                                       
CONECT    9    3                                                            
CONECT   10    4                                                            
CONECT   11    8                                                            
CONECT   12   13   17   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   24                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   12   16                                                       
CONECT   18   15                                                            
CONECT   19   12   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22    6   21                                                       
CONECT   23   21                                                            
CONECT   24   14   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

View in JSmol

Synonyms

Value	Source
(e)-1-O-Feruloyl-beta-D-glucopyranose	ChEBI
(e)-4'-Hydroxy-3'-methoxycinnamoyl-beta-D-glucopyranose	ChEBI
1-Feruloyl-D-glucose	ChEBI
1-O-(e)-Feruloyl-beta-D-glucose	ChEBI
1-O-(e)-p-Feruloyl-beta-D-glucopyranose	ChEBI
1-O-[(e)-Feruloyl]-beta-D-glucose	ChEBI
1-O-trans-Feruloyl-beta-D-glucopyranoside	ChEBI
Ferulic acid beta-D-glucopyranosyl ester	ChEBI
(e)-1-O-Feruloyl-b-D-glucopyranose	Generator
(e)-1-O-Feruloyl-β-D-glucopyranose	Generator
(e)-4'-Hydroxy-3'-methoxycinnamoyl-b-D-glucopyranose	Generator
(e)-4'-Hydroxy-3'-methoxycinnamoyl-β-D-glucopyranose	Generator
1-O-(e)-Feruloyl-b-D-glucose	Generator
1-O-(e)-Feruloyl-β-D-glucose	Generator
1-O-(e)-p-Feruloyl-b-D-glucopyranose	Generator
1-O-(e)-p-Feruloyl-β-D-glucopyranose	Generator
1-O-[(e)-Feruloyl]-b-D-glucose	Generator
1-O-[(e)-Feruloyl]-β-D-glucose	Generator
1-O-trans-Feruloyl-b-D-glucopyranoside	Generator
1-O-trans-Feruloyl-β-D-glucopyranoside	Generator
Ferulate b-D-glucopyranosyl ester	Generator
Ferulate beta-D-glucopyranosyl ester	Generator
Ferulate β-D-glucopyranosyl ester	Generator
Ferulic acid b-D-glucopyranosyl ester	Generator
Ferulic acid β-D-glucopyranosyl ester	Generator
trans-p-Feruloyl-b-D-glucopyranoside	Generator
trans-p-Feruloyl-β-D-glucopyranoside	Generator
1-O-(trans-Feruloyl)-beta-D-glucose	ChEBI
1-O-(trans-Feruloyl)-b-D-glucose	Generator
1-O-(trans-Feruloyl)-β-D-glucose	Generator

Chemical Formula

C₁₆H₂₀O₉

Average Mass

356.3246 Da

Monoisotopic Mass

356.11073 Da

IUPAC Name

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Traditional Name

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

CAS Registry Number

117405-51-3

SMILES

COC1=C(O)C=CC(\C=C\C(=O)O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)=C1

InChI Identifier

InChI=1S/C16H20O9/c1-23-10-6-8(2-4-9(10)18)3-5-12(19)25-16-15(22)14(21)13(20)11(7-17)24-16/h2-6,11,13-18,20-22H,7H2,1H3/b5-3+/t11-,13-,14+,15-,16+/m1/s1

InChI Key

JWRQVQWBNRGGPK-PMQCXRHVSA-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
Ananas comosus	LOTUS Database	35616633
Aruncus dioicus	LOTUS Database	35616633
Baccharis dracunculifolia	LOTUS Database	35616633
Bacopa monnieri	LOTUS Database	35616633
Balanophora fungosa	LOTUS Database	35616633
Balanophora japonica	LOTUS Database	35616633
Beta vulgaris	LOTUS Database	35616633
Camellia sinensis	Plant	KNApSAcK
Capsicum annuum	FooDB	KNAPSACK
Coussarea hydrangeifolia	LOTUS Database	35616633
Daphnia pulex	LOTUS Database	35616633
Digitalis lanata	LOTUS Database	35616633
Ligustrum obtusifolium	LOTUS Database	35616633
Linaria japonica	LOTUS Database	35616633
Myoporum bontioides	LOTUS Database	35616633
Persicaria lapathifolia	LOTUS Database	35616633
Raphanus sativus	LOTUS Database	35616633
Rheum rhabarbarum	LOTUS Database	35616633
Salix cheilophila	LOTUS Database	35616633
Sinoadina racemosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxycinnamic acid glycosides. These are glycosylated hydoxycinnamic acids derivatives.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acid glycosides

Alternative Parents

Substituents

Hydroxycinnamic acid glycoside
O-cinnamoyl glycoside
Coumaric acid or derivatives
Hexose monosaccharide
Cinnamic acid ester
Methoxyphenol
Anisole
Phenoxy compound
Phenol ether
Styrene
Methoxybenzene
Phenol
Alkyl aryl ether
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Oxane
Monosaccharide
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Acetal
Carboxylic acid derivative
Polyol
Ether
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Alcohol
Primary alcohol
Organooxygen compound
Carbonyl group
Organic oxygen compound
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

glycoside (CHEBI:81321 )

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	-0.44	ALOGPS
logP	-0.36	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	9.87	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	145.91 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	83.94 m³·mol⁻¹	ChemAxon
Polarizability	34.31 Å³	ChemAxon
Number of Rings	2	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001666

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C17759

BioCyc ID

CPD-15281

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13962928

PDB ID

Not Available

ChEBI ID

81321

Good Scents ID

Not Available

References

General References

Materska M, Piacente S, Stochmal A, Pizza C, Oleszek W, Perucka I: Isolation and structure elucidation of flavonoid and phenolic acid glycosides from pericarp of hot pepper fruit Capsicum annuum L. Phytochemistry. 2003 Aug;63(8):893-8. doi: 10.1016/s0031-9422(03)00282-6. [PubMed:12895536 ]
Materska M, Perucka I: Antioxidant activity of the main phenolic compounds isolated from hot pepper fruit (Capsicum annuum L). J Agric Food Chem. 2005 Mar 9;53(5):1750-6. doi: 10.1021/jf035331k. [PubMed:15740069 ]

Showing NP-Card for trans-p-Feruloyl-beta-D-glucopyranoside (NP0045707)

MOL for NP0045707 (trans-p-Feruloyl-beta-D-glucopyranoside)

3D MOL for NP0045707 (trans-p-Feruloyl-beta-D-glucopyranoside)

3D SDF for NP0045707 (trans-p-Feruloyl-beta-D-glucopyranoside)

3D-SDF for NP0045707 (trans-p-Feruloyl-beta-D-glucopyranoside)

PDB for NP0045707 (trans-p-Feruloyl-beta-D-glucopyranoside)

3D PDB for NP0045707 (trans-p-Feruloyl-beta-D-glucopyranoside)

SMILES for NP0045707 (trans-p-Feruloyl-beta-D-glucopyranoside)

INCHI for NP0045707 (trans-p-Feruloyl-beta-D-glucopyranoside)

Structure for NP0045707 (trans-p-Feruloyl-beta-D-glucopyranoside)

3D Structure for NP0045707 (trans-p-Feruloyl-beta-D-glucopyranoside)