NP-MRD: Showing NP-Card for (2r,3s,4r,5r,6s)-4,5-dihydroxy-6-[4-hydroxy-2-(3-methylbut-2-en-1-yl)phenoxy]-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate (NP0161174)

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Record Information

Version

2.0

Created at

2022-09-02 19:17:09 UTC

Updated at

2022-09-02 19:17:09 UTC

NP-MRD ID

NP0161174

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3s,4r,5r,6s)-4,5-dihydroxy-6-[4-hydroxy-2-(3-methylbut-2-en-1-yl)phenoxy]-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Description

2-(3-Methyl-2-butenyl)-4-hydroxyphenyl 4-O-(3,4-dihydroxycinnamoyl)-beta-D-glucopyranoside belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. (2r,3s,4r,5r,6s)-4,5-dihydroxy-6-[4-hydroxy-2-(3-methylbut-2-en-1-yl)phenoxy]-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate is found in Phagnalon rupestre. Based on a literature review very few articles have been published on 2-(3-Methyl-2-butenyl)-4-hydroxyphenyl 4-O-(3,4-dihydroxycinnamoyl)-beta-D-glucopyranoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022221172D          

 36 38  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309022221172D          

 36 38  0  0  1  0            999 V2000
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 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
 14 35  1  0  0  0  0
 35 36  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0161174

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=CC(O)=CC=C1O[C@@H]1O[C@H](CO)[C@@H](OC(=O)\C=C\C2=CC=C(O)C(O)=C2)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H30O10/c1-14(2)3-6-16-12-17(28)7-9-20(16)34-26-24(33)23(32)25(21(13-27)35-26)36-22(31)10-5-15-4-8-18(29)19(30)11-15/h3-5,7-12,21,23-30,32-33H,6,13H2,1-2H3/b10-5+/t21-,23-,24-,25-,26-/m1/s1

> <INCHI_KEY>
NCCLLRBZVMPSLE-HEWQUDLHSA-N

> <FORMULA>
C26H30O10

> <MOLECULAR_WEIGHT>
502.516

> <EXACT_MASS>
502.183897166

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
51.31213792028498

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4R,5R,6S)-4,5-dihydroxy-6-[4-hydroxy-2-(3-methylbut-2-en-1-yl)phenoxy]-2-(hydroxymethyl)oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
2.31

> <JCHEM_LOGP>
3.253374153333334

> <ALOGPS_LOGS>
-3.42

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.855824086634858

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.098016308666864

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981816497541283

> <JCHEM_POLAR_SURFACE_AREA>
166.14

> <JCHEM_REFRACTIVITY>
129.93650000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.91e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4R,5R,6S)-4,5-dihydroxy-6-[4-hydroxy-2-(3-methylbut-2-en-1-yl)phenoxy]-2-(hydroxymethyl)oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.001 -14.630   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.668 -14.630   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002 -13.860   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.336 -11.550   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      12.003 -11.550   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      13.337 -12.320   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      14.670 -10.010   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      13.337 -13.860   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      14.670 -14.630   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      16.004 -13.860   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      16.004 -12.320   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      17.338 -14.630   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.672 -13.860   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      20.005 -14.630   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      21.339 -13.860   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      22.673 -14.630   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      22.673 -16.170   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      24.006 -16.940   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      21.339 -16.940   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      21.339 -18.480   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      20.005 -16.170   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.003 -14.630   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      12.003 -16.170   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       9.336 -14.630   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    6   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   35                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20   33                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   32                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   25                                                       
CONECT   33   19   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   14   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Value	Source
2-(3-Methyl-2-butenyl)-4-hydroxyphenyl 4-O-(3,4-dihydroxycinnamoyl)-b-D-glucopyranoside	Generator
2-(3-Methyl-2-butenyl)-4-hydroxyphenyl 4-O-(3,4-dihydroxycinnamoyl)-β-D-glucopyranoside	Generator

Chemical Formula

C₂₆H₃₀O₁₀

Average Mass

502.5160 Da

Monoisotopic Mass

502.18390 Da

IUPAC Name

(2R,3S,4R,5R,6S)-4,5-dihydroxy-6-[4-hydroxy-2-(3-methylbut-2-en-1-yl)phenoxy]-2-(hydroxymethyl)oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

(2R,3S,4R,5R,6S)-4,5-dihydroxy-6-[4-hydroxy-2-(3-methylbut-2-en-1-yl)phenoxy]-2-(hydroxymethyl)oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=CC(O)=CC=C1O[C@@H]1O[C@H](CO)[C@@H](OC(=O)\C=C\C2=CC=C(O)C(O)=C2)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C26H30O10/c1-14(2)3-6-16-12-17(28)7-9-20(16)34-26-24(33)23(32)25(21(13-27)35-26)36-22(31)10-5-15-4-8-18(29)19(30)11-15/h3-5,7-12,21,23-30,32-33H,6,13H2,1-2H3/b10-5+/t21-,23-,24-,25-,26-/m1/s1

InChI Key

NCCLLRBZVMPSLE-HEWQUDLHSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Phagnalon rupestre	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hexose monosaccharide
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
O-glycosyl compound
4-alkoxyphenol
Phenoxy compound
Catechol
Phenol ether
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Monocyclic benzene moiety
Oxane
Fatty acyl
Monosaccharide
Benzenoid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Acetal
Primary alcohol
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxide
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	2.31	ALOGPS
logP	3.25	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	9.1	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	166.14 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	129.94 m³·mol⁻¹	ChemAxon
Polarizability	51.31 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

9930485

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11755782

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3s,4r,5r,6s)-4,5-dihydroxy-6-[4-hydroxy-2-(3-methylbut-2-en-1-yl)phenoxy]-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate (NP0161174)

MOL for NP0161174 ((2r,3s,4r,5r,6s)-4,5-dihydroxy-6-[4-hydroxy-2-(3-methylbut-2-en-1-yl)phenoxy]-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D MOL for NP0161174 ((2r,3s,4r,5r,6s)-4,5-dihydroxy-6-[4-hydroxy-2-(3-methylbut-2-en-1-yl)phenoxy]-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D SDF for NP0161174 ((2r,3s,4r,5r,6s)-4,5-dihydroxy-6-[4-hydroxy-2-(3-methylbut-2-en-1-yl)phenoxy]-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D-SDF for NP0161174 ((2r,3s,4r,5r,6s)-4,5-dihydroxy-6-[4-hydroxy-2-(3-methylbut-2-en-1-yl)phenoxy]-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

PDB for NP0161174 ((2r,3s,4r,5r,6s)-4,5-dihydroxy-6-[4-hydroxy-2-(3-methylbut-2-en-1-yl)phenoxy]-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D PDB for NP0161174 ((2r,3s,4r,5r,6s)-4,5-dihydroxy-6-[4-hydroxy-2-(3-methylbut-2-en-1-yl)phenoxy]-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

SMILES for NP0161174 ((2r,3s,4r,5r,6s)-4,5-dihydroxy-6-[4-hydroxy-2-(3-methylbut-2-en-1-yl)phenoxy]-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

INCHI for NP0161174 ((2r,3s,4r,5r,6s)-4,5-dihydroxy-6-[4-hydroxy-2-(3-methylbut-2-en-1-yl)phenoxy]-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

Structure for NP0161174 ((2r,3s,4r,5r,6s)-4,5-dihydroxy-6-[4-hydroxy-2-(3-methylbut-2-en-1-yl)phenoxy]-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D Structure for NP0161174 ((2r,3s,4r,5r,6s)-4,5-dihydroxy-6-[4-hydroxy-2-(3-methylbut-2-en-1-yl)phenoxy]-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)