NP-MRD: Showing NP-Card for (3r,4s,5r,6r)-5-{[(3s,4r,5r,6s)-6-ethyl-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4,6-trihydroxyoxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate (NP0204494)

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Record Information

Version

2.0

Created at

2022-09-05 00:10:46 UTC

Updated at

2022-09-05 00:10:46 UTC

NP-MRD ID

NP0204494

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,4s,5r,6r)-5-{[(3s,4r,5r,6s)-6-ethyl-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4,6-trihydroxyoxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Description

(3R,4S,5R,6R)-5-{[(3S,4R,5R,6S)-6-ethyl-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4,6-trihydroxyoxan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate belongs to the class of organic compounds known as hydroxycinnamic acid glycosides. These are glycosylated hydoxycinnamic acids derivatives. (3r,4s,5r,6r)-5-{[(3s,4r,5r,6s)-6-ethyl-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4,6-trihydroxyoxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate is found in Juncus acutus. Based on a literature review very few articles have been published on (3R,4S,5R,6R)-5-{[(3S,4R,5R,6S)-6-ethyl-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4,6-trihydroxyoxan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052202102D          

 34 36  0  0  1  0            999 V2000
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    5.0013   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309052202102D          

 34 36  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0204494

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H]1OC(O[C@H]2[C@H](O)OC(OC(=O)\C=C\C3=CC=C(O)C(O)=C3)[C@H](O)[C@@H]2O)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O13/c1-2-11-13(25)14(26)16(28)20(31-11)33-18-15(27)17(29)21(34-19(18)30)32-12(24)6-4-8-3-5-9(22)10(23)7-8/h3-7,11,13-23,25-30H,2H2,1H3/b6-4+/t11-,13-,14+,15-,16-,17+,18+,19+,20?,21?/m0/s1

> <INCHI_KEY>
UTBKBZAPMAXVDW-XCLYCKQCSA-N

> <FORMULA>
C21H28O13

> <MOLECULAR_WEIGHT>
488.442

> <EXACT_MASS>
488.152990962

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
47.18195831928142

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,4S,5R,6R)-5-{[(3S,4R,5R,6S)-6-ethyl-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4,6-trihydroxyoxan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <JCHEM_LOGP>
-0.4410714269999993

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.181461038148482

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.203970690629601

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6158716314572317

> <JCHEM_POLAR_SURFACE_AREA>
215.82999999999996

> <JCHEM_REFRACTIVITY>
109.9139

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4S,5R,6R)-5-{[(3S,4R,5R,6S)-6-ethyl-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4,6-trihydroxyoxan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.335 -12.320   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.001 -14.630   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.334 -16.170   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.667 -13.860   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0     -10.669  -9.240   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.668 -14.630   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.668 -16.170   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       8.002 -13.860   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       9.336 -14.630   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       9.336 -11.550   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   33                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   29                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   27                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   26                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   18                                                       
CONECT   26   12   27                                                       
CONECT   27   26    7   28                                                  
CONECT   28   27                                                            
CONECT   29    5   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    3   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Value	Source
(3R,4S,5R,6R)-5-{[(3S,4R,5R,6S)-6-ethyl-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4,6-trihydroxyoxan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₂₁H₂₈O₁₃

Average Mass

488.4420 Da

Monoisotopic Mass

488.15299 Da

IUPAC Name

(3R,4S,5R,6R)-5-{[(3S,4R,5R,6S)-6-ethyl-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4,6-trihydroxyoxan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

(3R,4S,5R,6R)-5-{[(3S,4R,5R,6S)-6-ethyl-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4,6-trihydroxyoxan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

CC[C@@H]1OC(O[C@H]2[C@H](O)OC(OC(=O)\C=C\C3=CC=C(O)C(O)=C3)[C@H](O)[C@@H]2O)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C21H28O13/c1-2-11-13(25)14(26)16(28)20(31-11)33-18-15(27)17(29)21(34-19(18)30)32-12(24)6-4-8-3-5-9(22)10(23)7-8/h3-7,11,13-23,25-30H,2H2,1H3/b6-4+/t11-,13-,14+,15-,16-,17+,18+,19+,20?,21?/m0/s1

InChI Key

UTBKBZAPMAXVDW-XCLYCKQCSA-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
Juncus acutus	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
Cinnamic acid ester
Coumaric acid or derivatives
O-glycosyl compound
Glycosyl compound
Disaccharide
Styrene
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acid ester
Fatty acyl
Benzenoid
Oxane
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Hemiacetal
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	-0.44	ChemAxon
pKa (Strongest Acidic)	9.2	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	215.83 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	109.91 m³·mol⁻¹	ChemAxon
Polarizability	47.18 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

162817168

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r,4s,5r,6r)-5-{[(3s,4r,5r,6s)-6-ethyl-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4,6-trihydroxyoxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate (NP0204494)

MOL for NP0204494 ((3r,4s,5r,6r)-5-{[(3s,4r,5r,6s)-6-ethyl-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4,6-trihydroxyoxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D MOL for NP0204494 ((3r,4s,5r,6r)-5-{[(3s,4r,5r,6s)-6-ethyl-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4,6-trihydroxyoxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D SDF for NP0204494 ((3r,4s,5r,6r)-5-{[(3s,4r,5r,6s)-6-ethyl-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4,6-trihydroxyoxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D-SDF for NP0204494 ((3r,4s,5r,6r)-5-{[(3s,4r,5r,6s)-6-ethyl-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4,6-trihydroxyoxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

PDB for NP0204494 ((3r,4s,5r,6r)-5-{[(3s,4r,5r,6s)-6-ethyl-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4,6-trihydroxyoxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D PDB for NP0204494 ((3r,4s,5r,6r)-5-{[(3s,4r,5r,6s)-6-ethyl-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4,6-trihydroxyoxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

SMILES for NP0204494 ((3r,4s,5r,6r)-5-{[(3s,4r,5r,6s)-6-ethyl-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4,6-trihydroxyoxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

INCHI for NP0204494 ((3r,4s,5r,6r)-5-{[(3s,4r,5r,6s)-6-ethyl-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4,6-trihydroxyoxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

Structure for NP0204494 ((3r,4s,5r,6r)-5-{[(3s,4r,5r,6s)-6-ethyl-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4,6-trihydroxyoxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D Structure for NP0204494 ((3r,4s,5r,6r)-5-{[(3s,4r,5r,6s)-6-ethyl-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4,6-trihydroxyoxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)