NP-MRD: Showing NP-Card for [(3s,4s,5r)-5-{[(2r,3s,4s,5s,6s)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-hydroxyphenoxy)oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl (2e)-2-methylbut-2-enoate (NP0240527)

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Record Information

Version

2.0

Created at

2022-09-07 00:22:33 UTC

Updated at

2022-09-07 00:22:34 UTC

NP-MRD ID

NP0240527

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(3s,4s,5r)-5-{[(2r,3s,4s,5s,6s)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-hydroxyphenoxy)oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl (2e)-2-methylbut-2-enoate

Description

[(3S,4S,5R)-5-{[(2R,3S,4S,5S,6S)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-hydroxyphenoxy)oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl (2E)-2-methylbut-2-enoate 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. [(3s,4s,5r)-5-{[(2r,3s,4s,5s,6s)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-hydroxyphenoxy)oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl (2e)-2-methylbut-2-enoate is found in Myrsine seguinii. Based on a literature review very few articles have been published on [(3S,4S,5R)-5-{[(2R,3S,4S,5S,6S)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-hydroxyphenoxy)oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl (2E)-2-methylbut-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072202222D          

 34 36  0  0  1  0            999 V2000
    1.6058    0.4806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8607   -0.3040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5017   -0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3706   -1.8732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0116   -2.3148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665   -3.0994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1624   -3.0994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819   -4.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -4.9820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1830   -5.6495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1526   -6.4032    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.7376   -3.9425    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


  Mrv1652309072202222D          

 34 36  0  0  1  0            999 V2000
    1.6058    0.4806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8607   -0.3040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0240527

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(/C)C(=O)OC[C@@]1(O)CO[C@H](O[C@@H]2[C@@H](OC3=CC=C(O)C=C3)O[C@@H](CO)[C@@H](O)[C@@H]2O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O12/c1-3-11(2)19(28)30-9-22(29)10-31-21(18(22)27)34-17-16(26)15(25)14(8-23)33-20(17)32-13-6-4-12(24)5-7-13/h3-7,14-18,20-21,23-27,29H,8-10H2,1-2H3/b11-3+/t14-,15+,16-,17-,18+,20-,21+,22+/m0/s1

> <INCHI_KEY>
RYHVNXLXTBESAE-NUMQRFBXSA-N

> <FORMULA>
C22H30O12

> <MOLECULAR_WEIGHT>
486.47

> <EXACT_MASS>
486.173726406

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
47.875656217217575

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(3S,4S,5R)-5-{[(2R,3S,4S,5S,6S)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-hydroxyphenoxy)oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl (2E)-2-methylbut-2-enoate

> <JCHEM_LOGP>
0.03448525399999958

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.796998488994873

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.817606824973767

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810925692673598

> <JCHEM_POLAR_SURFACE_AREA>
184.6

> <JCHEM_REFRACTIVITY>
112.66420000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(3S,4S,5R)-5-{[(2R,3S,4S,5S,6S)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-hydroxyphenoxy)oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       2.997   0.897   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.473  -0.567   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.443  -1.712   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.936  -1.392   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.919  -3.176   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.425  -3.497   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       1.888  -4.321   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.364  -5.786   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.303  -5.786   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.580  -7.835   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.104  -9.300   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.564  -9.300   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.342 -10.546   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.285 -11.953   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.816 -12.114   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.722 -10.868   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.443 -13.520   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.974 -13.681   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.538 -14.766   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.164 -16.173   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.259 -17.419   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.006 -14.605   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.620 -13.198   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.152 -13.037   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -3.057 -14.283   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.431 -15.690   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.336 -16.936   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -4.867 -16.775   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -5.773 -18.021   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -5.494 -15.368   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.589 -14.122   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.088  -7.835   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -1.377  -7.359   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   33                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   33                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   24                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   24                                                       
CONECT   24   23   15   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   26                                                       
CONECT   33   13    9   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Value	Source
[(3S,4S,5R)-5-{[(2R,3S,4S,5S,6S)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-hydroxyphenoxy)oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl (2E)-2-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₂H₃₀O₁₂

Average Mass

486.4700 Da

Monoisotopic Mass

486.17373 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C\C=C(/C)C(=O)OC[C@@]1(O)CO[C@H](O[C@@H]2[C@@H](OC3=CC=C(O)C=C3)O[C@@H](CO)[C@@H](O)[C@@H]2O)[C@H]1O

InChI Identifier

InChI=1S/C22H30O12/c1-3-11(2)19(28)30-9-22(29)10-31-21(18(22)27)34-17-16(26)15(25)14(8-23)33-20(17)32-13-6-4-12(24)5-7-13/h3-7,14-18,20-21,23-27,29H,8-10H2,1-2H3/b11-3+/t14-,15+,16-,17-,18+,20-,21+,22+/m0/s1

InChI Key

RYHVNXLXTBESAE-NUMQRFBXSA-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
Myrsine seguinii	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
Disaccharide
O-glycosyl compound
4-alkoxyphenol
Phenoxy compound
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Monocyclic benzene moiety
Oxane
Fatty acyl
Benzenoid
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Secondary alcohol
Carboxylic acid ester
Acetal
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Primary alcohol
Organic oxide
Carbonyl group
Hydrocarbon derivative
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

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

163190469

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(3s,4s,5r)-5-{[(2r,3s,4s,5s,6s)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-hydroxyphenoxy)oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl (2e)-2-methylbut-2-enoate (NP0240527)

MOL for NP0240527 ([(3s,4s,5r)-5-{[(2r,3s,4s,5s,6s)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-hydroxyphenoxy)oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl (2e)-2-methylbut-2-enoate)

3D MOL for NP0240527 ([(3s,4s,5r)-5-{[(2r,3s,4s,5s,6s)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-hydroxyphenoxy)oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl (2e)-2-methylbut-2-enoate)

3D SDF for NP0240527 ([(3s,4s,5r)-5-{[(2r,3s,4s,5s,6s)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-hydroxyphenoxy)oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl (2e)-2-methylbut-2-enoate)

3D-SDF for NP0240527 ([(3s,4s,5r)-5-{[(2r,3s,4s,5s,6s)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-hydroxyphenoxy)oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl (2e)-2-methylbut-2-enoate)

PDB for NP0240527 ([(3s,4s,5r)-5-{[(2r,3s,4s,5s,6s)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-hydroxyphenoxy)oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl (2e)-2-methylbut-2-enoate)

3D PDB for NP0240527 ([(3s,4s,5r)-5-{[(2r,3s,4s,5s,6s)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-hydroxyphenoxy)oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl (2e)-2-methylbut-2-enoate)

SMILES for NP0240527 ([(3s,4s,5r)-5-{[(2r,3s,4s,5s,6s)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-hydroxyphenoxy)oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl (2e)-2-methylbut-2-enoate)

INCHI for NP0240527 ([(3s,4s,5r)-5-{[(2r,3s,4s,5s,6s)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-hydroxyphenoxy)oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl (2e)-2-methylbut-2-enoate)

Structure for NP0240527 ([(3s,4s,5r)-5-{[(2r,3s,4s,5s,6s)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-hydroxyphenoxy)oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl (2e)-2-methylbut-2-enoate)

3D Structure for NP0240527 ([(3s,4s,5r)-5-{[(2r,3s,4s,5s,6s)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-hydroxyphenoxy)oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl (2e)-2-methylbut-2-enoate)