NP-MRD: Showing NP-Card for Ethyl 3-hydroxyoctanoate 3-O-beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranoside (NP0075336)

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Record Information

Version

2.0

Created at

2022-04-28 20:37:32 UTC

Updated at

2022-04-28 20:37:33 UTC

NP-MRD ID

NP0075336

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ethyl 3-hydroxyoctanoate 3-O-beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranoside

Description

Ethyl (3R)-3-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octanoate belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. Ethyl 3-hydroxyoctanoate 3-O-beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranoside is found in Physalis peruviana . Based on a literature review very few articles have been published on ethyl (3R)-3-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282222372D          

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M  END

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 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  4 20  1  1  0  0  0
 20 21  1  0  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  1  0  0  0
 26 29  1  6  0  0  0
 25 30  1  6  0  0  0
 24 31  1  6  0  0  0
 31 32  1  0  0  0  0
  3 33  1  1  0  0  0
  2 34  1  1  0  0  0
  1 35  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0075336

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC[C@H](CC(=O)OCC)O[C@@H]1O[C@H](CO[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C22H40O13/c1-3-5-6-7-11(8-14(24)31-4-2)33-22-20(30)18(28)16(26)13(35-22)10-32-21-19(29)17(27)15(25)12(9-23)34-21/h11-13,15-23,25-30H,3-10H2,1-2H3/t11-,12-,13-,15+,16+,17+,18+,19-,20-,21-,22-/m1/s1

> <INCHI_KEY>
QAIPLYVRKVVKMO-JIGDLYATSA-N

> <FORMULA>
C22H40O13

> <MOLECULAR_WEIGHT>
512.549

> <EXACT_MASS>
512.246891348

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
52.73429026354309

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
ethyl (3R)-3-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octanoate

> <ALOGPS_LOGP>
-0.80

> <JCHEM_LOGP>
-1.5697468900000002

> <ALOGPS_LOGS>
-1.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.432789975100903

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.910550174170844

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083422322401

> <JCHEM_POLAR_SURFACE_AREA>
204.82999999999998

> <JCHEM_REFRACTIVITY>
116.13539999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.60e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl (3R)-3-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      13.337 -20.020   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.670 -20.790   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.670 -22.330   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.337 -23.100   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      12.003 -22.330   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      12.003 -20.790   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      10.669 -20.020   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      10.669 -18.480   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336 -17.710   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336 -16.170   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.669 -15.400   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       8.002 -15.400   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.002 -13.860   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668 -13.090   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.003 -17.710   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.003 -16.170   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.337 -15.400   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.337 -13.860   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.670 -13.090   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.337 -24.640   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      14.670 -25.410   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      14.670 -26.950   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      16.004 -27.720   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      16.004 -29.260   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.670 -30.030   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.337 -29.260   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.337 -27.720   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      12.003 -26.950   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      12.003 -30.030   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      14.670 -31.570   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      17.338 -30.030   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      17.338 -31.570   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      16.004 -23.100   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      16.004 -20.020   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      13.337 -18.480   0.000  0.00  0.00           O+0
CONECT    1    2    6   35                                                  
CONECT    2    1    3   34                                                  
CONECT    3    2    4   33                                                  
CONECT    4    3    5   20                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15    8   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20    4   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   31                                                  
CONECT   25   24   26   30                                                  
CONECT   26   25   27   29                                                  
CONECT   27   26   22   28                                                  
CONECT   28   27                                                            
CONECT   29   26                                                            
CONECT   30   25                                                            
CONECT   31   24   32                                                       
CONECT   32   31                                                            
CONECT   33    3                                                            
CONECT   34    2                                                            
CONECT   35    1                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   72    0
END

View in JSmol

Synonyms

Value	Source
Ethyl (3R)-3-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octanoic acid	Generator

Chemical Formula

C₂₂H₄₀O₁₃

Average Mass

512.5490 Da

Monoisotopic Mass

512.24689 Da

IUPAC Name

ethyl (3R)-3-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octanoate

Traditional Name

ethyl (3R)-3-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octanoate

CAS Registry Number

Not Available

SMILES

CCCCC[C@H](CC(=O)OCC)O[C@@H]1O[C@H](CO[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C22H40O13/c1-3-5-6-7-11(8-14(24)31-4-2)33-22-20(30)18(28)16(26)13(35-22)10-32-21-19(29)17(27)15(25)12(9-23)34-21/h11-13,15-23,25-30H,3-10H2,1-2H3/t11-,12-,13-,15+,16+,17+,18+,19-,20-,21-,22-/m1/s1

InChI Key

QAIPLYVRKVVKMO-JIGDLYATSA-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
Physalis peruviana	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides of mono- and disaccharides

Alternative Parents

Substituents

Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
O-glycosyl compound
Glycosyl compound
Disaccharide
Fatty acid ester
Oxane
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic 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	-0.8	ALOGPS
logP	-1.6	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	11.91	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	204.83 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	116.14 m³·mol⁻¹	ChemAxon
Polarizability	52.73 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

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

162876419

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Ethyl 3-hydroxyoctanoate 3-O-beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranoside (NP0075336)

MOL for NP0075336 (Ethyl 3-hydroxyoctanoate 3-O-beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranoside)

3D MOL for NP0075336 (Ethyl 3-hydroxyoctanoate 3-O-beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranoside)

3D SDF for NP0075336 (Ethyl 3-hydroxyoctanoate 3-O-beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranoside)

3D-SDF for NP0075336 (Ethyl 3-hydroxyoctanoate 3-O-beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranoside)

PDB for NP0075336 (Ethyl 3-hydroxyoctanoate 3-O-beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranoside)

3D PDB for NP0075336 (Ethyl 3-hydroxyoctanoate 3-O-beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranoside)

SMILES for NP0075336 (Ethyl 3-hydroxyoctanoate 3-O-beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranoside)

INCHI for NP0075336 (Ethyl 3-hydroxyoctanoate 3-O-beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranoside)

Structure for NP0075336 (Ethyl 3-hydroxyoctanoate 3-O-beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranoside)

3D Structure for NP0075336 (Ethyl 3-hydroxyoctanoate 3-O-beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranoside)