NP-MRD: Showing NP-Card for ethyl 3-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octanoate (NP0162235)

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Record Information

Version

2.0

Created at

2022-09-02 20:35:21 UTC

Updated at

2022-09-02 20:35:21 UTC

NP-MRD ID

NP0162235

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Ethyl 3-hydroxyoctanoate O-[glucosyl-(1->6)-glucoside] 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 O-[glucosyl-(1->6)-glucoside] is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Ethyl 3-hydroxyoctanoate O-[glucosyl-(1->6)-glucoside] has been detected, but not quantified in, fruits. ethyl 3-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octanoate is found in Physalis peruviana. This could make ethyl 3-hydroxyoctanoate O-[glucosyl-(1->6)-glucoside] a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061310372D          

 35 36  0  0  0  0            999 V2000
    2.1434    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7158    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 35 22  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv0541 05061310372D          

 35 36  0  0  0  0            999 V2000
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 20 18  1  0  0  0  0
 21 19  1  0  0  0  0
 22 20  1  0  0  0  0
 23  9  1  0  0  0  0
 24 14  2  0  0  0  0
 25 15  1  0  0  0  0
 26 16  1  0  0  0  0
 27 17  1  0  0  0  0
 28 18  1  0  0  0  0
 29 19  1  0  0  0  0
 30 20  1  0  0  0  0
 31  4  1  0  0  0  0
 31 14  1  0  0  0  0
 32 10  1  0  0  0  0
 32 21  1  0  0  0  0
 33 11  1  0  0  0  0
 33 22  1  0  0  0  0
 34 12  1  0  0  0  0
 34 21  1  0  0  0  0
 35 13  1  0  0  0  0
 35 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0162235

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC(CC(=O)OCC)OC1OC(COC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O

> <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

> <INCHI_KEY>
QAIPLYVRKVVKMO-UHFFFAOYSA-N

> <FORMULA>
C22H40O13

> <MOLECULAR_WEIGHT>
512.5452

> <EXACT_MASS>
512.246891366

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
52.570830339147506

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
ethyl 3-{[3,4,5-trihydroxy-6-({[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>
204.82999999999996

> <JCHEM_REFRACTIVITY>
116.13539999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.60e+01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       4.001  10.010   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.003  10.010   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669   9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336   5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669  -1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002  -6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.003   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.669  -6.160   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.669   3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.336  -3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.668  -8.470   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       8.002   7.700   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       9.336  -8.470   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      13.337   0.000   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      12.003  -6.930   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      13.337   3.080   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      12.003  -3.850   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      10.669   4.620   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      10.669   7.700   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       8.002   3.080   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       9.336   0.770   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    5                                                       
CONECT    4    2   31                                                       
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6   11                                                       
CONECT    8   11   14                                                       
CONECT    9   12   23                                                       
CONECT   10   13   32                                                       
CONECT   11    7    8   33                                                  
CONECT   12    9   15   34                                                  
CONECT   13   10   16   35                                                  
CONECT   14    8   24   31                                                  
CONECT   15   12   17   25                                                  
CONECT   16   13   18   26                                                  
CONECT   17   15   19   27                                                  
CONECT   18   16   20   28                                                  
CONECT   19   17   21   29                                                  
CONECT   20   18   22   30                                                  
CONECT   21   19   32   34                                                  
CONECT   22   20   33   35                                                  
CONECT   23    9                                                            
CONECT   24   14                                                            
CONECT   25   15                                                            
CONECT   26   16                                                            
CONECT   27   17                                                            
CONECT   28   18                                                            
CONECT   29   19                                                            
CONECT   30   20                                                            
CONECT   31    4   14                                                       
CONECT   32   10   21                                                       
CONECT   33   11   22                                                       
CONECT   34   12   21                                                       
CONECT   35   13   22                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   72    0
END

View in JSmol

Synonyms

Value	Source
Ethyl 3-hydroxyoctanoic acid O-[glucosyl-(1->6)-glucoside]	Generator
Ethyl 3-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octanoic acid	Generator

Chemical Formula

C₂₂H₄₀O₁₃

Average Mass

512.5452 Da

Monoisotopic Mass

512.24689 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CCCCCC(CC(=O)OCC)OC1OC(COC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O

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

InChI Key

QAIPLYVRKVVKMO-UHFFFAOYSA-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
Physalis peruviana	LOTUS Database	35616633

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
Disaccharide
Glycosyl compound
O-glycosyl compound
Fatty acid ester
Oxane
Carboxylic acid ester
Secondary alcohol
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Polyol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Primary alcohol
Carbonyl group
Alcohol
Organooxygen compound
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	52.57 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

HMDB0038738

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018149

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

73981596

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for ethyl 3-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octanoate (NP0162235)

MOL for NP0162235 (ethyl 3-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octanoate)

3D MOL for NP0162235 (ethyl 3-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octanoate)

3D SDF for NP0162235 (ethyl 3-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octanoate)

3D-SDF for NP0162235 (ethyl 3-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octanoate)

PDB for NP0162235 (ethyl 3-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octanoate)

3D PDB for NP0162235 (ethyl 3-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octanoate)

SMILES for NP0162235 (ethyl 3-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octanoate)

INCHI for NP0162235 (ethyl 3-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octanoate)

Structure for NP0162235 (ethyl 3-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octanoate)

3D Structure for NP0162235 (ethyl 3-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octanoate)