NP-MRD: Showing NP-Card for 5-(acetyloxy)-2-[(acetyloxy)methyl]-4-[(2-methylpropanoyl)oxy]-6-(octyloxy)oxan-3-yl 2-methylpropanoate (NP0254627)

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Record Information

Version

2.0

Created at

2022-09-07 18:50:56 UTC

Updated at

2022-09-07 18:50:56 UTC

NP-MRD ID

NP0254627

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-(acetyloxy)-2-[(acetyloxy)methyl]-4-[(2-methylpropanoyl)oxy]-6-(octyloxy)oxan-3-yl 2-methylpropanoate

Description

3-(Acetyloxy)-6-[(acetyloxy)methyl]-5-[(2-methylpropanoyl)oxy]-2-(octyloxy)oxan-4-yl 2-methylpropanoate 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. 5-(acetyloxy)-2-[(acetyloxy)methyl]-4-[(2-methylpropanoyl)oxy]-6-(octyloxy)oxan-3-yl 2-methylpropanoate is found in Arctostaphylos pumila. 3-(Acetyloxy)-6-[(acetyloxy)methyl]-5-[(2-methylpropanoyl)oxy]-2-(octyloxy)oxan-4-yl 2-methylpropanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191521432D          

 36 36  0  0  0  0            999 V2000
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -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
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    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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    9.2881   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4302   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
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 25 32  1  0  0  0  0
 10 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004191521432D          

 36 36  0  0  0  0            999 V2000
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.8592   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 25 32  1  0  0  0  0
 10 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0254627

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCOC1OC(COC(C)=O)C(OC(=O)C(C)C)C(OC(=O)C(C)C)C1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H44O10/c1-8-9-10-11-12-13-14-31-26-23(33-19(7)28)22(36-25(30)17(4)5)21(35-24(29)16(2)3)20(34-26)15-32-18(6)27/h16-17,20-23,26H,8-15H2,1-7H3

> <INCHI_KEY>
PSCONMQJGRBKNB-UHFFFAOYSA-N

> <FORMULA>
C26H44O10

> <MOLECULAR_WEIGHT>
516.628

> <EXACT_MASS>
516.293447617

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
56.92717755013726

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-(acetyloxy)-2-[(acetyloxy)methyl]-4-[(2-methylpropanoyl)oxy]-6-(octyloxy)oxan-3-yl 2-methylpropanoate

> <ALOGPS_LOGP>
4.09

> <JCHEM_LOGP>
5.064306852333333

> <ALOGPS_LOGS>
-4.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.060957579173559

> <JCHEM_POLAR_SURFACE_AREA>
123.66000000000003

> <JCHEM_REFRACTIVITY>
127.96099999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
19

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.09e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-(acetyloxy)-2-[(acetyloxy)methyl]-4-[(2-methylpropanoyl)oxy]-6-(octyloxy)oxan-3-yl 2-methylpropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         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       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      13.337  -9.240   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      16.004  -9.240   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      17.338 -10.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.672  -9.240   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      18.672  -7.700   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      17.338  -6.930   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      16.004  -7.700   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      17.338  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.338 -11.550   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      18.672 -12.320   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      20.005 -11.550   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      20.005 -10.010   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      21.339 -12.320   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      22.673 -11.550   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      21.339 -13.860   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.004 -12.320   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      16.004 -13.860   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      17.338 -14.630   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      18.672 -13.860   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      17.338 -16.170   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      18.672 -16.940   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.004 -16.940   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      13.337 -12.320   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      13.337 -13.860   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      14.670 -14.630   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      12.003 -14.630   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   32                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   12   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   18   26   32                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   25   10   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   72    0
END

View in JSmol

Synonyms

Value	Source
3-(Acetyloxy)-6-[(acetyloxy)methyl]-5-[(2-methylpropanoyl)oxy]-2-(octyloxy)oxan-4-yl 2-methylpropanoic acid	Generator

Chemical Formula

C₂₆H₄₄O₁₀

Average Mass

516.6280 Da

Monoisotopic Mass

516.29345 Da

IUPAC Name

5-(acetyloxy)-2-[(acetyloxy)methyl]-4-[(2-methylpropanoyl)oxy]-6-(octyloxy)oxan-3-yl 2-methylpropanoate

Traditional Name

5-(acetyloxy)-2-[(acetyloxy)methyl]-4-[(2-methylpropanoyl)oxy]-6-(octyloxy)oxan-3-yl 2-methylpropanoate

CAS Registry Number

Not Available

SMILES

CCCCCCCCOC1OC(COC(C)=O)C(OC(=O)C(C)C)C(OC(=O)C(C)C)C1OC(C)=O

InChI Identifier

InChI=1S/C26H44O10/c1-8-9-10-11-12-13-14-31-26-23(33-19(7)28)22(36-25(30)17(4)5)21(35-24(29)16(2)3)20(34-26)15-32-18(6)27/h16-17,20-23,26H,8-15H2,1-7H3

InChI Key

PSCONMQJGRBKNB-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
Arctostaphylos pumila	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
Tetracarboxylic acid or derivatives
Alkyl glycoside
Glycosyl compound
O-glycosyl compound
Monosaccharide
Oxane
Carboxylic acid ester
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
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	4.09	ALOGPS
logP	5.06	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	123.66 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	127.96 m³·mol⁻¹	ChemAxon
Polarizability	56.93 Å³	ChemAxon
Number of Rings	1	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-(acetyloxy)-2-[(acetyloxy)methyl]-4-[(2-methylpropanoyl)oxy]-6-(octyloxy)oxan-3-yl 2-methylpropanoate (NP0254627)

MOL for NP0254627 (5-(acetyloxy)-2-[(acetyloxy)methyl]-4-[(2-methylpropanoyl)oxy]-6-(octyloxy)oxan-3-yl 2-methylpropanoate)

3D MOL for NP0254627 (5-(acetyloxy)-2-[(acetyloxy)methyl]-4-[(2-methylpropanoyl)oxy]-6-(octyloxy)oxan-3-yl 2-methylpropanoate)

3D SDF for NP0254627 (5-(acetyloxy)-2-[(acetyloxy)methyl]-4-[(2-methylpropanoyl)oxy]-6-(octyloxy)oxan-3-yl 2-methylpropanoate)

3D-SDF for NP0254627 (5-(acetyloxy)-2-[(acetyloxy)methyl]-4-[(2-methylpropanoyl)oxy]-6-(octyloxy)oxan-3-yl 2-methylpropanoate)

PDB for NP0254627 (5-(acetyloxy)-2-[(acetyloxy)methyl]-4-[(2-methylpropanoyl)oxy]-6-(octyloxy)oxan-3-yl 2-methylpropanoate)

3D PDB for NP0254627 (5-(acetyloxy)-2-[(acetyloxy)methyl]-4-[(2-methylpropanoyl)oxy]-6-(octyloxy)oxan-3-yl 2-methylpropanoate)

SMILES for NP0254627 (5-(acetyloxy)-2-[(acetyloxy)methyl]-4-[(2-methylpropanoyl)oxy]-6-(octyloxy)oxan-3-yl 2-methylpropanoate)

INCHI for NP0254627 (5-(acetyloxy)-2-[(acetyloxy)methyl]-4-[(2-methylpropanoyl)oxy]-6-(octyloxy)oxan-3-yl 2-methylpropanoate)

Structure for NP0254627 (5-(acetyloxy)-2-[(acetyloxy)methyl]-4-[(2-methylpropanoyl)oxy]-6-(octyloxy)oxan-3-yl 2-methylpropanoate)

3D Structure for NP0254627 (5-(acetyloxy)-2-[(acetyloxy)methyl]-4-[(2-methylpropanoyl)oxy]-6-(octyloxy)oxan-3-yl 2-methylpropanoate)