NP-MRD: Showing NP-Card for [3,4,5-tris(acetyloxy)-6-{[4-(2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)but-3-en-2-yl]oxy}oxan-2-yl]methyl acetate (NP0330638)

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Record Information

Version

2.0

Created at

2022-09-12 16:10:47 UTC

Updated at

2022-09-12 16:10:48 UTC

NP-MRD ID

NP0330638

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[3,4,5-tris(acetyloxy)-6-{[4-(2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)but-3-en-2-yl]oxy}oxan-2-yl]methyl acetate

Description

[3,4,5-Tris(acetyloxy)-6-{[4-(2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)but-3-en-2-yl]oxy}oxan-2-yl]methyl acetate 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. [3,4,5-tris(acetyloxy)-6-{[4-(2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)but-3-en-2-yl]oxy}oxan-2-yl]methyl acetate is found in Rosa transmorrisonensis. [3,4,5-Tris(acetyloxy)-6-{[4-(2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)but-3-en-2-yl]oxy}oxan-2-yl]methyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241505182D          

 38 39  0  0  0  0            999 V2000
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 30 38  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004241505182D          

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    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8661   -0.6996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2534   -0.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    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  2  0  0  0  0
  9 11  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 17 22  1  0  0  0  0
  4 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 27  2  1  4  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 29 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 30 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0330638

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(OC1OC(COC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O)C=CC1C(C)=CC(=O)CC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H38O11/c1-14-11-20(32)12-27(7,8)21(14)10-9-15(2)34-26-25(37-19(6)31)24(36-18(5)30)23(35-17(4)29)22(38-26)13-33-16(3)28/h9-11,15,21-26H,12-13H2,1-8H3

> <INCHI_KEY>
NILGFPDWHHOUSF-UHFFFAOYSA-N

> <FORMULA>
C27H38O11

> <MOLECULAR_WEIGHT>
538.59

> <EXACT_MASS>
538.241412044

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
55.868335051993746

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[3,4,5-tris(acetyloxy)-6-{[4-(2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)but-3-en-2-yl]oxy}oxan-2-yl]methyl acetate

> <ALOGPS_LOGP>
2.19

> <JCHEM_LOGP>
2.2601498756666647

> <ALOGPS_LOGS>
-4.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.009873428875517

> <JCHEM_POLAR_SURFACE_AREA>
140.73000000000002

> <JCHEM_REFRACTIVITY>
132.7264

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.08e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[3,4,5-tris(acetyloxy)-6-{[4-(2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)but-3-en-2-yl]oxy}oxan-2-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334 -10.010   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       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.667 -12.320   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.483  -1.306   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.206  -0.054   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   27                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   22                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    6   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   12   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   17    4   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27    2   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   35                                                  
CONECT   30   29   31   38                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   29   36   37                                             
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   30                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   78    0
END

View in JSmol

Synonyms

Value	Source
[3,4,5-Tris(acetyloxy)-6-{[4-(2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)but-3-en-2-yl]oxy}oxan-2-yl]methyl acetic acid	Generator

Chemical Formula

C₂₇H₃₈O₁₁

Average Mass

538.5900 Da

Monoisotopic Mass

538.24141 Da

IUPAC Name

[3,4,5-tris(acetyloxy)-6-{[4-(2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)but-3-en-2-yl]oxy}oxan-2-yl]methyl acetate

Traditional Name

[3,4,5-tris(acetyloxy)-6-{[4-(2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)but-3-en-2-yl]oxy}oxan-2-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

CC(OC1OC(COC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O)C=CC1C(C)=CC(=O)CC1(C)C

InChI Identifier

InChI=1S/C27H38O11/c1-14-11-20(32)12-27(7,8)21(14)10-9-15(2)34-26-25(37-19(6)31)24(36-18(5)30)23(35-17(4)29)22(38-26)13-33-16(3)28/h9-11,15,21-26H,12-13H2,1-8H3

InChI Key

NILGFPDWHHOUSF-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
Rosa transmorrisonensis	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
Sesquiterpenoid
Megastigmane sesquiterpenoid
Cyclofarsesane sesquiterpenoid
Ionone derivative
Tetracarboxylic acid or derivatives
Alkyl glycoside
Glycosyl compound
O-glycosyl compound
Cyclohexenone
Monosaccharide
Oxane
Ketone
Carboxylic acid ester
Cyclic ketone
Oxacycle
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen 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	2.19	ALOGPS
logP	2.26	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	140.73 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	132.73 m³·mol⁻¹	ChemAxon
Polarizability	55.87 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

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 [3,4,5-tris(acetyloxy)-6-{[4-(2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)but-3-en-2-yl]oxy}oxan-2-yl]methyl acetate (NP0330638)

MOL for NP0330638 ([3,4,5-tris(acetyloxy)-6-{[4-(2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)but-3-en-2-yl]oxy}oxan-2-yl]methyl acetate)

3D MOL for NP0330638 ([3,4,5-tris(acetyloxy)-6-{[4-(2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)but-3-en-2-yl]oxy}oxan-2-yl]methyl acetate)

3D SDF for NP0330638 ([3,4,5-tris(acetyloxy)-6-{[4-(2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)but-3-en-2-yl]oxy}oxan-2-yl]methyl acetate)

3D-SDF for NP0330638 ([3,4,5-tris(acetyloxy)-6-{[4-(2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)but-3-en-2-yl]oxy}oxan-2-yl]methyl acetate)

PDB for NP0330638 ([3,4,5-tris(acetyloxy)-6-{[4-(2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)but-3-en-2-yl]oxy}oxan-2-yl]methyl acetate)

3D PDB for NP0330638 ([3,4,5-tris(acetyloxy)-6-{[4-(2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)but-3-en-2-yl]oxy}oxan-2-yl]methyl acetate)

SMILES for NP0330638 ([3,4,5-tris(acetyloxy)-6-{[4-(2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)but-3-en-2-yl]oxy}oxan-2-yl]methyl acetate)

INCHI for NP0330638 ([3,4,5-tris(acetyloxy)-6-{[4-(2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)but-3-en-2-yl]oxy}oxan-2-yl]methyl acetate)

Structure for NP0330638 ([3,4,5-tris(acetyloxy)-6-{[4-(2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)but-3-en-2-yl]oxy}oxan-2-yl]methyl acetate)

3D Structure for NP0330638 ([3,4,5-tris(acetyloxy)-6-{[4-(2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)but-3-en-2-yl]oxy}oxan-2-yl]methyl acetate)