NP-MRD: Showing NP-Card for 4,5-bis(acetyloxy)-2-methyl-6-{[6-methyl-2-(4-methylcyclohex-3-en-1-yl)-5-oxohept-6-en-2-yl]oxy}oxan-3-yl acetate (NP0235978)

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Record Information

Version

2.0

Created at

2022-09-06 18:45:57 UTC

Updated at

2022-09-06 18:45:57 UTC

NP-MRD ID

NP0235978

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,5-bis(acetyloxy)-2-methyl-6-{[6-methyl-2-(4-methylcyclohex-3-en-1-yl)-5-oxohept-6-en-2-yl]oxy}oxan-3-yl acetate

Description

4,5-Bis(acetyloxy)-6-methyl-2-{[6-methyl-2-(4-methylcyclohex-3-en-1-yl)-5-oxohept-6-en-2-yl]oxy}oxan-3-yl 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. 4,5-bis(acetyloxy)-2-methyl-6-{[6-methyl-2-(4-methylcyclohex-3-en-1-yl)-5-oxohept-6-en-2-yl]oxy}oxan-3-yl acetate is found in Carthamus lanatus. Based on a literature review very few articles have been published on 4,5-bis(acetyloxy)-6-methyl-2-{[6-methyl-2-(4-methylcyclohex-3-en-1-yl)-5-oxohept-6-en-2-yl]oxy}oxan-3-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062220452D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309062220452D          

 36 37  0  0  0  0            999 V2000
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  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  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
  8 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
 13 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
 17 19  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 20 25  1  0  0  0  0
 11 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
  8 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 30 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0235978

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(OC(C)(CCC(=O)C(C)=C)C2CCC(C)=CC2)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H40O9/c1-15(2)22(31)13-14-27(8,21-11-9-16(3)10-12-21)36-26-25(35-20(7)30)24(34-19(6)29)23(17(4)32-26)33-18(5)28/h9,17,21,23-26H,1,10-14H2,2-8H3

> <INCHI_KEY>
VZFHXCOIBHQWQJ-UHFFFAOYSA-N

> <FORMULA>
C27H40O9

> <MOLECULAR_WEIGHT>
508.608

> <EXACT_MASS>
508.267232868

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
54.43972260722374

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,5-bis(acetyloxy)-2-methyl-6-{[6-methyl-2-(4-methylcyclohex-3-en-1-yl)-5-oxohept-6-en-2-yl]oxy}oxan-3-yl acetate

> <JCHEM_LOGP>
3.902066373666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.160659088147977

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9805277178235143

> <JCHEM_POLAR_SURFACE_AREA>
114.43

> <JCHEM_REFRACTIVITY>
130.13230000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4,5-bis(acetyloxy)-2-methyl-6-{[6-methyl-2-(4-methylcyclohex-3-en-1-yl)-5-oxohept-6-en-2-yl]oxy}oxan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.588  -0.357   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.255  -1.127   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.255  -2.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.921  -0.357   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.921   1.183   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.413  -1.127   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.746  -0.357   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.080  -1.127   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.310  -2.461   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.414  -1.897   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.414  -3.437   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.080  -4.207   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.080  -5.747   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.746  -6.517   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.414  -6.517   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.414  -8.057   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.080  -8.827   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.746  -8.057   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.080 -10.367   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.747  -5.747   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.081  -6.517   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.081  -8.057   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.747  -8.827   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.415  -8.827   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.747  -4.207   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.081  -3.437   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       8.415  -4.207   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.415  -5.747   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       9.748  -3.437   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.850   0.206   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.080   1.540   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.850   2.874   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.390   2.874   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.160   4.207   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.160   1.540   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.390   0.206   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   30                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   25                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   15   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   20   11   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30    8   31   36                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   30                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   74    0
END

View in JSmol

Synonyms

Value	Source
4,5-Bis(acetyloxy)-6-methyl-2-{[6-methyl-2-(4-methylcyclohex-3-en-1-yl)-5-oxohept-6-en-2-yl]oxy}oxan-3-yl acetic acid	Generator

Chemical Formula

C₂₇H₄₀O₉

Average Mass

508.6080 Da

Monoisotopic Mass

508.26723 Da

IUPAC Name

4,5-bis(acetyloxy)-2-methyl-6-{[6-methyl-2-(4-methylcyclohex-3-en-1-yl)-5-oxohept-6-en-2-yl]oxy}oxan-3-yl acetate

Traditional Name

4,5-bis(acetyloxy)-2-methyl-6-{[6-methyl-2-(4-methylcyclohex-3-en-1-yl)-5-oxohept-6-en-2-yl]oxy}oxan-3-yl acetate

CAS Registry Number

Not Available

SMILES

CC1OC(OC(C)(CCC(=O)C(C)=C)C2CCC(C)=CC2)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O

InChI Identifier

InChI=1S/C27H40O9/c1-15(2)22(31)13-14-27(8,21-11-9-16(3)10-12-21)36-26-25(35-20(7)30)24(34-19(6)29)23(17(4)32-26)33-18(5)28/h9,17,21,23-26H,1,10-14H2,2-8H3

InChI Key

VZFHXCOIBHQWQJ-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
Carthamus lanatus	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
Bisabolane sesquiterpenoid
Sesquiterpenoid
Alkyl glycoside
Glycosyl compound
O-glycosyl compound
Tricarboxylic acid or derivatives
Monosaccharide
Alpha-branched alpha,beta-unsaturated-ketone
Oxane
Acryloyl-group
Enone
Alpha,beta-unsaturated ketone
Ketone
Carboxylic acid ester
Oxacycle
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
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	3.9	ChemAxon
pKa (Strongest Acidic)	19.16	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	114.43 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	130.13 m³·mol⁻¹	ChemAxon
Polarizability	54.44 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

14488662

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4,5-bis(acetyloxy)-2-methyl-6-{[6-methyl-2-(4-methylcyclohex-3-en-1-yl)-5-oxohept-6-en-2-yl]oxy}oxan-3-yl acetate (NP0235978)

MOL for NP0235978 (4,5-bis(acetyloxy)-2-methyl-6-{[6-methyl-2-(4-methylcyclohex-3-en-1-yl)-5-oxohept-6-en-2-yl]oxy}oxan-3-yl acetate)

3D MOL for NP0235978 (4,5-bis(acetyloxy)-2-methyl-6-{[6-methyl-2-(4-methylcyclohex-3-en-1-yl)-5-oxohept-6-en-2-yl]oxy}oxan-3-yl acetate)

3D SDF for NP0235978 (4,5-bis(acetyloxy)-2-methyl-6-{[6-methyl-2-(4-methylcyclohex-3-en-1-yl)-5-oxohept-6-en-2-yl]oxy}oxan-3-yl acetate)

3D-SDF for NP0235978 (4,5-bis(acetyloxy)-2-methyl-6-{[6-methyl-2-(4-methylcyclohex-3-en-1-yl)-5-oxohept-6-en-2-yl]oxy}oxan-3-yl acetate)

PDB for NP0235978 (4,5-bis(acetyloxy)-2-methyl-6-{[6-methyl-2-(4-methylcyclohex-3-en-1-yl)-5-oxohept-6-en-2-yl]oxy}oxan-3-yl acetate)

3D PDB for NP0235978 (4,5-bis(acetyloxy)-2-methyl-6-{[6-methyl-2-(4-methylcyclohex-3-en-1-yl)-5-oxohept-6-en-2-yl]oxy}oxan-3-yl acetate)

SMILES for NP0235978 (4,5-bis(acetyloxy)-2-methyl-6-{[6-methyl-2-(4-methylcyclohex-3-en-1-yl)-5-oxohept-6-en-2-yl]oxy}oxan-3-yl acetate)

INCHI for NP0235978 (4,5-bis(acetyloxy)-2-methyl-6-{[6-methyl-2-(4-methylcyclohex-3-en-1-yl)-5-oxohept-6-en-2-yl]oxy}oxan-3-yl acetate)

Structure for NP0235978 (4,5-bis(acetyloxy)-2-methyl-6-{[6-methyl-2-(4-methylcyclohex-3-en-1-yl)-5-oxohept-6-en-2-yl]oxy}oxan-3-yl acetate)

3D Structure for NP0235978 (4,5-bis(acetyloxy)-2-methyl-6-{[6-methyl-2-(4-methylcyclohex-3-en-1-yl)-5-oxohept-6-en-2-yl]oxy}oxan-3-yl acetate)