NP-MRD: Showing NP-Card for 4,5-bis(acetyloxy)-6-methyl-2-{[6-methyl-2-(4-methylcyclohex-3-en-1-yl)hept-5-en-2-yl]oxy}oxan-3-yl acetate (NP0158220)

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Record Information

Version

2.0

Created at

2022-09-02 15:46:24 UTC

Updated at

2022-09-02 15:46:24 UTC

NP-MRD ID

NP0158220

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022217462D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309022217462D          

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  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  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
  6  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
 11 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
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 19 25  1  0  0  0  0
  9 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 26 31  1  0  0  0  0
  5 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0158220

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H42O8/c1-16(2)10-9-15-27(8,22-13-11-17(3)12-14-22)35-26-25(34-21(7)30)24(33-20(6)29)23(18(4)31-26)32-19(5)28/h10-11,18,22-26H,9,12-15H2,1-8H3

> <INCHI_KEY>
OLZQPRLALKGOBH-UHFFFAOYSA-N

> <FORMULA>
C27H42O8

> <MOLECULAR_WEIGHT>
494.625

> <EXACT_MASS>
494.287968312

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
54.762050144468674

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
4.58

> <JCHEM_LOGP>
4.5114160646666654

> <ALOGPS_LOGS>
-5.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.075313522553781

> <JCHEM_POLAR_SURFACE_AREA>
97.36000000000001

> <JCHEM_REFRACTIVITY>
130.51160000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.62e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.413   0.413   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.413  -1.127   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.921  -1.897   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -1.746  -1.897   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.746  -3.437   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.080  -4.207   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.414  -3.437   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.080  -5.747   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.746  -6.517   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.746  -8.057   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -3.080  -8.827   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.850  -7.494   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.414  -9.597   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.747  -8.827   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -7.081  -9.597   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.415  -8.827   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -9.748  -9.597   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -8.415  -7.287   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.310 -10.161   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.770 -10.161   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000 -11.495   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.770 -12.828   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000 -14.162   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.310 -12.828   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.080 -11.495   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.413  -5.747   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.921  -6.517   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.921  -8.057   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.413  -8.827   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.255  -8.827   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -0.413  -4.207   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.921  -3.437   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.255  -4.207   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.255  -5.747   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       3.588  -3.437   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   31                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   26                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13   19                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   11   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   19                                                       
CONECT   26    9   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   26    5   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   72    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₂₇H₄₂O₈

Average Mass

494.6250 Da

Monoisotopic Mass

494.28797 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C27H42O8/c1-16(2)10-9-15-27(8,22-13-11-17(3)12-14-22)35-26-25(34-21(7)30)24(33-20(6)29)23(18(4)31-26)32-19(5)28/h10-11,18,22-26H,9,12-15H2,1-8H3

InChI Key

OLZQPRLALKGOBH-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
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	4.58	ALOGPS
logP	4.51	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	97.36 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	130.51 m³·mol⁻¹	ChemAxon
Polarizability	54.76 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

14488666

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)-6-methyl-2-{[6-methyl-2-(4-methylcyclohex-3-en-1-yl)hept-5-en-2-yl]oxy}oxan-3-yl acetate (NP0158220)

MOL for NP0158220 (4,5-bis(acetyloxy)-6-methyl-2-{[6-methyl-2-(4-methylcyclohex-3-en-1-yl)hept-5-en-2-yl]oxy}oxan-3-yl acetate)

3D MOL for NP0158220 (4,5-bis(acetyloxy)-6-methyl-2-{[6-methyl-2-(4-methylcyclohex-3-en-1-yl)hept-5-en-2-yl]oxy}oxan-3-yl acetate)

3D SDF for NP0158220 (4,5-bis(acetyloxy)-6-methyl-2-{[6-methyl-2-(4-methylcyclohex-3-en-1-yl)hept-5-en-2-yl]oxy}oxan-3-yl acetate)

3D-SDF for NP0158220 (4,5-bis(acetyloxy)-6-methyl-2-{[6-methyl-2-(4-methylcyclohex-3-en-1-yl)hept-5-en-2-yl]oxy}oxan-3-yl acetate)

PDB for NP0158220 (4,5-bis(acetyloxy)-6-methyl-2-{[6-methyl-2-(4-methylcyclohex-3-en-1-yl)hept-5-en-2-yl]oxy}oxan-3-yl acetate)

3D PDB for NP0158220 (4,5-bis(acetyloxy)-6-methyl-2-{[6-methyl-2-(4-methylcyclohex-3-en-1-yl)hept-5-en-2-yl]oxy}oxan-3-yl acetate)

SMILES for NP0158220 (4,5-bis(acetyloxy)-6-methyl-2-{[6-methyl-2-(4-methylcyclohex-3-en-1-yl)hept-5-en-2-yl]oxy}oxan-3-yl acetate)

INCHI for NP0158220 (4,5-bis(acetyloxy)-6-methyl-2-{[6-methyl-2-(4-methylcyclohex-3-en-1-yl)hept-5-en-2-yl]oxy}oxan-3-yl acetate)

Structure for NP0158220 (4,5-bis(acetyloxy)-6-methyl-2-{[6-methyl-2-(4-methylcyclohex-3-en-1-yl)hept-5-en-2-yl]oxy}oxan-3-yl acetate)

3D Structure for NP0158220 (4,5-bis(acetyloxy)-6-methyl-2-{[6-methyl-2-(4-methylcyclohex-3-en-1-yl)hept-5-en-2-yl]oxy}oxan-3-yl acetate)