NP-MRD: Showing NP-Card for 3-{2-[3-(2-{4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxan]-5'-yl}ethyl)-2,2-dimethyl-6-methylidenecyclohexyl]ethenyl}-5h-furan-2-one (NP0157648)

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Record Information

Version

2.0

Created at

2022-09-02 15:05:16 UTC

Updated at

2022-09-02 15:05:16 UTC

NP-MRD ID

NP0157648

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-{2-[3-(2-{4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxan]-5'-yl}ethyl)-2,2-dimethyl-6-methylidenecyclohexyl]ethenyl}-5h-furan-2-one

Description

3-{2-[3-(2-{4-Hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]Octane-2,2'-oxane]-5'-yl}ethyl)-2,2-dimethyl-6-methylidenecyclohexyl]ethenyl}-2,5-dihydrofuran-2-one belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals. 3-{2-[3-(2-{4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxan]-5'-yl}ethyl)-2,2-dimethyl-6-methylidenecyclohexyl]ethenyl}-5h-furan-2-one is found in Tricholoma saponaceum. 3-{2-[3-(2-{4-Hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]Octane-2,2'-oxane]-5'-yl}ethyl)-2,2-dimethyl-6-methylidenecyclohexyl]ethenyl}-2,5-dihydrofuran-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251506572D          

 36 40  0  0  0  0            999 V2000
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M  END

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M  END


  Mrv1533004251506572D          

 36 40  0  0  0  0            999 V2000
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   -4.5985    3.8289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8124    4.6256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1208    5.0753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4793    4.5565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6826    4.7704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2275    2.4900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2423    3.3149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5520    2.9636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6937    1.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5176    1.9728    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5 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  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 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
 21 23  1  0  0  0  0
 24 23  1  4  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 26 30  1  0  0  0  0
 30 31  2  0  0  0  0
 23 32  1  0  0  0  0
 18 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 15 35  1  0  0  0  0
 35 36  1  0  0  0  0
 12 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0157648

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)OC2(C)CCC1(O)OC21CCC(CCC2CCC(=C)C(C=CC3=CCOC3=O)C2(C)C)CO1

> <INCHI_IDENTIFIER>
InChI=1S/C30H44O6/c1-20-7-10-23(26(2,3)24(20)12-9-22-14-18-33-25(22)31)11-8-21-13-15-30(34-19-21)28(6)16-17-29(32,36-30)27(4,5)35-28/h9,12,14,21,23-24,32H,1,7-8,10-11,13,15-19H2,2-6H3

> <INCHI_KEY>
NNRRIHOQCYFQRJ-UHFFFAOYSA-N

> <FORMULA>
C30H44O6

> <MOLECULAR_WEIGHT>
500.676

> <EXACT_MASS>
500.313789137

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
57.16931474233961

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{2-[3-(2-{4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxane]-5'-yl}ethyl)-2,2-dimethyl-6-methylidenecyclohexyl]ethenyl}-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
5.31

> <JCHEM_LOGP>
5.901252768000001

> <ALOGPS_LOGS>
-6.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.579506743909413

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.930734101105148

> <JCHEM_PKA_STRONGEST_BASIC>
-3.911883013643037

> <JCHEM_POLAR_SURFACE_AREA>
74.22000000000001

> <JCHEM_REFRACTIVITY>
140.02370000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.64e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{2-[3-(2-{4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxane]-5'-yl}ethyl)-2,2-dimethyl-6-methylidenecyclohexyl]ethenyl}-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       9.845   1.628   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.615   2.554   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.740   3.605   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       7.916   1.182   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.378   1.100   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.680  -0.272   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.615   2.132   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.081   3.047   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.775   3.845   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.474   5.218   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       6.237   3.764   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.539   2.391   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.840   1.019   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.303   0.937   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.463   2.229   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.925   2.147   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.086   3.438   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.452   3.357   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.150   1.984   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.688   1.903   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.528   3.194   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -6.065   3.113   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.829   4.567   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.669   5.858   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -6.206   5.776   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -7.046   7.067   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -8.584   7.147   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -8.983   8.635   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -7.692   9.474   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -6.495   8.505   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -5.007   8.905   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -2.291   4.648   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.319   6.188   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.030   5.532   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.162   3.601   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.699   3.683   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    9                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7   12                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    2   10   11                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11    5   13   36                                             
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   35                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   32                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   32                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   30                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   26   31                                                  
CONECT   31   30                                                            
CONECT   32   23   18   33   34                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   15   36                                                       
CONECT   36   35   12                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₄O₆

Average Mass

500.6760 Da

Monoisotopic Mass

500.31379 Da

IUPAC Name

3-{2-[3-(2-{4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxane]-5'-yl}ethyl)-2,2-dimethyl-6-methylidenecyclohexyl]ethenyl}-2,5-dihydrofuran-2-one

Traditional Name

3-{2-[3-(2-{4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxane]-5'-yl}ethyl)-2,2-dimethyl-6-methylidenecyclohexyl]ethenyl}-5H-furan-2-one

CAS Registry Number

Not Available

SMILES

CC1(C)OC2(C)CCC1(O)OC21CCC(CCC2CCC(=C)C(C=CC3=CCOC3=O)C2(C)C)CO1

InChI Identifier

InChI=1S/C30H44O6/c1-20-7-10-23(26(2,3)24(20)12-9-22-14-18-33-25(22)31)11-8-21-13-15-30(34-19-21)28(6)16-17-29(32,36-30)27(4,5)35-28/h9,12,14,21,23-24,32H,1,7-8,10-11,13,15-19H2,2-6H3

InChI Key

NNRRIHOQCYFQRJ-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
Tricholoma saponaceum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Ketals

Alternative Parents

Substituents

Ketal
Para-dioxane
2-furanone
Oxane
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Hemiacetal
Lactone
Oxacycle
Dialkyl ether
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	5.31	ALOGPS
logP	5.9	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	10.93	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.22 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	140.02 m³·mol⁻¹	ChemAxon
Polarizability	57.17 Å³	ChemAxon
Number of Rings	5	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

73090495

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-{2-[3-(2-{4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxan]-5'-yl}ethyl)-2,2-dimethyl-6-methylidenecyclohexyl]ethenyl}-5h-furan-2-one (NP0157648)

MOL for NP0157648 (3-{2-[3-(2-{4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxan]-5'-yl}ethyl)-2,2-dimethyl-6-methylidenecyclohexyl]ethenyl}-5h-furan-2-one)

3D MOL for NP0157648 (3-{2-[3-(2-{4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxan]-5'-yl}ethyl)-2,2-dimethyl-6-methylidenecyclohexyl]ethenyl}-5h-furan-2-one)

3D SDF for NP0157648 (3-{2-[3-(2-{4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxan]-5'-yl}ethyl)-2,2-dimethyl-6-methylidenecyclohexyl]ethenyl}-5h-furan-2-one)

3D-SDF for NP0157648 (3-{2-[3-(2-{4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxan]-5'-yl}ethyl)-2,2-dimethyl-6-methylidenecyclohexyl]ethenyl}-5h-furan-2-one)

PDB for NP0157648 (3-{2-[3-(2-{4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxan]-5'-yl}ethyl)-2,2-dimethyl-6-methylidenecyclohexyl]ethenyl}-5h-furan-2-one)

3D PDB for NP0157648 (3-{2-[3-(2-{4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxan]-5'-yl}ethyl)-2,2-dimethyl-6-methylidenecyclohexyl]ethenyl}-5h-furan-2-one)

SMILES for NP0157648 (3-{2-[3-(2-{4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxan]-5'-yl}ethyl)-2,2-dimethyl-6-methylidenecyclohexyl]ethenyl}-5h-furan-2-one)

INCHI for NP0157648 (3-{2-[3-(2-{4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxan]-5'-yl}ethyl)-2,2-dimethyl-6-methylidenecyclohexyl]ethenyl}-5h-furan-2-one)

Structure for NP0157648 (3-{2-[3-(2-{4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxan]-5'-yl}ethyl)-2,2-dimethyl-6-methylidenecyclohexyl]ethenyl}-5h-furan-2-one)

3D Structure for NP0157648 (3-{2-[3-(2-{4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxan]-5'-yl}ethyl)-2,2-dimethyl-6-methylidenecyclohexyl]ethenyl}-5h-furan-2-one)