NP-MRD: Showing NP-Card for 5'-(2-{2,2-dimethyl-4-methylidene-3-[2-(2-oxooxolan-3-ylidene)ethyl]cyclohexyl}ethyl)-3,3,5-trimethyl-4,7-dioxaspiro[bicyclo[3.2.1]octane-6,2'-oxan]-2-one (NP0329627)

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Record Information

Version

2.0

Created at

2022-09-12 14:11:05 UTC

Updated at

2022-09-12 14:11:05 UTC

NP-MRD ID

NP0329627

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5'-(2-{2,2-dimethyl-4-methylidene-3-[2-(2-oxooxolan-3-ylidene)ethyl]cyclohexyl}ethyl)-3,3,5-trimethyl-4,7-dioxaspiro[bicyclo[3.2.1]octane-6,2'-oxan]-2-one

Description

5'-(2-{2,2-Dimethyl-4-methylidene-3-[2-(2-oxooxolan-3-ylidene)ethyl]cyclohexyl}ethyl)-3,3,5-trimethyl-4,7-dioxaspiro[bicyclo[3.2.1]Octane-6,2'-oxane]-2-one belongs to the class of organic compounds known as 1,4-dioxepanes. These are dioxepanes with the two ring oxygen atoms at position 1 and 4, respectively. 5'-(2-{2,2-dimethyl-4-methylidene-3-[2-(2-oxooxolan-3-ylidene)ethyl]cyclohexyl}ethyl)-3,3,5-trimethyl-4,7-dioxaspiro[bicyclo[3.2.1]octane-6,2'-oxan]-2-one is found in Tricholoma terreum. Based on a literature review very few articles have been published on 5'-(2-{2,2-dimethyl-4-methylidene-3-[2-(2-oxooxolan-3-ylidene)ethyl]cyclohexyl}ethyl)-3,3,5-trimethyl-4,7-dioxaspiro[bicyclo[3.2.1]Octane-6,2'-oxane]-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122216112D          

 36 40  0  0  0  0            999 V2000
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M  END

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M  END


  Mrv1652309122216112D          

 36 40  0  0  0  0            999 V2000
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    7.2815    1.8111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7372    2.4989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3693    3.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8250    3.9251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5363    4.6980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1822    5.2113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8700    4.7557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6492    3.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1625    3.3149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  8 13  1  0  0  0  0
 11 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
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  2  0  0  0  0
  5 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
  2 28  1  0  0  0  0
 28 29  1  0  0  0  0
 30 29  1  4  0  0  0
 30 31  2  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
 34 35  1  0  0  0  0
 31 35  1  0  0  0  0
 35 36  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0329627

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CC(OC11CCC(CCC3CCC(=C)C(CC=C4CCOC4=O)C3(C)C)CO1)C(=O)C(C)(C)O2

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

> <INCHI_KEY>
GNCISGASFVPTHV-UHFFFAOYSA-N

> <FORMULA>
C30H44O6

> <MOLECULAR_WEIGHT>
500.676

> <EXACT_MASS>
500.313789137

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
57.00517819096241

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5'-(2-{2,2-dimethyl-4-methylidene-3-[2-(2-oxooxolan-3-ylidene)ethyl]cyclohexyl}ethyl)-3,3,5-trimethyl-4,7-dioxaspiro[bicyclo[3.2.1]octane-6,2'-oxane]-2-one

> <JCHEM_LOGP>
6.145320251333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.733560700883533

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8795394675639954

> <JCHEM_POLAR_SURFACE_AREA>
71.06

> <JCHEM_REFRACTIVITY>
138.10970000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
5'-(2-{2,2-dimethyl-4-methylidene-3-[2-(2-oxooxolan-3-ylidene)ethyl]cyclohexyl}ethyl)-3,3,5-trimethyl-4,7-dioxaspiro[bicyclo[3.2.1]octane-6,2'-oxane]-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      15.816   1.908   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.279   2.002   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.428   0.718   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.891   0.813   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.205   2.192   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.668   2.286   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.817   1.002   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.280   1.097   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.429  -0.187   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.892  -0.092   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.206   1.286   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.056   2.570   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.593   2.475   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.624   2.712   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.147   3.146   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.400   1.381   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.454  -0.058   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.338  -1.318   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.934  -0.307   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.791   0.725   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.039  -0.619   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.686   1.159   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.886   2.262   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.458   3.014   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      12.055   3.475   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.643   4.090   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.415   4.973   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.592   3.381   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.443   4.665   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.756   6.043   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      14.607   7.327   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.068   8.770   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      15.273   9.728   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      16.557   8.877   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      16.145   7.394   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      17.103   6.188   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   28                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   25                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   14   17                                             
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14   11   15                                                       
CONECT   15   14   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   11   18   19                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20   15   24                                                  
CONECT   24   23                                                            
CONECT   25    5   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25    2   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   35                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   31   36                                                  
CONECT   36   35                                                            
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

5'-(2-{2,2-dimethyl-4-methylidene-3-[2-(2-oxooxolan-3-ylidene)ethyl]cyclohexyl}ethyl)-3,3,5-trimethyl-4,7-dioxaspiro[bicyclo[3.2.1]octane-6,2'-oxane]-2-one

Traditional Name

5'-(2-{2,2-dimethyl-4-methylidene-3-[2-(2-oxooxolan-3-ylidene)ethyl]cyclohexyl}ethyl)-3,3,5-trimethyl-4,7-dioxaspiro[bicyclo[3.2.1]octane-6,2'-oxane]-2-one

CAS Registry Number

Not Available

SMILES

CC12CC(OC11CCC(CCC3CCC(=C)C(CC=C4CCOC4=O)C3(C)C)CO1)C(=O)C(C)(C)O2

InChI Identifier

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

InChI Key

GNCISGASFVPTHV-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 terreum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,4-dioxepanes. These are dioxepanes with the two ring oxygen atoms at position 1 and 4, respectively.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dioxepanes

Sub Class

1,4-dioxepanes

Direct Parent

1,4-dioxepanes

Alternative Parents

Substituents

Ketal
1,4-dioxepane
Oxane
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	6.15	ChemAxon
pKa (Strongest Acidic)	17.73	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	71.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	138.11 m³·mol⁻¹	ChemAxon
Polarizability	57.01 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

163059808

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5'-(2-{2,2-dimethyl-4-methylidene-3-[2-(2-oxooxolan-3-ylidene)ethyl]cyclohexyl}ethyl)-3,3,5-trimethyl-4,7-dioxaspiro[bicyclo[3.2.1]octane-6,2'-oxan]-2-one (NP0329627)

MOL for NP0329627 (5'-(2-{2,2-dimethyl-4-methylidene-3-[2-(2-oxooxolan-3-ylidene)ethyl]cyclohexyl}ethyl)-3,3,5-trimethyl-4,7-dioxaspiro[bicyclo[3.2.1]octane-6,2'-oxan]-2-one)

3D MOL for NP0329627 (5'-(2-{2,2-dimethyl-4-methylidene-3-[2-(2-oxooxolan-3-ylidene)ethyl]cyclohexyl}ethyl)-3,3,5-trimethyl-4,7-dioxaspiro[bicyclo[3.2.1]octane-6,2'-oxan]-2-one)

3D SDF for NP0329627 (5'-(2-{2,2-dimethyl-4-methylidene-3-[2-(2-oxooxolan-3-ylidene)ethyl]cyclohexyl}ethyl)-3,3,5-trimethyl-4,7-dioxaspiro[bicyclo[3.2.1]octane-6,2'-oxan]-2-one)

3D-SDF for NP0329627 (5'-(2-{2,2-dimethyl-4-methylidene-3-[2-(2-oxooxolan-3-ylidene)ethyl]cyclohexyl}ethyl)-3,3,5-trimethyl-4,7-dioxaspiro[bicyclo[3.2.1]octane-6,2'-oxan]-2-one)

PDB for NP0329627 (5'-(2-{2,2-dimethyl-4-methylidene-3-[2-(2-oxooxolan-3-ylidene)ethyl]cyclohexyl}ethyl)-3,3,5-trimethyl-4,7-dioxaspiro[bicyclo[3.2.1]octane-6,2'-oxan]-2-one)

3D PDB for NP0329627 (5'-(2-{2,2-dimethyl-4-methylidene-3-[2-(2-oxooxolan-3-ylidene)ethyl]cyclohexyl}ethyl)-3,3,5-trimethyl-4,7-dioxaspiro[bicyclo[3.2.1]octane-6,2'-oxan]-2-one)

SMILES for NP0329627 (5'-(2-{2,2-dimethyl-4-methylidene-3-[2-(2-oxooxolan-3-ylidene)ethyl]cyclohexyl}ethyl)-3,3,5-trimethyl-4,7-dioxaspiro[bicyclo[3.2.1]octane-6,2'-oxan]-2-one)

INCHI for NP0329627 (5'-(2-{2,2-dimethyl-4-methylidene-3-[2-(2-oxooxolan-3-ylidene)ethyl]cyclohexyl}ethyl)-3,3,5-trimethyl-4,7-dioxaspiro[bicyclo[3.2.1]octane-6,2'-oxan]-2-one)

Structure for NP0329627 (5'-(2-{2,2-dimethyl-4-methylidene-3-[2-(2-oxooxolan-3-ylidene)ethyl]cyclohexyl}ethyl)-3,3,5-trimethyl-4,7-dioxaspiro[bicyclo[3.2.1]octane-6,2'-oxan]-2-one)

3D Structure for NP0329627 (5'-(2-{2,2-dimethyl-4-methylidene-3-[2-(2-oxooxolan-3-ylidene)ethyl]cyclohexyl}ethyl)-3,3,5-trimethyl-4,7-dioxaspiro[bicyclo[3.2.1]octane-6,2'-oxan]-2-one)