NP-MRD: Showing NP-Card for 1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecane (NP0242284)

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Record Information

Version

1.0

Created at

2022-09-07 02:34:32 UTC

Updated at

2022-09-07 02:34:33 UTC

NP-MRD ID

NP0242284

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecane

Description

Isokessane, also known as b-kessane, belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms. Isokessane is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Isokessane has been detected, but not quantified in, a few different foods, such as fats and oils, herbs and spices, and tea. 1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecane is found in Geigeria aspera and Valeriana officinalis. This could make isokessane a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
    3.0682   -1.8106    0.6889 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4228   -0.9628   -0.3792 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0355    0.4001   -0.3455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8324    1.3523   -0.2696 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8913    0.5471    0.5782 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9552   -0.8104   -0.0349 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1487   -0.9058   -1.2978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2610   -0.4646   -1.1668 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4787    0.9728   -1.5753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9668    1.8565   -0.4932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4674    1.1194    0.7206 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4062    2.1701    1.8421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3296    0.1408    1.1673 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8599   -0.6559    0.1910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3440   -0.2725    0.0776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8268   -2.1336    0.5582 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9761   -1.2517    1.6442 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4190   -2.7277    0.7959 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0813   -2.1322    0.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5477   -1.4781   -1.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6884    0.6342   -1.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6064    0.5502    0.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4927    1.4774   -1.3105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1997    2.2650    0.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3494    0.4796    1.5952 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6626   -1.5507    0.7198 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6539   -0.2335   -2.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2737   -1.9329   -1.7027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8820   -1.0808   -1.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5960    1.0936   -1.6846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0693    1.1922   -2.5787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1790    2.5434   -0.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8048    2.5209   -0.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3493    2.7698    1.7176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3888    1.6902    2.8202 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4404    2.8125    1.6062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4363    0.8036    0.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8255   -0.7741    0.9638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7710   -0.6077   -0.8714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8340   -2.5932    0.5345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4458   -2.2921    1.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2234   -2.7208   -0.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  1
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
  6  2  1  0
 14  8  1  0
 11  5  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  6
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  1
  6 26  1  1
  7 27  1  0
  7 28  1  0
  8 29  1  6
  9 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
M  END


  Mrv1652307201900082D          

 16 18  0  0  0  0            999 V2000
    3.5676   -0.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0043   -0.2147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0903    0.8097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7802    2.2045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6630    0.6398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1188    1.2598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3846    0.1747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6003    0.7537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8418   -0.4592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2415   -0.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0240   -0.3504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4368    0.1123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3609    0.9338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5993    0.3568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6714    1.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8873    1.1299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  8  7  1  0  0  0  0
 10  1  1  0  0  0  0
 10  5  1  0  0  0  0
 11  7  1  0  0  0  0
 11  9  1  0  0  0  0
 12  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13  6  1  0  0  0  0
 13 12  1  0  0  0  0
 14  2  1  0  0  0  0
 14  3  1  0  0  0  0
 14 11  1  0  0  0  0
 15  4  1  0  0  0  0
 15  8  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0242284

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC2C1CC1CCC2(C)OC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H26O/c1-10-5-6-13-12(10)9-11-7-8-15(13,4)16-14(11,2)3/h10-13H,5-9H2,1-4H3

> <INCHI_KEY>
QRVMFXFSGYDNJI-UHFFFAOYSA-N

> <FORMULA>
C15H26O

> <MOLECULAR_WEIGHT>
222.372

> <EXACT_MASS>
222.198365457

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
27.331780852455744

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0^{2,6}]dodecane

> <ALOGPS_LOGP>
4.18

> <JCHEM_LOGP>
3.712842052666667

> <ALOGPS_LOGS>
-5.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.207917560818977

> <JCHEM_POLAR_SURFACE_AREA>
9.23

> <JCHEM_REFRACTIVITY>
66.8295

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.95e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0^{2,6}]dodecane

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 20-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUL-19         0                                  
HETATM    1  C   UNK     0       6.660  -1.544   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.008  -0.401   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.169   1.511   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.323   4.115   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.838   1.194   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.822   2.352   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.585   0.326   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.987   1.407   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.438  -0.857   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.051  -0.130   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.911  -0.654   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.549   0.210   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.407   1.743   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.119   0.666   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.120   2.589   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.656   2.109   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   14                                                            
CONECT    3   14                                                            
CONECT    4   15                                                            
CONECT    5    6   10                                                       
CONECT    6    5   13                                                       
CONECT    7    8   11                                                       
CONECT    8    7   15                                                       
CONECT    9   11   12                                                       
CONECT   10    1    5   12                                                  
CONECT   11    7    9   14                                                  
CONECT   12    9   10   13                                                  
CONECT   13    6   12   15                                                  
CONECT   14    2    3   11   16                                             
CONECT   15    4    8   13   16                                             
CONECT   16   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

View in JSmol

Synonyms

Value	Source
b-Kessane	HMDB

Chemical Formula

C₁₅H₂₆O

Average Mass

222.3720 Da

Monoisotopic Mass

222.19837 Da

IUPAC Name

1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0^{2,6}]dodecane

Traditional Name

1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0^{2,6}]dodecane

CAS Registry Number

Not Available

SMILES

CC1CCC2C1CC1CCC2(C)OC1(C)C

InChI Identifier

InChI=1S/C15H26O/c1-10-5-6-13-12(10)9-11-7-8-15(13,4)16-14(11,2)3/h10-13H,5-9H2,1-4H3

InChI Key

QRVMFXFSGYDNJI-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
Geigeria aspera	LOTUS Database	35616633
Valeriana officinalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxepanes

Sub Class

Not Available

Direct Parent

Oxepanes

Alternative Parents

Substituents

Oxepane
Oxane
Oxacycle
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
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	4.18	ALOGPS
logP	3.71	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	66.83 m³·mol⁻¹	ChemAxon
Polarizability	27.33 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0041575

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021582

KNApSAcK ID

C00020423

Chemspider ID

11380157

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

527491

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecane (NP0242284)

MOL for NP0242284 (1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecane)

3D MOL for NP0242284 (1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecane)

3D SDF for NP0242284 (1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecane)

3D-SDF for NP0242284 (1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecane)

PDB for NP0242284 (1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecane)

3D PDB for NP0242284 (1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecane)

SMILES for NP0242284 (1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecane)

INCHI for NP0242284 (1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecane)

Structure for NP0242284 (1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecane)

3D Structure for NP0242284 (1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0²,⁶]dodecane)