NP-MRD: Showing NP-Card for Kessane (NP0063560)

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Record Information

Version

2.0

Created at

2022-04-28 07:56:43 UTC

Updated at

2022-04-28 07:56:43 UTC

NP-MRD ID

NP0063560

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Kessane

Description

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. Kessane is found in Acacia nuperrima, Bothriochloa bladhii, Geigeria aspera, Heracleum dissectum, Olearia phlogopappa, Petasites albus , Petasites hybridus , Primula halleri, Valeriana fauriei and Valeriana officinalis . Kessane was first documented in 2017 (PMID: 29129053). Based on a literature review a small amount of articles have been published on Kessane (PMID: 33202983) (PMID: 31030559) (PMID: 29117116) (PMID: 28467692).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
   -3.1217    1.4617   -0.0207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2447    0.8098   -1.0285 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7377   -0.5768   -1.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6983   -1.5506   -0.8702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9981   -0.7561    0.1801 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8465    0.5632   -0.5956 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2422    1.6104    0.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1780    1.2835    0.5788 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2980    0.6114    1.9521 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7832   -0.7720    1.8540 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3935   -1.2232    0.4851 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3543   -2.7539    0.5482 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2323   -0.8607   -0.5186 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8430    0.3601   -0.3922 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2415    0.0833    0.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0924    1.0285   -1.7427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6499    2.2275    0.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6715    0.7215    0.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9454    1.9877   -0.5878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2093    1.4081   -1.9832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9044   -0.6794   -2.4789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6785   -0.7782   -0.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9910   -1.7299   -1.7184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1566   -2.4852   -0.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6330   -0.6132    1.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2490    0.3023   -1.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3756    2.5960   -0.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8040    1.6307    1.2287 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7746    2.2166    0.6295 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8192    1.2316    2.7414 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3990    0.6297    2.2039 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5017   -1.4731    2.3632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1461   -0.8357    2.4928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1872   -3.1832   -0.2935 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3949   -3.1359    0.5956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1129   -3.0334    1.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6698    1.0131    0.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9019   -0.2056   -0.6758 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2421   -0.7663    0.8700 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4599    1.9532   -1.8268 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8937    0.3192   -2.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1304    1.3635   -1.8615 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  1
 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  6
  7 27  1  0
  7 28  1  0
  8 29  1  1
  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


  Mrv1652304282209562D          

 16 18  0  0  1  0            999 V2000
    2.4368    1.0382    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3609    0.2167    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1188   -0.1093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6630    0.5107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2415    1.2199    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5676    1.9778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6714   -0.2362    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8873    0.0206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5993    0.7936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0240    1.5009    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8418    1.6097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3846    0.9758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6003    0.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1672    0.4883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0983    1.2342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7802   -1.0540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  5  6  1  6  0  0  0
  2  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
  1 11  1  6  0  0  0
 10 12  1  6  0  0  0
 12 13  1  0  0  0  0
  7 13  1  0  0  0  0
  9 14  1  0  0  0  0
  9 15  1  0  0  0  0
  7 16  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0063560

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@@H]2[C@@H]1C[C@H]1CC[C@]2(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/t10-,11-,12-,13-,15+/m1/s1

> <INCHI_KEY>
QRVMFXFSGYDNJI-HVNMYJMUSA-N

> <FORMULA>
C15H26O

> <MOLECULAR_WEIGHT>
222.372

> <EXACT_MASS>
222.198365457

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
27.238235392299067

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,5R,6R,8R)-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>
(1S,2R,5R,6R,8R)-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0^{2,6}]dodecane

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       4.549   1.938   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.407   0.404   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.822  -0.204   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.838   0.953   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.051   2.277   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.659   3.692   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.120  -0.441   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.656   0.038   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.119   1.481   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.912   2.802   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.438   3.005   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.585   1.821   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.987   0.741   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.312   0.911   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.183   2.304   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.323  -1.967   0.000  0.00  0.00           C+0
CONECT    1    2    5   11                                                  
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    1    6                                                  
CONECT    6    5                                                            
CONECT    7    2    8   13   16                                             
CONECT    8    7    9                                                       
CONECT    9    8   10   14   15                                             
CONECT   10    9   11   12                                                  
CONECT   11   10    1                                                       
CONECT   12   10   13                                                       
CONECT   13   12    7                                                       
CONECT   14    9                                                            
CONECT   15    9                                                            
CONECT   16    7                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₆O

Average Mass

222.3720 Da

Monoisotopic Mass

222.19837 Da

IUPAC Name

(1S,2R,5R,6R,8R)-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0^{2,6}]dodecane

Traditional Name

(1S,2R,5R,6R,8R)-1,5,9,9-tetramethyl-10-oxatricyclo[6.2.2.0^{2,6}]dodecane

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@@H]2[C@@H]1C[C@H]1CC[C@]2(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/t10-,11-,12-,13-,15+/m1/s1

InChI Key

QRVMFXFSGYDNJI-HVNMYJMUSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Acacia nuperrima	LOTUS Database	35616633
Bothriochloa bladhii	LOTUS Database	35616633
Geigeria aspera	LOTUS Database	35616633
Heracleum dissectum	LOTUS Database	35616633
Olearia phlogopappa	LOTUS Database	35616633
Petasites albus	Plant	KNApSAcK
Petasites hybridus	Plant	KNApSAcK
Primula halleri	Plant	KNApSAcK
Valeriana fauriei	LOTUS Database	35616633
Valeriana officinalis	Plant	KNApSAcK

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	27.24 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00020421

Chemspider ID

9485584

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11310616

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sadgrove NJ, Padilla-Gonzalez GF, Telford IRH, Greatrex BW, Jones GL, Andrew R, Bruhl JJ, Langat MK, Melnikovova I, Fernandez-Cusimamani E: Prostanthera (Lamiaceae) as a 'Cradle of Incense': Chemophenetics of Rare Essential Oils from Both New and Forgotten Australian 'Mint Bush' Species. Plants (Basel). 2020 Nov 13;9(11). pii: plants9111570. doi: 10.3390/plants9111570. [PubMed:33202983 ]
Dong FW, Li F, Ren JJ, Zhao CM, Diao HL, Li BJ, Li YP, Hu JM, He HP: Sesquiterpenoids from the roots and rhizomes of Valeriana amurensis and their effects on NGF-induced neurite outgrowth in PC12 cells. Nat Prod Res. 2021 Mar;35(5):757-762. doi: 10.1080/14786419.2019.1603223. Epub 2019 Apr 29. [PubMed:31030559 ]
Mileski KS, Trifunovic SS, Ciric AD, Sakic ZM, Ristic MS, Todorovic NM, Matevski VS, Marin PD, Tesevic VV, Dzamic AM: Research on Chemical Composition and Biological Properties Including Antiquorum Sensing Activity of Angelica pancicii Vandas Aerial Parts and Roots. J Agric Food Chem. 2017 Dec 20;65(50):10933-10949. doi: 10.1021/acs.jafc.7b04202. Epub 2017 Dec 8. [PubMed:29129053 ]
Parki A, Chaubey P, Prakash O, Kumar R, Pant AK: Seasonal Variation in Essential Oil Compositions and Antioxidant Properties of Acorus calamus L. Accessions. Medicines (Basel). 2017 Nov 8;4(4). pii: medicines4040081. doi: 10.3390/medicines4040081. [PubMed:29117116 ]
Chaib F, Allali H, Bennaceur M, Flamini G: Chemical Composition and Antimicrobial Activity of Essential Oils from the Aerial Parts of Asteriscus graveolens (Forssk.) Less. and Pulicaria incisa (Lam.) DC.: Two Asteraceae Herbs Growing Wild in the Hoggar. Chem Biodivers. 2017 Aug;14(8). doi: 10.1002/cbdv.201700092. Epub 2017 Jul 1. [PubMed:28467692 ]

Showing NP-Card for Kessane (NP0063560)

MOL for NP0063560 (Kessane)

3D MOL for NP0063560 (Kessane)

3D SDF for NP0063560 (Kessane)

3D-SDF for NP0063560 (Kessane)

PDB for NP0063560 (Kessane)

3D PDB for NP0063560 (Kessane)

SMILES for NP0063560 (Kessane)

INCHI for NP0063560 (Kessane)

Structure for NP0063560 (Kessane)

3D Structure for NP0063560 (Kessane)