NP-MRD: Showing NP-Card for Kobusone (NP0137067)

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Record Information

Version

2.0

Created at

2022-05-30 16:40:43 UTC

Updated at

2025-06-11 03:41:06 UTC

NP-MRD ID

NP0137067

Natural Product DOI

https://doi.org/10.57994/0911

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Kobusone

Description

Kobusone belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Kobusone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, kobusone has been detected, but not quantified in, root vegetables. Kobusone is found in Lavandula angustifolia and Neolitsea hiiranensis. This could make kobusone a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
   -2.5239   -1.0412    1.3762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3354   -0.3624    0.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3372   -0.8309   -0.9723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3280    1.1383    0.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9102    1.2082   -0.3147 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0793    1.7656    0.6100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1118    1.6877    1.8094 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3261    2.4342    0.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4794    1.4749   -0.0294 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0860    0.4640   -1.0385 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9824   -0.3551   -1.6985 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3575   -0.9182   -0.6268 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2336   -1.2359    0.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0898   -1.6971   -0.6917 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1168   -1.0135    0.2821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9266   -0.2709   -0.4572 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4443   -2.1287    1.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8959   -0.5901    2.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5860   -0.8159    1.6910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3386   -0.8413   -0.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0105   -1.8113   -1.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3948   -0.0546   -1.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0737    1.6930   -0.3807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3631    1.4849    1.2739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9227    1.7851   -1.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1427    2.8886   -0.8541 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5962    3.2917    0.8086 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3264    2.0629   -0.4142 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7623    1.0540    0.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1688    0.6659   -1.6214 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2323   -0.8209    0.4247 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3473   -2.3446    0.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7751   -0.9273    1.5232 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2636   -2.7469   -0.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6584   -1.5924   -1.7210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2688   -1.8359    0.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6510   -0.3227    0.9600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9035   -0.5410   -1.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  1
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 11 12  1  0
  2 16  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  6
  5 25  1  6
  4 23  1  0
  4 24  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  6
M  END


  Mrv0541 05061309202D          

 16 18  0  0  0  0            999 V2000
    5.8458   -1.3842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8972   -2.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7241   -1.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1544    0.6831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3822    0.3928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5916   -1.6518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7666   -1.6605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1666   -0.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3526   -0.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2179   -1.1149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9326    0.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9773   -0.3260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0319   -1.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1291   -1.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4562    1.0467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3509   -0.8629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  7  6  1  0  0  0  0
  9  8  1  0  0  0  0
 10  6  1  0  0  0  0
 10  9  1  0  0  0  0
 11  4  1  0  0  0  0
 11  9  1  0  0  0  0
 12  5  1  0  0  0  0
 13  1  1  0  0  0  0
 13  2  1  0  0  0  0
 13  8  1  0  0  0  0
 13 10  1  0  0  0  0
 14  3  1  0  0  0  0
 14  7  1  0  0  0  0
 14 12  1  0  0  0  0
 15 11  2  0  0  0  0
 16 12  1  0  0  0  0
 16 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137067

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CCC3C(CC3(C)C)C(=O)CCC1O2

> <INCHI_IDENTIFIER>
InChI=1S/C14H22O2/c1-13(2)8-9-10(13)6-7-14(3)12(16-14)5-4-11(9)15/h9-10,12H,4-8H2,1-3H3

> <INCHI_KEY>
UETZJEZFLKASPR-UHFFFAOYSA-N

> <FORMULA>
C14H22O2

> <MOLECULAR_WEIGHT>
222.3233

> <EXACT_MASS>
222.161979948

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
25.44551485681503

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,12,12-trimethyl-5-oxatricyclo[8.2.0.0⁴,⁶]dodecan-9-one

> <ALOGPS_LOGP>
2.50

> <JCHEM_LOGP>
2.755904054666667

> <ALOGPS_LOGS>
-3.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.49805561593643

> <JCHEM_PKA_STRONGEST_BASIC>
-4.224184024856662

> <JCHEM_POLAR_SURFACE_AREA>
29.6

> <JCHEM_REFRACTIVITY>
62.554100000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,12,12-trimethyl-5-oxatricyclo[8.2.0.0⁴,⁶]dodecan-9-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      10.912  -2.584   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.141  -3.852   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.218  -3.464   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.888   1.275   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.447   0.733   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.704  -3.083   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.164  -3.100   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.644  -0.813   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.125  -0.562   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.873  -2.081   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.341   0.764   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.691  -0.609   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.393  -2.333   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.974  -2.122   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.318   1.954   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.522  -1.611   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   13                                                            
CONECT    3   14                                                            
CONECT    4    5   11                                                       
CONECT    5    4   12                                                       
CONECT    6    7   10                                                       
CONECT    7    6   14                                                       
CONECT    8    9   13                                                       
CONECT    9    8   10   11                                                  
CONECT   10    6    9   13                                                  
CONECT   11    4    9   15                                                  
CONECT   12    5   14   16                                                  
CONECT   13    1    2    8   10                                             
CONECT   14    3    7   12   16                                             
CONECT   15   11                                                            
CONECT   16   12   14                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

View in JSmol

Synonyms

Value	Source
(-)-Kobusone	HMDB
6,7-Epoxy-15-nor-3-caryophyllanone	HMDB
Caryophyllene keto epoxide	HMDB

Chemical Formula

C₁₄H₂₂O₂

Average Mass

222.3233 Da

Monoisotopic Mass

222.16198 Da

IUPAC Name

4,12,12-trimethyl-5-oxatricyclo[8.2.0.0⁴,⁶]dodecan-9-one

Traditional Name

4,12,12-trimethyl-5-oxatricyclo[8.2.0.0⁴,⁶]dodecan-9-one

CAS Registry Number

Not Available

SMILES

CC12CCC3C(CC3(C)C)C(=O)CCC1O2

InChI Identifier

InChI=1S/C14H22O2/c1-13(2)8-9-10(13)6-7-14(3)12(16-14)5-4-11(9)15/h9-10,12H,4-8H2,1-3H3

InChI Key

UETZJEZFLKASPR-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)	Not Available	LIOS	Georgijs Stakanovs	2024-05-08	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CDCl3, experimental)	Not Available	LIOS	Georgijs Stakanovs	2024-05-08	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)	Not Available	Latvian Institute of Organic Synthesis	Georgijs Stakanovs	2023-09-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CDCl3, experimental)	Not Available	Latvian Institute of Organic Synthesis	Georgijs Stakanovs	2023-09-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CDCl3, experimental)	Not Available	Not Available	Georgijs Stakanovs	2023-09-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)	Not Available	Not Available	Georgijs Stakanovs	2023-09-13	View Spectrum

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

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100.578570142, CDCl₃, simulated)	st_george@inbox.lv	Latvian Institute of Organic Synthesis	Georgijs Stakanovs	2024-05-14	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101, CDCl₃, simulated)	st_george@inbox.lv	Latvian Institute of Organic Synthesis	Georgijs Stakanovs	2024-05-08	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Lavandula angustifolia	LOTUS Database	35616633
Neolitsea hiiranensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Ketones

Alternative Parents

Substituents

Ketone
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Organic oxide
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	2.5	ALOGPS
logP	2.76	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	18.5	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	29.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	62.55 m³·mol⁻¹	ChemAxon
Polarizability	25.45 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

HMDB0036790

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB015734

KNApSAcK ID

C00012492

Chemspider ID

2683359

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3440569

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

DOI: 10.1021/acs.jnatprod.3c00574

Showing NP-Card for Kobusone (NP0137067)

MOL for NP0137067 (Kobusone)

3D MOL for NP0137067 (Kobusone)

3D SDF for NP0137067 (Kobusone)

3D-SDF for NP0137067 (Kobusone)

PDB for NP0137067 (Kobusone)

3D PDB for NP0137067 (Kobusone)

SMILES for NP0137067 (Kobusone)

INCHI for NP0137067 (Kobusone)

Structure for NP0137067 (Kobusone)

3D Structure for NP0137067 (Kobusone)