NP-MRD: Showing NP-Card for 3-methyl-6-(1-methylethylidene)-cyclohex-2-en-1-one (NP0027702)

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Record Information

Version

2.0

Created at

2021-06-19 19:47:07 UTC

Updated at

2021-08-20 00:00:11 UTC

NP-MRD ID

NP0027702

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-methyl-6-(1-methylethylidene)-cyclohex-2-en-1-one

Provided By

JEOL Database JEOL Logo

Description

Piperitenone, also known as 3-terpinolenone or fema 3560, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Thus, piperitenone is considered to be an isoprenoid. 3-methyl-6-(1-methylethylidene)-cyclohex-2-en-1-one is found in Agathosma betulina, Aloysia triphylla, Artemisia judaica, Basella alba, Cantinoa mutabilis, Clinopodium grandiflorum, Clinopodium serpyllifolium, Cyclotrichium niveum, Foeniculum vulgare, Lippia javanica, Lippia rehmannii, Lonicera japonica, Mentha arvensis L. , Mentha spicata, Micromeria biflora, Micromeria croatica, Monardella hypoleuca, Perilla frutescens, Pistacia vera, Poliomintha incana, Pycnanthemum floridanum, Salvia rosmarinus, Tagetes patula, Thymbra capitata and Ziziphora hispanica. 3-methyl-6-(1-methylethylidene)-cyclohex-2-en-1-one was first documented in 2005 (PMID: 15868213). Based on a literature review very few articles have been published on Piperitenone (PMID: 24211775).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192121473D          

 25 25  0  0  0  0            999 V2000
   -1.8622   -2.3347    0.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4887   -1.0618   -0.5857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2323   -0.5872   -0.5726 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1438    0.7021   -1.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3216    1.0393   -1.2412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9737    1.5091   -1.8115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9132    2.8618   -1.8661 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1778    3.6842   -1.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9328    3.7215   -2.5717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0863    0.6468   -2.3524 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6004   -0.3429   -1.3029 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6381   -2.1416    0.8629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0079   -2.7873    0.6295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2451   -3.0664   -0.6036 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5808   -1.1043   -0.0745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2343    4.6234   -0.8309 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6357    3.1879   -0.3585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9534    3.9296   -1.9501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5780    4.2184   -1.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4272    4.4929   -3.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5641    3.1699   -3.2710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7065    0.0952   -3.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9424    1.2273   -2.7057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2181    0.1808   -0.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2481   -1.0699   -1.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0  0  0  0
 11  2  1  0  0  0  0
  4  5  2  0  0  0  0
  3  4  1  0  0  0  0
  6  7  2  3  0  0  0
  3  2  2  0  0  0  0
  7  8  1  0  0  0  0
  4  6  1  0  0  0  0
  7  9  1  0  0  0  0
  6 10  1  0  0  0  0
  2  1  1  0  0  0  0
  3 15  1  0  0  0  0
 10 22  1  0  0  0  0
 10 23  1  0  0  0  0
 11 24  1  0  0  0  0
 11 25  1  0  0  0  0
  8 16  1  0  0  0  0
  8 17  1  0  0  0  0
  8 18  1  0  0  0  0
  9 19  1  0  0  0  0
  9 20  1  0  0  0  0
  9 21  1  0  0  0  0
  1 12  1  0  0  0  0
  1 13  1  0  0  0  0
  1 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0027702

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C(C([H])([H])[H])C([H])([H])C([H])([H])C(=C(C([H])([H])[H])C([H])([H])[H])C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)6-10(9)11/h6H,4-5H2,1-3H3

> <INCHI_KEY>
HKZQJZIFODOLFR-UHFFFAOYSA-N

> <FORMULA>
C10H14O

> <MOLECULAR_WEIGHT>
150.2176

> <EXACT_MASS>
150.10446507

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
17.766770562483096

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-methyl-6-(propan-2-ylidene)cyclohex-2-en-1-one

> <ALOGPS_LOGP>
2.39

> <JCHEM_LOGP>
2.810682941666667

> <ALOGPS_LOGS>
-1.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.60419382288991

> <JCHEM_PKA_STRONGEST_BASIC>
-3.939944703066289

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
47.956100000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.05e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
piperitenone

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.862  -2.335   0.115  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.489  -1.062  -0.586  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.232  -0.587  -0.573  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.144   0.702  -1.207  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.322   1.039  -1.241  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.974   1.509  -1.812  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.913   2.862  -1.866  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.178   3.684  -1.218  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.933   3.721  -2.572  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.086   0.647  -2.352  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.600  -0.343  -1.303  0.00  0.00           C+0
HETATM   12  H   UNK     0      -2.638  -2.142   0.863  0.00  0.00           H+0
HETATM   13  H   UNK     0      -1.008  -2.787   0.630  0.00  0.00           H+0
HETATM   14  H   UNK     0      -2.245  -3.066  -0.604  0.00  0.00           H+0
HETATM   15  H   UNK     0       0.581  -1.104  -0.075  0.00  0.00           H+0
HETATM   16  H   UNK     0      -0.234   4.623  -0.831  0.00  0.00           H+0
HETATM   17  H   UNK     0       0.636   3.188  -0.359  0.00  0.00           H+0
HETATM   18  H   UNK     0       0.953   3.930  -1.950  0.00  0.00           H+0
HETATM   19  H   UNK     0      -2.578   4.218  -1.840  0.00  0.00           H+0
HETATM   20  H   UNK     0      -1.427   4.493  -3.164  0.00  0.00           H+0
HETATM   21  H   UNK     0      -2.564   3.170  -3.271  0.00  0.00           H+0
HETATM   22  H   UNK     0      -1.706   0.095  -3.223  0.00  0.00           H+0
HETATM   23  H   UNK     0      -2.942   1.227  -2.706  0.00  0.00           H+0
HETATM   24  H   UNK     0      -3.218   0.181  -0.563  0.00  0.00           H+0
HETATM   25  H   UNK     0      -3.248  -1.070  -1.808  0.00  0.00           H+0
CONECT    1    2   12   13   14                                             
CONECT    2   11    3    1                                                  
CONECT    3    4    2   15                                                  
CONECT    4    5    3    6                                                  
CONECT    5    4                                                            
CONECT    6    7    4   10                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7   16   17   18                                             
CONECT    9    7   19   20   21                                             
CONECT   10   11    6   22   23                                             
CONECT   11   10    2   24   25                                             
CONECT   12    1                                                            
CONECT   13    1                                                            
CONECT   14    1                                                            
CONECT   15    3                                                            
CONECT   16    8                                                            
CONECT   17    8                                                            
CONECT   18    8                                                            
CONECT   19    9                                                            
CONECT   20    9                                                            
CONECT   21    9                                                            
CONECT   22   10                                                            
CONECT   23   10                                                            
CONECT   24   11                                                            
CONECT   25   11                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END

View in JSmol

Synonyms

Value	Source
3-Methyl-6-(1-methylethylidene)-2-cyclohexen-1-one	HMDB
3-Methyl-6-(1-methylethylidene)-2-cyclohexen-1-one, 9ci	HMDB
3-Methyl-6-propan-2-ylidenecyclohex-2-en-1-one	HMDB
3-Terpinolenone	HMDB
6-Isopropylidene-3-methyl-2-cyclohexenone	HMDB
FEMA 3560	HMDB
Pulespenone	HMDB

Chemical Formula

C₁₀H₁₄O

Average Mass

150.2176 Da

Monoisotopic Mass

150.10447 Da

IUPAC Name

3-methyl-6-(propan-2-ylidene)cyclohex-2-en-1-one

Traditional Name

piperitenone

CAS Registry Number

Not Available

SMILES

[H]C1=C(C([H])([H])[H])C([H])([H])C([H])([H])C(=C(C([H])([H])[H])C([H])([H])[H])C1=O

InChI Identifier

InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)6-10(9)11/h6H,4-5H2,1-3H3

InChI Key

HKZQJZIFODOLFR-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Agathosma betulina	LOTUS Database	35616633
Aloysia triphylla	LOTUS Database	35616633
Artemisia judaica	LOTUS Database	35616633
Basella alba	LOTUS Database	35616633
Calamintha nepeta subsp.glandulosa.	KNApSAcK Database	22123792
Cannabis sativa	CannabisDB	Not Available
Cantinoa mutabilis	LOTUS Database	35616633
Clinopodium grandiflorum	LOTUS Database	35616633
Clinopodium serpyllifolium	LOTUS Database	35616633
Cyclotrichium niveum	LOTUS Database	35616633
Cymbopogon martinii	KNApSAcK Database	22123792
Foeniculum vulgare	LOTUS Database	35616633
Ligusticum jeholense	KNApSAcK Database	22123792
Lippia javanica	JEOL database	Manenzhe, N. J., et al, Phytochemistry 65, 2333 (2004)
Lippia rehmannii	LOTUS Database	35616633
Lippia spp.	KNApSAcK Database	22123792
Lonicera japonica	LOTUS Database	35616633
Mentha arvensis	Plant	KNApSAcK
Mentha arvensis L.	KNApSAcK Database	22123792
Mentha pulegium	KNApSAcK Database	22123792
Mentha spicata	LOTUS Database	35616633
Mentha spp.	KNApSAcK Database	22123792
Micromeria biflora	LOTUS Database	35616633
Micromeria croatica	LOTUS Database	35616633
Monardella hypoleuca	LOTUS Database	35616633
Perilla frutescens	LOTUS Database	35616633
Pistacia vera	LOTUS Database	35616633
Poliomintha incana	LOTUS Database	35616633
Pycnanthemum floridanum	LOTUS Database	35616633
Salvia rosmarinus	LOTUS Database	35616633
Schizonepeta tenuifolia	KNApSAcK Database	22123792
Tagetes patula	LOTUS Database	35616633
Thymbra capitata	LOTUS Database	35616633
Ziziphora hispanica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane monoterpenoids

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	106.00 to 107.00 °C. @ 10.00 mm Hg	The Good Scents Company Information System
Water Solubility	164.7 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.766 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	2.39	ALOGPS
logP	2.81	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	18.6	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	47.96 m³·mol⁻¹	ChemAxon
Polarizability	17.77 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0036999

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

381152

PDB ID

Not Available

ChEBI ID

17304

Good Scents ID

rw1031141

References

General References

Passone MA, Etcheverry M: Antifungal impact of volatile fractions of Peumus boldus and Lippia turbinata on Aspergillus section Flavi and residual levels of these oils in irradiated peanut. Int J Food Microbiol. 2014 Jan 3;168-169:17-23. doi: 10.1016/j.ijfoodmicro.2013.10.009. Epub 2013 Oct 23. [PubMed:24211775 ]
Romagnoli C, Bruni R, Andreotti E, Rai MK, Vicentini CB, Mares D: Chemical characterization and antifungal activity of essential oil of capitula from wild Indian Tagetes patula L. Protoplasma. 2005 Apr;225(1-2):57-65. doi: 10.1007/s00709-005-0084-8. Epub 2005 May 4. [PubMed:15868213 ]
Manenzhe, N. J., et al. (2004). Manenzhe, N. J., et al, Phytochemistry 65, 2333 (2004). Phytochem..

Showing NP-Card for 3-methyl-6-(1-methylethylidene)-cyclohex-2-en-1-one (NP0027702)

MOL for NP0027702 (3-methyl-6-(1-methylethylidene)-cyclohex-2-en-1-one)

3D MOL for NP0027702 (3-methyl-6-(1-methylethylidene)-cyclohex-2-en-1-one)

3D SDF for NP0027702 (3-methyl-6-(1-methylethylidene)-cyclohex-2-en-1-one)

3D-SDF for NP0027702 (3-methyl-6-(1-methylethylidene)-cyclohex-2-en-1-one)

PDB for NP0027702 (3-methyl-6-(1-methylethylidene)-cyclohex-2-en-1-one)

3D PDB for NP0027702 (3-methyl-6-(1-methylethylidene)-cyclohex-2-en-1-one)

SMILES for NP0027702 (3-methyl-6-(1-methylethylidene)-cyclohex-2-en-1-one)

INCHI for NP0027702 (3-methyl-6-(1-methylethylidene)-cyclohex-2-en-1-one)

Structure for NP0027702 (3-methyl-6-(1-methylethylidene)-cyclohex-2-en-1-one)

3D Structure for NP0027702 (3-methyl-6-(1-methylethylidene)-cyclohex-2-en-1-one)