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Showing NP-Card for 2,6,6-Trimethyl-2-cyclohexene-1,4-dione (NP0074087)

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Record Information
Version2.0
Created at2022-04-28 19:16:12 UTC
Updated at2022-04-28 19:16:12 UTC
NP-MRD IDNP0074087
Secondary Accession NumbersNone
Natural Product Identification
Common Name2,6,6-Trimethyl-2-cyclohexene-1,4-dione
Description2,6,6-Trimethyl-2-cyclohexene-1,4-dione, also known as ketoisophorone or 2-cyclohexen-1,4-dione, 2,6,6-trimethyl, belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. 2,6,6-Trimethyl-2-cyclohexene-1,4-dione is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 2,6,6-Trimethyl-2-cyclohexene-1,4-dione has been detected, but not quantified in, tea. 2,6,6-Trimethyl-2-cyclohexene-1,4-dione is found in Artemisia judaica, Averrhoa carambola , Crocus sativus , Euploea sylvester, Mandragora autumnalis , Nicotiana bonariensis and Tipuana tipu. 2,6,6-Trimethyl-2-cyclohexene-1,4-dione was first documented in 2006 (PMID: 17193245). This could make 2,6,6-trimethyl-2-cyclohexene-1,4-dione a potential biomarker for the consumption of these foods (PMID: 18496783) (PMID: 20849886) (PMID: 21232941) (PMID: 18811168).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0074087 (2,6,6-Trimethyl-2-cyclohexene-1,4-dione)


  Mrv0541 05061311422D          

 11 11  0  0  0  0            999 V2000
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  6  4  2  0  0  0  0
  7  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  2  1  0  0  0  0
  9  3  1  0  0  0  0
  9  5  1  0  0  0  0
  9  8  1  0  0  0  0
 10  7  2  0  0  0  0
 11  8  2  0  0  0  0
M  END
Download

3D MOL for NP0074087 (2,6,6-Trimethyl-2-cyclohexene-1,4-dione)

     RDKit          3D

 23 23  0  0  0  0  0  0  0  0999 V2000
    2.9222    0.5982    0.1333 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5844   -0.0675   -0.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4015   -1.3399    0.2959 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1157   -2.0054    0.1544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0508   -3.2335    0.3679 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0853   -1.2337   -0.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9093    0.2437   -0.1548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2654    0.7275    1.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9228    0.9140   -1.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4517    0.6949   -0.5329 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6479    1.7078   -1.2756 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5085   -0.0352    0.8219 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4648    0.5956   -0.8520 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8431    1.6184    0.5089 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2208   -1.9333    0.6779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4147   -1.5330   -1.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9064   -1.5545    0.4447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3551    0.4872    1.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1087    1.8132    1.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6226    0.2410    1.9909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3864    1.8046   -0.6023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3896    1.2771   -1.9691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7436    0.2129   -1.2954 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  2  0
 10  2  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  6 16  1  0
  6 17  1  0
  8 18  1  0
  8 19  1  0
  8 20  1  0
  9 21  1  0
  9 22  1  0
  9 23  1  0
M  END
Download

3D SDF for NP0074087 (2,6,6-Trimethyl-2-cyclohexene-1,4-dione)


  Mrv0541 05061311422D          

 11 11  0  0  0  0            999 V2000
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  6  4  2  0  0  0  0
  7  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  2  1  0  0  0  0
  9  3  1  0  0  0  0
  9  5  1  0  0  0  0
  9  8  1  0  0  0  0
 10  7  2  0  0  0  0
 11  8  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0074087

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(=O)CC(C)(C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H12O2/c1-6-4-7(10)5-9(2,3)8(6)11/h4H,5H2,1-3H3

> <INCHI_KEY>
AYJXHIDNNLJQDT-UHFFFAOYSA-N

> <FORMULA>
C9H12O2

> <MOLECULAR_WEIGHT>
152.1904

> <EXACT_MASS>
152.083729628

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
16.325381977702385

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,6,6-trimethylcyclohex-2-ene-1,4-dione

> <ALOGPS_LOGP>
1.51

> <JCHEM_LOGP>
2.1610962450000004

> <ALOGPS_LOGS>
-1.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.85103893019325

> <JCHEM_PKA_STRONGEST_BASIC>
-6.350677474425435

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
43.391400000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.73e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,6,6-trimethylcyclohex-2-ene-1,4-dione

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0074087 (2,6,6-Trimethyl-2-cyclohexene-1,4-dione)

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PDB for NP0074087 (2,6,6-Trimethyl-2-cyclohexene-1,4-dione)
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       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    9                                                            
CONECT    3    9                                                            
CONECT    4    6    7                                                       
CONECT    5    7    9                                                       
CONECT    6    1    4    8                                                  
CONECT    7    4    5   10                                                  
CONECT    8    6    9   11                                                  
CONECT    9    2    3    5    8                                             
CONECT   10    7                                                            
CONECT   11    8                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0074087 (2,6,6-Trimethyl-2-cyclohexene-1,4-dione)
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SMILES for NP0074087 (2,6,6-Trimethyl-2-cyclohexene-1,4-dione)
CC1=CC(=O)CC(C)(C)C1=O
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INCHI for NP0074087 (2,6,6-Trimethyl-2-cyclohexene-1,4-dione)
InChI=1S/C9H12O2/c1-6-4-7(10)5-9(2,3)8(6)11/h4H,5H2,1-3H3
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Synonyms
ValueSource
2,2,6-Trimethyl-2-cyclohexene-1,4-dione (cetoisophorone)HMDB
2,2,6-Trimethylcyclohex-2-en-1,4-dione (4-oxo-isophorone)HMDB
2,6,6-Trimethy-2-cyclohexene-1,4-dione (4-oxoisophorone)HMDB
2,6,6-Trimethyl-2-cyclohexen-1,4-dioneHMDB
2,6,6-Trimethylcyclohex-2-ene-1,4-dioneHMDB
2-Cyclohexen-1,4-dione, 2,6,6-trimethylHMDB
3,5,5-Trimethyl-2-cyclohexene-1,4-dioneHMDB
3,5,5-Trimethylcyclohex-2-en-1,4-dioneHMDB
3,5,5-Trimethylcyclohex-2-ene-1,4-dioneHMDB
4-KetoisophoroneHMDB
4-oxo-alpha-IsophoroneHMDB
4-OxoisophoroneHMDB
6-OxoisophoroneHMDB
FEMA 3421HMDB
Keto-isophoroneHMDB
KetoisophoroneHMDB
OxoisophoroneHMDB
OxopholoneHMDB
OxophoroneHMDB
Chemical FormulaC9H12O2
Average Mass152.1904 Da
Monoisotopic Mass152.08373 Da
IUPAC Name2,6,6-trimethylcyclohex-2-ene-1,4-dione
Traditional Name2,6,6-trimethylcyclohex-2-ene-1,4-dione
CAS Registry NumberNot Available
SMILES
CC1=CC(=O)CC(C)(C)C1=O
InChI Identifier
InChI=1S/C9H12O2/c1-6-4-7(10)5-9(2,3)8(6)11/h4H,5H2,1-3H3
InChI KeyAYJXHIDNNLJQDT-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Artemisia judaicaLOTUS Database
Averrhoa carambolaPlant
Crocus sativusPlant
Euploea sylvesterLOTUS Database
Mandragora autumnalisPlant
Nicotiana bonariensisPlant
Tipuana tipuPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentCyclohexenones  
Alternative Parents
Substituents
  • Cyclohexenone
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.51ALOGPS
logP2.16ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)18.85ChemAxon
pKa (Strongest Basic)-6.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity43.39 m³·mol⁻¹ChemAxon
Polarizability16.33 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0040216  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB004389  
KNApSAcK IDC00035002  
Chemspider ID56162  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound62374  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Jerkovic I, Mastelic J, Marijanovic Z: A variety of volatile compounds as markers in unifloral honey from dalmatian sage (Salvia officinalis L.). Chem Biodivers. 2006 Dec;3(12):1307-16. doi: 10.1002/cbdv.200690134. [PubMed:17193245  ] 
  2. Lechtenberg M, Schepmann D, Niehues M, Hellenbrand N, Wunsch B, Hensel A: Quality and functionality of saffron: quality control, species assortment and affinity of extract and isolated saffron compounds to NMDA and sigma1 (sigma-1) receptors. Planta Med. 2008 Jun;74(7):764-72. doi: 10.1055/s-2008-1074535. Epub 2008 May 21. [PubMed:18496783  ] 
  3. Raimondi S, Roncaglia L, Amaretti A, Leonardi A, Buzzini P, Forti L, Rossi M: Rapid method for screening enoate reductase activity in yeasts. J Microbiol Methods. 2010 Nov;83(2):106-10. doi: 10.1016/j.mimet.2010.09.007.  Epub 2010 Sep 16. [PubMed:20849886  ] 
  4. Goretti M, Ponzoni C, Caselli E, Marchegiani E, Cramarossa MR, Turchetti B, Forti L, Buzzini P: Bioreduction of alpha,beta-unsaturated ketones and aldehydes by non-conventional yeast (NCY) whole-cells. Bioresour Technol. 2011 Mar;102(5):3993-8. doi: 10.1016/j.biortech.2010.12.062.  Epub 2010 Dec 22. [PubMed:21232941  ] 
  5. Zhuang X, Klingeman WE, Hu J, Chen F: Emission of volatile chemicals from flowering dogwood (cornus Florida L.) flowers. J Agric Food Chem. 2008 Oct 22;56(20):9570-4. doi: 10.1021/jf801651v. Epub 2008  Sep 24. [PubMed:18811168  ]