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Showing NP-Card for 2,6,6-Trimethyl 1,4-cyclohexanedione (NP0074086)

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Record Information
Version2.0
Created at2022-04-28 19:16:09 UTC
Updated at2022-04-28 19:16:09 UTC
NP-MRD IDNP0074086
Secondary Accession NumbersNone
Natural Product Identification
Common Name2,6,6-Trimethyl 1,4-cyclohexanedione
DescriptionLevodione, also known as doip CPD, belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety. Levodione is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 2,6,6-Trimethyl 1,4-cyclohexanedione is found in Nicotiana bonariensis. 2,6,6-Trimethyl 1,4-cyclohexanedione was first documented in 2015 (PMID: 25639703). Based on a literature review a small amount of articles have been published on levodione (PMID: 32495457) (PMID: 31768035) (PMID: 29421034) (PMID: 27578886).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0074086 (2,6,6-Trimethyl 1,4-cyclohexanedione)


  Mrv1652304282221162D          

 11 11  0  0  1  0            999 V2000
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   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    0.0000    0.0000 C   0  0  2  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
   -0.7145    1.2375    0.0000 O   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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3272    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1018    1.9659    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
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  1  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
  4 11  1  1  0  0  0
M  END
Download

3D MOL for NP0074086 (2,6,6-Trimethyl 1,4-cyclohexanedione)

     RDKit          3D

 25 25  0  0  0  0  0  0  0  0999 V2000
    2.7216    0.8156    0.0966 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4543    0.0705    0.4414 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4379   -1.2212   -0.3431 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0740   -1.7619   -0.5042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1723   -2.9159   -0.2586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9952   -0.8540   -0.9768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0884    0.3013    0.0074 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6050   -0.2853    1.3039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0701    1.3341   -0.4439 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2507    0.8837    0.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3916    2.0787   -0.0165 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5186    0.6706    0.8527 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0938    0.5081   -0.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5138    1.9176    0.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5099   -0.1919    1.5228 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1164   -1.9561    0.1419 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8727   -1.0270   -1.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7988   -0.4177   -1.9605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9832   -1.3606   -0.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9082    0.4951    2.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8773   -1.0072    1.7550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5397   -0.8411    1.0434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4433    1.9180    0.4166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5722    2.0451   -1.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9012    0.8016   -0.9609 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  1
  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
  2 15  1  1
  3 16  1  0
  3 17  1  0
  6 18  1  0
  6 19  1  0
  8 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  0
  9 24  1  0
  9 25  1  0
M  END
Download

3D SDF for NP0074086 (2,6,6-Trimethyl 1,4-cyclohexanedione)


  Mrv1652304282221162D          

 11 11  0  0  1  0            999 V2000
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   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    0.0000    0.0000 C   0  0  2  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
   -0.7145    1.2375    0.0000 O   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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3272    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1018    1.9659    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
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  1  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
  4 11  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0074086

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC(=O)CC(C)(C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H14O2/c1-6-4-7(10)5-9(2,3)8(6)11/h6H,4-5H2,1-3H3/t6-/m1/s1

> <INCHI_KEY>
HVHHZSFNAYSPSA-ZCFIWIBFSA-N

> <FORMULA>
C9H14O2

> <MOLECULAR_WEIGHT>
154.209

> <EXACT_MASS>
154.099379691

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
16.83266855363999

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6R)-2,2,6-trimethylcyclohexane-1,4-dione

> <ALOGPS_LOGP>
1.52

> <JCHEM_LOGP>
1.9509633980000003

> <ALOGPS_LOGS>
-1.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.710190995200104

> <JCHEM_PKA_STRONGEST_BASIC>
-7.150388916274602

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
42.538799999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.91e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6R)-2,2,6-trimethylcyclohexane-1,4-dione

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0074086 (2,6,6-Trimethyl 1,4-cyclohexanedione)

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PDB for NP0074086 (2,6,6-Trimethyl 1,4-cyclohexanedione)
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       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.000   0.000   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  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.334   2.310   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       0.611   3.670   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.057   3.670   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2    3    8                                                  
CONECT    2    1                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9   10                                             
CONECT    8    7    1                                                       
CONECT    9    7                                                            
CONECT   10    7                                                            
CONECT   11    4                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0074086 (2,6,6-Trimethyl 1,4-cyclohexanedione)
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SMILES for NP0074086 (2,6,6-Trimethyl 1,4-cyclohexanedione)
C[C@@H]1CC(=O)CC(C)(C)C1=O
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INCHI for NP0074086 (2,6,6-Trimethyl 1,4-cyclohexanedione)
InChI=1S/C9H14O2/c1-6-4-7(10)5-9(2,3)8(6)11/h6H,4-5H2,1-3H3/t6-/m1/s1
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View in JSmol
Synonyms
ValueSource
(-)-(6R)-2,2,6-Trimethyl-1,4-cyclohexandioneChEBI
(6R)-2,2,6-Trimethyl-1,4-cyclohexanedioneChEBI
(R)-2,2,6-Trimethyl-1,4-cyclohexanedioneChEBI
DOIP CPDMeSH
DihydrooxoisophoroneMeSH
Chemical FormulaC9H14O2
Average Mass154.2090 Da
Monoisotopic Mass154.09938 Da
IUPAC Name(6R)-2,2,6-trimethylcyclohexane-1,4-dione
Traditional Name(6R)-2,2,6-trimethylcyclohexane-1,4-dione
CAS Registry NumberNot Available
SMILES
C[C@@H]1CC(=O)CC(C)(C)C1=O
InChI Identifier
InChI=1S/C9H14O2/c1-6-4-7(10)5-9(2,3)8(6)11/h6H,4-5H2,1-3H3/t6-/m1/s1
InChI KeyHVHHZSFNAYSPSA-ZCFIWIBFSA-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
Nicotiana bonariensisPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentCyclic ketones  
Alternative Parents
Substituents
  • Cyclic ketone
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
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
logP1.52ALOGPS
logP1.95ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)17.71ChemAxon
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity42.54 m³·mol⁻¹ChemAxon
Polarizability16.83 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8351734  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10176229  
PDB IDNot Available
ChEBI ID86400  
Good Scents IDNot Available
References
General References
  1. Horita S, Kataoka M, Kitamura N, Nakagawa T, Miyakawa T, Ohtsuka J, Nagata K, Shimizu S, Tanokura M: An engineered old yellow enzyme that enables efficient synthesis of (4R,6R)-Actinol in a one-pot reduction system. Chembiochem. 2015 Feb 9;16(3):440-5. doi: 10.1002/cbic.201402555. Epub 2015 Jan 14. [PubMed:25639703  ] 
  2. Choi DS, Kim J, Hollmann F, Park CB: Solar-Assisted eBiorefinery: Photoelectrochemical Pairing of Oxyfunctionalization and Hydrogenation Reactions. Angew Chem Int Ed Engl. 2020 Sep 7;59(37):15886-15890. doi: 10.1002/anie.202006893. Epub 2020 Jul 2. [PubMed:32495457  ] 
  3. Black WB, Zhang L, Mak WS, Maxel S, Cui Y, King E, Fong B, Sanchez Martinez A, Siegel JB, Li H: Engineering a nicotinamide mononucleotide redox cofactor system for biocatalysis. Nat Chem Biol. 2020 Jan;16(1):87-94. doi: 10.1038/s41589-019-0402-7. Epub 2019 Nov 25. [PubMed:31768035  ] 
  4. Dezvarei S, Lee JHZ, Bell SG: Stereoselective hydroxylation of isophorone by variants of the cytochromes P450 CYP102A1 and CYP101A1. Enzyme Microb Technol. 2018 Apr;111:29-37. doi: 10.1016/j.enzmictec.2018.01.002.  Epub 2018 Jan 5. [PubMed:29421034  ] 
  5. Lerchner A, Daake M, Jarasch A, Skerra A: Fusion of an alcohol dehydrogenase with an aminotransferase using a PAS linker to improve coupled enzymatic alcohol-to-amine conversion. Protein Eng Des Sel. 2016 Dec;29(12):557-562. doi: 10.1093/protein/gzw039. Epub 2016 Aug 29. [PubMed:27578886  ]