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Showing NP-Card for 3,5,5-Trimethyl-2-cyclohexen-1-one (NP0046124)

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Record Information
Version2.0
Created at2022-03-17 19:48:53 UTC
Updated at2022-03-17 19:48:53 UTC
NP-MRD IDNP0046124
Secondary Accession NumbersNone
Natural Product Identification
Common Name3,5,5-Trimethyl-2-cyclohexen-1-one
Description3,5,5-Trimethyl-2-cyclohexen-1-one, also known as isoforone or isoacetophorone, 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. 3,5,5-Trimethyl-2-cyclohexen-1-one is a flavouring ingredient. 3,5,5-Trimethyl-2-cyclohexen-1-one is an extremely weak basic (essentially neutral) compound (based on its pKa). 3,5,5-Trimethyl-2-cyclohexen-1-one is a sweet, camphor, and camphoraceous tasting compound. Outside of the human body, 3,5,5-Trimethyl-2-cyclohexen-1-one is found, on average, in the highest concentration within kohlrabis. 3,5,5-Trimethyl-2-cyclohexen-1-one has also been detected, but not quantified in, several different foods, such as saffrons, cherry tomato, garden tomato (var.), White mustards, and garden tomato. 3,5,5-Trimethyl-2-cyclohexen-1-one is found in Amauris echeria, Artemisia judaica, Prunus armeniaca L. (K604-19,K113-40,K33-81) , Prunus salcina Lindl. (Friar), Taxus baccata , Vaccinium macrocarpon and Vaccinium microcarpa. 3,5,5-Trimethyl-2-cyclohexen-1-one was first documented in 2013 (PMID: 23183344). This could make 3,5,5-trimethyl-2-cyclohexen-1-one a potential biomarker for the consumption of these foods (PMID: 23472460) (PMID: 23506080) (PMID: 23923622).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0046124 (3,5,5-Trimethyl-2-cyclohexen-1-one)


  Mrv0541 05061305482D          

 10 10  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
    1.2448    1.8695    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
    0.7145   -0.4125    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
    0.0000    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
    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
  7  1  1  0  0  0  0
  7  4  2  0  0  0  0
  7  5  1  0  0  0  0
  8  4  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  6  1  0  0  0  0
 10  8  2  0  0  0  0
M  END
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3D MOL for NP0046124 (3,5,5-Trimethyl-2-cyclohexen-1-one)

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3D SDF for NP0046124 (3,5,5-Trimethyl-2-cyclohexen-1-one)

  Mrv0541 05061305482D          

 10 10  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
    1.2448    1.8695    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
    0.7145   -0.4125    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
    0.0000    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
    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
  7  1  1  0  0  0  0
  7  4  2  0  0  0  0
  7  5  1  0  0  0  0
  8  4  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  6  1  0  0  0  0
 10  8  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0046124

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H14O/c1-7-4-8(10)6-9(2,3)5-7/h4H,5-6H2,1-3H3

> <INCHI_KEY>
HJOVHMDZYOCNQW-UHFFFAOYSA-N

> <FORMULA>
C9H14O

> <MOLECULAR_WEIGHT>
138.2069

> <EXACT_MASS>
138.10446507

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
16.218812635610615

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,5,5-trimethylcyclohex-2-en-1-one

> <ALOGPS_LOGP>
1.90

> <JCHEM_LOGP>
2.3164452423333337

> <ALOGPS_LOGS>
-1.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.526413703417468

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
42.64640000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.89e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isophorone

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0046124 (3,5,5-Trimethyl-2-cyclohexen-1-one)
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PDB for NP0046124 (3,5,5-Trimethyl-2-cyclohexen-1-one)
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       2.324   3.490   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.344   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       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   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
CONECT    1    7                                                            
CONECT    2    9                                                            
CONECT    3    9                                                            
CONECT    4    7    8                                                       
CONECT    5    7    9                                                       
CONECT    6    8    9                                                       
CONECT    7    1    4    5                                                  
CONECT    8    4    6   10                                                  
CONECT    9    2    3    5    6                                             
CONECT   10    8                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END

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3D PDB for NP0046124 (3,5,5-Trimethyl-2-cyclohexen-1-one)
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SMILES for NP0046124 (3,5,5-Trimethyl-2-cyclohexen-1-one)
CC1=CC(=O)CC(C)(C)C1
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INCHI for NP0046124 (3,5,5-Trimethyl-2-cyclohexen-1-one)
InChI=1S/C9H14O/c1-7-4-8(10)6-9(2,3)5-7/h4H,5-6H2,1-3H3
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Synonyms
ValueSource
1,1,3-Trimethyl-3-cyclohexene-5-oneChEBI
3,5,5-Trimethyl-2-cyclohexen-1-ONChEBI
IsoacetophoroneChEBI
IsoforoneChEBI
IsooctopheroneChEBI
IzoforonChEBI
1,1, 3-Trimethyl-3-cyclohexene-5-oneHMDB
1,5,5-Trimethyl-1-cyclohexen-3-oneHMDB
3,3,5-Trimethyl-2-cyclohexen-1-oneHMDB
3,5, 5-Trimethyl-2-cyclohexene-1-oneHMDB
3,5,5-Trimethyl-2-cyclohexene-1-oneHMDB
3,5,5-Trimethyl-2-cyclohexenoneHMDB
3,5,5-Trimethylcyclohex-2-enoneHMDB
3,5,5-Trimethylcyclohexen oneHMDB
3,5,5-Trimethylcyclohexen-2-one-1HMDB
3,5,5-TrimethylcyclohexenoneHMDB
3,5,5-Trimetil-2-cicloesen-1-oneHMDB
a-IsophoroneHMDB
alpha -IsophoronHMDB
alpha -IsophoroneHMDB
alpha-IsophoroneHMDB
DIIsophoroneHMDB
FEMA 3553HMDB
IsoforonHMDB
IsophoronHMDB
IsophoroneHMDB
Isophorone, reagHMDB
Nchem.180-comp3HMDB
Chemical FormulaC9H14O
Average Mass138.2069 Da
Monoisotopic Mass138.10447 Da
IUPAC Name3,5,5-trimethylcyclohex-2-en-1-one
Traditional Nameisophorone
CAS Registry Number78-59-1
SMILES
CC1=CC(=O)CC(C)(C)C1
InChI Identifier
InChI=1S/C9H14O/c1-7-4-8(10)6-9(2,3)5-7/h4H,5-6H2,1-3H3
InChI KeyHJOVHMDZYOCNQW-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Amauris echeriaLOTUS Database
Artemisia judaicaLOTUS Database
Brassica oleracea var. gongylodesFooDB
Crocus sativusFooDB
Prunus armeniaca L. (K604-19,K113-40,K33-81)Plant
Prunus salcina Lindl. (Friar)Plant
Sinapis albaFooDB
Taxus baccataPlant
Vaccinium macrocarponLOTUS Database
Vaccinium microcarpaPlant
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 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
logP1.9ALOGPS
logP2.32ChemAxon
logS-1.9ALOGPS
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity42.65 m³·mol⁻¹ChemAxon
Polarizability16.22 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031195  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003216  
KNApSAcK IDC00030540  
Chemspider ID6296  
KEGG Compound IDC14743  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIsophorone  
METLIN IDNot Available
PubChem Compound6544  
PDB IDNot Available
ChEBI ID34800  
Good Scents IDNot Available
References
General References
  1. Wei H, Yan X, Li X, He S, Sun C: The degradation of Isophorone by catalytic wet air oxidation on Ru/TiZrO4. J Hazard Mater. 2013 Jan 15;244-245:478-88. doi: 10.1016/j.jhazmat.2012.10.069. Epub 2012 Nov 5. [PubMed:23183344  ] 
  2. Kiran I, Ozsen O, Celik T, Ilhan S, Gursu BY, Demirci F: Microbial transformations of isophorone by Alternaria alternata and Neurospora crassa. Nat Prod Commun. 2013 Jan;8(1):59-61. [PubMed:23472460  ] 
  3. Zheng Z, Yu Z, Yang M, Jin F, Zhang Q, Zhou H, Wu J, Tian Y: Substituent group variations directing the molecular packing, electronic structure, and aggregation-induced emission property of isophorone derivatives. J Org Chem. 2013 Apr 5;78(7):3222-34. doi: 10.1021/jo400116j. Epub 2013 Mar 25. [PubMed:23506080  ] 
  4. Zong S, Liu X, Cao C, Luo Y, Ren L, Zhang H: Development of semiochemical attractants for monitoring and controlling Chlorophorus caragana. Z Naturforsch C J Biosci. 2013 May-Jun;68(5-6):243-52. [PubMed:23923622  ]