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Showing NP-Card for 3,5,5-Trimethyl-3-cyclohexen-1-one (NP0049617)

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Record Information
Version2.0
Created at2022-03-17 21:15:22 UTC
Updated at2022-03-17 21:15:23 UTC
NP-MRD IDNP0049617
Secondary Accession NumbersNone
Natural Product Identification
Common Name3,5,5-Trimethyl-3-cyclohexen-1-one
Description3,5,5-Trimethyl-3-cyclohexen-1-one, also known as.Beta-isophorone or b-phorone, 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-3-cyclohexen-1-one is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3,5,5-Trimethyl-3-cyclohexen-1-one has been detected, but not quantified in, a few different foods, such as fruits, herbs and spices, and saffrons. 3,5,5-Trimethyl-3-cyclohexen-1-one is found in Amauris echeria and Mandragora autumnalis . This could make 3,5,5-trimethyl-3-cyclohexen-1-one a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0049617 (3,5,5-Trimethyl-3-cyclohexen-1-one)


  Mrv0541 05061311462D          

 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  1  0  0  0  0
  7  5  2  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 NP0049617 (3,5,5-Trimethyl-3-cyclohexen-1-one)

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3D SDF for NP0049617 (3,5,5-Trimethyl-3-cyclohexen-1-one)

  Mrv0541 05061311462D          

 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  1  0  0  0  0
  7  5  2  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>
NP0049617

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H14O/c1-7-4-8(10)6-9(2,3)5-7/h5H,4,6H2,1-3H3

> <INCHI_KEY>
LKOKKQDYMZUSCG-UHFFFAOYSA-N

> <FORMULA>
C9H14O

> <MOLECULAR_WEIGHT>
138.2069

> <EXACT_MASS>
138.10446507

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
16.265843796339873

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.72

> <JCHEM_LOGP>
1.9567000960000007

> <ALOGPS_LOGS>
-1.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.62223190852583

> <JCHEM_PKA_STRONGEST_BASIC>
-7.444445923103984

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
42.669700000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.57e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,5,5-trimethylcyclohex-3-en-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0049617 (3,5,5-Trimethyl-3-cyclohexen-1-one)
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PDB for NP0049617 (3,5,5-Trimethyl-3-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 NP0049617 (3,5,5-Trimethyl-3-cyclohexen-1-one)
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SMILES for NP0049617 (3,5,5-Trimethyl-3-cyclohexen-1-one)
CC1=CC(C)(C)CC(=O)C1
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INCHI for NP0049617 (3,5,5-Trimethyl-3-cyclohexen-1-one)
InChI=1S/C9H14O/c1-7-4-8(10)6-9(2,3)5-7/h5H,4,6H2,1-3H3
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Synonyms
ValueSource
.beta-isophoroneHMDB
3,5,5-Trimethyl-3-cyclohexene-1-oneHMDB
3,5,5-Trimethylcyclohex-3-enoneHMDB
b-IsophoroneHMDB
b-PhoroneHMDB
beta -IsophoroneHMDB
beta -PhoroneHMDB
beta-IsophoroneHMDB
beta-PhoroneHMDB
Crocusatin eHMDB
Chemical FormulaC9H14O
Average Mass138.2069 Da
Monoisotopic Mass138.10447 Da
IUPAC Name3,5,5-trimethylcyclohex-3-en-1-one
Traditional Name3,5,5-trimethylcyclohex-3-en-1-one
CAS Registry Number471-01-2
SMILES
CC1=CC(C)(C)CC(=O)C1
InChI Identifier
InChI=1S/C9H14O/c1-7-4-8(10)6-9(2,3)5-7/h5H,4,6H2,1-3H3
InChI KeyLKOKKQDYMZUSCG-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Amauris echeriaLOTUS Database
Crocus sativusFooDB
Mandragora autumnalisPlant
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
logP1.72ALOGPS
logP1.96ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)16.62ChemAxon
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity42.67 m³·mol⁻¹ChemAxon
Polarizability16.27 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0040338  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB020063  
KNApSAcK IDC00032863  
Chemspider ID9704  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10108  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available