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Showing NP-Card for 3-Oxo-alpha-lonone (NP0047145)

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Record Information
Version2.0
Created at2022-03-17 20:35:23 UTC
Updated at2022-03-17 20:35:23 UTC
NP-MRD IDNP0047145
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Oxo-alpha-lonone
Description3-Oxo-alpha-lonone, also known as 3-oxo-α-lonone, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 3-Oxo-alpha-lonone is found in Vitis vinifera. 3-Oxo-alpha-lonone is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0047145 (3-Oxo-alpha-lonone)


  Mrv0541 02241212582D          

 15 15  0  0  0  0            999 V2000
   -1.2964    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0109   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0109   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5820   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5820   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7254   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1325   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8798    0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0829    0.7969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1325    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8470   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5615    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5615    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2759   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  3  7  2  0  0  0  0
  5  8  1  0  0  0  0
  1  9  1  0  0  0  0
  1 10  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
M  END
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3D MOL for NP0047145 (3-Oxo-alpha-lonone)

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3D SDF for NP0047145 (3-Oxo-alpha-lonone)

  Mrv0541 02241212582D          

 15 15  0  0  0  0            999 V2000
   -1.2964    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0109   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0109   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5820   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5820   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7254   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1325   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8798    0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0829    0.7969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1325    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8470   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5615    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5615    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2759   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  3  7  2  0  0  0  0
  5  8  1  0  0  0  0
  1  9  1  0  0  0  0
  1 10  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047145

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)\C=C\C1C(C)=CC(=O)CC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C13H18O2/c1-9-7-11(15)8-13(3,4)12(9)6-5-10(2)14/h5-7,12H,8H2,1-4H3/b6-5+

> <INCHI_KEY>
MLYOGKJJENFVJN-AATRIKPKSA-N

> <FORMULA>
C13H18O2

> <MOLECULAR_WEIGHT>
206.2808

> <EXACT_MASS>
206.13067982

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
23.239639116622982

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5,5-trimethyl-4-[(1E)-3-oxobut-1-en-1-yl]cyclohex-2-en-1-one

> <ALOGPS_LOGP>
2.16

> <JCHEM_LOGP>
2.499808916

> <ALOGPS_LOGS>
-2.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.341153927760665

> <JCHEM_PKA_STRONGEST_BASIC>
-4.555160106277608

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
62.706799999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.30e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,5,5-trimethyl-4-[(1E)-3-oxobut-1-en-1-yl]cyclohex-2-en-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0047145 (3-Oxo-alpha-lonone)
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PDB for NP0047145 (3-Oxo-alpha-lonone)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.420   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.754  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.754  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.420  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.086  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.086  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -5.087  -3.080   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.247  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.509   1.089   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.021   1.488   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.247   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.581  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.915   0.000   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.915   1.540   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.248  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2    6    9   10                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    1    5   11                                                  
CONECT    7    3                                                            
CONECT    8    5                                                            
CONECT    9    1                                                            
CONECT   10    1                                                            
CONECT   11    6   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

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3D PDB for NP0047145 (3-Oxo-alpha-lonone)
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SMILES for NP0047145 (3-Oxo-alpha-lonone)
CC(=O)\C=C\C1C(C)=CC(=O)CC1(C)C
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INCHI for NP0047145 (3-Oxo-alpha-lonone)
InChI=1S/C13H18O2/c1-9-7-11(15)8-13(3,4)12(9)6-5-10(2)14/h5-7,12H,8H2,1-4H3/b6-5+
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Synonyms
ValueSource
3-oxo-a-LononeGenerator
3-oxo-Α-lononeGenerator
Chemical FormulaC13H18O2
Average Mass206.2808 Da
Monoisotopic Mass206.13068 Da
IUPAC Name3,5,5-trimethyl-4-[(1E)-3-oxobut-1-en-1-yl]cyclohex-2-en-1-one
Traditional Name3,5,5-trimethyl-4-[(1E)-3-oxobut-1-en-1-yl]cyclohex-2-en-1-one
CAS Registry NumberNot Available
SMILES
CC(=O)\C=C\C1C(C)=CC(=O)CC1(C)C
InChI Identifier
InChI=1S/C13H18O2/c1-9-7-11(15)8-13(3,4)12(9)6-5-10(2)14/h5-7,12H,8H2,1-4H3/b6-5+
InChI KeyMLYOGKJJENFVJN-AATRIKPKSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Vitis viniferaLOTUS Database
Vitis vinifera L.FooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassSesquiterpenoids  
Direct ParentSesquiterpenoids  
Alternative Parents
Substituents
  • Sesquiterpenoid
    • 

  • Megastigmane sesquiterpenoid
    • 

  • Cyclofarsesane sesquiterpenoid
    • 

  • Ionone derivative
    • 

  • Cyclohexenone
    • 

  • Acryloyl-group
    • 

  • Enone
    • 

  • Alpha,beta-unsaturated ketone
    • 

  • Ketone
    • 

  • Cyclic ketone
    • 

  • Organooxygen compound
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Carbonyl group
    • 

  • 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
logP2.16ALOGPS
logP2.5ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)19.34ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity62.71 m³·mol⁻¹ChemAxon
Polarizability23.24 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB007536  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5363685  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available