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Showing NP-Card for 4-(4-Acetoxyphenyl)-2-butanone (NP0337154)

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Record Information
Version2.0
Created at2024-09-11 09:32:53 UTC
Updated at2024-09-11 09:32:53 UTC
NP-MRD IDNP0337154
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-(4-Acetoxyphenyl)-2-butanone
DescriptionCuelure, also known as fema 3652 or HDSF, belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group. Cuelure is an extremely weak basic (essentially neutral) compound (based on its pKa). Cuelure is a berry, blueberry, and jam tasting compound. 4-(4-Acetoxyphenyl)-2-butanone was first documented in 2007 (PMID: 17849860). Outside of the human body, (PMID: 19253638) (PMID: 17619106).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0337154 (4-(4-Acetoxyphenyl)-2-butanone)


  Mrv0541 05061307132D          

 15 15  0  0  0  0            999 V2000
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    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
    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
  9  1  1  0  0  0  0
  9  3  1  0  0  0  0
 10  2  1  0  0  0  0
 11  4  1  0  0  0  0
 11  5  2  0  0  0  0
 11  6  1  0  0  0  0
 12  7  2  0  0  0  0
 12  8  1  0  0  0  0
 13  9  2  0  0  0  0
 14 10  2  0  0  0  0
 15 10  1  0  0  0  0
 15 12  1  0  0  0  0
M  END
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3D MOL for NP0337154 (4-(4-Acetoxyphenyl)-2-butanone)

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3D SDF for NP0337154 (4-(4-Acetoxyphenyl)-2-butanone)

  Mrv0541 05061307132D          

 15 15  0  0  0  0            999 V2000
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    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
    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
  9  1  1  0  0  0  0
  9  3  1  0  0  0  0
 10  2  1  0  0  0  0
 11  4  1  0  0  0  0
 11  5  2  0  0  0  0
 11  6  1  0  0  0  0
 12  7  2  0  0  0  0
 12  8  1  0  0  0  0
 13  9  2  0  0  0  0
 14 10  2  0  0  0  0
 15 10  1  0  0  0  0
 15 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0337154

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)CCC1=CC=C(OC(C)=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H14O3/c1-9(13)3-4-11-5-7-12(8-6-11)15-10(2)14/h5-8H,3-4H2,1-2H3

> <INCHI_KEY>
UMIKWXDGXDJQJK-UHFFFAOYSA-N

> <FORMULA>
C12H14O3

> <MOLECULAR_WEIGHT>
206.2378

> <EXACT_MASS>
206.094294314

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
22.200412812289272

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(3-oxobutyl)phenyl acetate

> <ALOGPS_LOGP>
1.91

> <JCHEM_LOGP>
1.9924492673333332

> <ALOGPS_LOGS>
-3.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.591543875969542

> <JCHEM_PKA_STRONGEST_BASIC>
-6.9033191420944355

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
56.65010000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.42e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(3-oxobutyl)phenyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0337154 (4-(4-Acetoxyphenyl)-2-butanone)
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PDB for NP0337154 (4-(4-Acetoxyphenyl)-2-butanone)
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      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   4.620   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
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3    4    9                                                       
CONECT    4    3   11                                                       
CONECT    5    7   11                                                       
CONECT    6    8   11                                                       
CONECT    7    5   12                                                       
CONECT    8    6   12                                                       
CONECT    9    1    3   13                                                  
CONECT   10    2   14   15                                                  
CONECT   11    4    5    6                                                  
CONECT   12    7    8   15                                                  
CONECT   13    9                                                            
CONECT   14   10                                                            
CONECT   15   10   12                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

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3D PDB for NP0337154 (4-(4-Acetoxyphenyl)-2-butanone)
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SMILES for NP0337154 (4-(4-Acetoxyphenyl)-2-butanone)
CC(=O)CCC1=CC=C(OC(C)=O)C=C1
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INCHI for NP0337154 (4-(4-Acetoxyphenyl)-2-butanone)
InChI=1S/C12H14O3/c1-9(13)3-4-11-5-7-12(8-6-11)15-10(2)14/h5-8H,3-4H2,1-2H3
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Synonyms
ValueSource
1-Hexadecanesulfonyl fluorideHMDB
1-HEXADECYLsulfonyl fluorideHMDB
2-Butanone, 4-(p-hydroxyphenyl)-, acetateHMDB
4-(3-Oxobutyl)phenyl acetateHMDB
4-(4-Acetoxyphenyl)-2-butanoneHMDB
4-(p-ACETOXYPHENYL)-2-butanoneHMDB
4-(p-Hydroxyphenyl)-2-butanone, acetateHMDB
4-[4-(Acetyloxy)phenyl]-2-butanoneHMDB
Acetate OF 4-(hydroxyphenyl)-2-butanoneHMDB
Cue-lureHMDB
FEMA 3652HMDB
HDSFHMDB
p-(3-Oxobutyl)phenyl acetateHMDB
Para-(2-acetylethyl)phenyl acetateHMDB
Pherocon QFFHMDB
Q-LureHMDB
4-(3-Oxobutyl)phenyl acetic acidGenerator
Chemical FormulaC12H14O3
Average Mass206.2378 Da
Monoisotopic Mass206.09429 Da
IUPAC Name4-(3-oxobutyl)phenyl acetate
Traditional Name4-(3-oxobutyl)phenyl acetate
CAS Registry NumberNot Available
SMILES
CC(=O)CCC1=CC=C(OC(C)=O)C=C1
InChI Identifier
InChI=1S/C12H14O3/c1-9(13)3-4-11-5-7-12(8-6-11)15-10(2)14/h5-8H,3-4H2,1-2H3
InChI KeyUMIKWXDGXDJQJK-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassPhenol esters  
Sub ClassNot Available
Direct ParentPhenol esters  
Alternative Parents
Substituents
  • Phenol ester
    • 

  • Phenoxy compound
    • 

  • Monocyclic benzene moiety
    • 

  • Ketone
    • 

  • Carboxylic acid ester
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic 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
logP1.91ALOGPS
logP1.99ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)19.59ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity56.65 m³·mol⁻¹ChemAxon
Polarizability22.2 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0033594  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011678  
KNApSAcK IDNot Available
Chemspider ID18057  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound19137  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Chang CL, Cho IK, Li QX: Insecticidal activity of basil oil, trans-anethole, estragole, and linalool to adult fruit flies of Ceratitis capitata, Bactrocera dorsalis, and Bactrocera cucurbitae. J Econ Entomol. 2009 Feb;102(1):203-9. doi: 10.1603/029.102.0129. [PubMed:19253638  ] 
  2. Jang EB, Casana-Giner V, Oliver JE: Field captures of wild melon fly (Diptera: Tephritidae) with an improved male attractant, raspberry ketone formate. J Econ Entomol. 2007 Aug;100(4):1124-8. doi:  10.1603/0022-0493(2007)100[1124:fcowmf]2.0.co;2. [PubMed:17849860  ] 
  3. Suckling DM, Jang EB, Carvalho LA, Nagata JT, Schneider EL, El-Sayed AM: Can menage-a-trois be used for controlling insects? J Chem Ecol. 2007 Aug;33(8):1494-504. doi: 10.1007/s10886-007-9327-9. Epub 2007  Jul 6. [PubMed:17619106  ]