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Showing NP-Card for piperonyl acetate (NP0163228)

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Record Information
Version2.0
Created at2022-09-02 21:47:54 UTC
Updated at2022-09-02 21:47:54 UTC
NP-MRD IDNP0163228
Secondary Accession NumbersNone
Natural Product Identification
Common Namepiperonyl acetate
DescriptionPiperonyl acetate, also known as fema 2912 or heliotropin acetate, belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms. Piperonyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa). Piperonyl acetate is a sweet, bitter, and floral tasting compound. Outside of the human body, Piperonyl acetate has been detected, but not quantified in, green vegetables. piperonyl acetate is found in Cichorium endivia. This could make piperonyl acetate a potential biomarker for the consumption of these foods.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0163228 (piperonyl acetate)


  Mrv0541 05061306352D          

 14 15  0  0  0  0            999 V2000
    6.8513    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  7  1  1  0  0  0  0
  8  2  1  0  0  0  0
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  3  1  0  0  0  0
 10  4  1  0  0  0  0
 10  9  2  0  0  0  0
 11  7  2  0  0  0  0
 12  5  1  0  0  0  0
 12  7  1  0  0  0  0
 13  6  1  0  0  0  0
 13  9  1  0  0  0  0
 14  6  1  0  0  0  0
 14 10  1  0  0  0  0
M  END
Download

3D MOL for NP0163228 (piperonyl acetate)

     RDKit          3D

 24 25  0  0  0  0  0  0  0  0999 V2000
   -4.7019   -0.3268   -0.1684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4283   -1.0857   -0.3063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4615   -2.3207   -0.5435 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1828   -0.5001   -0.1862 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0002   -1.2649   -0.3258 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1704   -0.3620   -0.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0212    0.9780    0.1108 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0831    1.7788    0.2712 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3637    1.2540    0.1780 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5884   -0.0810   -0.0770 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4598   -0.8734   -0.2359 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9603   -0.3379   -0.1181 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5845    0.9300   -0.1967 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6214    1.8505    0.3001 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8899    0.1579   -1.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5332   -0.9514    0.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5562    0.4763    0.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9205   -1.7467   -1.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0063   -2.0168    0.5102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0328    1.4010    0.1860 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9481    2.8524    0.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6366   -1.9268   -0.4371 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8775    1.1879   -1.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4409    0.9272    0.5006 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6 11  2  0
 11 10  1  0
 10  9  2  0
  9 14  1  0
 14 13  1  0
 13 12  1  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
 12 10  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  5 18  1  0
  5 19  1  0
 11 22  1  0
 13 23  1  0
 13 24  1  0
  8 21  1  0
  7 20  1  0
M  END
Download

3D SDF for NP0163228 (piperonyl acetate)


  Mrv0541 05061306352D          

 14 15  0  0  0  0            999 V2000
    6.8513    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  7  1  1  0  0  0  0
  8  2  1  0  0  0  0
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  3  1  0  0  0  0
 10  4  1  0  0  0  0
 10  9  2  0  0  0  0
 11  7  2  0  0  0  0
 12  5  1  0  0  0  0
 12  7  1  0  0  0  0
 13  6  1  0  0  0  0
 13  9  1  0  0  0  0
 14  6  1  0  0  0  0
 14 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0163228

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC1=CC2=C(OCO2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O4/c1-7(11)12-5-8-2-3-9-10(4-8)14-6-13-9/h2-4H,5-6H2,1H3

> <INCHI_KEY>
PFWYHTORQZAGCA-UHFFFAOYSA-N

> <FORMULA>
C10H10O4

> <MOLECULAR_WEIGHT>
194.184

> <EXACT_MASS>
194.057908808

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
19.260681453139817

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2H-1,3-benzodioxol-5-ylmethyl acetate

> <ALOGPS_LOGP>
1.40

> <JCHEM_LOGP>
1.2702549266666667

> <ALOGPS_LOGS>
-1.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.739866004588901

> <JCHEM_POLAR_SURFACE_AREA>
44.760000000000005

> <JCHEM_REFRACTIVITY>
47.79230000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.17e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
piperonyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0163228 (piperonyl acetate)

Download
PDB for NP0163228 (piperonyl acetate)
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      12.789   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.788  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.455  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      11.455  -2.310   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      10.122   0.000   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       3.322   2.016   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       3.322  -0.476   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    3    8                                                       
CONECT    3    2    9                                                       
CONECT    4    8   10                                                       
CONECT    5    8   12                                                       
CONECT    6   13   14                                                       
CONECT    7    1   11   12                                                  
CONECT    8    2    4    5                                                  
CONECT    9    3   10   13                                                  
CONECT   10    4    9   14                                                  
CONECT   11    7                                                            
CONECT   12    5    7                                                       
CONECT   13    6    9                                                       
CONECT   14    6   10                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

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3D PDB for NP0163228 (piperonyl acetate)
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SMILES for NP0163228 (piperonyl acetate)
CC(=O)OCC1=CC2=C(OCO2)C=C1
Download
INCHI for NP0163228 (piperonyl acetate)
InChI=1S/C10H10O4/c1-7(11)12-5-8-2-3-9-10(4-8)14-6-13-9/h2-4H,5-6H2,1H3
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View in JSmol
Synonyms
ValueSource
Piperonyl acetic acidGenerator
(3,4-Methylenedioxy)benzyl acetateHMDB
1,3-Benzodioxol, 5-(acetoxymethyl)HMDB
1,3-Benzodioxol-5-ylmethyl acetateHMDB
1,3-Benzodioxole-5-methanol, 5-acetateHMDB
1,3-Benzodioxole-5-methanol, acetateHMDB
3,4-Methylenedioxybenzyl acetateHMDB
Acetic acid, (3, 4-methylenedioxy)benzyl esterHMDB
Acetic acid, (3,4-methylenedioxy)benzyl esterHMDB
FEMA 2912HMDB
Heliotropin acetateHMDB
Heliotropyl acetateHMDB
Methyl 1,3-benzodioxol-5-ylacetateHMDB
Piperonal acetateHMDB
Piperonyl alcohol, acetateHMDB
Piperonyl alcohol, acetate (6ci,7ci,8ci)HMDB
PiperonylacetateHMDB
(2H-1,3-Benzodioxol-5-yl)methyl acetic acidGenerator
1,3-Benzodioxole-5-methanol acetateMeSH
Piperonyl acetateMeSH
Chemical FormulaC10H10O4
Average Mass194.1840 Da
Monoisotopic Mass194.05791 Da
IUPAC Name2H-1,3-benzodioxol-5-ylmethyl acetate
Traditional Namepiperonyl acetate
CAS Registry NumberNot Available
SMILES
CC(=O)OCC1=CC2=C(OCO2)C=C1
InChI Identifier
InChI=1S/C10H10O4/c1-7(11)12-5-8-2-3-9-10(4-8)14-6-13-9/h2-4H,5-6H2,1H3
InChI KeyPFWYHTORQZAGCA-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Cichorium endiviaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassBenzodioxoles  
Sub ClassNot Available
Direct ParentBenzodioxoles  
Alternative Parents
Substituents
  • Benzodioxole
    • 

  • Benzenoid
    • 

  • Carboxylic acid ester
    • 

  • Oxacycle
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Acetal
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
logP1.4ALOGPS
logP1.27ChemAxon
logS-2ALOGPS
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area44.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.79 m³·mol⁻¹ChemAxon
Polarizability19.26 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0032614  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB010555  
KNApSAcK IDNot Available
Chemspider ID9101  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9473  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]