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Showing NP-Card for 3-phenyl-2-propenyl acetate (NP0183868)

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Record Information
Version2.0
Created at2022-09-03 22:51:29 UTC
Updated at2022-09-03 22:51:29 UTC
NP-MRD IDNP0183868
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-phenyl-2-propenyl acetate
DescriptionCinnamyl acetate, also known as PHCH=chch2oac, belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety. 3-phenyl-2-propenyl acetate is found in Bidens graveolens, Cinnamomum aromaticum, Cinnamomum osmophloeum, Cinnamomum sieboldii, Cinnamomum verum, Coreopsis woytkowskii, Cucumis melo, Illicium verum, Litchi chinensis, Nicotiana langsdorffii, Pandanus tectorius and Rhodiola rosea. 3-phenyl-2-propenyl acetate was first documented in 2004 (PMID: 15237942). Cinnamyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 18031892) (PMID: 23586860).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0183868 (3-phenyl-2-propenyl acetate)


  Mrv1533004161514352D          

 13 13  0  0  0  0            999 V2000
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    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
    0.7145    2.0625    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    0.8250    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
    0.7145   -0.4125    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
M  END
Download

3D MOL for NP0183868 (3-phenyl-2-propenyl acetate)

     RDKit          3D

 25 25  0  0  0  0  0  0  0  0999 V2000
    4.4282   -0.8403   -0.6783 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1985   -0.4631    0.0901 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3313   -1.3295    0.3295 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9793    0.8232    0.5526 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8573    1.2316    1.2708 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5784    1.0381    0.5227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3728    0.2719    0.9863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6344    0.0415    0.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8816    0.6509   -0.8913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1070    0.4112   -1.5191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0569   -0.4127   -0.9604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7549   -1.0051    0.2619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5819   -0.8019    0.9058 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9890    0.0593   -0.9874 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2134   -1.4384   -1.5605 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0873   -1.4103    0.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7329    0.7814    2.2559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9576    2.3385    1.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5156    1.5733   -0.4067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1909   -0.2284    1.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1595    1.3028   -1.3579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3139    0.8889   -2.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9854   -0.5718   -1.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5107   -1.6581    0.7022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3188   -1.2530    1.8640 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  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  5 17  1  0
  5 18  1  0
  6 19  1  0
  7 20  1  0
  9 21  1  0
 10 22  1  0
 11 23  1  0
 12 24  1  0
 13 25  1  0
M  END
Download

3D SDF for NP0183868 (3-phenyl-2-propenyl acetate)


  Mrv1533004161514352D          

 13 13  0  0  0  0            999 V2000
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    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
    0.7145    2.0625    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    0.8250    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
    0.7145   -0.4125    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0183868

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H12O2/c1-10(12)13-9-5-8-11-6-3-2-4-7-11/h2-8H,9H2,1H3

> <INCHI_KEY>
WJSDHUCWMSHDCR-UHFFFAOYSA-N

> <FORMULA>
C11H12O2

> <MOLECULAR_WEIGHT>
176.215

> <EXACT_MASS>
176.083729626

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
19.694287954230564

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-phenylprop-2-en-1-yl acetate

> <ALOGPS_LOGP>
2.92

> <JCHEM_LOGP>
2.2569371323333334

> <ALOGPS_LOGS>
-3.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.004438223439601

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
52.34400000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.40e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-phenyl-2-propenyl acetate

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0183868 (3-phenyl-2-propenyl acetate)

Download
PDB for NP0183868 (3-phenyl-2-propenyl acetate)
HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.000   9.240   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -0.000   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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

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3D PDB for NP0183868 (3-phenyl-2-propenyl acetate)
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SMILES for NP0183868 (3-phenyl-2-propenyl acetate)
CC(=O)OCC=CC1=CC=CC=C1
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INCHI for NP0183868 (3-phenyl-2-propenyl acetate)
InChI=1S/C11H12O2/c1-10(12)13-9-5-8-11-6-3-2-4-7-11/h2-8H,9H2,1H3
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View in JSmol
Synonyms
ValueSource
1-Acetoxy-3-phenyl-2-propeneChEBI
1-Phenyl-3-acetoxyprop-1-eneChEBI
3-Phenyl-2-propen-1-ol acetateChEBI
3-Phenyl-2-propen-1-yl acetateChEBI
3-Phenyl-2-propenyl acetateChEBI
3-Phenylallyl acetateChEBI
Acetic acid cinnamyl esterChEBI
gamma-Phenylallyl acetateChEBI
PHCH=CHCH2oacChEBI
3-Phenyl-2-propen-1-ol acetic acidGenerator
3-Phenyl-2-propen-1-yl acetic acidGenerator
3-Phenyl-2-propenyl acetic acidGenerator
3-Phenylallyl acetic acidGenerator
Acetate cinnamyl esterGenerator
g-Phenylallyl acetateGenerator
g-Phenylallyl acetic acidGenerator
gamma-Phenylallyl acetic acidGenerator
Γ-phenylallyl acetateGenerator
Γ-phenylallyl acetic acidGenerator
Cinnamyl acetic acidGenerator
3-Phenylprop-2-en-1-yl acetic acidGenerator
Chemical FormulaC11H12O2
Average Mass176.2150 Da
Monoisotopic Mass176.08373 Da
IUPAC Name3-phenylprop-2-en-1-yl acetate
Traditional Name3-phenyl-2-propenyl acetate
CAS Registry NumberNot Available
SMILES
CC(=O)OCC=CC1=CC=CC=C1
InChI Identifier
InChI=1S/C11H12O2/c1-10(12)13-9-5-8-11-6-3-2-4-7-11/h2-8H,9H2,1H3
InChI KeyWJSDHUCWMSHDCR-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
Bidens graveolensLOTUS Database
Cinnamomum aromaticumLOTUS Database
Cinnamomum osmophloeumLOTUS Database
Cinnamomum sieboldiiLOTUS Database
Cinnamomum verumLOTUS Database
Coreopsis woytkowskiiLOTUS Database
Cucumis meloLOTUS Database
Illicium verumLOTUS Database
Litchi chinensisLOTUS Database
Nicotiana langsdorffiiLOTUS Database
Pandanus tectoriusLOTUS Database
Rhodiola roseaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassBenzene and substituted derivatives  
Sub ClassStyrenes  
Direct ParentStyrenes  
Alternative Parents
Substituents
  • Styrene
    • 

  • 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 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
logP2.92ALOGPS
logP2.26ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity52.34 m³·mol⁻¹ChemAxon
Polarizability19.69 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 IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCinnamyl acetate  
METLIN IDNot Available
PubChem Compound7660  
PDB IDNot Available
ChEBI ID31402  
Good Scents IDNot Available
References
General References
  1. Cheng SS, Liu JY, Tsai KH, Chen WJ, Chang ST: Chemical composition and mosquito larvicidal activity of essential oils from leaves of different Cinnamomum osmophloeum provenances. J Agric Food Chem. 2004 Jul 14;52(14):4395-400. doi: 10.1021/jf0497152. [PubMed:15237942  ] 
  2. Bhatia SP, Wellington GA, Cocchiara J, Lalko J, Letizia CS, Api AM: Fragrance material review on cinnamyl acetate. Food Chem Toxicol. 2007;45 Suppl 1:S53-7. doi: 10.1016/j.fct.2007.09.012. Epub 2007 Sep 14. [PubMed:18031892  ] 
  3. Geng B, Wang M, Qi W, Su R, He Z: Cinnamyl acetate synthesis by lipase-catalyzed transesterification in a solvent-free system. Biotechnol Appl Biochem. 2012 Jul-Aug;59(4):270-5. doi: 10.1002/bab.1023. Epub 2012 Jun 28. [PubMed:23586860  ] 
  4. LOTUS database [Link]