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Showing NP-Card for Cinnamyl acetate (NP0045447)

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Record Information
Version2.0
Created at2022-03-17 19:20:07 UTC
Updated at2022-03-17 19:20:07 UTC
NP-MRD IDNP0045447
Secondary Accession NumbersNone
Natural Product Identification
Common NameCinnamyl acetate
DescriptionCinnamyl acetate, also known as fema 2293, belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety. Cinnamyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa). Cinnamyl acetate is a sweet, balsam, and cinnamon tasting compound. Outside of the human body, Cinnamyl acetate is found, on average, in the highest concentration within ceylon cinnamons. Cinnamyl acetate has also been detected, but not quantified in, several different foods, such as fruits, figs, herbs and spices, sweet bay, and chinese cinnamons. This could make cinnamyl acetate a potential biomarker for the consumption of these foods. Cinnamyl acetate is found in Cinnamomum burmannii Nees ex BI , Nicotiana alata, Nicotiana bonariensis, Nicotiana langsdorffii, Rhodiola rosea L. and Syzygium jambos. Another two experiments examined the skin irritation caused by 0.1 ML cinnamyl acetate on guinea pigs and rabbits via a direct application on the skin (open application).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0045447 (Cinnamyl acetate)


  Mrv0541 02241216452D          

 13 13  0  0  0  0            999 V2000
   -1.0717    1.2370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3292    1.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3292    2.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3292    1.2370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3292    0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3292   -1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3292   -2.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3292   -2.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -2.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3292   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 13  2  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
M  END
Download

3D MOL for NP0045447 (Cinnamyl acetate)

     RDKit          3D

 25 25  0  0  0  0  0  0  0  0999 V2000
    4.6328    0.7334   -0.5693 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4763   -0.1055   -0.0798 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5681   -1.3486   -0.0705 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3082    0.4816    0.3619 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1783   -0.3415    0.8347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7077   -1.1798   -0.2694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4881   -1.1609   -0.7431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5983   -0.3773   -0.3230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5487   -0.1005   -1.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6922    0.5599   -0.9897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9528    0.9687    0.3031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0529    0.7181    1.3146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8835    0.0369    0.9518 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1953    0.1899   -1.3585 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2802    0.8704    0.3337 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2252    1.6974   -0.8937 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5234   -0.9871    1.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4996    0.4429    1.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4607   -1.8991   -0.7344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6740   -1.8776   -1.6047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3692   -0.4122   -2.3611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4180    0.7627   -1.7967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8812    1.4861    0.4805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2410    1.0309    2.3313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2560   -0.1889    1.8169 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 NP0045447 (Cinnamyl acetate)


  Mrv0541 02241216452D          

 13 13  0  0  0  0            999 V2000
   -1.0717    1.2370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3292    1.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3292    2.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3292    1.2370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3292    0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3292   -1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3292   -2.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3292   -2.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -2.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3292   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 13  2  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045447

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC\C=C/C1=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/b8-5-

> <INCHI_KEY>
WJSDHUCWMSHDCR-YVMONPNESA-N

> <FORMULA>
C11H12O2

> <MOLECULAR_WEIGHT>
176.2118

> <EXACT_MASS>
176.083729628

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
19.413476795381165

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-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>
(2Z)-3-phenylprop-2-en-1-yl acetate

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0045447 (Cinnamyl acetate)

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PDB for NP0045447 (Cinnamyl acetate)
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  O   UNK     0      -2.001   2.309   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.615   3.079   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.615   4.619   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.615   2.309   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.615   0.769   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.001  -0.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.001  -1.539   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.615  -2.309   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.615  -3.849   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.615  -4.619   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.001  -3.849   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.001  -2.309   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.615  -1.539   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    8   12                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

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3D PDB for NP0045447 (Cinnamyl acetate)
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SMILES for NP0045447 (Cinnamyl acetate)
CC(=O)OC\C=C/C1=CC=CC=C1
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INCHI for NP0045447 (Cinnamyl acetate)
InChI=1S/C11H12O2/c1-10(12)13-9-5-8-11-6-3-2-4-7-11/h2-8H,9H2,1H3/b8-5-
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View in JSmol
Synonyms
ValueSource
Cinnamyl acetic acidGenerator
(2E)-3-Phenyl-2-propenyl acetateHMDB
(e)-Cinnamyl acetateHMDB
3-Phenyl-2-propenyl acetateHMDB
FEMA 2293HMDB
trans-Cinnamyl acetateHMDB
(2Z)-3-Phenylprop-2-en-1-yl acetic acidGenerator
Chemical FormulaC11H12O2
Average Mass176.2118 Da
Monoisotopic Mass176.08373 Da
IUPAC Name(2Z)-3-phenylprop-2-en-1-yl acetate
Traditional Name(2Z)-3-phenylprop-2-en-1-yl acetate
CAS Registry Number21040-45-9
SMILES
CC(=O)OC\C=C/C1=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/b8-5-
InChI KeyWJSDHUCWMSHDCR-YVMONPNESA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Cinnamomum aromaticumFooDB
Cinnamomum burmannii Nees ex BIPlant
Cinnamomum verumFooDB
Ficus caricaFooDB
Laurus nobilis L.FooDB
Nicotiana alataPlant
Nicotiana bonariensisPlant
Nicotiana langsdorffiiPlant
Psidium guajavaFooDB
Rhodiola roseaPlant
Syzygium jambosLOTUS 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 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
logP2.92ALOGPS
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
Polarizability19.41 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0029699  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000889  
KNApSAcK IDC00035072  
Chemspider ID4475104  
KEGG Compound IDC12299  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCinnamyl acetate  
METLIN IDNot Available
PubChem Compound5315912  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available