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Showing NP-Card for Methyl cinnamate (NP0047756)

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Record Information
Version2.0
Created at2022-03-17 20:45:27 UTC
Updated at2025-02-11 15:44:12 UTC
NP-MRD IDNP0047756
Natural Product DOIhttps://doi.org/10.57994/1347
Secondary Accession NumbersNone
Natural Product Identification
Common NameMethyl cinnamate
DescriptionMethyl cinnamate, also known as fema 2698, belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid. Methyl cinnamate is an extremely weak basic (essentially neutral) compound (based on its pKa). Methyl cinnamate is a sweet, balsam, and cherry tasting compound. Outside of the human body, Methyl cinnamate is found, on average, in the highest concentration within a few different foods, such as sweet basils, cumins, and safflowers. Methyl cinnamate has also been detected, but not quantified in, several different foods, such as pepper (spice), fruits, peppermints, chinese cinnamons, and sweet bay. This could make methyl cinnamate a potential biomarker for the consumption of these foods. It is known to attract males of various orchid bees, such as Aglae caerulea. The oral LD50 for rats is 2610 mg/kg. Methyl cinnamate is the methyl ester of cinnamic acid and is a white or transparent solid with a strong, aromatic odor. White Ruffle (Crespa blanca)Stanhopea embreei, an orchidVanillaModerately toxic by ingestion. The flavor is fruity and strawberry-like; and the odor is sweet, balsamic with fruity odor, reminiscent of cinnamon and strawberry. Methyl cinnamate is found in Alpinia formosana, Alpinia mutica, Alpinia spp. , Alpinia zerumbet, Aragoa lucidula, Artemisia judaica, Artemisia salsoloides, Balanophora fungosa, Conocephalum conicum, Eucalyptus delegatensis, Lindera erythrocarpa, Lychnophora ericoides , Melaleuca viridiflora, Ocotea quixos, Narcissus tazetta, Neolentinus lepideus, Ocimum, Ocimum gratissimum, Ocotea odorifera, Ozothamnus diosmifolius, Paeonia lactiflora, Pimenta racemosa, Plumeria rubra, Spiraea thunbergii, Trifolium pratense, Zanthoxylum armatum and Zanthoxylum piperitum. Purple Lovingly (Querendona Morada)Ocimum americanum cv.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0047756 (Methyl cinnamate)


  Mrv0541 05061307232D          

 12 12  0  0  0  0            999 V2000
   -2.1434    2.0625    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
    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
    0.7145    2.0625    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    1.2375    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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  8  7  2  0  0  0  0
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11 10  2  0  0  0  0
 12  1  1  0  0  0  0
 12 10  1  0  0  0  0
M  END
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3D MOL for NP0047756 (Methyl cinnamate)

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3D SDF for NP0047756 (Methyl cinnamate)

  Mrv0541 05061307232D          

 12 12  0  0  0  0            999 V2000
   -2.1434    2.0625    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
    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
    0.7145    2.0625    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    1.2375    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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  8  7  2  0  0  0  0
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11 10  2  0  0  0  0
 12  1  1  0  0  0  0
 12 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047756

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)\C=C/C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O2/c1-12-10(11)8-7-9-5-3-2-4-6-9/h2-8H,1H3/b8-7-

> <INCHI_KEY>
CCRCUPLGCSFEDV-FPLPWBNLSA-N

> <FORMULA>
C10H10O2

> <MOLECULAR_WEIGHT>
162.1852

> <EXACT_MASS>
162.068079564

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
17.509046833274233

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2Z)-3-phenylprop-2-enoate

> <ALOGPS_LOGP>
2.58

> <JCHEM_LOGP>
2.515313649333333

> <ALOGPS_LOGS>
-2.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.801363696744574

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
47.829

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.20e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2Z)-3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0047756 (Methyl cinnamate)
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PDB for NP0047756 (Methyl cinnamate)
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      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   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       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    9                                                       
CONECT    6    4    9                                                       
CONECT    7    8    9                                                       
CONECT    8    7   10                                                       
CONECT    9    5    6    7                                                  
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12    1   10                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

Download
3D PDB for NP0047756 (Methyl cinnamate)
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SMILES for NP0047756 (Methyl cinnamate)
COC(=O)\C=C/C1=CC=CC=C1
Download
INCHI for NP0047756 (Methyl cinnamate)
InChI=1S/C10H10O2/c1-12-10(11)8-7-9-5-3-2-4-6-9/h2-8H,1H3/b8-7-
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View in JSmol
Synonyms
ValueSource
Methyl cinnamic acidGenerator
3-Phenyl-methyl ester(2E)-2-propenoic acidHMDB
3-Phenyl-methyl ester(e)-2-propenoic acidHMDB
Cinnamic acid,methyl ester (trans)HMDB
FEMA 2698HMDB
Methyl (2E)-3-phenyl-2-propenoateHMDB
Methyl (2E)-3-phenylacrylateHMDB
Methyl (e)-cinnamateHMDB
Methyl cinnamate, (e)HMDB
Methyl ester(e)-cinnamic acidHMDB
Methyl trans-cinnamateHMDB
trans-Methyl cinnamateHMDB
Methyl (2Z)-3-phenylprop-2-enoic acidGenerator
Chemical FormulaC10H10O2
Average Mass162.1852 Da
Monoisotopic Mass162.06808 Da
IUPAC Namemethyl (2Z)-3-phenylprop-2-enoate
Traditional Namemethyl (2Z)-3-phenylprop-2-enoate
CAS Registry Number103-26-4
SMILES
COC(=O)\C=C/C1=CC=CC=C1
InChI Identifier
InChI=1S/C10H10O2/c1-12-10(11)8-7-9-5-3-2-4-6-9/h2-8H,1H3/b8-7-
InChI KeyCCRCUPLGCSFEDV-FPLPWBNLSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-03View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-03View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-03View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-03View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-03View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600.133705802, CD3OD, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-03View Spectrum
Species
Species of Origin
Species NameSourceReference
Alpinia formosanaLOTUS Database
Alpinia muticaLOTUS Database
Alpinia spp.Plant
Alpinia zerumbetLOTUS Database
Aragoa lucidulaLOTUS Database
Artemisia judaicaLOTUS Database
Artemisia salsoloidesLOTUS Database
Balanophora fungosaLOTUS Database
Carthamus tinctoriusFooDB
Cinnamomum aromaticumFooDB
Cinnamomum verumFooDB
Conocephalum conicumLOTUS Database
Cuminum cyminumFooDB
Eucalyptus delegatensisLOTUS Database
Laurus nobilis L.FooDB
Lindera erythrocarpaLOTUS Database
Lychnophora ericoidesPlant
Melaleuca viridifloraLOTUS Database
Mentha x piperitaFooDB
Mespilodaphne quixosLOTUS Database
Narcissus tazettaLOTUS Database
Neolentinus lepideusLOTUS Database
Ocimum-
Ocimum basilicumFooDB
Ocimum gratissimumLOTUS Database
Ocotea odoriferaLOTUS Database
Ozothamnus diosmifoliusLOTUS Database
Paeonia lactifloraLOTUS Database
Pimenta racemosaLOTUS Database
Piper nigrum L.FooDB
Plumeria rubraLOTUS Database
Psidium guajavaFooDB
Spiraea thunbergiiLOTUS Database
Trifolium pratenseLOTUS Database
Zanthoxylum armatumLOTUS Database
Zanthoxylum piperitumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassCinnamic acids and derivatives  
Sub ClassCinnamic acid esters  
Direct ParentCinnamic acid esters  
Alternative Parents
Substituents
  • Cinnamic acid ester
    • 

  • Styrene
    • 

  • Fatty acid ester
    • 

  • Monocyclic benzene moiety
    • 

  • Fatty acyl
    • 

  • Benzenoid
    • 

  • Methyl ester
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Carboxylic acid ester
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organic oxide
    • 

  • Organic oxygen 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
logP2.58ALOGPS
logP2.52ChemAxon
logS-2.9ALOGPS
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.83 m³·mol⁻¹ChemAxon
Polarizability17.51 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0033833  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012001  
KNApSAcK IDNot Available
Chemspider ID4933863  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethyl cinnamate  
METLIN IDNot Available
PubChem Compound6428458  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References