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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:53:05 UTC

Update Date

2023-02-21 17:28:35 UTC

HMDB ID

HMDB0041219

Secondary Accession Numbers

HMDB41219

Metabolite Identification

Common Name

Allyl cinnamate

Description

Allyl cinnamate belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid. Allyl cinnamate is a balsam, fruity, and peach tasting compound. Based on a literature review very few articles have been published on Allyl cinnamate.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

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   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.001   5.390   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.667   7.700   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1   10                                                       
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4   11                                                       
CONECT    7    5   11                                                       
CONECT    8    9   11                                                       
CONECT    9    8   12                                                       
CONECT   10    2   14                                                       
CONECT   11    6    7    8                                                  
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   10   12                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

COMPND    HMDB0041219
HETATM    1  C1  UNL     1       4.505   1.333   0.653  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.377   0.882   0.072  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.332  -0.403  -0.649  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.407  -1.277  -0.077  1.00  0.00           O  
HETATM    5  C4  UNL     1       1.013  -0.947  -0.015  1.00  0.00           C  
HETATM    6  O2  UNL     1       0.792   0.160  -0.522  1.00  0.00           O  
HETATM    7  C5  UNL     1       0.124  -1.891   0.592  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.133  -1.729   0.782  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.932  -0.585   0.460  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.638   0.738   0.444  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.535   1.691  -0.028  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.770   1.356  -0.503  1.00  0.00           C  
HETATM   13  C11 UNL     1      -4.106   0.019  -0.499  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.232  -0.928  -0.039  1.00  0.00           C  
HETATM   15  H1  UNL     1       4.552   2.270   1.182  1.00  0.00           H  
HETATM   16  H2  UNL     1       5.380   0.718   0.572  1.00  0.00           H  
HETATM   17  H3  UNL     1       2.511   1.515   0.163  1.00  0.00           H  
HETATM   18  H4  UNL     1       3.193  -0.273  -1.746  1.00  0.00           H  
HETATM   19  H5  UNL     1       4.325  -0.878  -0.537  1.00  0.00           H  
HETATM   20  H6  UNL     1       0.546  -2.884   0.948  1.00  0.00           H  
HETATM   21  H7  UNL     1      -1.666  -2.617   1.275  1.00  0.00           H  
HETATM   22  H8  UNL     1      -0.724   1.087   0.881  1.00  0.00           H  
HETATM   23  H9  UNL     1      -2.218   2.713  -0.007  1.00  0.00           H  
HETATM   24  H10 UNL     1      -4.465   2.109  -0.871  1.00  0.00           H  
HETATM   25  H11 UNL     1      -5.093  -0.223  -0.880  1.00  0.00           H  
HETATM   26  H12 UNL     1      -3.547  -1.954  -0.059  1.00  0.00           H  
CONECT    1    2    2   15   16
CONECT    2    3   17
CONECT    3    4   18   19
CONECT    4    5
CONECT    5    6    6    7
CONECT    7    8    8   20
CONECT    8    9   21
CONECT    9   10   10   14
CONECT   10   11   22
CONECT   11   12   12   23
CONECT   12   13   24
CONECT   13   14   14   25
CONECT   14   26
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Allyl cinnamic acid	Generator
Allyl (2E)-3-phenyl-2-propenoate	HMDB
Allyl 3-phenylacrylate	HMDB
Allylester kyseliny skoricove	HMDB
Cinnamic acid, allyl ester	HMDB
FEMA 2022	HMDB
Propenyl cinnamate	HMDB
Vinyl carbinyl cinnamate	HMDB
Prop-2-en-1-yl (2Z)-3-phenylprop-2-enoic acid	Generator

Chemical Formula

C₁₂H₁₂O₂

Average Molecular Weight

188.2225

Monoisotopic Molecular Weight

188.083729628

IUPAC Name

prop-2-en-1-yl (2Z)-3-phenylprop-2-enoate

Traditional Name

prop-2-en-1-yl (2Z)-3-phenylprop-2-enoate

CAS Registry Number

56289-56-6

SMILES

C=CCOC(=O)\C=C/C1=CC=CC=C1

InChI Identifier

InChI=1S/C12H12O2/c1-2-10-14-12(13)9-8-11-6-4-3-5-7-11/h2-9H,1,10H2/b9-8-

InChI Key

KCMITHMNVLRGJU-HJWRWDBZSA-N

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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Cinnamic acid esters

Direct Parent

Cinnamic acid esters

Alternative Parents

Substituents

Cinnamic acid ester
Styrene
Fatty acid ester
Monocyclic benzene moiety
Benzenoid
Fatty acyl
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Membrane (HMDB: HMDB0041219)
Cell membrane (HMDB: HMDB0041219)

Source

Exogenous

Exogenous (HMDB: HMDB0041219)

Food

Food (HMDB: HMDB0041219)

Endogenous

Plant

Plant (HMDB: HMDB0041219)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0041219)

Biological role

Nutrient (HMDB: HMDB0041219)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.031 g/L	ALOGPS
logP	3.19	ALOGPS
logP	3.25	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	56.99 m³·mol⁻¹	ChemAxon
Polarizability	20.86 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	143.497	31661259
DarkChem	[M-H]-	144.245	31661259
DeepCCS	[M+H]+	140.563	30932474
DeepCCS	[M-H]-	138.202	30932474
DeepCCS	[M-2H]-	173.2	30932474
DeepCCS	[M+Na]+	148.282	30932474
AllCCS	[M+H]+	140.6	32859911
AllCCS	[M+H-H2O]+	136.4	32859911
AllCCS	[M+NH4]+	144.5	32859911
AllCCS	[M+Na]+	145.6	32859911
AllCCS	[M-H]-	143.0	32859911
AllCCS	[M+Na-2H]-	143.5	32859911
AllCCS	[M+HCOO]-	144.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	8.31 minutes	32390414
Predicted by Siyang on May 30, 2022	15.7858 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.94 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2544.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	533.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	204.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	341.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	323.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	653.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	736.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	132.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1465.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	538.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1409.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	398.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	452.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	473.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	463.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	25.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Allyl cinnamate	C=CCOC(=O)\C=C/C1=CC=CC=C1	2286.1	Standard polar	33892256
Allyl cinnamate	C=CCOC(=O)\C=C/C1=CC=CC=C1	1460.9	Standard non polar	33892256
Allyl cinnamate	C=CCOC(=O)\C=C/C1=CC=CC=C1	1592.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Allyl cinnamate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f8c-6900000000-9998634589ef6e2efd0d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allyl cinnamate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allyl cinnamate 10V, Positive-QTOF	splash10-000l-4900000000-1d3c65432297957409a4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allyl cinnamate 20V, Positive-QTOF	splash10-0006-9300000000-b6d0fb0431c87421bbbf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allyl cinnamate 40V, Positive-QTOF	splash10-0f6x-9300000000-2f71bda605b3fa73ad3a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allyl cinnamate 10V, Negative-QTOF	splash10-002r-1900000000-0905bbafae2bba903517	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allyl cinnamate 20V, Negative-QTOF	splash10-002b-1900000000-3d91690ee70295f787c5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allyl cinnamate 40V, Negative-QTOF	splash10-0fb9-3900000000-3802535462f272e28012	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allyl cinnamate 10V, Negative-QTOF	splash10-0udr-0900000000-6674aba6e14542ef0c81	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allyl cinnamate 20V, Negative-QTOF	splash10-0udi-2900000000-4bb7a79809a1d7cdfba8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allyl cinnamate 40V, Negative-QTOF	splash10-0fb9-9500000000-f452e81933486484445a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allyl cinnamate 10V, Positive-QTOF	splash10-0019-1900000000-7a0a978ebc8f19d5ffb8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allyl cinnamate 20V, Positive-QTOF	splash10-0uec-2900000000-5ee5d9222cdcb79f9b28	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allyl cinnamate 40V, Positive-QTOF	splash10-0udi-3900000000-98dce8e660c447e58e4e	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021118

KNApSAcK ID

Not Available

Chemspider ID

21427301

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24884162

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Allyl cinnamate (HMDB0041219)

MOL for HMDB0041219 (Allyl cinnamate)

3D MOL for HMDB0041219 (Allyl cinnamate)

3D SDF for HMDB0041219 (Allyl cinnamate)

3D-SDF for HMDB0041219 (Allyl cinnamate)

PDB for HMDB0041219 (Allyl cinnamate)

3D PDB for HMDB0041219 (Allyl cinnamate)

SMILES for HMDB0041219 (Allyl cinnamate)

INCHI for HMDB0041219 (Allyl cinnamate)

Structure for HMDB0041219 (Allyl cinnamate)

3D Structure for HMDB0041219 (Allyl cinnamate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra