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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:57:38 UTC

Update Date

2023-02-21 17:25:57 UTC

HMDB ID

HMDB0037700

Secondary Accession Numbers

HMDB37700

Metabolite Identification

Common Name

Propyl cinnamate

Description

Propyl cinnamate belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid. Propyl cinnamate is an amber, musty, and vine tasting compound. Based on a literature review very few articles have been published on Propyl 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    HMDB0037700
HETATM    1  C1  UNL     1       3.847   0.822  -0.332  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.139  -0.313  -1.073  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.893  -1.477  -0.141  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.105  -1.177   0.968  1.00  0.00           O  
HETATM    5  C4  UNL     1       0.756  -0.731   0.828  1.00  0.00           C  
HETATM    6  O2  UNL     1       0.401  -0.653  -0.335  1.00  0.00           O  
HETATM    7  C5  UNL     1       0.081  -0.462   2.053  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.141  -0.107   2.205  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.110   0.079   1.162  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.267  -0.545  -0.028  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.196  -0.171  -1.011  1.00  0.00           C  
HETATM   12  C10 UNL     1      -4.036   0.895  -0.803  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.909   1.551   0.396  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.001   1.181   1.346  1.00  0.00           C  
HETATM   15  H1  UNL     1       4.944   0.773  -0.465  1.00  0.00           H  
HETATM   16  H2  UNL     1       3.410   1.798  -0.584  1.00  0.00           H  
HETATM   17  H3  UNL     1       3.621   0.655   0.759  1.00  0.00           H  
HETATM   18  H4  UNL     1       3.876  -0.646  -1.855  1.00  0.00           H  
HETATM   19  H5  UNL     1       2.221   0.039  -1.523  1.00  0.00           H  
HETATM   20  H6  UNL     1       3.889  -1.759   0.254  1.00  0.00           H  
HETATM   21  H7  UNL     1       2.542  -2.376  -0.694  1.00  0.00           H  
HETATM   22  H8  UNL     1       0.644  -0.559   3.031  1.00  0.00           H  
HETATM   23  H9  UNL     1      -1.500   0.080   3.280  1.00  0.00           H  
HETATM   24  H10 UNL     1      -1.705  -1.455  -0.222  1.00  0.00           H  
HETATM   25  H11 UNL     1      -3.251  -0.723  -1.934  1.00  0.00           H  
HETATM   26  H12 UNL     1      -4.746   1.173  -1.567  1.00  0.00           H  
HETATM   27  H13 UNL     1      -4.580   2.394   0.554  1.00  0.00           H  
HETATM   28  H14 UNL     1      -2.925   1.715   2.278  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3   18   19
CONECT    3    4   20   21
CONECT    4    5
CONECT    5    6    6    7
CONECT    7    8    8   22
CONECT    8    9   23
CONECT    9   10   10   14
CONECT   10   11   24
CONECT   11   12   12   25
CONECT   12   13   26
CONECT   13   14   14   27
CONECT   14   28
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Propyl cinnamic acid	Generator
2-Propenoic acid, 3-phenyl-, propyl ester	HMDB
3-Phenyl-propyl ester(2E)-2-propenoic acid	HMDB
Cinnamic acid, propyl ester	HMDB
FEMA 2938	HMDB
N-Propyl cinnamate	HMDB
Propyl 3-phenyl-2-propenoate	HMDB
Propyl 3-phenylpropenoate	HMDB
Propyl beta-phenylacrylate	HMDB
Propylester kyseliny skoricove	HMDB
Propyl (2Z)-3-phenylprop-2-enoic acid	Generator

Chemical Formula

C₁₂H₁₄O₂

Average Molecular Weight

190.2384

Monoisotopic Molecular Weight

190.099379692

IUPAC Name

propyl (2Z)-3-phenylprop-2-enoate

Traditional Name

propyl (2Z)-3-phenylprop-2-enoate

CAS Registry Number

7778-83-8

SMILES

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

InChI Identifier

InChI=1S/C12H14O2/c1-2-10-14-12(13)9-8-11-6-4-3-5-7-11/h3-9H,2,10H2,1H3/b9-8-

InChI Key

OLLPXZHNCXACMM-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: HMDB0037700)
Cell membrane (HMDB: HMDB0037700)

Source

Exogenous

Food

Food (HMDB: HMDB0037700)

Endogenous

Plant

Plant (HMDB: HMDB0037700)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0037700)

Biological role

Nutrient (HMDB: HMDB0037700)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	13 °C	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	0.054 g/L	ALOGPS
logP	3.43	ALOGPS
logP	3.39	ChemAxon
logS	-3.5	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	57.1 m³·mol⁻¹	ChemAxon
Polarizability	21.78 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]+	145.786	31661259
DarkChem	[M-H]-	143.626	31661259
DeepCCS	[M+H]+	144.126	30932474
DeepCCS	[M-H]-	140.945	30932474
DeepCCS	[M-2H]-	177.164	30932474
DeepCCS	[M+Na]+	152.715	30932474
AllCCS	[M+H]+	142.3	32859911
AllCCS	[M+H-H2O]+	138.2	32859911
AllCCS	[M+NH4]+	146.2	32859911
AllCCS	[M+Na]+	147.3	32859911
AllCCS	[M-H]-	146.4	32859911
AllCCS	[M+Na-2H]-	147.1	32859911
AllCCS	[M+HCOO]-	147.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Propyl cinnamate	CCCOC(=O)\C=C/C1=CC=CC=C1	2186.9	Standard polar	33892256
Propyl cinnamate	CCCOC(=O)\C=C/C1=CC=CC=C1	1511.8	Standard non polar	33892256
Propyl cinnamate	CCCOC(=O)\C=C/C1=CC=CC=C1	1605.8	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 - Propyl cinnamate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f8c-4900000000-d301e1b55e41d6dea4c0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Propyl cinnamate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Propyl 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 - Propyl cinnamate 10V, Positive-QTOF	splash10-0006-2900000000-7f49b6d75536b9ae8ac4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propyl cinnamate 20V, Positive-QTOF	splash10-0006-9600000000-03a1d4d5426cf8bc8daf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propyl cinnamate 40V, Positive-QTOF	splash10-0006-9200000000-f8b38bce2a0b22c246a2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propyl cinnamate 10V, Negative-QTOF	splash10-002r-1900000000-889f323616efee839b90	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propyl cinnamate 20V, Negative-QTOF	splash10-004j-1900000000-524d12dc7457a542a791	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propyl cinnamate 40V, Negative-QTOF	splash10-0fb9-2900000000-e7599e5e7e7e0c0204d6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propyl cinnamate 10V, Negative-QTOF	splash10-0f79-0900000000-c8a0f8fc8e17bc6cfacb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propyl cinnamate 20V, Negative-QTOF	splash10-0f6x-7900000000-f7da48a009f7a2fda1fa	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propyl cinnamate 40V, Negative-QTOF	splash10-0fb9-9400000000-08bafe7fd586d8973358	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propyl cinnamate 10V, Positive-QTOF	splash10-001l-1900000000-2531d31dbe94ecfc307e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propyl cinnamate 20V, Positive-QTOF	splash10-0ue9-2900000000-c5305b654704de210d57	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propyl cinnamate 40V, Positive-QTOF	splash10-0udi-4900000000-528ee325a716d943d76d	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

FDB016828

KNApSAcK ID

Not Available

Chemspider ID

30777197

KEGG Compound ID

C06360

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

86306394

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 Propyl cinnamate (HMDB0037700)

MOL for HMDB0037700 (Propyl cinnamate)

3D MOL for HMDB0037700 (Propyl cinnamate)

3D SDF for HMDB0037700 (Propyl cinnamate)

3D-SDF for HMDB0037700 (Propyl cinnamate)

PDB for HMDB0037700 (Propyl cinnamate)

3D PDB for HMDB0037700 (Propyl cinnamate)

SMILES for HMDB0037700 (Propyl cinnamate)

INCHI for HMDB0037700 (Propyl cinnamate)

Structure for HMDB0037700 (Propyl cinnamate)

3D Structure for HMDB0037700 (Propyl cinnamate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra