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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:57:41 UTC

Update Date

2023-02-21 17:25:57 UTC

HMDB ID

HMDB0037701

Secondary Accession Numbers

HMDB37701

Metabolite Identification

Common Name

Isopropyl cinnamate

Description

Isopropyl cinnamate belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid. Isopropyl cinnamate is a balsam, berry, and cinnamyl tasting compound. Based on a literature review very few articles have been published on Isopropyl 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      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   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    1    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    HMDB0037701
HETATM    1  C1  UNL     1       2.615   0.634  -1.140  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.438  -0.490  -0.114  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.359  -1.783  -0.932  1.00  0.00           C  
HETATM    4  O1  UNL     1       1.227  -0.237   0.546  1.00  0.00           O  
HETATM    5  C4  UNL     1       1.050  -0.047   1.873  1.00  0.00           C  
HETATM    6  O2  UNL     1       2.167  -0.123   2.542  1.00  0.00           O  
HETATM    7  C5  UNL     1      -0.111   0.203   2.651  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.312   0.377   2.220  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.719   0.374   0.850  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.996  -0.156   0.549  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.547  -0.111  -0.691  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.886   0.463  -1.748  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.649   0.994  -1.512  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.101   0.939  -0.234  1.00  0.00           C  
HETATM   15  H1  UNL     1       2.631   1.619  -0.615  1.00  0.00           H  
HETATM   16  H2  UNL     1       3.522   0.467  -1.735  1.00  0.00           H  
HETATM   17  H3  UNL     1       1.742   0.609  -1.821  1.00  0.00           H  
HETATM   18  H4  UNL     1       3.305  -0.530   0.555  1.00  0.00           H  
HETATM   19  H5  UNL     1       3.166  -1.803  -1.691  1.00  0.00           H  
HETATM   20  H6  UNL     1       2.481  -2.677  -0.297  1.00  0.00           H  
HETATM   21  H7  UNL     1       1.348  -1.807  -1.431  1.00  0.00           H  
HETATM   22  H8  UNL     1       0.028   0.256   3.781  1.00  0.00           H  
HETATM   23  H9  UNL     1      -2.142   0.551   2.992  1.00  0.00           H  
HETATM   24  H10 UNL     1      -3.549  -0.622   1.374  1.00  0.00           H  
HETATM   25  H11 UNL     1      -4.531  -0.523  -0.910  1.00  0.00           H  
HETATM   26  H12 UNL     1      -3.320   0.501  -2.737  1.00  0.00           H  
HETATM   27  H13 UNL     1      -1.054   1.467  -2.286  1.00  0.00           H  
HETATM   28  H14 UNL     1      -0.162   1.457  -0.110  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3    4   18
CONECT    3   19   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
Isopropyl cinnamic acid	Generator
1-Methylethyl 3-phenylpropenoate	HMDB
Cinnamic acid, isopropyl ester	HMDB
FEMA 2939	HMDB
Isopropyl (2E)-3-phenyl-2-propenoate	HMDB
Isopropyl 3-phenylpropenoate	HMDB
Isopropylester kyseliny skoricove	HMDB
Propan-2-yl (2Z)-3-phenylprop-2-enoic acid	Generator

Chemical Formula

C₁₂H₁₄O₂

Average Molecular Weight

190.2384

Monoisotopic Molecular Weight

190.099379692

IUPAC Name

propan-2-yl (2Z)-3-phenylprop-2-enoate

Traditional Name

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

CAS Registry Number

7780-06-5

SMILES

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

InChI Identifier

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

InChI Key

RGACABDFLVLVCT-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: HMDB0037701)
Cell membrane (HMDB: HMDB0037701)

Source

Exogenous

Food

Food (HMDB: HMDB0037701)

Endogenous

Plant

Plant (HMDB: HMDB0037701)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0037701)

Biological role

Nutrient (HMDB: HMDB0037701)

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	0.069 g/L	ALOGPS
logP	3.38	ALOGPS
logP	3.29	ChemAxon
logS	-3.4	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	4	ChemAxon
Refractivity	57 m³·mol⁻¹	ChemAxon
Polarizability	21.16 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]+	146.065	31661259
DarkChem	[M-H]-	143.314	31661259
DeepCCS	[M+H]+	144.396	30932474
DeepCCS	[M-H]-	142.037	30932474
DeepCCS	[M-2H]-	177.235	30932474
DeepCCS	[M+Na]+	152.845	30932474
AllCCS	[M+H]+	142.7	32859911
AllCCS	[M+H-H2O]+	138.5	32859911
AllCCS	[M+NH4]+	146.5	32859911
AllCCS	[M+Na]+	147.6	32859911
AllCCS	[M-H]-	145.4	32859911
AllCCS	[M+Na-2H]-	146.1	32859911
AllCCS	[M+HCOO]-	147.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isopropyl cinnamate	CC(C)OC(=O)\C=C/C1=CC=CC=C1	2139.9	Standard polar	33892256
Isopropyl cinnamate	CC(C)OC(=O)\C=C/C1=CC=CC=C1	1436.6	Standard non polar	33892256
Isopropyl cinnamate	CC(C)OC(=O)\C=C/C1=CC=CC=C1	1513.8	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 - Isopropyl cinnamate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f8c-4900000000-e74143d03a3dca209d9f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isopropyl 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 - Isopropyl cinnamate 10V, Positive-QTOF	splash10-000x-1900000000-0071dc77ec18ac6833a8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl cinnamate 20V, Positive-QTOF	splash10-01qc-5900000000-ddbc594e0796710263ce	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl cinnamate 40V, Positive-QTOF	splash10-0f6x-9300000000-13c6f12e8804cbdd7bef	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl cinnamate 10V, Negative-QTOF	splash10-000i-3900000000-84dd27a1124601710bc7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl cinnamate 20V, Negative-QTOF	splash10-0a4i-9700000000-b4b82d77674ce825fc7c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl cinnamate 40V, Negative-QTOF	splash10-0a4i-9300000000-3a29a6135672f9a5da68	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl cinnamate 10V, Negative-QTOF	splash10-000i-0900000000-f2caa0578ee476455a3d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl cinnamate 20V, Negative-QTOF	splash10-0udi-1900000000-1eebbd6b7d1696ae0586	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl cinnamate 40V, Negative-QTOF	splash10-0fb9-9500000000-a198564ace003f453695	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl cinnamate 10V, Positive-QTOF	splash10-001i-0900000000-a2a8ef9607e3f8fb6db0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl cinnamate 20V, Positive-QTOF	splash10-0ue9-0900000000-ebd6fc609248641dd7f7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl cinnamate 40V, Positive-QTOF	splash10-0udi-3900000000-275b5d0f6eda7c023315	2021-09-23	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

FDB016829

KNApSAcK ID

Not Available

Chemspider ID

10004867

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11830220

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 Isopropyl cinnamate (HMDB0037701)

MOL for HMDB0037701 (Isopropyl cinnamate)

3D MOL for HMDB0037701 (Isopropyl cinnamate)

3D SDF for HMDB0037701 (Isopropyl cinnamate)

3D-SDF for HMDB0037701 (Isopropyl cinnamate)

PDB for HMDB0037701 (Isopropyl cinnamate)

3D PDB for HMDB0037701 (Isopropyl cinnamate)

SMILES for HMDB0037701 (Isopropyl cinnamate)

INCHI for HMDB0037701 (Isopropyl cinnamate)

Structure for HMDB0037701 (Isopropyl cinnamate)

3D Structure for HMDB0037701 (Isopropyl cinnamate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra