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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:52:42 UTC

Update Date

2023-02-21 17:25:53 UTC

HMDB ID

HMDB0037627

Secondary Accession Numbers

HMDB37627

Metabolite Identification

Common Name

Benzyl tiglate

Description

Benzyl tiglate belongs to the class of organic compounds known as benzyloxycarbonyls. These are organic compounds containing a carbonyl group substituted with a benzyloxyl group. Benzyl tiglate has been detected, but not quantified in, cloves (Syzygium aromaticum). This could make benzyl tiglate a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Benzyl tiglate.

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       0.000   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   3.850   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       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   10                                                            
CONECT    3    1   10                                                       
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5   11                                                       
CONECT    8    6   11                                                       
CONECT    9   11   14                                                       
CONECT   10    2    3   12                                                  
CONECT   11    7    8    9                                                  
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14    9   12                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

COMPND    HMDB0037627
HETATM    1  C1  UNL     1       1.734   1.673  -0.231  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.967   0.890  -0.415  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.940  -0.422  -0.416  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.208  -1.172  -0.605  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.688  -1.139  -0.233  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.691  -2.409  -0.237  1.00  0.00           O  
HETATM    7  O2  UNL     1       0.471  -0.525  -0.051  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.714  -1.318   0.122  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.904  -0.455   0.300  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.648  -0.040  -0.801  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.754   0.757  -0.687  1.00  0.00           C  
HETATM   12  C10 UNL     1      -4.127   1.151   0.594  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.414   0.759   1.709  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.305  -0.042   1.566  1.00  0.00           C  
HETATM   15  H1  UNL     1       1.975   2.771  -0.274  1.00  0.00           H  
HETATM   16  H2  UNL     1       0.996   1.519  -1.059  1.00  0.00           H  
HETATM   17  H3  UNL     1       1.267   1.523   0.772  1.00  0.00           H  
HETATM   18  H4  UNL     1       3.933   1.397  -0.557  1.00  0.00           H  
HETATM   19  H5  UNL     1       4.481  -1.716   0.327  1.00  0.00           H  
HETATM   20  H6  UNL     1       5.030  -0.529  -0.920  1.00  0.00           H  
HETATM   21  H7  UNL     1       4.058  -1.965  -1.379  1.00  0.00           H  
HETATM   22  H8  UNL     1      -0.584  -2.046   0.940  1.00  0.00           H  
HETATM   23  H9  UNL     1      -0.869  -1.875  -0.826  1.00  0.00           H  
HETATM   24  H10 UNL     1      -2.315  -0.375  -1.778  1.00  0.00           H  
HETATM   25  H11 UNL     1      -4.288   1.046  -1.563  1.00  0.00           H  
HETATM   26  H12 UNL     1      -5.005   1.782   0.665  1.00  0.00           H  
HETATM   27  H13 UNL     1      -3.769   1.109   2.674  1.00  0.00           H  
HETATM   28  H14 UNL     1      -1.743  -0.351   2.444  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3    3   18
CONECT    3    4    5
CONECT    4   19   20   21
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   22   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
Benzyl tiglic acid	Generator
FEMA 3330	HMDB
Benzyl (2Z)-2-methylbut-2-enoic acid	Generator

Chemical Formula

C₁₂H₁₄O₂

Average Molecular Weight

190.2384

Monoisotopic Molecular Weight

190.099379692

IUPAC Name

benzyl (2Z)-2-methylbut-2-enoate

Traditional Name

benzyl (2Z)-2-methylbut-2-enoate

CAS Registry Number

37576-88-8

SMILES

C\C=C(\C)C(=O)OCC1=CC=CC=C1

InChI Identifier

InChI=1S/C12H14O2/c1-3-10(2)12(13)14-9-11-7-5-4-6-8-11/h3-8H,9H2,1-2H3/b10-3-

InChI Key

QRGSTISKDZCDHV-KMKOMSMNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzyloxycarbonyls. These are organic compounds containing a carbonyl group substituted with a benzyloxyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzyloxycarbonyls

Direct Parent

Benzyloxycarbonyls

Alternative Parents

Substituents

Benzyloxycarbonyl
Fatty acid ester
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
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 Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0037627)
Cell membrane (HMDB: HMDB0037627)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037627)

Source

Exogenous

Exogenous (HMDB: HMDB0037627)

Food

Food (HMDB: HMDB0037627)

Herb and spice

Spice

Cloves (FooDB: FOOD00179)

Endogenous

Plant

Plant (HMDB: HMDB0037627)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0037627)

Biological role

Nutrient (HMDB: HMDB0037627)

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	0.13 g/L	ALOGPS
logP	3.35	ALOGPS
logP	3.42	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	-6.9	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	56.7 m³·mol⁻¹	ChemAxon
Polarizability	21.43 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]+	146.699	31661259
DarkChem	[M-H]-	143.713	31661259
DeepCCS	[M+H]+	142.531	30932474
DeepCCS	[M-H]-	140.136	30932474
DeepCCS	[M-2H]-	174.806	30932474
DeepCCS	[M+Na]+	149.414	30932474
AllCCS	[M+H]+	141.3	32859911
AllCCS	[M+H-H2O]+	137.2	32859911
AllCCS	[M+NH4]+	145.1	32859911
AllCCS	[M+Na]+	146.2	32859911
AllCCS	[M-H]-	144.7	32859911
AllCCS	[M+Na-2H]-	145.3	32859911
AllCCS	[M+HCOO]-	146.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Benzyl tiglate	C\C=C(\C)C(=O)OCC1=CC=CC=C1	2181.0	Standard polar	33892256
Benzyl tiglate	C\C=C(\C)C(=O)OCC1=CC=CC=C1	1448.1	Standard non polar	33892256
Benzyl tiglate	C\C=C(\C)C(=O)OCC1=CC=CC=C1	1457.9	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 - Benzyl tiglate GC-MS (Non-derivatized) - 70eV, Positive	splash10-000x-9000000000-f01d715b91a3ffcc681f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzyl tiglate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzyl tiglate 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 - Benzyl tiglate 10V, Positive-QTOF	splash10-0006-9800000000-61a66ae83f08b7f7d478	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl tiglate 20V, Positive-QTOF	splash10-0006-9100000000-126b32aff155e77452b8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl tiglate 40V, Positive-QTOF	splash10-0f6x-9000000000-a3ede86c369e0236506d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl tiglate 10V, Negative-QTOF	splash10-000i-2900000000-29512c400de808d38199	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl tiglate 20V, Negative-QTOF	splash10-053j-9300000000-170016f4930d7367594e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl tiglate 40V, Negative-QTOF	splash10-056r-9000000000-a9db08ce7da135951c60	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl tiglate 10V, Negative-QTOF	splash10-000i-3900000000-906a541dd73b00e9e119	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl tiglate 20V, Negative-QTOF	splash10-002e-9000000000-20817558def392499dec	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl tiglate 40V, Negative-QTOF	splash10-0udj-9000000000-3811882f062db9c6577b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl tiglate 10V, Positive-QTOF	splash10-00l6-9000000000-f73114ad5bcea261929b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl tiglate 20V, Positive-QTOF	splash10-0006-9000000000-f9fef1551f97736d1b0c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzyl tiglate 40V, Positive-QTOF	splash10-0006-9000000000-b5f0ab37d7489c243ad4	2021-09-22	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

FDB016741

KNApSAcK ID

C00048327

Chemspider ID

4519666

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5368342

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 Benzyl tiglate (HMDB0037627)

MOL for HMDB0037627 (Benzyl tiglate)

3D MOL for HMDB0037627 (Benzyl tiglate)

3D SDF for HMDB0037627 (Benzyl tiglate)

3D-SDF for HMDB0037627 (Benzyl tiglate)

PDB for HMDB0037627 (Benzyl tiglate)

3D PDB for HMDB0037627 (Benzyl tiglate)

SMILES for HMDB0037627 (Benzyl tiglate)

INCHI for HMDB0037627 (Benzyl tiglate)

Structure for HMDB0037627 (Benzyl tiglate)

3D Structure for HMDB0037627 (Benzyl tiglate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra