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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:50:04 UTC

Update Date

2023-02-21 17:22:14 UTC

HMDB ID

HMDB0032488

Secondary Accession Numbers

HMDB32488

Metabolite Identification

Common Name

Prenyl benzoate

Description

Prenyl benzoate belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Prenyl benzoate is a balsam, chocolate, and fruity tasting compound. Prenyl benzoate is used as a food additive (EAFUS: Everything Added to Food in the United States).

Structure

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

HEADER    PROTEIN                                 12-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-20         0                                  
HETATM    1  C   UNK     0    8665.2878667.400   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8666.6218666.630   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8665.2878668.939   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0    8667.9568667.400   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8669.2888666.630   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8670.6238667.400   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8671.9558666.630   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8670.6238668.939   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8663.9548666.630   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8662.6208667.400   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8661.2878666.630   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8661.2878665.090   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8662.6208664.320   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8663.9548665.090   0.000  0.00  0.00           C+0
CONECT    1    2    3    9                                                  
CONECT    2    1    4                                                       
CONECT    3    1                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9   10   14    1                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

COMPND    HMDB0032488
HETATM    1  C1  UNL     1      -4.315   1.567   0.338  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.345   0.441   0.267  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.590  -0.726  -0.602  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.236   0.494   1.007  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.247  -0.613   0.960  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.017  -0.104   0.514  1.00  0.00           O  
HETATM    7  C6  UNL     1       1.098  -0.946   0.389  1.00  0.00           C  
HETATM    8  O2  UNL     1       0.963  -2.157   0.668  1.00  0.00           O  
HETATM    9  C7  UNL     1       2.422  -0.460  -0.069  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.485  -1.325  -0.184  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.714  -0.874  -0.609  1.00  0.00           C  
HETATM   12  C10 UNL     1       4.869   0.466  -0.920  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.795   1.322  -0.799  1.00  0.00           C  
HETATM   14  C12 UNL     1       2.566   0.872  -0.375  1.00  0.00           C  
HETATM   15  H1  UNL     1      -3.772   2.529   0.450  1.00  0.00           H  
HETATM   16  H2  UNL     1      -4.957   1.632  -0.557  1.00  0.00           H  
HETATM   17  H3  UNL     1      -4.992   1.364   1.195  1.00  0.00           H  
HETATM   18  H4  UNL     1      -2.841  -0.811  -1.434  1.00  0.00           H  
HETATM   19  H5  UNL     1      -4.623  -0.652  -1.012  1.00  0.00           H  
HETATM   20  H6  UNL     1      -3.559  -1.673  -0.029  1.00  0.00           H  
HETATM   21  H7  UNL     1      -2.038   1.345   1.653  1.00  0.00           H  
HETATM   22  H8  UNL     1      -1.158  -1.109   1.947  1.00  0.00           H  
HETATM   23  H9  UNL     1      -1.556  -1.383   0.227  1.00  0.00           H  
HETATM   24  H10 UNL     1       3.318  -2.374   0.071  1.00  0.00           H  
HETATM   25  H11 UNL     1       5.546  -1.579  -0.694  1.00  0.00           H  
HETATM   26  H12 UNL     1       5.822   0.810  -1.247  1.00  0.00           H  
HETATM   27  H13 UNL     1       3.898   2.383  -1.040  1.00  0.00           H  
HETATM   28  H14 UNL     1       1.716   1.560  -0.281  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3    4    4
CONECT    3   18   19   20
CONECT    4    5   21
CONECT    5    6   22   23
CONECT    6    7
CONECT    7    8    8    9
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
Prenyl benzoic acid	Generator
2-Buten-1-ol, 3-methyl-, 1-benzoate	HMDB
2-Buten-1-ol, 3-methyl-, benzoate	HMDB
3-Methyl-2-butenyl benzoate	HMDB
3-Methylbut-2-enyl benzoate	HMDB
Benzoic acid, 3-methyl-2-butenyl ester	HMDB
3-Methylbut-2-en-1-yl benzoic acid	HMDB
2-Methyl-4-benzoyloxy-2-butene	HMDB
3-Methylbut-2-en-1-yl benzoate	HMDB
Prenyl benzoate	HMDB

Chemical Formula

C₁₂H₁₄O₂

Average Molecular Weight

190.2384

Monoisotopic Molecular Weight

190.099379692

IUPAC Name

3-methylbut-2-en-1-yl benzoate

Traditional Name

3-methylbut-2-en-1-yl benzoate

CAS Registry Number

5205-11-8

SMILES

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

InChI Identifier

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

InChI Key

INVWRXWYYVMFQC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Benzoate ester
Benzoyl
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Membrane (HMDB: HMDB0032488)
Cell membrane (HMDB: HMDB0032488)

Source

Endogenous

Endogenous (HMDB: HMDB0032488)

Exogenous

Food

Food (HMDB: HMDB0032488)

Exogenous (HMDB: HMDB0032488)

Process

Not Available

Role

Not Available

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	0.22 g/L	ALOGPS
logP	3.26	ALOGPS
logP	3.34	ChemAxon
logS	-2.9	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	57.2 m³·mol⁻¹	ChemAxon
Polarizability	21.64 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]+	143.908	31661259
DarkChem	[M-H]-	140.713	31661259
DeepCCS	[M+H]+	140.386	30932474
DeepCCS	[M-H]-	137.817	30932474
DeepCCS	[M-2H]-	173.488	30932474
DeepCCS	[M+Na]+	148.953	30932474
AllCCS	[M+H]+	140.8	32859911
AllCCS	[M+H-H2O]+	136.7	32859911
AllCCS	[M+NH4]+	144.6	32859911
AllCCS	[M+Na]+	145.7	32859911
AllCCS	[M-H]-	144.3	32859911
AllCCS	[M+Na-2H]-	144.9	32859911
AllCCS	[M+HCOO]-	145.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Prenyl benzoate	CC(C)=CCOC(=O)C1=CC=CC=C1	2055.0	Standard polar	33892256
Prenyl benzoate	CC(C)=CCOC(=O)C1=CC=CC=C1	1450.8	Standard non polar	33892256
Prenyl benzoate	CC(C)=CCOC(=O)C1=CC=CC=C1	1500.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Prenyl benzoate EI-B (Non-derivatized)	splash10-066r-9200000000-ff260d9f3b3a70eb5fad	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Prenyl benzoate EI-B (Non-derivatized)	splash10-066r-9200000000-ff260d9f3b3a70eb5fad	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prenyl benzoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-8900000000-a77748d4560e922aa386	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prenyl benzoate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prenyl benzoate 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 - Prenyl benzoate 10V, Positive-QTOF	splash10-00kf-3900000000-dbb1f54e62eaf09db734	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prenyl benzoate 20V, Positive-QTOF	splash10-014i-9400000000-e54a9dba0aff874b342f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prenyl benzoate 40V, Positive-QTOF	splash10-0pb9-9500000000-1bb12544f004d1575dd8	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prenyl benzoate 10V, Negative-QTOF	splash10-000i-2900000000-646a50b7fec8b1c80873	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prenyl benzoate 20V, Negative-QTOF	splash10-00fr-4900000000-1a3b196addae213345dc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prenyl benzoate 40V, Negative-QTOF	splash10-004i-9400000000-592a725bd920f2a1dfec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prenyl benzoate 10V, Negative-QTOF	splash10-000i-1900000000-23a91098cada61d0d1d7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prenyl benzoate 20V, Negative-QTOF	splash10-004i-9300000000-cb6e67f4da0d697f3d06	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prenyl benzoate 40V, Negative-QTOF	splash10-004i-9000000000-fc58e0949de9ca4842ff	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prenyl benzoate 10V, Positive-QTOF	splash10-014i-9400000000-d7a457eea2e2d36db9ec	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prenyl benzoate 20V, Positive-QTOF	splash10-066r-9400000000-729673372ebf1ece252a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prenyl benzoate 40V, Positive-QTOF	splash10-0a4l-9600000000-4f0ab5ceeac9bd78aa6b	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

FDB010134

KNApSAcK ID

Not Available

Chemspider ID

19991

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21265

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

(). EAFUS: Everything Added to Food in the United States.. .

Enzymes

Enzyme Details

1. 4-hydroxybenzoate polyprenyltransferase, mitochondrial

General function:: Involved in prenyltransferase activity
Specific function:: Catalyzes the prenylation of para-hydroxybenzoate (PHB) with an all-trans polyprenyl group. Mediates the second step in the final reaction sequence of coenzyme Q (CoQ) biosynthesis, which is the condensation of the polyisoprenoid side chain with PHB.
Gene Name:: COQ2
Uniprot ID:: Q96H96
Molecular weight:: 45593.67

Reactions

Solanesyl-PP + 4-Hydroxybenzoic acid → Pyrophosphate + Prenyl benzoate	details

Showing metabocard for Prenyl benzoate (HMDB0032488)

MOL for HMDB0032488 (Prenyl benzoate)

3D MOL for HMDB0032488 (Prenyl benzoate)

3D SDF for HMDB0032488 (Prenyl benzoate)

3D-SDF for HMDB0032488 (Prenyl benzoate)

PDB for HMDB0032488 (Prenyl benzoate)

3D PDB for HMDB0032488 (Prenyl benzoate)

SMILES for HMDB0032488 (Prenyl benzoate)

INCHI for HMDB0032488 (Prenyl benzoate)

Structure for HMDB0032488 (Prenyl benzoate)

3D Structure for HMDB0032488 (Prenyl benzoate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra

Enzymes

Reactions