Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:44:54 UTC

Update Date

2023-02-21 17:21:12 UTC

HMDB ID

HMDB0031699

Secondary Accession Numbers

HMDB31699

Metabolite Identification

Common Name

S-(3-Methyl-2-butenyl) 2-methylpropanethioate

Description

S-(3-Methyl-2-butenyl) 2-methylpropanethioate, also known as S-prenyl thioisobutyrate, belongs to the class of organic compounds known as thioesters. These are organic compounds containing an ester of thiocarboxylic acid, with the general structure RC(=S)XR' (R=H, alkyl, aryl; R'=alkyl, aryl; X=O,S). Based on a literature review very few articles have been published on S-(3-Methyl-2-butenyl) 2-methylpropanethioate.

Structure

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

COMPND    HMDB0031699
HETATM    1  C1  UNL     1      -3.798  -0.462   1.270  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.004  -0.165   0.036  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.670   0.579  -1.072  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.749  -0.563  -0.048  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.939  -0.283  -1.257  1.00  0.00           C  
HETATM    6  S1  UNL     1       0.533   0.706  -0.905  1.00  0.00           S  
HETATM    7  C6  UNL     1       1.666  -0.255   0.111  1.00  0.00           C  
HETATM    8  O1  UNL     1       1.370  -1.386   0.445  1.00  0.00           O  
HETATM    9  C7  UNL     1       2.939   0.422   0.491  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.848  -0.456   1.298  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.609   0.900  -0.764  1.00  0.00           C  
HETATM   12  H1  UNL     1      -3.937   0.478   1.870  1.00  0.00           H  
HETATM   13  H2  UNL     1      -3.307  -1.190   1.930  1.00  0.00           H  
HETATM   14  H3  UNL     1      -4.802  -0.844   1.022  1.00  0.00           H  
HETATM   15  H4  UNL     1      -4.753   0.634  -0.880  1.00  0.00           H  
HETATM   16  H5  UNL     1      -3.531   0.008  -2.037  1.00  0.00           H  
HETATM   17  H6  UNL     1      -3.191   1.580  -1.117  1.00  0.00           H  
HETATM   18  H7  UNL     1      -1.290  -1.101   0.763  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.627  -1.255  -1.692  1.00  0.00           H  
HETATM   20  H9  UNL     1      -1.509   0.236  -2.036  1.00  0.00           H  
HETATM   21  H10 UNL     1       2.660   1.295   1.152  1.00  0.00           H  
HETATM   22  H11 UNL     1       3.212  -1.144   1.925  1.00  0.00           H  
HETATM   23  H12 UNL     1       4.552  -1.050   0.680  1.00  0.00           H  
HETATM   24  H13 UNL     1       4.460   0.207   1.955  1.00  0.00           H  
HETATM   25  H14 UNL     1       3.496   0.122  -1.550  1.00  0.00           H  
HETATM   26  H15 UNL     1       3.083   1.858  -1.050  1.00  0.00           H  
HETATM   27  H16 UNL     1       4.681   1.129  -0.537  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    4    4
CONECT    3   15   16   17
CONECT    4    5   18
CONECT    5    6   19   20
CONECT    6    7
CONECT    7    8    8    9
CONECT    9   10   11   21
CONECT   10   22   23   24
CONECT   11   25   26   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
S-(3-Methyl-2-butenyl) 2-methylpropanethioic acid	Generator
S-Prenyl thioisobutyrate	HMDB
2-Methyl-1-[(3-methylbut-2-en-1-yl)sulphanyl]propan-1-one	HMDB

Chemical Formula

C₉H₁₆OS

Average Molecular Weight

172.288

Monoisotopic Molecular Weight

172.092185824

IUPAC Name

2-methyl-1-[(3-methylbut-2-en-1-yl)sulfanyl]propan-1-one

Traditional Name

2-methyl-1-[(3-methylbut-2-en-1-yl)sulfanyl]propan-1-one

CAS Registry Number

53626-94-1

SMILES

CC(C)C(=O)SCC=C(C)C

InChI Identifier

InChI=1S/C9H16OS/c1-7(2)5-6-11-9(10)8(3)4/h5,8H,6H2,1-4H3

InChI Key

GZNOAIURTRJISH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thioesters. These are organic compounds containing an ester of thiocarboxylic acid, with the general structure RC(=S)XR' (R=H, alkyl, aryl; R'=alkyl, aryl; X=O,S).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Thiocarboxylic acids and derivatives

Sub Class

Thioesters

Direct Parent

Thioesters

Alternative Parents

Substituents

Carbothioic s-ester
Thiocarboxylic acid ester
Sulfenyl compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0031699)
Cell membrane (HMDB: HMDB0031699)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031699)

Source

Endogenous

Endogenous (HMDB: HMDB0031699)

Plant

Plant (HMDB: HMDB0031699)

Exogenous

Food

Food (HMDB: HMDB0031699)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0031699)

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	212.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	185.8 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.510 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.28 g/L	ALOGPS
logP	3.07	ALOGPS
logP	3.18	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Basic)	-6.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	52.08 m³·mol⁻¹	ChemAxon
Polarizability	20.67 Å³	ChemAxon
Number of Rings	0	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]+	142.147	31661259
DarkChem	[M-H]-	135.415	31661259
DeepCCS	[M+H]+	141.472	30932474
DeepCCS	[M-H]-	138.759	30932474
DeepCCS	[M-2H]-	175.075	30932474
DeepCCS	[M+Na]+	150.552	30932474
AllCCS	[M+H]+	136.2	32859911
AllCCS	[M+H-H2O]+	132.5	32859911
AllCCS	[M+NH4]+	139.6	32859911
AllCCS	[M+Na]+	140.6	32859911
AllCCS	[M-H]-	139.2	32859911
AllCCS	[M+Na-2H]-	141.2	32859911
AllCCS	[M+HCOO]-	143.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
S-(3-Methyl-2-butenyl) 2-methylpropanethioate	CC(C)C(=O)SCC=C(C)C	1630.1	Standard polar	33892256
S-(3-Methyl-2-butenyl) 2-methylpropanethioate	CC(C)C(=O)SCC=C(C)C	1226.2	Standard non polar	33892256
S-(3-Methyl-2-butenyl) 2-methylpropanethioate	CC(C)C(=O)SCC=C(C)C	1241.1	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 - S-(3-Methyl-2-butenyl) 2-methylpropanethioate GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kf-9200000000-e1c51dee87bcb6cabd39	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - S-(3-Methyl-2-butenyl) 2-methylpropanethioate 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 - S-(3-Methyl-2-butenyl) 2-methylpropanethioate 10V, Positive-QTOF	splash10-0fk9-3900000000-ac8df960bec2ef41e4d5	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(3-Methyl-2-butenyl) 2-methylpropanethioate 20V, Positive-QTOF	splash10-01b9-9300000000-94174f66ffb9a20a9c2c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(3-Methyl-2-butenyl) 2-methylpropanethioate 40V, Positive-QTOF	splash10-0gbc-9100000000-fe440921078bb3cfa260	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(3-Methyl-2-butenyl) 2-methylpropanethioate 10V, Negative-QTOF	splash10-0v4i-3900000000-45f3944827aee7ce5599	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(3-Methyl-2-butenyl) 2-methylpropanethioate 20V, Negative-QTOF	splash10-0gb9-7900000000-a4906df48a0957252368	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(3-Methyl-2-butenyl) 2-methylpropanethioate 40V, Negative-QTOF	splash10-014i-9100000000-43403c38b7812ab60926	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(3-Methyl-2-butenyl) 2-methylpropanethioate 10V, Positive-QTOF	splash10-0gi3-9600000000-9a413b999ae8586840d8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(3-Methyl-2-butenyl) 2-methylpropanethioate 20V, Positive-QTOF	splash10-01b9-9000000000-88a02485e7fb804f48b1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(3-Methyl-2-butenyl) 2-methylpropanethioate 40V, Positive-QTOF	splash10-05mo-9000000000-a9ca438364bad3eed680	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(3-Methyl-2-butenyl) 2-methylpropanethioate 10V, Negative-QTOF	splash10-0udi-0900000000-fb50c2725b07e45ce4c4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(3-Methyl-2-butenyl) 2-methylpropanethioate 20V, Negative-QTOF	splash10-0udi-6900000000-fefdbed65413277ed7e8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - S-(3-Methyl-2-butenyl) 2-methylpropanethioate 40V, Negative-QTOF	splash10-0udi-8900000000-24a7373c4f5c5303ad56	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

FDB008362

KNApSAcK ID

C00057429

Chemspider ID

28475392

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71438214

PDB ID

Not Available

ChEBI ID

173792

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1583171

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 S-(3-Methyl-2-butenyl) 2-methylpropanethioate (HMDB0031699)

MOL for HMDB0031699 (S-(3-Methyl-2-butenyl) 2-methylpropanethioate)

3D MOL for HMDB0031699 (S-(3-Methyl-2-butenyl) 2-methylpropanethioate)

3D SDF for HMDB0031699 (S-(3-Methyl-2-butenyl) 2-methylpropanethioate)

3D-SDF for HMDB0031699 (S-(3-Methyl-2-butenyl) 2-methylpropanethioate)

PDB for HMDB0031699 (S-(3-Methyl-2-butenyl) 2-methylpropanethioate)

3D PDB for HMDB0031699 (S-(3-Methyl-2-butenyl) 2-methylpropanethioate)

SMILES for HMDB0031699 (S-(3-Methyl-2-butenyl) 2-methylpropanethioate)

INCHI for HMDB0031699 (S-(3-Methyl-2-butenyl) 2-methylpropanethioate)

Structure for HMDB0031699 (S-(3-Methyl-2-butenyl) 2-methylpropanethioate)

3D Structure for HMDB0031699 (S-(3-Methyl-2-butenyl) 2-methylpropanethioate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra