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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:36:37 UTC

Update Date

2023-02-21 17:26:54 UTC

HMDB ID

HMDB0039227

Secondary Accession Numbers

HMDB39227

Metabolite Identification

Common Name

3-Mercapto-3-methyl-1-butyl acetate

Description

3-Mercapto-3-methyl-1-butyl acetate belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group). 3-Mercapto-3-methyl-1-butyl acetate is a sweet, fruity, and sulfurous tasting compound. 3-Mercapto-3-methyl-1-butyl acetate has been detected, but not quantified in, fruits. This could make 3-mercapto-3-methyl-1-butyl acetate a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3-Mercapto-3-methyl-1-butyl acetate.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Mercapto-3-methyl-1-butyl acetic acid	Generator
5-(O-Chlorophenyl)-5-ethyl-barbituric acid	HMDB
5-(O-Chlorophenyl)-5-ethylbarbituric acid	HMDB
acido 5-(O-Clorofenil)-5-etilbarbiturico	HMDB
3-Methyl-3-sulfanylbutyl acetic acid	Generator
3-Methyl-3-sulphanylbutyl acetate	Generator
3-Methyl-3-sulphanylbutyl acetic acid	Generator
3-m-3MBA	MeSH
3-Mercapto-3-methylbutyl acetate	MeSH

Chemical Formula

C₇H₁₄O₂S

Average Molecular Weight

162.25

Monoisotopic Molecular Weight

162.071450382

IUPAC Name

3-methyl-3-sulfanylbutyl acetate

Traditional Name

3-methyl-3-sulfanylbutyl acetate

CAS Registry Number

50746-09-3

SMILES

CC(=O)OCCC(C)(C)S

InChI Identifier

InChI=1S/C7H14O2S/c1-6(8)9-5-4-7(2,3)10/h10H,4-5H2,1-3H3

InChI Key

HEZWKNVLHZGPOE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

Carboxylic acid esters

Alternative Parents

Substituents

Carboxylic acid ester
Monocarboxylic acid or derivatives
Alkylthiol
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

Sweet

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0039227)
Cytoplasm (HMDB: HMDB0039227)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039227)

Source

Exogenous

Food

Food (HMDB: HMDB0039227)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0039227)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0039227)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	69.00 °C. @ 6.00 mm Hg	The Good Scents Company Information System
Water Solubility	0	The Good Scents Company Information System
LogP	2.009 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.71 g/L	ALOGPS
logP	2.26	ALOGPS
logP	1.03	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	9.97	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	43.75 m³·mol⁻¹	ChemAxon
Polarizability	17.91 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]+	136.955	31661259
DarkChem	[M-H]-	131.77	31661259
DeepCCS	[M+H]+	137.207	30932474
DeepCCS	[M-H]-	134.561	30932474
DeepCCS	[M-2H]-	170.499	30932474
DeepCCS	[M+Na]+	145.941	30932474
AllCCS	[M+H]+	134.6	32859911
AllCCS	[M+H-H2O]+	130.7	32859911
AllCCS	[M+NH4]+	138.1	32859911
AllCCS	[M+Na]+	139.1	32859911
AllCCS	[M-H]-	137.8	32859911
AllCCS	[M+Na-2H]-	140.4	32859911
AllCCS	[M+HCOO]-	143.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Mercapto-3-methyl-1-butyl acetate	CC(=O)OCCC(C)(C)S	1708.7	Standard polar	33892256
3-Mercapto-3-methyl-1-butyl acetate	CC(=O)OCCC(C)(C)S	1091.8	Standard non polar	33892256
3-Mercapto-3-methyl-1-butyl acetate	CC(=O)OCCC(C)(C)S	1117.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Mercapto-3-methyl-1-butyl acetate,1TMS,isomer #1	CC(=O)OCCC(C)(C)S[Si](C)(C)C	1314.8	Semi standard non polar	33892256
3-Mercapto-3-methyl-1-butyl acetate,1TMS,isomer #1	CC(=O)OCCC(C)(C)S[Si](C)(C)C	1391.7	Standard non polar	33892256
3-Mercapto-3-methyl-1-butyl acetate,1TBDMS,isomer #1	CC(=O)OCCC(C)(C)S[Si](C)(C)C(C)(C)C	1550.8	Semi standard non polar	33892256
3-Mercapto-3-methyl-1-butyl acetate,1TBDMS,isomer #1	CC(=O)OCCC(C)(C)S[Si](C)(C)C(C)(C)C	1610.0	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Mercapto-3-methyl-1-butyl acetate GC-MS (Non-derivatized) - 70eV, Positive	splash10-00bc-9200000000-d32e4c6c43025da7495a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Mercapto-3-methyl-1-butyl acetate 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 - 3-Mercapto-3-methyl-1-butyl acetate 10V, Positive-QTOF	splash10-03di-2900000000-765720981542aed826ae	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-3-methyl-1-butyl acetate 20V, Positive-QTOF	splash10-0uy0-9600000000-e857304e376b0092f0be	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-3-methyl-1-butyl acetate 40V, Positive-QTOF	splash10-014i-9200000000-d17c43472ce40c339259	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-3-methyl-1-butyl acetate 10V, Negative-QTOF	splash10-03fr-4900000000-7d194aac48cb1058a59c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-3-methyl-1-butyl acetate 20V, Negative-QTOF	splash10-0a4i-9300000000-2f64581952b86b42ee39	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-3-methyl-1-butyl acetate 40V, Negative-QTOF	splash10-0a4l-9000000000-dd19626b95f7096af667	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-3-methyl-1-butyl acetate 10V, Negative-QTOF	splash10-0a4i-9200000000-00534201cb933881030c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-3-methyl-1-butyl acetate 20V, Negative-QTOF	splash10-0a4i-9000000000-c01bbbf5bed889264ddb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-3-methyl-1-butyl acetate 40V, Negative-QTOF	splash10-0a4i-9000000000-ec3571c239d0c5c37921	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-3-methyl-1-butyl acetate 10V, Positive-QTOF	splash10-004i-9400000000-1adea7f01b1d95dd25f5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-3-methyl-1-butyl acetate 20V, Positive-QTOF	splash10-00bd-9000000000-a5ccf75dd35d8aafd546	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Mercapto-3-methyl-1-butyl acetate 40V, Positive-QTOF	splash10-004l-9000000000-0fea64b02d95bd22f5e6	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+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

Cytoplasm
Extracellular

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

FDB018760

KNApSAcK ID

Not Available

Chemspider ID

4925940

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6420388

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1593941

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 3-Mercapto-3-methyl-1-butyl acetate (HMDB0039227)

MOL for HMDB0039227 (3-Mercapto-3-methyl-1-butyl acetate)

3D MOL for HMDB0039227 (3-Mercapto-3-methyl-1-butyl acetate)

3D SDF for HMDB0039227 (3-Mercapto-3-methyl-1-butyl acetate)

3D-SDF for HMDB0039227 (3-Mercapto-3-methyl-1-butyl acetate)

PDB for HMDB0039227 (3-Mercapto-3-methyl-1-butyl acetate)

3D PDB for HMDB0039227 (3-Mercapto-3-methyl-1-butyl acetate)

SMILES for HMDB0039227 (3-Mercapto-3-methyl-1-butyl acetate)

INCHI for HMDB0039227 (3-Mercapto-3-methyl-1-butyl acetate)

Structure for HMDB0039227 (3-Mercapto-3-methyl-1-butyl acetate)

3D Structure for HMDB0039227 (3-Mercapto-3-methyl-1-butyl acetate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra