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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:45:24 UTC

Update Date

2023-02-21 17:26:34 UTC

HMDB ID

HMDB0038439

Secondary Accession Numbers

HMDB38439

Metabolite Identification

Common Name

(-)-5-(2-Propenyl)-2-oxazolidinethione

Description

(-)-5-(2-Propenyl)-2-oxazolidinethione belongs to the class of organic compounds known as oxazolidines. Oxazolidines are compounds containing an oxazolidine moiety, which consists of a saturated aliphatic five-member ring with one oxygen atom, one nitrogen, three carbon atoms, and two double bonds (-)-5-(2-Propenyl)-2-oxazolidinethione has been detected, but not quantified in, brassicas. This could make (-)-5-(2-propenyl)-2-oxazolidinethione a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (-)-5-(2-Propenyl)-2-oxazolidinethione.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
CQP	HMDB
Isoquinoline-5-sulfonamide 48	HMDB

Chemical Formula

C₆H₉NOS

Average Molecular Weight

143.207

Monoisotopic Molecular Weight

143.040484605

IUPAC Name

5-(prop-2-en-1-yl)-1,3-oxazolidine-2-thione

Traditional Name

5-(prop-2-en-1-yl)-1,3-oxazolidine-2-thione

CAS Registry Number

15216-29-2

SMILES

C=CCC1CNC(=S)O1

InChI Identifier

InChI=1S/C6H9NOS/c1-2-3-5-4-7-6(9)8-5/h2,5H,1,3-4H2,(H,7,9)

InChI Key

QEKDLBSHZCJKRO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxazolidines. Oxazolidines are compounds containing an oxazolidine moiety, which consists of a saturated aliphatic five-member ring with one oxygen atom, one nitrogen, three carbon atoms, and two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azolidines

Sub Class

Oxazolidines

Direct Parent

Oxazolidines

Alternative Parents

Substituents

Thiocarbamic acid ester
Oxazolidine
Thiocarbamic acid derivative
Oxacycle
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0038439)
Cytoplasm (HMDB: HMDB0038439)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038439)

Source

Exogenous

Exogenous (HMDB: HMDB0038439)

Food

Food (HMDB: HMDB0038439)

Vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Endogenous

Plant

Plant (HMDB: HMDB0038439)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0038439)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	60 - 61 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	2993 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.71 g/L	ALOGPS
logP	0.44	ALOGPS
logP	1.61	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	8.72	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	21.26 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	40.6 m³·mol⁻¹	ChemAxon
Polarizability	15.12 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	131.671	31661259
DarkChem	[M-H]-	126.931	31661259
DeepCCS	[M+H]+	133.819	30932474
DeepCCS	[M-H]-	131.773	30932474
DeepCCS	[M-2H]-	167.843	30932474
DeepCCS	[M+Na]+	142.531	30932474
AllCCS	[M+H]+	129.6	32859911
AllCCS	[M+H-H2O]+	125.0	32859911
AllCCS	[M+NH4]+	133.9	32859911
AllCCS	[M+Na]+	135.1	32859911
AllCCS	[M-H]-	128.1	32859911
AllCCS	[M+Na-2H]-	130.2	32859911
AllCCS	[M+HCOO]-	132.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.39 minutes	32390414
Predicted by Siyang on May 30, 2022	9.3723 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.65 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	118.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	859.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	318.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	94.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	205.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	75.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	264.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	324.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	306.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	654.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	164.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	817.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	200.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	228.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	560.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	320.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	78.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(-)-5-(2-Propenyl)-2-oxazolidinethione	C=CCC1CNC(=S)O1	2449.2	Standard polar	33892256
(-)-5-(2-Propenyl)-2-oxazolidinethione	C=CCC1CNC(=S)O1	1333.8	Standard non polar	33892256
(-)-5-(2-Propenyl)-2-oxazolidinethione	C=CCC1CNC(=S)O1	1592.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(-)-5-(2-Propenyl)-2-oxazolidinethione,1TMS,isomer #1	C=CCC1CN([Si](C)(C)C)C(=S)O1	1425.1	Semi standard non polar	33892256
(-)-5-(2-Propenyl)-2-oxazolidinethione,1TMS,isomer #1	C=CCC1CN([Si](C)(C)C)C(=S)O1	1446.0	Standard non polar	33892256
(-)-5-(2-Propenyl)-2-oxazolidinethione,1TBDMS,isomer #1	C=CCC1CN([Si](C)(C)C(C)(C)C)C(=S)O1	1645.0	Semi standard non polar	33892256
(-)-5-(2-Propenyl)-2-oxazolidinethione,1TBDMS,isomer #1	C=CCC1CN([Si](C)(C)C(C)(C)C)C(=S)O1	1687.0	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-5-(2-Propenyl)-2-oxazolidinethione GC-MS (Non-derivatized) - 70eV, Positive	splash10-004l-9100000000-59f6a76bc5b6ef57aabc	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-5-(2-Propenyl)-2-oxazolidinethione 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 - (-)-5-(2-Propenyl)-2-oxazolidinethione 10V, Positive-QTOF	splash10-000f-9800000000-ee0b551200f51bb88710	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-5-(2-Propenyl)-2-oxazolidinethione 20V, Positive-QTOF	splash10-002o-6900000000-fd2cc760176f4b2934d6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-5-(2-Propenyl)-2-oxazolidinethione 40V, Positive-QTOF	splash10-02tc-9000000000-b9d5bc3fd3af20c1e530	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-5-(2-Propenyl)-2-oxazolidinethione 10V, Negative-QTOF	splash10-0006-3900000000-a722caa6b27ae3fd2bb8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-5-(2-Propenyl)-2-oxazolidinethione 20V, Negative-QTOF	splash10-0a4i-6900000000-7a9be2c1224ffc42a6f4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-5-(2-Propenyl)-2-oxazolidinethione 40V, Negative-QTOF	splash10-0a4i-9000000000-8ad7d5cb20868af2470d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-5-(2-Propenyl)-2-oxazolidinethione 10V, Negative-QTOF	splash10-0a4i-2900000000-1a6b253509bfa3417664	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-5-(2-Propenyl)-2-oxazolidinethione 20V, Negative-QTOF	splash10-0a4i-9300000000-a126ec7418b962da8595	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-5-(2-Propenyl)-2-oxazolidinethione 40V, Negative-QTOF	splash10-0a4i-9000000000-1cb1195e5908c5ed2449	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-5-(2-Propenyl)-2-oxazolidinethione 10V, Positive-QTOF	splash10-0006-3900000000-b29116fc7ef9c4f1fb6d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-5-(2-Propenyl)-2-oxazolidinethione 20V, Positive-QTOF	splash10-05nf-9200000000-3b2ff9a95f4ff31a350e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-5-(2-Propenyl)-2-oxazolidinethione 40V, Positive-QTOF	splash10-00ko-9000000000-0d11ae9ce98f4b54ab54	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	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

FDB017797

KNApSAcK ID

Not Available

Chemspider ID

2300696

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3036745

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1868341

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 (-)-5-(2-Propenyl)-2-oxazolidinethione (HMDB0038439)

MOL for HMDB0038439 ((-)-5-(2-Propenyl)-2-oxazolidinethione)

3D MOL for HMDB0038439 ((-)-5-(2-Propenyl)-2-oxazolidinethione)

3D SDF for HMDB0038439 ((-)-5-(2-Propenyl)-2-oxazolidinethione)

3D-SDF for HMDB0038439 ((-)-5-(2-Propenyl)-2-oxazolidinethione)

PDB for HMDB0038439 ((-)-5-(2-Propenyl)-2-oxazolidinethione)

3D PDB for HMDB0038439 ((-)-5-(2-Propenyl)-2-oxazolidinethione)

SMILES for HMDB0038439 ((-)-5-(2-Propenyl)-2-oxazolidinethione)

INCHI for HMDB0038439 ((-)-5-(2-Propenyl)-2-oxazolidinethione)

Structure for HMDB0038439 ((-)-5-(2-Propenyl)-2-oxazolidinethione)

3D Structure for HMDB0038439 ((-)-5-(2-Propenyl)-2-oxazolidinethione)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra