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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:42:23 UTC

Update Date

2023-02-21 17:20:25 UTC

HMDB ID

HMDB0031337

Secondary Accession Numbers

HMDB31337

Metabolite Identification

Common Name

Thiiranebutanenitrile

Description

Thiiranebutanenitrile, also known as (3-cyanopropyl)thiirane, belongs to the class of organic compounds known as thiiranes. These are heterocyclic compounds containing a saturated three-member ring with two carbon atoms and one sulfur atom. Based on a literature review very few articles have been published on Thiiranebutanenitrile.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(+-)-ThIIranebutanenitrile	HMDB
(3-Cyanopropyl)thiirane	HMDB
1-Cyano-4,5-epithiopentane	HMDB
Thiiranebutanenitrile, 9ci	HMDB

Chemical Formula

C₆H₉NS

Average Molecular Weight

127.207

Monoisotopic Molecular Weight

127.045569983

IUPAC Name

4-(thiiran-2-yl)butanenitrile

Traditional Name

4-(thiiran-2-yl)butanenitrile

CAS Registry Number

58130-94-2

SMILES

N#CCCCC1CS1

InChI Identifier

InChI=1S/C6H9NS/c7-4-2-1-3-6-5-8-6/h6H,1-3,5H2

InChI Key

GWYOVZVXBRVBBE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thiiranes. These are heterocyclic compounds containing a saturated three-member ring with two carbon atoms and one sulfur atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Thiiranes

Sub Class

Not Available

Direct Parent

Thiiranes

Alternative Parents

Substituents

Dialkylthioether
Thioether
Thiirane
Nitrile
Carbonitrile
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
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: HMDB0031337)
Cytoplasm (HMDB: HMDB0031337)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031337)

Source

Endogenous

Endogenous (HMDB: HMDB0031337)

Plant

Plant (HMDB: HMDB0031337)

Exogenous

Food

Food (HMDB: HMDB0031337)

Vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Exogenous (HMDB: HMDB0031337)

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	259.00 to 260.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	4574 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.716 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.63 g/L	ALOGPS
logP	1.88	ALOGPS
logP	1.07	ChemAxon
logS	-1.7	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	23.79 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	36.09 m³·mol⁻¹	ChemAxon
Polarizability	14.12 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]+	125.573	31661259
DarkChem	[M-H]-	121.735	31661259
DeepCCS	[M+H]+	131.552	30932474
DeepCCS	[M-H]-	129.453	30932474
DeepCCS	[M-2H]-	165.007	30932474
DeepCCS	[M+Na]+	139.553	30932474
AllCCS	[M+H]+	125.8	32859911
AllCCS	[M+H-H2O]+	121.4	32859911
AllCCS	[M+NH4]+	129.9	32859911
AllCCS	[M+Na]+	131.0	32859911
AllCCS	[M-H]-	132.0	32859911
AllCCS	[M+Na-2H]-	134.5	32859911
AllCCS	[M+HCOO]-	137.3	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.	3.74 minutes	32390414
Predicted by Siyang on May 30, 2022	14.0518 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.12 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	51.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1904.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	513.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	182.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	359.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	256.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	545.8 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	651.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	208.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1160.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	363.2 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	1171.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	353.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	383.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	511.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	539.5 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	176.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Thiiranebutanenitrile	N#CCCCC1CS1	2031.4	Standard polar	33892256
Thiiranebutanenitrile	N#CCCCC1CS1	1150.3	Standard non polar	33892256
Thiiranebutanenitrile	N#CCCCC1CS1	1247.5	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 - Thiiranebutanenitrile GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9000000000-5d3a1f6610d4779df934	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Thiiranebutanenitrile 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 - Thiiranebutanenitrile 10V, Positive-QTOF	splash10-004i-1900000000-9d93737fbb718af3ff83	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiiranebutanenitrile 20V, Positive-QTOF	splash10-00lr-9200000000-cef308bc247ef8e42922	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiiranebutanenitrile 40V, Positive-QTOF	splash10-0zgi-9000000000-25dd63b209d849a8c374	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiiranebutanenitrile 10V, Negative-QTOF	splash10-004i-4900000000-b39fa8a280505200ce73	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiiranebutanenitrile 20V, Negative-QTOF	splash10-004i-7900000000-5ce0b1eeaacd27cb32c6	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiiranebutanenitrile 40V, Negative-QTOF	splash10-0a4i-9000000000-1ed15ab70126c78a2770	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiiranebutanenitrile 10V, Negative-QTOF	splash10-004i-0900000000-b818a559af05310c4d1b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiiranebutanenitrile 20V, Negative-QTOF	splash10-056u-5900000000-84300fa0b300127ee92e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiiranebutanenitrile 40V, Negative-QTOF	splash10-052f-9100000000-fe5e59b36243df30810d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiiranebutanenitrile 10V, Positive-QTOF	splash10-002r-9800000000-3594934e3e8af2531d22	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiiranebutanenitrile 20V, Positive-QTOF	splash10-0udi-9000000000-c332458bd3f4bfd03fe1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiiranebutanenitrile 40V, Positive-QTOF	splash10-0fr6-9000000000-c481325445adf5aef28c	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	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]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	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

FDB003401

KNApSAcK ID

C00054321

Chemspider ID

131181

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

148822

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1120311

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 Thiiranebutanenitrile (HMDB0031337)

MOL for HMDB0031337 (Thiiranebutanenitrile)

3D MOL for HMDB0031337 (Thiiranebutanenitrile)

3D SDF for HMDB0031337 (Thiiranebutanenitrile)

3D-SDF for HMDB0031337 (Thiiranebutanenitrile)

PDB for HMDB0031337 (Thiiranebutanenitrile)

3D PDB for HMDB0031337 (Thiiranebutanenitrile)

SMILES for HMDB0031337 (Thiiranebutanenitrile)

INCHI for HMDB0031337 (Thiiranebutanenitrile)

Structure for HMDB0031337 (Thiiranebutanenitrile)

3D Structure for HMDB0031337 (Thiiranebutanenitrile)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra