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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2007-04-12 22:45:27 UTC

Update Date

2023-02-21 17:17:14 UTC

HMDB ID

HMDB0006095

Secondary Accession Numbers

HMDB06095

Metabolite Identification

Common Name

3-Methylsulfinylpropyl isothiocyanate

Description

Consumption of broccoli sprouts has shown to be effective at inhibiting Helicobacter pylori growth with sulforaphane being at least one of the active agents. Sulforaphane is an anticancer and antimicrobial compound which can be obtained by eating cruciferous vegetables such as brussel sprouts, broccoli, cauliflower, bok choy, kale, collards, arugula, broccoli sprouts, chinese broccoli, broccoli raab, kohlrabi, mustard, turnip, radish, watercress and cabbage. The enzyme myrosinase transforms glucoraphanin (a glucosinolate) into sulforaphane upon damage to the plant (such as from chewing). The young sprouts of broccoli and cauliflower are particularly rich in glucoraphanin.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-Isothiocyanatopropyl methyl sulfoxide	ChEBI
IMSP	ChEBI
Methylsulfinylpropylisothiocyanate	ChEBI
3-Isothiocyanatopropyl methyl sulphoxide	Generator
Methylsulfinylpropylisothiocyanic acid	Generator
Methylsulphinylpropylisothiocyanate	Generator
Methylsulphinylpropylisothiocyanic acid	Generator
3-Methylsulfinylpropyl isothiocyanic acid	Generator
3-Methylsulphinylpropyl isothiocyanate	Generator
3-Methylsulphinylpropyl isothiocyanic acid	Generator
1-Isothiocyanato-3-(methylsulphinyl)propane	MeSH
1-Isothiocyanato-3-(methylsulfinyl)propane	MeSH
(R)-1-Isothiocyanato-3-(methylsulphinyl)propane	Generator

Chemical Formula

C₅H₉NOS₂

Average Molecular Weight

163.261

Monoisotopic Molecular Weight

163.012555295

IUPAC Name

1-isothiocyanato-3-methanesulfinylpropane

Traditional Name

iberin

CAS Registry Number

505-44-2

SMILES

CS(=O)CCCN=C=S

InChI Identifier

InChI=1S/C5H9NOS2/c1-9(7)4-2-3-6-5-8/h2-4H2,1H3

InChI Key

LELAOEBVZLPXAZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sulfoxides. Sulfoxides are compounds containing a sulfoxide functional group, with the structure RS(=O)R' (R,R' not H).

Kingdom

Organic compounds

Super Class

Organosulfur compounds

Class

Sulfoxides

Sub Class

Not Available

Direct Parent

Sulfoxides

Alternative Parents

Substituents

Sulfoxide
Isothiocyanate
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Sulfinyl compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (FooDB: )

Source

Endogenous

Endogenous (FooDB: )

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Vegetable

Cruciferous (FooDB: )

Brassica

Brassicas (FooDB: FOOD00857)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

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	2.87 g/L	ALOGPS
logP	0.69	ALOGPS
logP	-0.3	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	29.43 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	44.92 m³·mol⁻¹	ChemAxon
Polarizability	17.16 Å³	ChemAxon
Number of Rings	0	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]+	133.646	31661259
DarkChem	[M-H]-	128.775	31661259
DeepCCS	[M+H]+	130.448	30932474
DeepCCS	[M-H]-	128.297	30932474
DeepCCS	[M-2H]-	163.973	30932474
DeepCCS	[M+Na]+	138.636	30932474
AllCCS	[M+H]+	134.1	32859911
AllCCS	[M+H-H2O]+	130.3	32859911
AllCCS	[M+NH4]+	137.7	32859911
AllCCS	[M+Na]+	138.7	32859911
AllCCS	[M-H]-	137.4	32859911
AllCCS	[M+Na-2H]-	140.3	32859911
AllCCS	[M+HCOO]-	143.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Methylsulfinylpropyl isothiocyanate	CS(=O)CCCN=C=S	2221.5	Standard polar	33892256
3-Methylsulfinylpropyl isothiocyanate	CS(=O)CCCN=C=S	1450.3	Standard non polar	33892256
3-Methylsulfinylpropyl isothiocyanate	CS(=O)CCCN=C=S	1417.6	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 - 3-Methylsulfinylpropyl isothiocyanate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0mdi-9100000000-cba8365c48cdd07cae16	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methylsulfinylpropyl isothiocyanate 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-Methylsulfinylpropyl isothiocyanate 10V, Positive-QTOF	splash10-03di-1900000000-0f45d378074d3cee9fb1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylsulfinylpropyl isothiocyanate 20V, Positive-QTOF	splash10-0bt9-5900000000-5c92d444115013948405	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylsulfinylpropyl isothiocyanate 40V, Positive-QTOF	splash10-0006-9000000000-ad018f5caa95c24942fe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylsulfinylpropyl isothiocyanate 10V, Negative-QTOF	splash10-03di-9400000000-3156b9c5eaa02f6c4c70	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylsulfinylpropyl isothiocyanate 20V, Negative-QTOF	splash10-03di-9000000000-cbc7ae5d57c39a5f66be	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylsulfinylpropyl isothiocyanate 40V, Negative-QTOF	splash10-08fr-9000000000-1a81c645e78474f5e1e0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylsulfinylpropyl isothiocyanate 10V, Negative-QTOF	splash10-03di-6900000000-67dd71397391c1848440	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylsulfinylpropyl isothiocyanate 20V, Negative-QTOF	splash10-03di-9300000000-229345e9b4ce8990cbaf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylsulfinylpropyl isothiocyanate 40V, Negative-QTOF	splash10-0a4i-9000000000-dbe2377aeefa575913e5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylsulfinylpropyl isothiocyanate 10V, Positive-QTOF	splash10-0udi-4900000000-40d813da252f99b6c988	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylsulfinylpropyl isothiocyanate 20V, Positive-QTOF	splash10-0zfr-9700000000-35cceb22e4f361385ddd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylsulfinylpropyl isothiocyanate 40V, Positive-QTOF	splash10-05fr-9000000000-915fc15db1ff11b2de64	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.09 +/- 0.08 uM	Adult (>18 years old)	Both	Normal	16289008	details

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

FDB008196

KNApSAcK ID

C00047246

Chemspider ID

10023

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10455

PDB ID

Not Available

ChEBI ID

89494

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

Not Available

Showing metabocard for 3-Methylsulfinylpropyl isothiocyanate (HMDB0006095)

MOL for HMDB0006095 (3-Methylsulfinylpropyl isothiocyanate)

3D MOL for HMDB0006095 (3-Methylsulfinylpropyl isothiocyanate)

3D SDF for HMDB0006095 (3-Methylsulfinylpropyl isothiocyanate)

3D-SDF for HMDB0006095 (3-Methylsulfinylpropyl isothiocyanate)

PDB for HMDB0006095 (3-Methylsulfinylpropyl isothiocyanate)

3D PDB for HMDB0006095 (3-Methylsulfinylpropyl isothiocyanate)

SMILES for HMDB0006095 (3-Methylsulfinylpropyl isothiocyanate)

INCHI for HMDB0006095 (3-Methylsulfinylpropyl isothiocyanate)

Structure for HMDB0006095 (3-Methylsulfinylpropyl isothiocyanate)

3D Structure for HMDB0006095 (3-Methylsulfinylpropyl isothiocyanate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra