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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:53:31 UTC

Update Date

2022-03-07 02:53:34 UTC

HMDB ID

HMDB0033061

Secondary Accession Numbers

HMDB33061

Metabolite Identification

Common Name

1-(Methylsulfinyl)propyl propyl disulfide

Description

1-(Methylsulfinyl)propyl propyl disulfide, also known as 1-methanesulphinyl-1-(propyldisulphanyl)propane, 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). 1-(Methylsulfinyl)propyl propyl disulfide has been detected, but not quantified in, several different foods, such as garden onion (var.), red onion, welsh onions (Allium fistulosum), green onion, and onion-family vegetables. This could make 1-(methylsulfinyl)propyl propyl disulfide a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 1-(Methylsulfinyl)propyl propyl disulfide.

Structure

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

COMPND    HMDB0033061
HETATM    1  C1  UNL     1       4.236   0.459   0.295  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.243  -0.677   0.391  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.278  -0.679  -0.776  1.00  0.00           C  
HETATM    4  S1  UNL     1       1.379   0.861  -0.787  1.00  0.00           S  
HETATM    5  S2  UNL     1       0.157   0.914   0.954  1.00  0.00           S  
HETATM    6  C4  UNL     1      -1.420   0.196   0.537  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.201   1.018  -0.465  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.471   2.408   0.094  1.00  0.00           C  
HETATM    9  S3  UNL     1      -1.335  -1.477  -0.051  1.00  0.00           S  
HETATM   10  C7  UNL     1      -3.046  -1.986  -0.408  1.00  0.00           C  
HETATM   11  O1  UNL     1      -0.838  -2.442   1.038  1.00  0.00           O  
HETATM   12  H1  UNL     1       4.769   0.485  -0.670  1.00  0.00           H  
HETATM   13  H2  UNL     1       5.009   0.318   1.079  1.00  0.00           H  
HETATM   14  H3  UNL     1       3.767   1.443   0.497  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.739  -0.602   1.363  1.00  0.00           H  
HETATM   16  H5  UNL     1       3.842  -1.626   0.410  1.00  0.00           H  
HETATM   17  H6  UNL     1       1.655  -1.579  -0.691  1.00  0.00           H  
HETATM   18  H7  UNL     1       2.908  -0.815  -1.703  1.00  0.00           H  
HETATM   19  H8  UNL     1      -2.051   0.187   1.474  1.00  0.00           H  
HETATM   20  H9  UNL     1      -1.649   1.066  -1.417  1.00  0.00           H  
HETATM   21  H10 UNL     1      -3.201   0.570  -0.644  1.00  0.00           H  
HETATM   22  H11 UNL     1      -1.691   2.575   0.877  1.00  0.00           H  
HETATM   23  H12 UNL     1      -2.402   3.150  -0.719  1.00  0.00           H  
HETATM   24  H13 UNL     1      -3.440   2.421   0.622  1.00  0.00           H  
HETATM   25  H14 UNL     1      -3.760  -1.389   0.220  1.00  0.00           H  
HETATM   26  H15 UNL     1      -3.303  -1.735  -1.460  1.00  0.00           H  
HETATM   27  H16 UNL     1      -3.171  -3.066  -0.189  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3   15   16
CONECT    3    4   17   18
CONECT    4    5
CONECT    5    6
CONECT    6    7    9   19
CONECT    7    8   20   21
CONECT    8   22   23   24
CONECT    9   10   11   11
CONECT   10   25   26   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-(Methylsulphinyl)propyl propyl disulphide	Generator
1-Methanesulphinyl-1-(propyldisulphanyl)propane	HMDB

Chemical Formula

C₇H₁₆OS₃

Average Molecular Weight

212.396

Monoisotopic Molecular Weight

212.036327204

IUPAC Name

1-methanesulfinyl-1-(propyldisulfanyl)propane

Traditional Name

1-methanesulfinyl-1-(propyldisulfanyl)propane

CAS Registry Number

132216-21-8

SMILES

CCCSSC(CC)S(C)=O

InChI Identifier

InChI=1S/C7H16OS3/c1-4-6-9-10-7(5-2)11(3)8/h7H,4-6H2,1-3H3

InChI Key

SEEVCAXKLHCWMN-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

Dialkyldisulfide
Sulfoxide
Organic disulfide
Sulfenyl compound
Sulfinyl compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033061)
Cytoplasm (HMDB: HMDB0033061)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033061)

Source

Exogenous

Exogenous (HMDB: HMDB0033061)

Food

Food (HMDB: HMDB0033061)

Herb and spice

Herb

Welsh onion (FooDB: FOOD00241)

Vegetable

Onion-family vegetable

Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Endogenous

Plant

Plant (HMDB: HMDB0033061)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033061)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1310 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	2.94 g/L	ALOGPS
logP	2.31	ALOGPS
logP	1.75	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Basic)	-6.7	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	6	ChemAxon
Refractivity	59.28 m³·mol⁻¹	ChemAxon
Polarizability	23.14 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]+	147.214	31661259
DarkChem	[M-H]-	141.629	31661259
DeepCCS	[M+H]+	145.396	30932474
DeepCCS	[M-H]-	142.302	30932474
DeepCCS	[M-2H]-	179.522	30932474
DeepCCS	[M+Na]+	154.472	30932474
AllCCS	[M+H]+	145.4	32859911
AllCCS	[M+H-H2O]+	142.1	32859911
AllCCS	[M+NH4]+	148.5	32859911
AllCCS	[M+Na]+	149.3	32859911
AllCCS	[M-H]-	148.3	32859911
AllCCS	[M+Na-2H]-	150.6	32859911
AllCCS	[M+HCOO]-	153.1	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.	4.31 minutes	32390414
Predicted by Siyang on May 30, 2022	14.1349 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.81 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	26.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1823.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	354.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	139.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	211.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	90.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	407.6 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	430.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	98.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	944.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	386.8 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	1135.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	294.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	307.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	358.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	332.2 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	40.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-(Methylsulfinyl)propyl propyl disulfide	CCCSSC(CC)S(C)=O	2109.3	Standard polar	33892256
1-(Methylsulfinyl)propyl propyl disulfide	CCCSSC(CC)S(C)=O	1548.0	Standard non polar	33892256
1-(Methylsulfinyl)propyl propyl disulfide	CCCSSC(CC)S(C)=O	1531.2	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 - 1-(Methylsulfinyl)propyl propyl disulfide GC-MS (Non-derivatized) - 70eV, Positive	splash10-054o-9700000000-41b655b58f489921b4a5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(Methylsulfinyl)propyl propyl disulfide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(Methylsulfinyl)propyl propyl disulfide 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 - 1-(Methylsulfinyl)propyl propyl disulfide 10V, Positive-QTOF	splash10-01ot-4920000000-64f9efa1eab001fa48da	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(Methylsulfinyl)propyl propyl disulfide 20V, Positive-QTOF	splash10-0a4l-9800000000-f86a5346972db26949b7	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(Methylsulfinyl)propyl propyl disulfide 40V, Positive-QTOF	splash10-004l-9100000000-efb9c10016d829274469	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(Methylsulfinyl)propyl propyl disulfide 10V, Negative-QTOF	splash10-03di-9100000000-b37a5efecbfef6a772f8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(Methylsulfinyl)propyl propyl disulfide 20V, Negative-QTOF	splash10-03di-9100000000-75ef4e0849c0cabecc73	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(Methylsulfinyl)propyl propyl disulfide 40V, Negative-QTOF	splash10-03di-9000000000-f51d72d356c0a8670927	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(Methylsulfinyl)propyl propyl disulfide 10V, Positive-QTOF	splash10-00tr-4900000000-c50472a68ecdf2ba7343	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(Methylsulfinyl)propyl propyl disulfide 20V, Positive-QTOF	splash10-004i-9200000000-27f66f5d7a23fe8957f1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(Methylsulfinyl)propyl propyl disulfide 40V, Positive-QTOF	splash10-002f-9000000000-fe40cb37fa4c348b4864	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(Methylsulfinyl)propyl propyl disulfide 10V, Negative-QTOF	splash10-03di-9210000000-e059c4d855f463f8ec6f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(Methylsulfinyl)propyl propyl disulfide 20V, Negative-QTOF	splash10-03mi-9000000000-ff244893be210255925f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(Methylsulfinyl)propyl propyl disulfide 40V, Negative-QTOF	splash10-03k9-9000000000-e8e58fd209c455e91e0d	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

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

FDB011054

KNApSAcK ID

Not Available

Chemspider ID

35013536

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14704627

PDB ID

Not Available

ChEBI ID

174075

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1833121

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 1-(Methylsulfinyl)propyl propyl disulfide (HMDB0033061)

MOL for HMDB0033061 (1-(Methylsulfinyl)propyl propyl disulfide)

3D MOL for HMDB0033061 (1-(Methylsulfinyl)propyl propyl disulfide)

3D SDF for HMDB0033061 (1-(Methylsulfinyl)propyl propyl disulfide)

3D-SDF for HMDB0033061 (1-(Methylsulfinyl)propyl propyl disulfide)

PDB for HMDB0033061 (1-(Methylsulfinyl)propyl propyl disulfide)

3D PDB for HMDB0033061 (1-(Methylsulfinyl)propyl propyl disulfide)

SMILES for HMDB0033061 (1-(Methylsulfinyl)propyl propyl disulfide)

INCHI for HMDB0033061 (1-(Methylsulfinyl)propyl propyl disulfide)

Structure for HMDB0033061 (1-(Methylsulfinyl)propyl propyl disulfide)

3D Structure for HMDB0033061 (1-(Methylsulfinyl)propyl propyl disulfide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra