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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:55:31 UTC

Update Date

2022-03-07 02:56:12 UTC

HMDB ID

HMDB0039458

Secondary Accession Numbers

HMDB39458

Metabolite Identification

Common Name

Di-2-propenyl heptasulfide

Description

Di-2-propenyl heptasulfide belongs to the class of organic compounds known as allyl sulfur compounds. Allyl sulfur compounds are compounds containing an allylsulfur group, with the general structure H2C(=CH2)CS. Di-2-propenyl heptasulfide has been detected, but not quantified in, several different foods, such as welsh onions (Allium fistulosum), soft-necked garlics (Allium sativum L. var. sativum), garden onion (var.), onion-family vegetables, and garden onions (Allium cepa). This could make di-2-propenyl heptasulfide a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Di-2-propenyl heptasulfide.

Structure

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

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -6.724  -3.231   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.281  -3.231   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.390  -4.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.947  -4.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.056  -3.231   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.613  -3.231   0.000  0.00  0.00           C+0
HETATM    7  S   UNK     0      -2.723  -4.001   0.000  0.00  0.00           S+0
HETATM    8  S   UNK     0       5.279  -4.001   0.000  0.00  0.00           S+0
HETATM    9  S   UNK     0      -1.389  -3.231   0.000  0.00  0.00           S+0
HETATM   10  S   UNK     0       3.946  -3.231   0.000  0.00  0.00           S+0
HETATM   11  S   UNK     0      -0.055  -4.001   0.000  0.00  0.00           S+0
HETATM   12  S   UNK     0       2.612  -4.001   0.000  0.00  0.00           S+0
HETATM   13  S   UNK     0       1.278  -3.231   0.000  0.00  0.00           S+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   13                                                       
CONECT   13   11   12                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Di-2-propenyl heptasulphide	Generator
4,5,6,7,8,9,10-Heptathia-1,12-tridecadiene	HMDB
Allyl heptasulfide	HMDB
Diallyl heptasulfide	HMDB
Bis(prop-2-en-1-yl)heptasulphane	Generator

Chemical Formula

C₆H₁₀S₇

Average Molecular Weight

306.599

Monoisotopic Molecular Weight

305.88274515

IUPAC Name

bis(prop-2-en-1-yl)heptasulfane

Traditional Name

bis(prop-2-en-1-yl)heptasulfane

CAS Registry Number

139693-24-6

SMILES

C=CCSSSSSSSCC=C

InChI Identifier

InChI=1S/C6H10S7/c1-3-5-7-9-11-13-12-10-8-6-4-2/h3-4H,1-2,5-6H2

InChI Key

GSEBMLLGHBSQFW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as allyl sulfur compounds. Allyl sulfur compounds are compounds containing an allylsulfur group, with the general structure H2C(=CH2)CS.

Kingdom

Organic compounds

Super Class

Organosulfur compounds

Class

Allyl sulfur compounds

Sub Class

Not Available

Direct Parent

Allyl sulfur compounds

Alternative Parents

Substituents

Allyl sulfur compound
Sulfenyl compound
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: HMDB0039458)
Cytoplasm (HMDB: HMDB0039458)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039458)

Source

Exogenous

Exogenous (HMDB: HMDB0039458)

Food

Food (HMDB: HMDB0039458)

Herb and spice

Herb

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: HMDB0039458)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0039458)

Industrial application

Manufacturing industry

Material processing agent

Solid material processing agent

Protective agent

Antioxidant (HMDB: HMDB0039458)
Antioxidant (HMDB: HMDB0039458)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	121.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	539.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	10.15 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	0.039 g/L	ALOGPS
logP	2.12	ALOGPS
logP	5.73	ChemAxon
logS	-3.9	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	74.2 m³·mol⁻¹	ChemAxon
Polarizability	29.05 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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]+	166.758	31661259
DarkChem	[M-H]-	165.087	31661259
DeepCCS	[M+H]+	147.874	30932474
DeepCCS	[M-H]-	145.472	30932474
DeepCCS	[M-2H]-	181.993	30932474
DeepCCS	[M+Na]+	157.243	30932474
AllCCS	[M+H]+	149.8	32859911
AllCCS	[M+H-H2O]+	147.2	32859911
AllCCS	[M+NH4]+	152.1	32859911
AllCCS	[M+Na]+	152.7	32859911
AllCCS	[M-H]-	132.4	32859911
AllCCS	[M+Na-2H]-	133.0	32859911
AllCCS	[M+HCOO]-	133.8	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.	4.95 minutes	32390414
Predicted by Siyang on May 30, 2022	22.5264 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.95 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	121.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2269.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	681.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	256.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	487.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	335.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	660.4 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	668.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	157.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1640.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	695.5 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	1366.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	554.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	493.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	574.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	534.6 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	90.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Di-2-propenyl heptasulfide	C=CCSSSSSSSCC=C	3255.1	Standard polar	33892256
Di-2-propenyl heptasulfide	C=CCSSSSSSSCC=C	2160.5	Standard non polar	33892256
Di-2-propenyl heptasulfide	C=CCSSSSSSSCC=C	2123.1	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 - Di-2-propenyl heptasulfide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-94216616bee6b5661805	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Di-2-propenyl heptasulfide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Di-2-propenyl heptasulfide 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 - Di-2-propenyl heptasulfide 10V, Positive-QTOF	splash10-0a4i-6349000000-136c3cc5ee33420c5697	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Di-2-propenyl heptasulfide 20V, Positive-QTOF	splash10-0fkc-9461000000-9c11b3de5a00177a061e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Di-2-propenyl heptasulfide 40V, Positive-QTOF	splash10-006x-9110000000-d03cf98ab726705ff785	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Di-2-propenyl heptasulfide 10V, Negative-QTOF	splash10-0udi-4935000000-5037b24eef680b30637e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Di-2-propenyl heptasulfide 20V, Negative-QTOF	splash10-0fk9-9542000000-bcf20534fc06aa01f9a0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Di-2-propenyl heptasulfide 40V, Negative-QTOF	splash10-02a6-9860000000-e063e62a0e9ad066c8ff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Di-2-propenyl heptasulfide 10V, Negative-QTOF	splash10-03di-2910000000-58f8284704ef32dc4618	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Di-2-propenyl heptasulfide 20V, Negative-QTOF	splash10-01r2-5900000000-fddd2f9767f338672d3b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Di-2-propenyl heptasulfide 40V, Negative-QTOF	splash10-0002-9600000000-1e8276992c82af91d6b3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Di-2-propenyl heptasulfide 10V, Positive-QTOF	splash10-0udi-2941000000-da729aa82763ef9f41f1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Di-2-propenyl heptasulfide 20V, Positive-QTOF	splash10-0fk9-9400000000-04460e6f6090416a40d2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Di-2-propenyl heptasulfide 40V, Positive-QTOF	splash10-0h93-9100000000-ce331f00c1a24e2ed55f	2021-09-23	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

FDB019059

KNApSAcK ID

C00054604

Chemspider ID

30777346

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53854515

PDB ID

Not Available

ChEBI ID

169612

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1595271

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 Di-2-propenyl heptasulfide (HMDB0039458)

MOL for HMDB0039458 (Di-2-propenyl heptasulfide)

3D MOL for HMDB0039458 (Di-2-propenyl heptasulfide)

3D SDF for HMDB0039458 (Di-2-propenyl heptasulfide)

3D-SDF for HMDB0039458 (Di-2-propenyl heptasulfide)

PDB for HMDB0039458 (Di-2-propenyl heptasulfide)

3D PDB for HMDB0039458 (Di-2-propenyl heptasulfide)

SMILES for HMDB0039458 (Di-2-propenyl heptasulfide)

INCHI for HMDB0039458 (Di-2-propenyl heptasulfide)

Structure for HMDB0039458 (Di-2-propenyl heptasulfide)

3D Structure for HMDB0039458 (Di-2-propenyl heptasulfide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra