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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:45:01 UTC

Update Date

2023-02-21 17:21:15 UTC

HMDB ID

HMDB0031719

Secondary Accession Numbers

HMDB31719

Metabolite Identification

Common Name

1,2,4,6-Tetrathiepane

Description

1,2,4,6-Tetrathiepane, also known as rocaglamide, belongs to the class of organic compounds known as dithioacetals. Dithioacetals are compounds containing a dithioacetal functional group with the general structure R2C(SR')2. Based on a literature review a significant number of articles have been published on 1,2,4,6-Tetrathiepane.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,2,4,6-Tetrathiacycloheptane	HMDB
Rocaglamide	HMDB
Rocaglamide (FR aglaia elliptifolia)	HMDB

Chemical Formula

C₃H₆S₄

Average Molecular Weight

170.34

Monoisotopic Molecular Weight

169.935232952

IUPAC Name

1,2,4,6-tetrathiepane

Traditional Name

1,2,4,6-tetrathiepane

CAS Registry Number

292-45-5

SMILES

C1SCSSCS1

InChI Identifier

InChI=1S/C3H6S4/c1-4-2-6-7-3-5-1/h1-3H2

InChI Key

LCABDMYFXTZXMI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dithioacetals. Dithioacetals are compounds containing a dithioacetal functional group with the general structure R2C(SR')2.

Kingdom

Organic compounds

Super Class

Organosulfur compounds

Class

Thioacetals

Sub Class

Dithioacetals

Direct Parent

Dithioacetals

Alternative Parents

Substituents

Thioacetal
Organic disulfide
Organoheterocyclic compound
Dialkylthioether
Thioether
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031719)
Cytoplasm (HMDB: HMDB0031719)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031719)

Source

Endogenous

Endogenous (HMDB: HMDB0031719)

Plant

Plant (HMDB: HMDB0031719)

Exogenous

Food

Food (HMDB: HMDB0031719)

Vegetable

Mushroom

Exogenous (HMDB: HMDB0031719)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	79 °C	Not Available
Boiling Point	307.00 to 308.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	754.7 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.900 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.56 g/L	ALOGPS
logP	1.31	ALOGPS
logP	2.06	ChemAxon
logS	-2.5	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	44.45 m³·mol⁻¹	ChemAxon
Polarizability	16.15 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]+	132.379	31661259
DarkChem	[M-H]-	125.143	31661259
DeepCCS	[M+H]+	131.569	30932474
DeepCCS	[M-H]-	129.649	30932474
DeepCCS	[M-2H]-	165.159	30932474
DeepCCS	[M+Na]+	139.64	30932474
AllCCS	[M+H]+	128.5	32859911
AllCCS	[M+H-H2O]+	124.2	32859911
AllCCS	[M+NH4]+	132.5	32859911
AllCCS	[M+Na]+	133.6	32859911
AllCCS	[M-H]-	128.8	32859911
AllCCS	[M+Na-2H]-	131.9	32859911
AllCCS	[M+HCOO]-	135.3	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.	2.11 minutes	32390414
Predicted by Siyang on May 30, 2022	11.6214 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.69 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	146.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1813.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	684.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	269.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	495.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	305.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	654.6 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	727.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	412.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1335.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	478.4 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	1473.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	496.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	492.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	739.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	562.2 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	185.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,2,4,6-Tetrathiepane	C1SCSSCS1	2401.0	Standard polar	33892256
1,2,4,6-Tetrathiepane	C1SCSSCS1	1460.7	Standard non polar	33892256
1,2,4,6-Tetrathiepane	C1SCSSCS1	1464.7	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 - 1,2,4,6-Tetrathiepane GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9700000000-d5a1812a3910a69b0b51	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2,4,6-Tetrathiepane 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 - 1,2,4,6-Tetrathiepane 10V, Positive-QTOF	splash10-00di-1900000000-b9a07b8ce539004a2e62	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,4,6-Tetrathiepane 20V, Positive-QTOF	splash10-0092-9400000000-f9fd1ac09078667f2b4b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,4,6-Tetrathiepane 40V, Positive-QTOF	splash10-004i-9100000000-0d660ca74518a41d63c7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,4,6-Tetrathiepane 10V, Negative-QTOF	splash10-0100-5900000000-f8ea0acad9e5d425639c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,4,6-Tetrathiepane 20V, Negative-QTOF	splash10-00dl-9600000000-7df27fb3879ee502d767	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,4,6-Tetrathiepane 40V, Negative-QTOF	splash10-0006-9000000000-e12e61fa49fbda2b4e8c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,4,6-Tetrathiepane 10V, Positive-QTOF	splash10-00di-2900000000-c02309d8751f5df315a7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,4,6-Tetrathiepane 20V, Positive-QTOF	splash10-0097-9300000000-880d50c7bd9a79c536d2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,4,6-Tetrathiepane 40V, Positive-QTOF	splash10-0002-9000000000-bbe39ba325fa177258c0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,4,6-Tetrathiepane 10V, Negative-QTOF	splash10-004i-9000000000-53dddc1a389ffc476d3b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,4,6-Tetrathiepane 20V, Negative-QTOF	splash10-004i-9000000000-357ba416f402a6ae25ce	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,4,6-Tetrathiepane 40V, Negative-QTOF	splash10-004i-9200000000-7ffd583373bad39d10d6	2021-09-22	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+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

FDB008382

KNApSAcK ID

C00058070

Chemspider ID

453955

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

520423

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1119961

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 1,2,4,6-Tetrathiepane (HMDB0031719)

MOL for HMDB0031719 (1,2,4,6-Tetrathiepane)

3D MOL for HMDB0031719 (1,2,4,6-Tetrathiepane)

3D SDF for HMDB0031719 (1,2,4,6-Tetrathiepane)

3D-SDF for HMDB0031719 (1,2,4,6-Tetrathiepane)

PDB for HMDB0031719 (1,2,4,6-Tetrathiepane)

3D PDB for HMDB0031719 (1,2,4,6-Tetrathiepane)

SMILES for HMDB0031719 (1,2,4,6-Tetrathiepane)

INCHI for HMDB0031719 (1,2,4,6-Tetrathiepane)

Structure for HMDB0031719 (1,2,4,6-Tetrathiepane)

3D Structure for HMDB0031719 (1,2,4,6-Tetrathiepane)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra