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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:41:22 UTC

Update Date

2023-02-21 17:19:56 UTC

HMDB ID

HMDB0031162

Secondary Accession Numbers

HMDB31162

Metabolite Identification

Common Name

3,3'-Thiobispropanoic acid

Description

3,3'-Thiobispropanoic acid, also known as thiodipropionic acid, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Based on a literature review very few articles have been published on 3,3'-Thiobispropanoic acid.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3,3'-Thiobispropanoate	Generator
Thiodipropionic acid	MeSH
3,3'-Thiobis(propanoic acid)	HMDB
3,3'-Thiobis-propanoic acid	HMDB
3,3'-Thiodi-propionic acid	HMDB
3,3'-Thiodipropanoic acid	HMDB
3,3'-Thiodipropionic acid, 8ci	HMDB
4-Thiaheptanedioic acid	HMDB
beta ,beta '-Thiodipropionic acid	HMDB
Bis(2-carboxyethyl) sulfide	HMDB
Diethyl sulfide 2,2'-dicarboxylic acid	HMDB
Diethyl sulfide b,b'-dicarboxylic acid	HMDB
Sulfide, bis(2-carboxyethyl)	HMDB
Thiodihydracrylic acid	HMDB
Tyox a	HMDB
3-[(2-Carboxyethyl)sulfanyl]propanoate	Generator
3-[(2-Carboxyethyl)sulphanyl]propanoate	Generator
3-[(2-Carboxyethyl)sulphanyl]propanoic acid	Generator

Chemical Formula

C₆H₁₀O₄S

Average Molecular Weight

178.206

Monoisotopic Molecular Weight

178.029979498

IUPAC Name

3-[(2-carboxyethyl)sulfanyl]propanoic acid

Traditional Name

propanoic acid, 3,3'-thiobis-

CAS Registry Number

111-17-1

SMILES

OC(=O)CCSCCC(O)=O

InChI Identifier

InChI=1S/C6H10O4S/c7-5(8)1-3-11-4-2-6(9)10/h1-4H2,(H,7,8)(H,9,10)

InChI Key

ODJQKYXPKWQWNK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Dicarboxylic acids and derivatives

Direct Parent

Dicarboxylic acids and derivatives

Alternative Parents

Substituents

Fatty acid
Dicarboxylic acid or derivatives
Dialkylthioether
Sulfenyl compound
Thioether
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Source

Endogenous

Endogenous (HMDB: HMDB0031162)

Exogenous

Food

Food (HMDB: HMDB0031162)

Exogenous (HMDB: HMDB0031162)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0031162)

Role

Biological role

Energy source (HMDB: HMDB0031162)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0031162)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	134 °C	Not Available
Boiling Point	409.28 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	37.2 mg/mL at 26 °C	Not Available
LogP	-0.062 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	7.2 g/L	ALOGPS
logP	0.19	ALOGPS
logP	0.45	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	3.86	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	40.56 m³·mol⁻¹	ChemAxon
Polarizability	17.46 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	137.417	31661259
DarkChem	[M-H]-	132.032	31661259
DeepCCS	[M+H]+	133.156	30932474
DeepCCS	[M-H]-	129.889	30932474
DeepCCS	[M-2H]-	166.438	30932474
DeepCCS	[M+Na]+	141.769	30932474
AllCCS	[M+H]+	136.7	32859911
AllCCS	[M+H-H2O]+	133.1	32859911
AllCCS	[M+NH4]+	140.1	32859911
AllCCS	[M+Na]+	141.1	32859911
AllCCS	[M-H]-	138.0	32859911
AllCCS	[M+Na-2H]-	139.9	32859911
AllCCS	[M+HCOO]-	142.2	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.	3.66 minutes	32390414
Predicted by Siyang on May 30, 2022	9.8285 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.68 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	101.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1193.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	307.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	79.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	181.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	64.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	258.0 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	354.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	153.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	672.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	253.1 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	878.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	223.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	231.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	513.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	275.4 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	303.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,3'-Thiobispropanoic acid	OC(=O)CCSCCC(O)=O	2803.9	Standard polar	33892256
3,3'-Thiobispropanoic acid	OC(=O)CCSCCC(O)=O	1396.6	Standard non polar	33892256
3,3'-Thiobispropanoic acid	OC(=O)CCSCCC(O)=O	1640.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,3'-Thiobispropanoic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CCSCCC(=O)O	1680.2	Semi standard non polar	33892256
3,3'-Thiobispropanoic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCSCCC(=O)O[Si](C)(C)C	1782.6	Semi standard non polar	33892256
3,3'-Thiobispropanoic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCSCCC(=O)O	1936.6	Semi standard non polar	33892256
3,3'-Thiobispropanoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCSCCC(=O)O[Si](C)(C)C(C)(C)C	2234.7	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 - 3,3'-Thiobispropanoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-9700000000-354ca3b42ce11453c095	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,3'-Thiobispropanoic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00g3-9720000000-f8705be155fbe507be6a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,3'-Thiobispropanoic acid 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,3'-Thiobispropanoic acid 45V, Negative-QTOF	splash10-0a4i-0900000000-475c17dc4ba04668fbba	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,3'-Thiobispropanoic acid 6V, Positive-QTOF	splash10-001c-9600000000-b96069a2546eb1aaf185	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,3'-Thiobispropanoic acid 60V, Negative-QTOF	splash10-0a4i-0900000000-8b28db6445f07df794c8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,3'-Thiobispropanoic acid 15V, Negative-QTOF	splash10-0a4i-0900000000-0a15201cc7386c886989	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,3'-Thiobispropanoic acid 30V, Negative-QTOF	splash10-0a4i-0900000000-47ec0acd9aec72ffb0e3	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Thiobispropanoic acid 10V, Positive-QTOF	splash10-01t9-3900000000-76f06b92632950ed9fd6	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Thiobispropanoic acid 20V, Positive-QTOF	splash10-0ab9-9600000000-0e51c2e8c07363346866	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Thiobispropanoic acid 40V, Positive-QTOF	splash10-0ab9-9100000000-05dd54ffe8222cbaa1cc	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Thiobispropanoic acid 10V, Negative-QTOF	splash10-056r-1900000000-228e87ee9db972c186a3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Thiobispropanoic acid 20V, Negative-QTOF	splash10-0a4i-5900000000-9f32c5fd062110ac24c1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Thiobispropanoic acid 40V, Negative-QTOF	splash10-0ac9-9200000000-22a7a2cd736e0d4a3b61	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Thiobispropanoic acid 10V, Positive-QTOF	splash10-07br-4900000000-81416df867458f622e7a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Thiobispropanoic acid 20V, Positive-QTOF	splash10-0abi-9200000000-e84dfe81aaeb45f4f56b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Thiobispropanoic acid 40V, Positive-QTOF	splash10-0a4l-9000000000-a9a3636c88bb4cda21bb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Thiobispropanoic acid 10V, Negative-QTOF	splash10-0a4r-9600000000-678e4a2c9c944e7f6745	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Thiobispropanoic acid 20V, Negative-QTOF	splash10-053r-9100000000-f383a96fc4dfeadf58fa	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Thiobispropanoic acid 40V, Negative-QTOF	splash10-0540-9000000000-a4211ff62117158e6a65	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)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	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+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
Membrane

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

FDB003177

KNApSAcK ID

Not Available

Chemspider ID

7805

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

8096

PDB ID

Not Available

ChEBI ID

1093323

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1182081

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 3,3'-Thiobispropanoic acid (HMDB0031162)

MOL for HMDB0031162 (3,3'-Thiobispropanoic acid)

3D MOL for HMDB0031162 (3,3'-Thiobispropanoic acid)

3D SDF for HMDB0031162 (3,3'-Thiobispropanoic acid)

3D-SDF for HMDB0031162 (3,3'-Thiobispropanoic acid)

PDB for HMDB0031162 (3,3'-Thiobispropanoic acid)

3D PDB for HMDB0031162 (3,3'-Thiobispropanoic acid)

SMILES for HMDB0031162 (3,3'-Thiobispropanoic acid)

INCHI for HMDB0031162 (3,3'-Thiobispropanoic acid)

Structure for HMDB0031162 (3,3'-Thiobispropanoic acid)

3D Structure for HMDB0031162 (3,3'-Thiobispropanoic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra