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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 11:26:26 UTC

Update Date

2021-09-26 23:06:18 UTC

HMDB ID

HMDB0253211

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Tramiprosate

Description

Tramiprosate, also known as 3APS or tramiprosic acid, belongs to the class of organic compounds known as organosulfonic acids. Organosulfonic acids are compounds containing the sulfonic acid group, which has the general structure RS(=O)2OH (R is not a hydrogen atom). Homotaurine has been reported as a GABA antagonist, as well as a GABA agonist. Tramiprosate is a very strong basic compound (based on its pKa). Acamprosate was approved by the FDA in 2004 to treat alcohol dependence. It is analogous to taurine, but with an extra carbon in its chain. In vitro studies have found that homotaurine is a GABAA partial agonist as well as a GABAB receptor partial agonist with low efficacy, becoming an antagonist and a displacing full agonist of GABA or baclofen at this receptor. In preclinical studies it had been found to bind to soluble amyloid beta and inhibit the formation of neurotoxic aggregates. One study in rats showed that homotaurine suppressed ethanol-stimulated dopamine release, as well as ethanol intake and preference in rats in a way similar to the N-acetyl derivative of homotaurine, acamprosate. Homotaurine has also shown anticonvulsant activities, reduction in skeletal muscle tonus, and hypothermic activity. It has GABAergic activity, apparently by mimicking GABA, which it resembles. In a study in rats, homotaurine reversed the catatonia induced by baclofen (the prototypical GABAB agonist), and was able to produce analgesia via the GABAB receptor, an effect that was abolished when CGP-35348, a GABAB receptor antagonist was applied. Homotaurine was investigated in a Phase III clinical trial as a potential treatment for Alzheimer's disease that did not show efficacy. A study in cognitive impairment done in 2018 did show positive benefits. This compound has been identified in human blood as reported by (PMID: 31557052 ). Tramiprosate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Tramiprosate is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Amino-1-propanesulfonic acid	Kegg
3APS	Kegg
3-Amino-1-propanesulfonate	Generator
3-Amino-1-propanesulphonate	Generator
3-Amino-1-propanesulphonic acid	Generator
Tramiprosic acid	Generator
3-Aminopropylsulfonic acid	MeSH
3-APS	MeSH
3-Aminopropanesulfonic acid	MeSH
3-Aminopropane-1-sulfonate	Generator
3-Aminopropane-1-sulphonate	Generator
3-Aminopropane-1-sulphonic acid	Generator
Tramiprosate	MeSH

Chemical Formula

C₃H₉NO₃S

Average Molecular Weight

139.173

Monoisotopic Molecular Weight

139.030313849

IUPAC Name

3-aminopropane-1-sulfonic acid

Traditional Name

homotaurine

CAS Registry Number

Not Available

SMILES

NCCCS(O)(=O)=O

InChI Identifier

InChI=1S/C3H9NO3S/c4-2-1-3-8(5,6)7/h1-4H2,(H,5,6,7)

InChI Key

SNKZJIOFVMKAOJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as organosulfonic acids. Organosulfonic acids are compounds containing the sulfonic acid group, which has the general structure RS(=O)2OH (R is not a hydrogen atom).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic sulfonic acids and derivatives

Sub Class

Organosulfonic acids and derivatives

Direct Parent

Organosulfonic acids

Alternative Parents

Substituents

Alkanesulfonic acid
Sulfonyl
Organosulfonic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organosulfur compound
Organonitrogen compound
Primary aliphatic amine
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

organosulfonic acid (CHEBI:1457 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0253211)

Process

Not Available

Role

Not Available

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-2	ALOGPS
logP	-2.6	ChemAxon
logS	-0.27	ALOGPS
pKa (Strongest Acidic)	-0.99	ChemAxon
pKa (Strongest Basic)	10.19	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	80.39 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	29.47 m³·mol⁻¹	ChemAxon
Polarizability	12.84 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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
DeepCCS	[M+H]+	132.2	30932474
DeepCCS	[M-H]-	129.435	30932474
DeepCCS	[M-2H]-	165.644	30932474
DeepCCS	[M+Na]+	140.426	30932474
AllCCS	[M+H]+	131.3	32859911
AllCCS	[M+H-H2O]+	127.2	32859911
AllCCS	[M+NH4]+	135.1	32859911
AllCCS	[M+Na]+	136.2	32859911
AllCCS	[M-H]-	127.2	32859911
AllCCS	[M+Na-2H]-	130.5	32859911
AllCCS	[M+HCOO]-	134.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tramiprosate	NCCCS(O)(=O)=O	2157.3	Standard polar	33892256
Tramiprosate	NCCCS(O)(=O)=O	1137.0	Standard non polar	33892256
Tramiprosate	NCCCS(O)(=O)=O	1414.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tramiprosate,1TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)CCCN	1468.6	Semi standard non polar	33892256
Tramiprosate,1TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)CCCN	1378.6	Standard non polar	33892256
Tramiprosate,1TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)CCCN	2459.7	Standard polar	33892256
Tramiprosate,1TMS,isomer #2	C[Si](C)(C)NCCCS(=O)(=O)O	1558.6	Semi standard non polar	33892256
Tramiprosate,1TMS,isomer #2	C[Si](C)(C)NCCCS(=O)(=O)O	1396.6	Standard non polar	33892256
Tramiprosate,1TMS,isomer #2	C[Si](C)(C)NCCCS(=O)(=O)O	2540.5	Standard polar	33892256
Tramiprosate,2TMS,isomer #1	C[Si](C)(C)NCCCS(=O)(=O)O[Si](C)(C)C	1611.8	Semi standard non polar	33892256
Tramiprosate,2TMS,isomer #1	C[Si](C)(C)NCCCS(=O)(=O)O[Si](C)(C)C	1567.4	Standard non polar	33892256
Tramiprosate,2TMS,isomer #1	C[Si](C)(C)NCCCS(=O)(=O)O[Si](C)(C)C	2016.5	Standard polar	33892256
Tramiprosate,2TMS,isomer #2	C[Si](C)(C)N(CCCS(=O)(=O)O)[Si](C)(C)C	1752.6	Semi standard non polar	33892256
Tramiprosate,2TMS,isomer #2	C[Si](C)(C)N(CCCS(=O)(=O)O)[Si](C)(C)C	1657.4	Standard non polar	33892256
Tramiprosate,2TMS,isomer #2	C[Si](C)(C)N(CCCS(=O)(=O)O)[Si](C)(C)C	2418.9	Standard polar	33892256
Tramiprosate,3TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)CCCN([Si](C)(C)C)[Si](C)(C)C	1801.1	Semi standard non polar	33892256
Tramiprosate,3TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)CCCN([Si](C)(C)C)[Si](C)(C)C	1818.2	Standard non polar	33892256
Tramiprosate,3TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)CCCN([Si](C)(C)C)[Si](C)(C)C	1991.8	Standard polar	33892256
Tramiprosate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)CCCN	1697.3	Semi standard non polar	33892256
Tramiprosate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)CCCN	1668.4	Standard non polar	33892256
Tramiprosate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)CCCN	2545.4	Standard polar	33892256
Tramiprosate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCCS(=O)(=O)O	1825.6	Semi standard non polar	33892256
Tramiprosate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCCS(=O)(=O)O	1686.8	Standard non polar	33892256
Tramiprosate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCCS(=O)(=O)O	2645.6	Standard polar	33892256
Tramiprosate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCCS(=O)(=O)O[Si](C)(C)C(C)(C)C	2105.0	Semi standard non polar	33892256
Tramiprosate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCCS(=O)(=O)O[Si](C)(C)C(C)(C)C	2117.4	Standard non polar	33892256
Tramiprosate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCCS(=O)(=O)O[Si](C)(C)C(C)(C)C	2159.0	Standard polar	33892256
Tramiprosate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CCCS(=O)(=O)O)[Si](C)(C)C(C)(C)C	2212.5	Semi standard non polar	33892256
Tramiprosate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CCCS(=O)(=O)O)[Si](C)(C)C(C)(C)C	2186.4	Standard non polar	33892256
Tramiprosate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CCCS(=O)(=O)O)[Si](C)(C)C(C)(C)C	2441.3	Standard polar	33892256
Tramiprosate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)CCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2475.2	Semi standard non polar	33892256
Tramiprosate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)CCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2602.4	Standard non polar	33892256
Tramiprosate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)CCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2228.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tramiprosate GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9000000000-a6a2e92e973b68960011	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tramiprosate 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 - Tramiprosate 10V, Positive-QTOF	splash10-00dl-0900000000-66959ba94ad341ad274c	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tramiprosate 20V, Positive-QTOF	splash10-0596-9500000000-4ed2663fc785f4bfb4f4	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tramiprosate 40V, Positive-QTOF	splash10-0006-9100000000-4a6ab032f63a76ef1b06	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tramiprosate 10V, Negative-QTOF	splash10-000i-4900000000-ae57944de6daece918e3	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tramiprosate 20V, Negative-QTOF	splash10-001r-9400000000-50e0a389268a422da0e2	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tramiprosate 40V, Negative-QTOF	splash10-001i-9000000000-d1e30bd9ede34408db01	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tramiprosate 10V, Negative-QTOF	splash10-000i-0900000000-0735f59de97763ca9c41	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tramiprosate 20V, Negative-QTOF	splash10-000i-2900000000-fa5cb6db18dfcefad36c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tramiprosate 40V, Negative-QTOF	splash10-001i-9000000000-a6fb8cd4d3dc149be309	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tramiprosate 10V, Positive-QTOF	splash10-0006-1900000000-f7878a5851d46a1eb734	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tramiprosate 20V, Positive-QTOF	splash10-0006-9200000000-1917a8769ba544b9822a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tramiprosate 40V, Positive-QTOF	splash10-0a4i-9000000000-1a1461a90577cb4e1137	2021-10-12	Wishart 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 but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB06527

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C03349

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Homotaurine

METLIN ID

Not Available

PubChem Compound

1646

PDB ID

Not Available

ChEBI ID

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Tramiprosate (HMDB0253211)

MOL for HMDB0253211 (Tramiprosate)

3D MOL for HMDB0253211 (Tramiprosate)

3D SDF for HMDB0253211 (Tramiprosate)

3D-SDF for HMDB0253211 (Tramiprosate)

PDB for HMDB0253211 (Tramiprosate)

3D PDB for HMDB0253211 (Tramiprosate)

SMILES for HMDB0253211 (Tramiprosate)

INCHI for HMDB0253211 (Tramiprosate)

Structure for HMDB0253211 (Tramiprosate)

3D Structure for HMDB0253211 (Tramiprosate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra