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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2015-01-30 22:06:26 UTC

Update Date

2022-09-22 18:34:29 UTC

HMDB ID

HMDB0062164

Secondary Accession Numbers

HMDB62164

Metabolite Identification

Common Name

Thioproline

Description

Thioproline, also known as gamma-thioproline or heparegen, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Thioproline is a very strong basic compound (based on its pKa). An optically active version of thioproline having L-configuration.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(4R)-4-Thiazolidinecarboxylic acid	ChEBI
(R)-(-)-4-Thiazolidinecarboxylic acid	ChEBI
(R)-4-Thiazolidinecarboxylic acid	ChEBI
4-Thiaproline	ChEBI
gamma-Thioproline	ChEBI
L-Thiaproline	ChEBI
L-Thiazolidine-4-carboxylic acid	ChEBI
Thiazolidinecarboxylic acid	ChEBI
(4R)-4-Thiazolidinecarboxylate	Generator
(R)-(-)-4-Thiazolidinecarboxylate	Generator
(R)-4-Thiazolidinecarboxylate	Generator
g-Thioproline	Generator
Γ-thioproline	Generator
L-Thiazolidine-4-carboxylate	Generator
Thiazolidinecarboxylate	Generator
L-4-Thiazolidinecarboxylic acid	HMDB
gamma-Thiaproline	HMDB
Thiaproline	HMDB
Thiazolidine-4-carboxylic acid	HMDB
Heparegen	HMDB
Norgamem	HMDB
Thiazolidine-4-carboxylic acid, sodium salt	HMDB
Thiazolidine-4-carboxylic acid, (R)-isomer	HMDB
Thioproline	MeSH

Chemical Formula

C₄H₇NO₂S

Average Molecular Weight

133.169

Monoisotopic Molecular Weight

133.019749163

IUPAC Name

(4R)-1,3-thiazolidine-4-carboxylic acid

Traditional Name

(4R)-1,3-thiazolidine-4-carboxylic acid

CAS Registry Number

34592-47-7

SMILES

OC(=O)[C@@H]1CSCN1

InChI Identifier

InChI=1S/C4H7NO2S/c6-4(7)3-1-8-2-5-3/h3,5H,1-2H2,(H,6,7)/t3-/m0/s1

InChI Key

DZLNHFMRPBPULJ-VKHMYHEASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Thiazolidine
Amino acid
Carboxylic acid
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Secondary amine
Thioether
Hemithioaminal
Dialkylthioether
Organoheterocyclic compound
Azacycle
Organic nitrogen compound
Amine
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

thiazolidinemonocarboxylic acid (CHEBI:45171 )
thioproline (CHEBI:45171 )

Ontology

Not Available

Placenta (HMDB: HMDB0062164)

Excreta

Biofluid or Excreta

Urine (PMID: 27012787)
Feces (PMID: 29808030)

Source

Exogenous

Exogenous (HMDB: HMDB0062164)

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
Water Solubility	84 g/L	ALOGPS
logP	-2.5	ALOGPS
logP	-2.7	ChemAxon
logS	-0.2	ALOGPS
pKa (Strongest Acidic)	2.59	ChemAxon
pKa (Strongest Basic)	7.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.33 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	30.82 m³·mol⁻¹	ChemAxon
Polarizability	12.48 Å³	ChemAxon
Number of Rings	1	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]+	125.37	30932474
DeepCCS	[M-H]-	122.501	30932474
DeepCCS	[M-2H]-	159.152	30932474
DeepCCS	[M+Na]+	134.34	30932474
AllCCS	[M+H]+	127.6	32859911
AllCCS	[M+H-H2O]+	123.0	32859911
AllCCS	[M+NH4]+	131.8	32859911
AllCCS	[M+Na]+	133.0	32859911
AllCCS	[M-H]-	126.0	32859911
AllCCS	[M+Na-2H]-	128.6	32859911
AllCCS	[M+HCOO]-	131.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Thioproline	OC(=O)[C@@H]1CSCN1	2419.0	Standard polar	33892256
Thioproline	OC(=O)[C@@H]1CSCN1	1236.1	Standard non polar	33892256
Thioproline	OC(=O)[C@@H]1CSCN1	1425.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Thioproline,1TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1CSCN1	1437.9	Semi standard non polar	33892256
Thioproline,1TMS,isomer #2	C[Si](C)(C)N1CSC[C@H]1C(=O)O	1522.5	Semi standard non polar	33892256
Thioproline,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1CSCN1[Si](C)(C)C	1568.2	Semi standard non polar	33892256
Thioproline,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1CSCN1[Si](C)(C)C	1499.4	Standard non polar	33892256
Thioproline,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1CSCN1[Si](C)(C)C	1874.0	Standard polar	33892256
Thioproline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CSCN1	1665.4	Semi standard non polar	33892256
Thioproline,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1CSC[C@H]1C(=O)O	1760.0	Semi standard non polar	33892256
Thioproline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CSCN1[Si](C)(C)C(C)(C)C	2015.0	Semi standard non polar	33892256
Thioproline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CSCN1[Si](C)(C)C(C)(C)C	1949.9	Standard non polar	33892256
Thioproline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CSCN1[Si](C)(C)C(C)(C)C	2070.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Thioproline 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 - Thioproline 10V, Positive-QTOF	splash10-001i-2900000000-4c7415eb5213815fcf90	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thioproline 20V, Positive-QTOF	splash10-0019-9800000000-4d42ab7305bc5b6c53d4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thioproline 40V, Positive-QTOF	splash10-08g0-9000000000-0543dfbddb2254f46d26	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thioproline 10V, Negative-QTOF	splash10-001i-3900000000-584ea9d5a453dff96c8a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thioproline 20V, Negative-QTOF	splash10-0zgi-9600000000-89fbcd989a3bde6ecc27	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thioproline 40V, Negative-QTOF	splash10-0f89-9200000000-d8bc6a99fc8c3eaccb40	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thioproline 10V, Positive-QTOF	splash10-001i-1900000000-6f425206faeb84c62457	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thioproline 20V, Positive-QTOF	splash10-00m0-9700000000-037376d41eb70f14feb9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thioproline 40V, Positive-QTOF	splash10-0002-9000000000-4a3724c597ca7d7c8e17	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thioproline 10V, Negative-QTOF	splash10-001i-9000000000-6103f78feab98bdf47a5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thioproline 20V, Negative-QTOF	splash10-001i-9000000000-dba40d2fe895aa552397	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thioproline 40V, Negative-QTOF	splash10-001i-9000000000-76da8cad1ce59915d0f6	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Urine	Detected and Quantified	0.28-0.69 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	27012787	details
Urine	Detected and Quantified	0.26-0.46 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	27012787	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB02846

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

CPD0-1571

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

93176

PDB ID

Not Available

ChEBI ID

45171

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

Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for Thioproline (HMDB0062164)

MOL for HMDB0062164 (Thioproline)

3D MOL for HMDB0062164 (Thioproline)

3D SDF for HMDB0062164 (Thioproline)

3D-SDF for HMDB0062164 (Thioproline)

PDB for HMDB0062164 (Thioproline)

3D PDB for HMDB0062164 (Thioproline)

SMILES for HMDB0062164 (Thioproline)

INCHI for HMDB0062164 (Thioproline)

Structure for HMDB0062164 (Thioproline)

3D Structure for HMDB0062164 (Thioproline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra