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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 17:29:14 UTC

Update Date

2021-09-26 23:12:51 UTC

HMDB ID

HMDB0256869

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Protionamide

Description

Protionamide, also known as trevintix or abbr pto, belongs to the class of organic compounds known as pyridines and derivatives. Pyridines and derivatives are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms. Based on a literature review very few articles have been published on Protionamide. This compound has been identified in human blood as reported by (PMID: 31557052 ). Protionamide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Protionamide 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

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -1.334  -2.310   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       2.667   1.540   0.000  0.00  0.00           N+0
HETATM   12  S   UNK     0      -2.667   0.000   0.000  0.00  0.00           S+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    8                                                       
CONECT    4    5    7                                                       
CONECT    5    4   11                                                       
CONECT    6    7    8                                                       
CONECT    7    4    6    9                                                  
CONECT    8    3    6   11                                                  
CONECT    9    7   10   12                                                  
CONECT   10    9                                                            
CONECT   11    5    8                                                       
CONECT   12    9                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Trevintix	Kegg
ABBR pto	Kegg
Prothionamide	MeSH
Sanavita brand OF prothionamide	MeSH
Fatol brand OF prothionamide	MeSH
Peteha	MeSH
Wernigerode brand OF prothionamide	MeSH
Ektebin	MeSH
Protionamide	KEGG
2-Propylpyridine-4-carboimidothioate	Generator

Chemical Formula

C₉H₁₂N₂S

Average Molecular Weight

180.27

Monoisotopic Molecular Weight

180.072119568

IUPAC Name

2-propylpyridine-4-carboimidothioic acid

Traditional Name

tuberex

CAS Registry Number

Not Available

SMILES

CCCC1=NC=CC(=C1)C(S)=N

InChI Identifier

InChI=1S/C9H12N2S/c1-2-3-8-6-7(9(10)12)4-5-11-8/h4-6H,2-3H2,1H3,(H2,10,12)

InChI Key

VRDIULHPQTYCLN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyridines and derivatives. Pyridines and derivatives are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Not Available

Direct Parent

Pyridines and derivatives

Alternative Parents

Substituents

Pyridine
Heteroaromatic compound
Thioamide
Azacycle
Thiocarboxylic acid amide
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Thiocarbonyl group
Organosulfur compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0256869)

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	2.38	ALOGPS
logP	2.22	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Basic)	7.31	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	36.74 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	63.86 m³·mol⁻¹	ChemAxon
Polarizability	20.07 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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
DeepCCS	[M+H]+	143.279	30932474
DeepCCS	[M-H]-	140.742	30932474
DeepCCS	[M-2H]-	176.873	30932474
DeepCCS	[M+Na]+	152.21	30932474
AllCCS	[M+H]+	138.3	32859911
AllCCS	[M+H-H2O]+	133.9	32859911
AllCCS	[M+NH4]+	142.3	32859911
AllCCS	[M+Na]+	143.5	32859911
AllCCS	[M-H]-	140.7	32859911
AllCCS	[M+Na-2H]-	141.9	32859911
AllCCS	[M+HCOO]-	143.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Protionamide	CCCC1=NC=CC(=C1)C(S)=N	2583.1	Standard polar	33892256
Protionamide	CCCC1=NC=CC(=C1)C(S)=N	1713.4	Standard non polar	33892256
Protionamide	CCCC1=NC=CC(=C1)C(S)=N	1871.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Protionamide,1TMS,isomer #1	CCCC1=CC(C(=N)S[Si](C)(C)C)=CC=N1	1899.1	Semi standard non polar	33892256
Protionamide,1TMS,isomer #1	CCCC1=CC(C(=N)S[Si](C)(C)C)=CC=N1	1694.6	Standard non polar	33892256
Protionamide,1TMS,isomer #1	CCCC1=CC(C(=N)S[Si](C)(C)C)=CC=N1	2400.2	Standard polar	33892256
Protionamide,1TMS,isomer #2	CCCC1=CC(C(S)=N[Si](C)(C)C)=CC=N1	1852.1	Semi standard non polar	33892256
Protionamide,1TMS,isomer #2	CCCC1=CC(C(S)=N[Si](C)(C)C)=CC=N1	1641.2	Standard non polar	33892256
Protionamide,1TMS,isomer #2	CCCC1=CC(C(S)=N[Si](C)(C)C)=CC=N1	2220.9	Standard polar	33892256
Protionamide,2TMS,isomer #1	CCCC1=CC(C(=N[Si](C)(C)C)S[Si](C)(C)C)=CC=N1	1883.2	Semi standard non polar	33892256
Protionamide,2TMS,isomer #1	CCCC1=CC(C(=N[Si](C)(C)C)S[Si](C)(C)C)=CC=N1	1758.5	Standard non polar	33892256
Protionamide,2TMS,isomer #1	CCCC1=CC(C(=N[Si](C)(C)C)S[Si](C)(C)C)=CC=N1	2180.7	Standard polar	33892256
Protionamide,1TBDMS,isomer #1	CCCC1=CC(C(=N)S[Si](C)(C)C(C)(C)C)=CC=N1	2142.8	Semi standard non polar	33892256
Protionamide,1TBDMS,isomer #1	CCCC1=CC(C(=N)S[Si](C)(C)C(C)(C)C)=CC=N1	1938.3	Standard non polar	33892256
Protionamide,1TBDMS,isomer #1	CCCC1=CC(C(=N)S[Si](C)(C)C(C)(C)C)=CC=N1	2455.8	Standard polar	33892256
Protionamide,1TBDMS,isomer #2	CCCC1=CC(C(S)=N[Si](C)(C)C(C)(C)C)=CC=N1	2059.3	Semi standard non polar	33892256
Protionamide,1TBDMS,isomer #2	CCCC1=CC(C(S)=N[Si](C)(C)C(C)(C)C)=CC=N1	1869.5	Standard non polar	33892256
Protionamide,1TBDMS,isomer #2	CCCC1=CC(C(S)=N[Si](C)(C)C(C)(C)C)=CC=N1	2338.5	Standard polar	33892256
Protionamide,2TBDMS,isomer #1	CCCC1=CC(C(=N[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C)=CC=N1	2330.4	Semi standard non polar	33892256
Protionamide,2TBDMS,isomer #1	CCCC1=CC(C(=N[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C)=CC=N1	2151.0	Standard non polar	33892256
Protionamide,2TBDMS,isomer #1	CCCC1=CC(C(=N[Si](C)(C)C(C)(C)C)S[Si](C)(C)C(C)(C)C)=CC=N1	2387.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Protionamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fwa-3900000000-d686302cfa409885a2f9	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Protionamide 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 - Protionamide LC-ESI-qTof , Positive-QTOF	splash10-0udi-3900000000-ebf07b82c23f40b432ab	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Protionamide , positive-QTOF	splash10-001i-1900000000-4e2e325a8024a29d1946	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Protionamide , positive-QTOF	splash10-0udi-3900000000-ebf07b82c23f40b432ab	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protionamide 10V, Positive-QTOF	splash10-03di-0900000000-f4c0758fc099d07fe382	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protionamide 20V, Positive-QTOF	splash10-03di-0900000000-fab730e0cf6bdb40f5a4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protionamide 40V, Positive-QTOF	splash10-03dm-4900000000-7d10dadc0f4c10a1f934	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protionamide 10V, Negative-QTOF	splash10-004j-0900000000-b5a8c53716c2d67b56e7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protionamide 20V, Negative-QTOF	splash10-004j-2900000000-4291d9a3dca91c2b33df	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Protionamide 40V, Negative-QTOF	splash10-0a59-9500000000-199e08e6d6d4e58164c0	2016-08-03	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

DB12667

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

579891

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Prothionamide

METLIN ID

Not Available

PubChem Compound

Not Available

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 Protionamide (HMDB0256869)

MOL for HMDB0256869 (Protionamide)

3D MOL for HMDB0256869 (Protionamide)

3D SDF for HMDB0256869 (Protionamide)

3D-SDF for HMDB0256869 (Protionamide)

PDB for HMDB0256869 (Protionamide)

3D PDB for HMDB0256869 (Protionamide)

SMILES for HMDB0256869 (Protionamide)

INCHI for HMDB0256869 (Protionamide)

Structure for HMDB0256869 (Protionamide)

3D Structure for HMDB0256869 (Protionamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra