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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-15 18:09:01 UTC

Update Date

2023-02-21 17:30:06 UTC

HMDB ID

HMDB0060624

Secondary Accession Numbers

HMDB60624

Metabolite Identification

Common Name

Ethionamide sulphoxide

Description

Ethionamide sulphoxide is a metabolite of ethionamide. Ethionamide (2-ethylthioisonicotinamide, Trecator SC) is an antibiotic used in the treatment of tuberculosis. Ethionamide works to induce expression of EthA, a NAD derivative which is toxic to fungi. The resistance mechanism of this drug is through EthR, resistance is common. Therefore, EthR inhibitors are of great interest. It is a prodrug. It has been proposed for use in combination with gatifloxacin. The action may be through disruption of mycolic acid. (Wikipedia)

Structure

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

HEADER    PROTEIN                                 15-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-JUN-13         0                                  
HETATM    1  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       2.667   1.540   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   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       0.000   1.540   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      -2.667   0.000   0.000  0.00  0.00           N+0
HETATM   11  S   UNK     0      -1.334  -2.310   0.000  0.00  0.00           S+0
HETATM   12  O   UNK     0      -1.334  -3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7    3                                                       
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Ethionamide sulfoxide	ChEBI
Ethionamide sulphoxide	ChEBI

Chemical Formula

C₈H₁₀N₂OS

Average Molecular Weight

182.243

Monoisotopic Molecular Weight

182.051383642

IUPAC Name

(2-ethylpyridin-4-yl)(sulfinylidene)methanamine

Traditional Name

(2-ethylpyridin-4-yl)(sulfinylidene)methanamine

CAS Registry Number

Not Available

SMILES

CCC1=NC=CC(=C1)C(N)=S=O

InChI Identifier

InChI=1S/C8H10N2OS/c1-2-7-5-6(3-4-10-7)8(9)12-11/h3-5H,2,9H2,1H3

InChI Key

QDQQNGZRIJPDGA-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
Azacycle
Sulfinyl compound
Sulfine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
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 (HMDB: HMDB0060624)

Organ

Kidney (HMDB: HMDB0060624)
Liver (HMDB: HMDB0060624)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060624)

Cellular substructure

Cytoplasm (HMDB: HMDB0060624)

Source

Endogenous

Endogenous (HMDB: HMDB0060624)

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	71.3 g/L	ALOGPS
logP	0.23	ALOGPS
logP	0.8	ChemAxon
logS	-0.41	ALOGPS
pKa (Strongest Acidic)	7.53	ChemAxon
pKa (Strongest Basic)	4.47	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.98 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	47.95 m³·mol⁻¹	ChemAxon
Polarizability	18.62 Å³	ChemAxon
Number of Rings	1	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]+	140.315	31661259
DarkChem	[M-H]-	136.837	31661259
DeepCCS	[M+H]+	140.075	30932474
DeepCCS	[M-H]-	137.729	30932474
DeepCCS	[M-2H]-	173.649	30932474
DeepCCS	[M+Na]+	148.819	30932474
AllCCS	[M+H]+	138.5	32859911
AllCCS	[M+H-H2O]+	134.1	32859911
AllCCS	[M+NH4]+	142.5	32859911
AllCCS	[M+Na]+	143.7	32859911
AllCCS	[M-H]-	138.1	32859911
AllCCS	[M+Na-2H]-	139.3	32859911
AllCCS	[M+HCOO]-	140.6	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. Predicted by Afia on May 17, 2022.	3.1 minutes	32390414
Predicted by Siyang on May 30, 2022	9.3223 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.31 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	669.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	299.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	75.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	174.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	56.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	290.9 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	254.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	368.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	618.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	37.0 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	728.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	168.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	239.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	510.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	349.5 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	221.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ethionamide sulphoxide	CCC1=NC=CC(=C1)C(N)=S=O	2683.3	Standard polar	33892256
Ethionamide sulphoxide	CCC1=NC=CC(=C1)C(N)=S=O	1742.9	Standard non polar	33892256
Ethionamide sulphoxide	CCC1=NC=CC(=C1)C(N)=S=O	1862.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ethionamide sulphoxide,1TMS,isomer #1	CCC1=CC(C(N[Si](C)(C)C)=S=O)=CC=N1	1921.4	Semi standard non polar	33892256
Ethionamide sulphoxide,1TMS,isomer #1	CCC1=CC(C(N[Si](C)(C)C)=S=O)=CC=N1	1592.2	Standard non polar	33892256
Ethionamide sulphoxide,1TMS,isomer #1	CCC1=CC(C(N[Si](C)(C)C)=S=O)=CC=N1	2638.7	Standard polar	33892256
Ethionamide sulphoxide,2TMS,isomer #1	CCC1=CC(C(=S=O)N([Si](C)(C)C)[Si](C)(C)C)=CC=N1	1957.3	Semi standard non polar	33892256
Ethionamide sulphoxide,2TMS,isomer #1	CCC1=CC(C(=S=O)N([Si](C)(C)C)[Si](C)(C)C)=CC=N1	1770.9	Standard non polar	33892256
Ethionamide sulphoxide,2TMS,isomer #1	CCC1=CC(C(=S=O)N([Si](C)(C)C)[Si](C)(C)C)=CC=N1	2308.1	Standard polar	33892256
Ethionamide sulphoxide,1TBDMS,isomer #1	CCC1=CC(C(N[Si](C)(C)C(C)(C)C)=S=O)=CC=N1	2158.7	Semi standard non polar	33892256
Ethionamide sulphoxide,1TBDMS,isomer #1	CCC1=CC(C(N[Si](C)(C)C(C)(C)C)=S=O)=CC=N1	1819.7	Standard non polar	33892256
Ethionamide sulphoxide,1TBDMS,isomer #1	CCC1=CC(C(N[Si](C)(C)C(C)(C)C)=S=O)=CC=N1	2696.9	Standard polar	33892256
Ethionamide sulphoxide,2TBDMS,isomer #1	CCC1=CC(C(=S=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=N1	2439.7	Semi standard non polar	33892256
Ethionamide sulphoxide,2TBDMS,isomer #1	CCC1=CC(C(=S=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=N1	2193.7	Standard non polar	33892256
Ethionamide sulphoxide,2TBDMS,isomer #1	CCC1=CC(C(=S=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=N1	2433.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ethionamide sulphoxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-2900000000-e1e57c15859b4306c6bf	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethionamide sulphoxide 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 - Ethionamide sulphoxide 10V, Positive-QTOF	splash10-00lr-0900000000-cc0dcc80ecd495acbefa	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethionamide sulphoxide 20V, Positive-QTOF	splash10-00lr-0900000000-20f6be49e087dc9c38db	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethionamide sulphoxide 40V, Positive-QTOF	splash10-0a6r-9600000000-3c6a5f1dedd78e140dc1	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethionamide sulphoxide 10V, Negative-QTOF	splash10-001i-0900000000-8862d0db3ba360dc524a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethionamide sulphoxide 20V, Negative-QTOF	splash10-001i-3900000000-c674145c3a95a060d127	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethionamide sulphoxide 40V, Negative-QTOF	splash10-00fs-9100000000-2eeb13718a3e3f1a0466	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethionamide sulphoxide 10V, Positive-QTOF	splash10-001i-0900000000-9e05192d1bd755c0f756	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethionamide sulphoxide 20V, Positive-QTOF	splash10-001i-0900000000-cffdf45561ef57a7f9a8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethionamide sulphoxide 40V, Positive-QTOF	splash10-0a4i-9500000000-8afdbc66318c758b4af0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethionamide sulphoxide 10V, Negative-QTOF	splash10-001i-1900000000-7774abd10ade777d372b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethionamide sulphoxide 20V, Negative-QTOF	splash10-003s-9700000000-7e99e9e2a9cbcc30de98	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethionamide sulphoxide 40V, Negative-QTOF	splash10-004j-9200000000-eb1791a4bad974853ef9	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

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

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71316501

PDB ID

Not Available

ChEBI ID

87805

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

Deshpande AY, Gurav S, Punde R, Zambre V, Kulkarni R, Pandey S, Mungantiwar A, Mullangi R: Development and validation of a highly sensitive LC-MS/MS method for simultaneous quantitation of ethionamide and ethionamide sulfoxide in human plasma: application to a human pharmacokinetic study. Biomed Chromatogr. 2011 Sep;25(9):985-94. doi: 10.1002/bmc.1554. Epub 2011 Jan 26. [PubMed:21268048 ]
Grunert M, Werner E, Iwainsky H, Eule H: [Associated chemical and microbiological studies on the antitubercular properties of ethionamide sulfoxide]. Z Erkr Atmungsorgane Folia Bronchol. 1970 Dec;133(1):406-8. [PubMed:5204733 ]
Bieder A, Brunel P, Roquet-Ghaye J, Kreis B: [Evolution of serum concentrations of ethionamide (TH 1413) and ethionamide sulfoxide (TH 1405) after oral administration of these tuberculostatic agents in man]. Rev Fr Etud Clin Biol. 1966 Apr;11(4):419-23. [PubMed:5944589 ]

Showing metabocard for Ethionamide sulphoxide (HMDB0060624)

MOL for HMDB0060624 (Ethionamide sulphoxide)

3D MOL for HMDB0060624 (Ethionamide sulphoxide)

3D SDF for HMDB0060624 (Ethionamide sulphoxide)

3D-SDF for HMDB0060624 (Ethionamide sulphoxide)

PDB for HMDB0060624 (Ethionamide sulphoxide)

3D PDB for HMDB0060624 (Ethionamide sulphoxide)

SMILES for HMDB0060624 (Ethionamide sulphoxide)

INCHI for HMDB0060624 (Ethionamide sulphoxide)

Structure for HMDB0060624 (Ethionamide sulphoxide)

3D Structure for HMDB0060624 (Ethionamide sulphoxide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra