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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:01:54 UTC

Update Date

2022-03-07 02:54:02 UTC

HMDB ID

HMDB0034228

Secondary Accession Numbers

HMDB34228

Metabolite Identification

Common Name

Thiolutin

Description

Thiolutin is found in alcoholic beverages. Thiolutin is isolated from several strains of Streptomyces albus and Streptomyces pimprina. Antibiotic which inhibits microbiological growth in beer Some sources erroneously specify "aureothricin" as a synonym of thiolutin. Aureothricin is an antibiotic very similar to Thiolutin, and is created as a by-product during the Thiolutin fermentation. Thiolutin is a sulfur-containing antibiotic, which is a potent inhibitor of bacterial and yeast RNA polymerases. It was found to inhibit in vitro RNA synthesis directed by all three yeast RNA polymerases (I, II, and III). Thiolutin is also an inhibitor of mannan and glucan formation in Saccharomyces cerevisiae and used for the analysis of mRNA stability. Studies have shown that thiolutin inhibits adhesion of human umbilical vein endothelial cells (HUVECs) to vitronectin and thus suppresses tumor cell-induced angiogenesis in vivo

Structure

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


  Mrv0541 02241216092D          

 14 15  0  0  0  0            999 V2000
   -0.6602    0.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4034   -0.1647    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8988    0.4951    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4034    1.1556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6602    0.9079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0830    1.1556    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5776    0.4951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1647   -0.1647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.9079    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2382   -1.1556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8988   -0.6602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4034   -1.9814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4034    0.5776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    1.9814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  1  8  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 14  1  0  0  0  0
  7  8  1  0  0  0  0
  7 13  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034228

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C(=O)C(NC(C)=O)=C2SSC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C8H8N2O2S2/c1-4(11)9-6-7-5(3-13-14-7)10(2)8(6)12/h3H,1-2H3,(H,9,11)

> <INCHI_KEY>
MHMRAFONCSQAIA-UHFFFAOYSA-N

> <FORMULA>
C8H8N2O2S2

> <MOLECULAR_WEIGHT>
228.291

> <EXACT_MASS>
228.00271889

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
21.952411352473877

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-{4-methyl-5-oxo-4H,5H-[1,2]dithiolo[4,3-b]pyrrol-6-yl}acetamide

> <ALOGPS_LOGP>
0.82

> <JCHEM_LOGP>
-0.5274866153333333

> <ALOGPS_LOGS>
-2.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.501974404604912

> <JCHEM_PKA_STRONGEST_BASIC>
-4.620144100700394

> <JCHEM_POLAR_SURFACE_AREA>
49.410000000000004

> <JCHEM_REFRACTIVITY>
60.346500000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.73e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
thiolutin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.232   0.155   0.000  0.00  0.00           C+0
HETATM    2  S   UNK     0      -2.620  -0.307   0.000  0.00  0.00           S+0
HETATM    3  S   UNK     0      -3.544   0.924   0.000  0.00  0.00           S+0
HETATM    4  C   UNK     0      -2.620   2.157   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.232   1.695   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       0.155   2.157   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       1.078   0.924   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.307  -0.307   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       0.770  -1.695   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       2.311  -2.157   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.544  -1.232   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.620  -3.699   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.620   1.078   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.770   3.699   0.000  0.00  0.00           C+0
CONECT    1    2    5    8                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    1    4    6                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8   13                                                  
CONECT    8    1    7    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    7                                                            
CONECT   14    6                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
6-Acetamido-4-methyl-1,2-dithiolo[4,3-b]pyrrol-5(4H)-one	ChEBI
Acetopyrrothin	ChEBI
Acetopyrrothine	ChEBI
N-(4,5-Dihydro-4-methyl-5-oxo-1,2-dithiolo[4,3-b]pyrrol-6-yl)acetamide	ChEBI
N-(4-Methyl-5-oxodithiolo[4,3-b]pyrrol-6-yl)acetamide	ChEBI
Farcinicine	HMDB
N-Acetylpyrrothine	HMDB
N-{4-methyl-5-oxo-4H,5H-[1,2]dithiolo[4,3-b]pyrrol-6-yl}ethanimidate	Generator
Thiolutin	MeSH

Chemical Formula

C₈H₈N₂O₂S₂

Average Molecular Weight

228.291

Monoisotopic Molecular Weight

228.00271889

IUPAC Name

N-{4-methyl-5-oxo-4H,5H-[1,2]dithiolo[4,3-b]pyrrol-6-yl}acetamide

Traditional Name

thiolutin

CAS Registry Number

87-11-6

SMILES

CN1C(=O)C(NC(C)=O)=C2SSC=C12

InChI Identifier

InChI=1S/C8H8N2O2S2/c1-4(11)9-6-7-5(3-13-14-7)10(2)8(6)12/h3H,1-2H3,(H,9,11)

InChI Key

MHMRAFONCSQAIA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acetylarylamines. These are acetamides where one or more amide hydrogens is substituted by an aryl group.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

N-arylamides

Direct Parent

N-acetylarylamines

Alternative Parents

Substituents

N-acetylarylamine
N-methylpyrrole
Substituted pyrrole
Pyrrole
1,2-dithiole
Dithiole
Acetamide
Heteroaromatic compound
Carboxamide group
Secondary carboxylic acid amide
Lactam
Organoheterocyclic compound
Carboxylic acid derivative
Azacycle
Carbonyl group
Organopnictogen compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0034228)
Cytoplasm (HMDB: HMDB0034228)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034228)

Source

Exogenous

Food

Food (HMDB: HMDB0034228)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Not Available

Nutrient (HMDB: HMDB0034228)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	273 - 276 °C	Not Available
Boiling Point	152.00 to 156.00 °C. @ 17.00 mm Hg	The Good Scents Company Information System
Water Solubility	0.21 mg/mL	Not Available
LogP	2.298 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.73 g/L	ALOGPS
logP	0.82	ALOGPS
logP	-0.53	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	12.5	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.41 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	60.35 m³·mol⁻¹	ChemAxon
Polarizability	21.95 Å³	ChemAxon
Number of Rings	2	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
DarkChem	[M+H]+	148.508	31661259
DarkChem	[M-H]-	140.815	31661259
DeepCCS	[M-2H]-	171.863	30932474
DeepCCS	[M+Na]+	146.662	30932474
AllCCS	[M+H]+	145.0	32859911
AllCCS	[M+H-H2O]+	141.1	32859911
AllCCS	[M+NH4]+	148.6	32859911
AllCCS	[M+Na]+	149.7	32859911
AllCCS	[M-H]-	144.6	32859911
AllCCS	[M+Na-2H]-	145.0	32859911
AllCCS	[M+HCOO]-	145.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Thiolutin	CN1C(=O)C(NC(C)=O)=C2SSC=C12	2886.1	Standard polar	33892256
Thiolutin	CN1C(=O)C(NC(C)=O)=C2SSC=C12	2012.4	Standard non polar	33892256
Thiolutin	CN1C(=O)C(NC(C)=O)=C2SSC=C12	2207.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Thiolutin,1TMS,isomer #1	CC(=O)N(C1=C2SSC=C2N(C)C1=O)[Si](C)(C)C	2063.8	Semi standard non polar	33892256
Thiolutin,1TMS,isomer #1	CC(=O)N(C1=C2SSC=C2N(C)C1=O)[Si](C)(C)C	2282.2	Standard non polar	33892256
Thiolutin,1TBDMS,isomer #1	CC(=O)N(C1=C2SSC=C2N(C)C1=O)[Si](C)(C)C(C)(C)C	2276.3	Semi standard non polar	33892256
Thiolutin,1TBDMS,isomer #1	CC(=O)N(C1=C2SSC=C2N(C)C1=O)[Si](C)(C)C(C)(C)C	2550.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Thiolutin GC-MS (Non-derivatized) - 70eV, Positive	splash10-054o-3910000000-519ee727a019d3a93d69	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Thiolutin 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 - Thiolutin 10V, Positive-QTOF	splash10-004i-7590000000-85817f7eb87b0115bd93	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiolutin 20V, Positive-QTOF	splash10-004r-0590000000-515631cb29113ba3b962	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiolutin 40V, Positive-QTOF	splash10-052s-9200000000-f7ff9dbd9f3a2082f78f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiolutin 10V, Negative-QTOF	splash10-004i-0890000000-9e6266701a4ec9c61060	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiolutin 20V, Negative-QTOF	splash10-003r-1970000000-03b1d843e3d93fbf40bc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiolutin 40V, Negative-QTOF	splash10-0zgi-2900000000-2d15a380d25bc120cdf3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiolutin 10V, Positive-QTOF	splash10-002r-0980000000-5f26834e99b886e3f03b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiolutin 20V, Positive-QTOF	splash10-002r-0960000000-7693ffa3bb0a88d601d7	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiolutin 40V, Positive-QTOF	splash10-0159-2900000000-a10fda5b87d577f08ad2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiolutin 10V, Negative-QTOF	splash10-004i-0090000000-95faf19c58c835a83e00	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiolutin 20V, Negative-QTOF	splash10-0059-0590000000-0ab84e20d5f22fd4f7af	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiolutin 40V, Negative-QTOF	splash10-004i-1920000000-229b3b69617b7784c357	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB012539

KNApSAcK ID

C00054277

Chemspider ID

6608

KEGG Compound ID

Not Available

BioCyc ID

CPD-17934

BiGG ID

Not Available

Wikipedia Link

Thiolutin

METLIN ID

Not Available

PubChem Compound

6870

PDB ID

Not Available

ChEBI ID

156450

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1021681

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Dai S, Jia Y, Wu SL, Isenberg JS, Ridnour LA, Bandle RW, Wink DA, Roberts DD, Karger BL: Comprehensive characterization of heat shock protein 27 phosphorylation in human endothelial cells stimulated by the microbial dithiole thiolutin. J Proteome Res. 2008 Oct;7(10):4384-95. doi: 10.1021/pr800376w. Epub 2008 Aug 23. [PubMed:18720982 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Thiolutin (HMDB0034228)

MOL for HMDB0034228 (Thiolutin)

3D MOL for HMDB0034228 (Thiolutin)

3D SDF for HMDB0034228 (Thiolutin)

3D-SDF for HMDB0034228 (Thiolutin)

PDB for HMDB0034228 (Thiolutin)

3D PDB for HMDB0034228 (Thiolutin)

SMILES for HMDB0034228 (Thiolutin)

INCHI for HMDB0034228 (Thiolutin)

Structure for HMDB0034228 (Thiolutin)

3D Structure for HMDB0034228 (Thiolutin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra