NP-MRD: Showing NP-Card for Thiolutin (NP0005120)

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Record Information

Version

2.0

Created at

2020-12-09 02:27:45 UTC

Updated at

2021-08-19 23:59:37 UTC

NP-MRD ID

NP0005120

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Thiolutin

Provided By

NPAtlas

Description

Thiolutin, also known as acetopyrrothine or farcinicine, 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. Thiolutin has been detected, but not quantified in, alcoholic beverages. This could make thiolutin a potential biomarker for the consumption of these foods. Thiolutin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Thiolutin is found in Saccharothrix algeriensis, Streptomyces kasugaensis and Streptomyces luteosporeus. Thiolutin was first documented in 1951 (PMID: 14847786). Based on a literature review a small amount of articles have been published on Thiolutin (PMID: 11433393) (PMID: 17036064) (PMID: 17914747) (PMID: 18720982).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118173D          

 22 23  0  0  0  0            999 V2000
    4.0863   -0.4510   -0.0988 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6759   -0.2284    0.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3899    0.0659    1.4414 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6302   -0.3356   -0.6969 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2711   -0.1284   -0.3870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4210    1.0947   -0.4500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0319    2.7040   -0.8683 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9258    3.4682   -0.5304 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6267    1.9877   -0.0570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7920    0.9056   -0.0587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8485   -0.4454    0.2228 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0228   -1.1544    0.6660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6693   -1.0278    0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4061   -2.2561    0.2081 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5670    0.4463   -0.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7075   -0.7679    0.7602 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2010   -1.2742   -0.8606 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8954   -0.5828   -1.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7124    1.9357    0.2335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1298   -2.1486    0.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9246   -1.2483    1.7847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9135   -0.5592    0.4203 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13  5  1  0  0  0  0
 10  6  1  0  0  0  0
  1 15  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  4 18  1  0  0  0  0
  9 19  1  0  0  0  0
 12 20  1  0  0  0  0
 12 21  1  0  0  0  0
 12 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0005120

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N(C(=O)C([H])([H])[H])C1=C2SSC([H])=C2N(C1=O)C([H])([H])[H]

> <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_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
21.95241134028825

> <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-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       4.086  -0.451  -0.099  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.676  -0.228   0.256  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.390   0.066   1.441  0.00  0.00           O+0
HETATM    4  N   UNK     0       1.630  -0.336  -0.697  0.00  0.00           N+0
HETATM    5  C   UNK     0       0.271  -0.128  -0.387  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.421   1.095  -0.450  0.00  0.00           C+0
HETATM    7  S   UNK     0      -0.032   2.704  -0.868  0.00  0.00           S+0
HETATM    8  S   UNK     0      -1.926   3.468  -0.530  0.00  0.00           S+0
HETATM    9  C   UNK     0      -2.627   1.988  -0.057  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.792   0.906  -0.059  0.00  0.00           C+0
HETATM   11  N   UNK     0      -1.849  -0.445   0.223  0.00  0.00           N+0
HETATM   12  C   UNK     0      -3.023  -1.154   0.666  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.669  -1.028   0.033  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.406  -2.256   0.208  0.00  0.00           O+0
HETATM   15  H   UNK     0       4.567   0.446  -0.530  0.00  0.00           H+0
HETATM   16  H   UNK     0       4.707  -0.768   0.760  0.00  0.00           H+0
HETATM   17  H   UNK     0       4.201  -1.274  -0.861  0.00  0.00           H+0
HETATM   18  H   UNK     0       1.895  -0.583  -1.681  0.00  0.00           H+0
HETATM   19  H   UNK     0      -3.712   1.936   0.234  0.00  0.00           H+0
HETATM   20  H   UNK     0      -3.130  -2.149   0.193  0.00  0.00           H+0
HETATM   21  H   UNK     0      -2.925  -1.248   1.785  0.00  0.00           H+0
HETATM   22  H   UNK     0      -3.914  -0.559   0.420  0.00  0.00           H+0
CONECT    1    2   15   16   17                                             
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   18                                                  
CONECT    5    4    6   13                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   19                                                  
CONECT   10    9   11    6                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11   20   21   22                                             
CONECT   13   11   14    5                                                  
CONECT   14   13                                                            
CONECT   15    1                                                            
CONECT   16    1                                                            
CONECT   17    1                                                            
CONECT   18    4                                                            
CONECT   19    9                                                            
CONECT   20   12                                                            
CONECT   21   12                                                            
CONECT   22   12                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol View NMR Assignments

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	HMDB
Thiolutin	MeSH

Chemical Formula

C₈H₈N₂O₂S₂

Average Mass

228.2910 Da

Monoisotopic Mass

228.00272 Da

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

Not Available

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Saccharothrix algeriensis	LOTUS Database	35616633
Streptomyces kasugaensis	LOTUS Database	35616633
Streptomyces luteosporeus	NPAtlas	14847786

Species Where Detected

Species Name	Source	Reference
Streptomyces albus	KNApSAcK Database	22123792
Streptomyces pimprina	KNApSAcK Database	22123792

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

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	152.00 to 156.00 °C. @ 17.00 mm Hg	The Good Scents Company Information System
Water Solubility	133.2 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.298 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
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

External Links

NPAtlas ID

NPA005113

HMDB ID

HMDB0034228

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

rw1021681

References

General References

COHEN R: Four new fungicides for Coccidioides immitis: 1. Sodium caprylate. 2. Ethyl vanillate 3. Fradicin. 4. Thiolutin. Arch Pediatr. 1951 Jun;68(6):259-64. [PubMed:14847786 ]
Minamiguchi K, Kumagai H, Masuda T, Kawada M, Ishizuka M, Takeuchi T: Thiolutin, an inhibitor of HUVEC adhesion to vitronectin, reduces paxillin in HUVECs and suppresses tumor cell-induced angiogenesis. Int J Cancer. 2001 Aug 1;93(3):307-16. doi: 10.1002/ijc.1321. [PubMed:11433393 ]
Kebaara BW, Nielsen LE, Nickerson KW, Atkin AL: Determination of mRNA half-lives in Candida albicans using thiolutin as a transcription inhibitor. Genome. 2006 Aug;49(8):894-9. doi: 10.1139/g06-046. [PubMed:17036064 ]
Pelechano V, Perez-Ortin JE: The transcriptional inhibitor thiolutin blocks mRNA degradation in yeast. Yeast. 2008 Feb;25(2):85-92. doi: 10.1002/yea.1548. [PubMed:17914747 ]
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 ]

Showing NP-Card for Thiolutin (NP0005120)

MOL for NP0005120 (Thiolutin)

3D MOL for NP0005120 (Thiolutin)

3D SDF for NP0005120 (Thiolutin)

3D-SDF for NP0005120 (Thiolutin)

PDB for NP0005120 (Thiolutin)

3D PDB for NP0005120 (Thiolutin)

SMILES for NP0005120 (Thiolutin)

INCHI for NP0005120 (Thiolutin)

Structure for NP0005120 (Thiolutin)

3D Structure for NP0005120 (Thiolutin)