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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 20:45:38 UTC

Update Date

2022-11-23 22:29:20 UTC

HMDB ID

HMDB0258921

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Tetramisole

Description

6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole, also known as ascaverm or tetramisole, belongs to the class of organic compounds known as imidazothiazoles. These are organic polycyclic compounds containing an imidazole ring fused to a thiazole ring. Imidazole is 5-membered ring consisting of three carbon atoms, and two nitrogen centers at the 1- and 3-positions. Thiazole is a 6-membered ring that contains both sulfur and nitrogen. Based on a literature review very few articles have been published on 6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole. This compound has been identified in human blood as reported by (PMID: 31557052 ). Tetramisole is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Tetramisole 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


  Mrv1652309112122452D          

 14 16  0  0  0  0            999 V2000
    1.2695   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542    0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8388    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3237   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8388   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1487   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5612    0.4595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3862    0.4595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7987   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3862   -0.9694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5612   -0.9694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  7  8  1  0  0  0  0
  4  8  1  0  0  0  0
  1  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0258921

> <DATABASE_NAME>
hmdb

> <SMILES>
C1CN2CC(N=C2S1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H12N2S/c1-2-4-9(5-3-1)10-8-13-6-7-14-11(13)12-10/h1-5,10H,6-8H2

> <INCHI_KEY>
HLFSDGLLUJUHTE-UHFFFAOYSA-N

> <FORMULA>
C11H12N2S

> <MOLECULAR_WEIGHT>
204.29

> <EXACT_MASS>
204.072119568

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
22.24610068559575

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-phenyl-2H,3H,5H,6H-imidazo[2,1-b][1,3]thiazole

> <ALOGPS_LOGP>
2.20

> <JCHEM_LOGP>
2.3582269016666664

> <ALOGPS_LOGS>
-2.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
6.975299007898724

> <JCHEM_POLAR_SURFACE_AREA>
15.6

> <JCHEM_REFRACTIVITY>
60.078400000000016

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.44e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
levamisole

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       2.370  -1.722   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM    3  S   UNK     0       2.370   0.770   0.000  0.00  0.00           S+0
HETATM    4  C   UNK     0       3.834   0.294   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       5.299   0.770   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       6.204  -0.476   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.299  -1.722   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       3.834  -1.246   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       7.744  -0.476   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.514   0.858   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.054   0.858   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.824  -0.476   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.054  -1.810   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.514  -1.810   0.000  0.00  0.00           C+0
CONECT    1    2    8                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7    4    1                                                  
CONECT    9    6   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   32    0
END

COMPND    HMDB0258921
HETATM    1  C1  UNL     1      -4.125  -0.107  -0.362  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.165   0.447  -1.153  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.846   0.510  -0.763  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.508  -0.012   0.474  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.091   0.065   0.874  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.777  -0.903   0.057  1.00  0.00           C  
HETATM    7  N1  UNL     1       2.041  -0.128   0.094  1.00  0.00           N  
HETATM    8  C7  UNL     1       3.469  -0.326   0.103  1.00  0.00           C  
HETATM    9  C8  UNL     1       4.061   0.606  -0.955  1.00  0.00           C  
HETATM   10  S1  UNL     1       3.145   2.123  -0.447  1.00  0.00           S  
HETATM   11  C9  UNL     1       1.689   1.250   0.145  1.00  0.00           C  
HETATM   12  N2  UNL     1       0.472   1.377   0.594  1.00  0.00           N  
HETATM   13  C10 UNL     1      -2.456  -0.570   1.278  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.767  -0.620   0.865  1.00  0.00           C  
HETATM   15  H1  UNL     1      -5.167  -0.141  -0.702  1.00  0.00           H  
HETATM   16  H2  UNL     1      -3.438   0.858  -2.131  1.00  0.00           H  
HETATM   17  H3  UNL     1      -1.141   0.959  -1.433  1.00  0.00           H  
HETATM   18  H4  UNL     1       0.067  -0.184   1.926  1.00  0.00           H  
HETATM   19  H5  UNL     1       0.461  -0.957  -0.993  1.00  0.00           H  
HETATM   20  H6  UNL     1       0.886  -1.877   0.540  1.00  0.00           H  
HETATM   21  H7  UNL     1       3.723  -1.364  -0.066  1.00  0.00           H  
HETATM   22  H8  UNL     1       3.858   0.068   1.088  1.00  0.00           H  
HETATM   23  H9  UNL     1       3.725   0.246  -1.932  1.00  0.00           H  
HETATM   24  H10 UNL     1       5.127   0.719  -0.814  1.00  0.00           H  
HETATM   25  H11 UNL     1      -2.227  -0.983   2.244  1.00  0.00           H  
HETATM   26  H12 UNL     1      -4.568  -1.056   1.470  1.00  0.00           H  
CONECT    1    2    2   14   15
CONECT    2    3   16
CONECT    3    4    4   17
CONECT    4    5   13
CONECT    5    6   12   18
CONECT    6    7   19   20
CONECT    7    8   11
CONECT    8    9   21   22
CONECT    9   10   23   24
CONECT   10   11
CONECT   11   12   12
CONECT   13   14   14   25
CONECT   14   26
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Ascaverm	Kegg
Tetramisole	Kegg
Nilverm	MeSH

Chemical Formula

C₁₁H₁₂N₂S

Average Molecular Weight

204.29

Monoisotopic Molecular Weight

204.072119568

IUPAC Name

6-phenyl-2H,3H,5H,6H-imidazo[2,1-b][1,3]thiazole

Traditional Name

levamisole

CAS Registry Number

Not Available

SMILES

C1CN2CC(N=C2S1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C11H12N2S/c1-2-4-9(5-3-1)10-8-13-6-7-14-11(13)12-10/h1-5,10H,6-8H2

InChI Key

HLFSDGLLUJUHTE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as imidazothiazoles. These are organic polycyclic compounds containing an imidazole ring fused to a thiazole ring. Imidazole is 5-membered ring consisting of three carbon atoms, and two nitrogen centers at the 1- and 3-positions. Thiazole is a 6-membered ring that contains both sulfur and nitrogen.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazothiazoles

Sub Class

Not Available

Direct Parent

Imidazothiazoles

Alternative Parents

Substituents

Imidazothiazole
Benzenoid
Monocyclic benzene moiety
Thiazolidine
2-imidazoline
Isothiourea
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

imidazothiazole (CHEBI:77278 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

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	2.2	ALOGPS
logP	2.36	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Basic)	6.98	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	15.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	60.08 m³·mol⁻¹	ChemAxon
Polarizability	22.25 Å³	ChemAxon
Number of Rings	3	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]+	140.099	30932474
DeepCCS	[M-H]-	137.704	30932474
DeepCCS	[M-2H]-	172.644	30932474
DeepCCS	[M+Na]+	147.22	30932474
AllCCS	[M+H]+	146.1	32859911
AllCCS	[M+H-H2O]+	142.1	32859911
AllCCS	[M+NH4]+	149.8	32859911
AllCCS	[M+Na]+	150.9	32859911
AllCCS	[M-H]-	145.6	32859911
AllCCS	[M+Na-2H]-	145.6	32859911
AllCCS	[M+HCOO]-	145.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
TETRAMISOLE	C1CN2CC(N=C2S1)C1=CC=CC=C1	2676.5	Standard polar	33892256
TETRAMISOLE	C1CN2CC(N=C2S1)C1=CC=CC=C1	1853.3	Standard non polar	33892256
TETRAMISOLE	C1CN2CC(N=C2S1)C1=CC=CC=C1	1989.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tetramisole GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-6900000000-5160cd42f946bfd44b1d	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tetramisole 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 - Tetramisole 30V, Positive-QTOF	splash10-00b9-2900000000-2abb17a381dbc6fa4682	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetramisole 50V, Positive-QTOF	splash10-01ec-1900000000-ca0f7799112d42972b0d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetramisole 20V, Positive-QTOF	splash10-0a4i-0590000000-8e6a510684f807e7bf29	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetramisole 10V, Positive-QTOF	splash10-0a4i-0090000000-7b5e4e71832c5808c581	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetramisole 30V, Positive-QTOF	splash10-00b9-2900000000-b19ea929fe684b26355e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetramisole 10V, Positive-QTOF	splash10-0a4i-0090000000-4a3cc348fa14a506c8bd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetramisole 20V, Positive-QTOF	splash10-0a4i-0190000000-49a9ae546ec3a269617e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetramisole 40V, Positive-QTOF	splash10-0006-7900000000-9f0ba2bb89893c9a6632	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetramisole 30V, Positive-QTOF	splash10-00b9-2900000000-eb1cb3a71ea671b3303f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetramisole 50V, Positive-QTOF	splash10-0006-9500000000-5215d5723213d256e0db	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetramisole 50V, Positive-QTOF	splash10-0006-9500000000-143f624b24a42901e987	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetramisole 40V, Positive-QTOF	splash10-00b9-0900000000-408cd49d75c26186b6e2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetramisole 30V, Positive-QTOF	splash10-056r-0930000000-339380648feb3e65ef30	2021-09-20	HMDB team, MONA	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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3776

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

77278

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 Tetramisole (HMDB0258921)

MOL for HMDB0258921 (Tetramisole)

3D MOL for HMDB0258921 (Tetramisole)

3D SDF for HMDB0258921 (Tetramisole)

3D-SDF for HMDB0258921 (Tetramisole)

PDB for HMDB0258921 (Tetramisole)

3D PDB for HMDB0258921 (Tetramisole)

SMILES for HMDB0258921 (Tetramisole)

INCHI for HMDB0258921 (Tetramisole)

Structure for HMDB0258921 (Tetramisole)

3D Structure for HMDB0258921 (Tetramisole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra