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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:27:32 UTC

Update Date

2021-09-26 22:55:31 UTC

HMDB ID

HMDB0246439

Secondary Accession Numbers

None

Metabolite Identification

Common Name

p-Hydroxylevamisole

Description

4-{2H,3H,5H,6H-imidazo[2,1-b][1,3]thiazol-6-yl}phenol belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. Based on a literature review very few articles have been published on 4-{2H,3H,5H,6H-imidazo[2,1-b][1,3]thiazol-6-yl}phenol. This compound has been identified in human blood as reported by (PMID: 31557052 ). P-hydroxylevamisole is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically p-Hydroxylevamisole 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


  Mrv1652309112101272D          

 15 17  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
    6.6237   -0.2549    0.0000 O   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
 12 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0246439

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C(C=C1)C1CN2CCSC2=N1

> <INCHI_IDENTIFIER>
InChI=1S/C11H12N2OS/c14-9-3-1-8(2-4-9)10-7-13-5-6-15-11(13)12-10/h1-4,10,14H,5-7H2

> <INCHI_KEY>
QBEDXUHDXKEDES-UHFFFAOYSA-N

> <FORMULA>
C11H12N2OS

> <MOLECULAR_WEIGHT>
220.29

> <EXACT_MASS>
220.067034188

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
23.31918309954843

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{2H,3H,5H,6H-imidazo[2,1-b][1,3]thiazol-6-yl}phenol

> <ALOGPS_LOGP>
1.82

> <JCHEM_LOGP>
2.0546615799999994

> <ALOGPS_LOGS>
-2.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.478164771571716

> <JCHEM_PKA_STRONGEST_BASIC>
6.973721844929794

> <JCHEM_POLAR_SURFACE_AREA>
35.83

> <JCHEM_REFRACTIVITY>
62.05930000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.56e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-{2H,3H,5H,6H-imidazo[2,1-b][1,3]thiazol-6-yl}phenol

> <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
HETATM   15  O   UNK     0      12.364  -0.476   0.000  0.00  0.00           O+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   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
CONECT   15   12                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END

COMPND    HMDB0246439
HETATM    1  O1  UNL     1      -5.293  -0.582  -0.093  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.941  -0.287   0.070  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.995  -1.285   0.071  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.653  -1.041   0.228  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.212   0.242   0.392  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.212   0.582   0.565  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.023   0.372  -0.699  1.00  0.00           C  
HETATM    8  N1  UNL     1       2.284  -0.178  -0.213  1.00  0.00           N  
HETATM    9  C7  UNL     1       3.637  -0.328  -0.596  1.00  0.00           C  
HETATM   10  C8  UNL     1       4.197  -1.624  -0.107  1.00  0.00           C  
HETATM   11  S1  UNL     1       3.325  -1.757   1.509  1.00  0.00           S  
HETATM   12  C9  UNL     1       1.955  -0.707   1.058  1.00  0.00           C  
HETATM   13  N2  UNL     1       0.828  -0.304   1.496  1.00  0.00           N  
HETATM   14  C10 UNL     1      -2.141   1.277   0.396  1.00  0.00           C  
HETATM   15  C11 UNL     1      -3.486   1.012   0.237  1.00  0.00           C  
HETATM   16  H1  UNL     1      -5.722  -0.614  -1.023  1.00  0.00           H  
HETATM   17  H2  UNL     1      -3.330  -2.311  -0.059  1.00  0.00           H  
HETATM   18  H3  UNL     1      -0.923  -1.838   0.226  1.00  0.00           H  
HETATM   19  H4  UNL     1       0.329   1.617   0.940  1.00  0.00           H  
HETATM   20  H5  UNL     1       0.533  -0.260  -1.436  1.00  0.00           H  
HETATM   21  H6  UNL     1       1.160   1.381  -1.148  1.00  0.00           H  
HETATM   22  H7  UNL     1       4.252   0.520  -0.233  1.00  0.00           H  
HETATM   23  H8  UNL     1       3.728  -0.347  -1.709  1.00  0.00           H  
HETATM   24  H9  UNL     1       3.940  -2.498  -0.699  1.00  0.00           H  
HETATM   25  H10 UNL     1       5.292  -1.485   0.058  1.00  0.00           H  
HETATM   26  H11 UNL     1      -1.785   2.302   0.527  1.00  0.00           H  
HETATM   27  H12 UNL     1      -4.215   1.822   0.240  1.00  0.00           H  
CONECT    1    2   16
CONECT    2    3    3   15
CONECT    3    4   17
CONECT    4    5    5   18
CONECT    5    6   14
CONECT    6    7   13   19
CONECT    7    8   20   21
CONECT    8    9   12
CONECT    9   10   22   23
CONECT   10   11   24   25
CONECT   11   12
CONECT   12   13   13
CONECT   14   15   15   26
CONECT   15   27
END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₁H₁₂N₂OS

Average Molecular Weight

220.29

Monoisotopic Molecular Weight

220.067034188

IUPAC Name

4-{2H,3H,5H,6H-imidazo[2,1-b][1,3]thiazol-6-yl}phenol

Traditional Name

4-{2H,3H,5H,6H-imidazo[2,1-b][1,3]thiazol-6-yl}phenol

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1)C1CN2CCSC2=N1

InChI Identifier

InChI=1S/C11H12N2OS/c14-9-3-1-8(2-4-9)10-7-13-5-6-15-11(13)12-10/h1-4,10,14H,5-7H2

InChI Key

QBEDXUHDXKEDES-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

1-hydroxy-2-unsubstituted benzenoids

Direct Parent

1-hydroxy-2-unsubstituted benzenoids

Alternative Parents

Substituents

1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Azole
2-imidazoline
Thiazolidine
Isothiourea
Azacycle
Organoheterocyclic compound
Carboximidamide
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organonitrogen compound
Amine
Organooxygen compound
Organic nitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	1.82	ALOGPS
logP	2.05	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	9.48	ChemAxon
pKa (Strongest Basic)	6.97	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	35.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	62.06 m³·mol⁻¹	ChemAxon
Polarizability	23.32 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]+	145.585	30932474
DeepCCS	[M-H]-	142.699	30932474
DeepCCS	[M-2H]-	178.804	30932474
DeepCCS	[M+Na]+	154.342	30932474
AllCCS	[M+H]+	149.7	32859911
AllCCS	[M+H-H2O]+	145.9	32859911
AllCCS	[M+NH4]+	153.3	32859911
AllCCS	[M+Na]+	154.3	32859911
AllCCS	[M-H]-	149.1	32859911
AllCCS	[M+Na-2H]-	149.1	32859911
AllCCS	[M+HCOO]-	149.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
p-Hydroxylevamisole	OC1=CC=C(C=C1)C1CN2CCSC2=N1	3029.7	Standard polar	33892256
p-Hydroxylevamisole	OC1=CC=C(C=C1)C1CN2CCSC2=N1	2156.6	Standard non polar	33892256
p-Hydroxylevamisole	OC1=CC=C(C=C1)C1CN2CCSC2=N1	2369.5	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 - p-Hydroxylevamisole GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-4910000000-2b57730dd4b1abd0f07a	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - p-Hydroxylevamisole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - p-Hydroxylevamisole GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - p-Hydroxylevamisole GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	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 - p-Hydroxylevamisole 10V, Positive-QTOF	splash10-00di-0090000000-f3efe59c21707af45b3f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Hydroxylevamisole 20V, Positive-QTOF	splash10-00di-0190000000-b134a7cda0ed0a183f59	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Hydroxylevamisole 40V, Positive-QTOF	splash10-00mo-4900000000-0e30ca1ba7188f870fc1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Hydroxylevamisole 10V, Negative-QTOF	splash10-014i-0090000000-7053f17cda719ca2a7b7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Hydroxylevamisole 20V, Negative-QTOF	splash10-014i-1290000000-bb2d5c1457f659a21194	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Hydroxylevamisole 40V, Negative-QTOF	splash10-0cdj-7910000000-d0de21f8dd85a79accb7	2021-10-12	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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8618877

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10443458

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 p-Hydroxylevamisole (HMDB0246439)

MOL for HMDB0246439 (p-Hydroxylevamisole)

3D MOL for HMDB0246439 (p-Hydroxylevamisole)

3D SDF for HMDB0246439 (p-Hydroxylevamisole)

3D-SDF for HMDB0246439 (p-Hydroxylevamisole)

PDB for HMDB0246439 (p-Hydroxylevamisole)

3D PDB for HMDB0246439 (p-Hydroxylevamisole)

SMILES for HMDB0246439 (p-Hydroxylevamisole)

INCHI for HMDB0246439 (p-Hydroxylevamisole)

Structure for HMDB0246439 (p-Hydroxylevamisole)

3D Structure for HMDB0246439 (p-Hydroxylevamisole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra