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Showing NP-Card for 5-(2-Hydroxyethyl)-4-methylthiazole (NP0001247)

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Record Information
Version2.0
Created at2012-09-11 17:53:05 UTC
Updated at2024-09-17 15:44:40 UTC
NP-MRD IDNP0001247
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-(2-Hydroxyethyl)-4-methylthiazole
Description5-(2-Hydroxyethyl)-4-methylthiazole, also known as 4-methyl-5-(2'-hydroxyethyl)-thiazole or 4-methyl-5-thiazolethanol, belongs to the class of organic compounds known as 4,5-disubstituted thiazoles. 4,5-Disubstituted thiazoles are compounds containing a thiazole ring substituted at positions 4 and 5 only. 5-(2-Hydroxyethyl)-4-methylthiazole exists in all living species, ranging from bacteria to humans. 5-(2-Hydroxyethyl)-4-methylthiazole is a sulfur tasting compound. 5-(2-Hydroxyethyl)-4-methylthiazole has been detected, but not quantified, in several different foods, such as kohlrabis, red bell peppers, citrus, avocado, and black-eyed pea. This could make 5-(2-hydroxyethyl)-4-methylthiazole a potential biomarker for the consumption of these foods. A 1,3-thiazole that is thiazole substituted by a methyl group at position 4 and a 2-hydroxyethyl group at position 5.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001247 (5-(2-Hydroxyethyl)-4-methylthiazole)


  Mrv1652304152023112D          

  9  9  0  0  0  0            999 V2000
    1.9078   -0.1819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1627    0.6027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5752   -0.6667    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.9876    0.6027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2427   -0.1819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6777    1.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1232   -0.4369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5101    0.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2745   -0.1398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  3  5  1  0  0  0  0
  1  2  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  2  6  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
M  END
Download

3D MOL for NP0001247 (5-(2-Hydroxyethyl)-4-methylthiazole)

HMDB0032985
     RDKit          3D
5-(2-Hydroxyethyl)-4-methylthiazole
 18 18  0  0  0  0  0  0  0  0999 V2000
   -1.9530   -1.5081   -0.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4745   -0.0703   -0.0791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3026    0.9149   -0.2074 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8773    2.1652   -0.1612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1990    1.9584    0.0830 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1512    0.2304    0.1095 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0190   -0.6840    0.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2549    0.0329   -0.1967 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4756    1.2184    0.5284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8178   -1.8469   -1.1690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3416   -2.1074    0.5873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9927   -1.6001    0.2246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4557    3.1020   -0.2538 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8727   -1.5288   -0.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0974   -1.1076    1.2674 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1121   -0.6744    0.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3215    0.1767   -1.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4123    1.3288    0.7888 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  6  2  2  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  4 13  1  0
  7 14  1  0
  7 15  1  0
  8 16  1  0
  8 17  1  0
  9 18  1  0
M  END
Download

3D SDF for NP0001247 (5-(2-Hydroxyethyl)-4-methylthiazole)


  Mrv1652304152023112D          

  9  9  0  0  0  0            999 V2000
    1.9078   -0.1819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1627    0.6027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5752   -0.6667    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.9876    0.6027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2427   -0.1819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6777    1.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1232   -0.4369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5101    0.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2745   -0.1398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  3  5  1  0  0  0  0
  1  2  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  2  6  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001247

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(CCO)SC=N1

> <INCHI_IDENTIFIER>
InChI=1S/C6H9NOS/c1-5-6(2-3-8)9-4-7-5/h4,8H,2-3H2,1H3

> <INCHI_KEY>
BKAWJIRCKVUVED-UHFFFAOYSA-N

> <FORMULA>
C6H9NOS

> <MOLECULAR_WEIGHT>
143.207

> <EXACT_MASS>
143.040484605

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
14.923318009148648

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(4-methyl-1,3-thiazol-5-yl)ethan-1-ol

> <ALOGPS_LOGP>
0.67

> <JCHEM_LOGP>
0.4171596229999998

> <ALOGPS_LOGS>
-1.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.619949149474245

> <JCHEM_PKA_STRONGEST_BASIC>
3.1150787325803235

> <JCHEM_POLAR_SURFACE_AREA>
33.120000000000005

> <JCHEM_REFRACTIVITY>
37.323299999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.26e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-methyl-5-thiazoleethanol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0001247 (5-(2-Hydroxyethyl)-4-methylthiazole)

HMDB0032985
     RDKit          3D
5-(2-Hydroxyethyl)-4-methylthiazole
 18 18  0  0  0  0  0  0  0  0999 V2000
   -1.9530   -1.5081   -0.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4745   -0.0703   -0.0791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3026    0.9149   -0.2074 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8773    2.1652   -0.1612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1990    1.9584    0.0830 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1512    0.2304    0.1095 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0190   -0.6840    0.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2549    0.0329   -0.1967 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4756    1.2184    0.5284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8178   -1.8469   -1.1690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3416   -2.1074    0.5873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9927   -1.6001    0.2246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4557    3.1020   -0.2538 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8727   -1.5288   -0.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0974   -1.1076    1.2674 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1121   -0.6744    0.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3215    0.1767   -1.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4123    1.3288    0.7888 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  6  2  2  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  4 13  1  0
  7 14  1  0
  7 15  1  0
  8 16  1  0
  8 17  1  0
  9 18  1  0
M  END
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PDB for NP0001247 (5-(2-Hydroxyethyl)-4-methylthiazole)

HEADER    PROTEIN                                 15-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-20         0                                  
HETATM    1  C   UNK     0       3.561  -0.340   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.037   1.125   0.000  0.00  0.00           C+0
HETATM    3  S   UNK     0       4.807  -1.245   0.000  0.00  0.00           S+0
HETATM    4  N   UNK     0       5.577   1.125   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       6.053  -0.340   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.132   2.371   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.097  -0.816   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.952   0.215   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.512  -0.261   0.000  0.00  0.00           O+0
CONECT    1    3    2    7                                                  
CONECT    2    1    4    6                                                  
CONECT    3    1    5                                                       
CONECT    4    2    5                                                       
CONECT    5    3    4                                                       
CONECT    6    2                                                            
CONECT    7    1    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
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3D PDB for NP0001247 (5-(2-Hydroxyethyl)-4-methylthiazole)

COMPND    HMDB0032985
HETATM    1  C1  UNL     1      -1.953  -1.508  -0.115  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.475  -0.070  -0.079  1.00  0.00           C  
HETATM    3  N1  UNL     1      -2.303   0.915  -0.207  1.00  0.00           N  
HETATM    4  C3  UNL     1      -1.877   2.165  -0.161  1.00  0.00           C  
HETATM    5  S1  UNL     1      -0.199   1.958   0.083  1.00  0.00           S  
HETATM    6  C4  UNL     1      -0.151   0.230   0.110  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.019  -0.684   0.281  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.255   0.033  -0.197  1.00  0.00           C  
HETATM    9  O1  UNL     1       2.476   1.218   0.528  1.00  0.00           O  
HETATM   10  H1  UNL     1      -1.818  -1.847  -1.169  1.00  0.00           H  
HETATM   11  H2  UNL     1      -1.342  -2.107   0.587  1.00  0.00           H  
HETATM   12  H3  UNL     1      -2.993  -1.600   0.225  1.00  0.00           H  
HETATM   13  H4  UNL     1      -2.456   3.102  -0.254  1.00  0.00           H  
HETATM   14  H5  UNL     1       0.873  -1.529  -0.455  1.00  0.00           H  
HETATM   15  H6  UNL     1       1.097  -1.108   1.267  1.00  0.00           H  
HETATM   16  H7  UNL     1       3.112  -0.674   0.055  1.00  0.00           H  
HETATM   17  H8  UNL     1       2.322   0.177  -1.288  1.00  0.00           H  
HETATM   18  H9  UNL     1       3.412   1.329   0.789  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3    6    6
CONECT    3    4    4
CONECT    4    5   13
CONECT    5    6
CONECT    6    7
CONECT    7    8   14   15
CONECT    8    9   16   17
CONECT    9   18
END
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SMILES for NP0001247 (5-(2-Hydroxyethyl)-4-methylthiazole)

CC1=C(CCO)SC=N1
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INCHI for NP0001247 (5-(2-Hydroxyethyl)-4-methylthiazole)

InChI=1S/C6H9NOS/c1-5-6(2-3-8)9-4-7-5/h4,8H,2-3H2,1H3
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View in JSmolView NMR Assignments
Synonyms
ValueSource
4-Methyl-5-(2'-hydroxyethyl)-thiazoleChEBI
4-Methyl-5-(2-hydroxyethyl)-thiazoleChEBI
4-Methyl-5-thiazolethanolChEBI
HemineurineChEBI
4-Methyl-5-(2-hydroxyethyl)thiazoleKegg
HETKegg
2-(4-Methyl-1,3-thiazol-5-yl)ethanolHMDB
2-(4-Methyl-5-thiazolyl)ethanolHMDB
2-(4-METHYL-thiazol-5-yl)-ethanolHMDB
2-(4-Methylthiazol-5-yl)ethanolHMDB
2-(4-Methylthiazole-5-yl)ethanolHMDB
4-METHYL-5-(beta-hydroxyethyl)-thiazoleHMDB
4-Methyl-5-(beta-hydroxyethyl)thiazoleHMDB
4-Methyl-5-hydroxethylthiazoleHMDB
4-Methyl-5-hydroxyethylthiazoleHMDB
4-Methyl-5-thiazoleethanolHMDB
4-Methyl-5-thiazoleethanol, 9ciHMDB
4-Methyl-5-thiazolylethanolHMDB
4-Metyl-5-(beta-hydroxyethyl)thiazoleHMDB
5-(2-Hydroxyethyl)-4-methylthiazole (sulfurol)HMDB
5-(beta-Hydroxyethyl)-4-methylthiazoleHMDB
5-(Hydroxyethyl)-4-methylthiazoleHMDB
FEMA 3204HMDB
MHTHMDB
SulfurolHMDB
Thiamine breakdown product 4-methyl-5-thiazoleethanol- fromHMDB
Thiamine thiazoleHMDB
Thiazole, 5-(2-hydroxyethyl)-4-methylHMDB
TZEHMDB
Thiamine thiazole hydrochlorideHMDB
Thiamine thiazole phosphateHMDB
4-Methyl-5-(2-thiazoleethanol)HMDB
4-Methyl-5-(β-hydroxyethyl)thiazoleHMDB
5-(Β-hydroxyethyl)-4-methylthiazoleHMDB
THZHMDB
5-(2-Hydroxyethyl)-4-methylthiazoleMeSH
Chemical FormulaC6H9NOS
Average Mass143.2070 Da
Monoisotopic Mass143.04048 Da
IUPAC Name2-(4-methyl-1,3-thiazol-5-yl)ethan-1-ol
Traditional Name4-methyl-5-thiazoleethanol
CAS Registry Number137-00-8
SMILES
CC1=C(CCO)SC=N1
InChI Identifier
InChI=1S/C6H9NOS/c1-5-6(2-3-8)9-4-7-5/h4,8H,2-3H2,1H3
InChI KeyBKAWJIRCKVUVED-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Brassica napusKNApSAcK Database
Panax ginsengLOTUS Database
Species Where Detected
Species NameSourceReference
Boletus edulisKNApSAcK Database
Escherichia coli K12KNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 4,5-disubstituted thiazoles. 4,5-Disubstituted thiazoles are compounds containing a thiazole ring substituted at positions 4 and 5 only.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassThiazoles
Direct Parent4,5-disubstituted thiazoles
Alternative Parents
Substituents
  • 4,5-disubstituted 1,3-thiazole
  • Heteroaromatic compound
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling Point135.00 °C. @ 7.00 mm HgThe Good Scents Company Information System
Water Solubility9081 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.275 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility2.26 g/LALOGPS
logP0.67ALOGPS
logP0.42ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)15.62ChemAxon
pKa (Strongest Basic)3.12ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area33.12 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity37.32 m³·mol⁻¹ChemAxon
Polarizability14.92 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0032985
DrugBank IDDB02969
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030512
KNApSAcK IDC00007610
Chemspider ID1104
KEGG Compound IDC04294
BioCyc IDTHZ
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1136
PDB IDTZE
ChEBI ID17957
Good Scents IDrw1023221
References
General References
  1. Song Z, Pan J, Xie L, Gong G, Han S, Zhang W, Hu Y: Expression, Purification, and Activity of ActhiS, a Thiazole Biosynthesis Enzyme from Acremonium chrysogenum. Biochemistry (Mosc). 2017 Jul;82(7):852-860. doi: 10.1134/S0006297917070112. [PubMed:28918750 ]
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