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Showing metabocard for Trimethyloxazole (HMDB0040148)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:41:35 UTC
Update Date2023-02-21 17:27:46 UTC
HMDB IDHMDB0040148
Secondary Accession Numbers
  • HMDB40148
Metabolite Identification
Common NameTrimethyloxazole
DescriptionTrimethyloxazole belongs to the class of organic compounds known as 2,4,5-trisubstituted oxazoles. 2,4,5-trisubstituted oxazoles are compounds containing an oxazole ring substituted at positions 2, 4 and 5 only. Oxazole is a five-membered aromatic heterocycle with one oxygen, one nitrogen, and three carbon atoms. Isomers include 1,2-oxazole and 1,3-oxazole. Trimethyloxazole is a mustard, nut skin, and nutty tasting compound. trimethyloxazole is found, on average, in the highest concentration in kohlrabis. Trimethyloxazole has also been detected, but not quantified, in nuts and potato.
Structure
Data?1677000466
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0040148 (Trimethyloxazole)


  Mrv1652305271900312D          

  8  8  0  0  0  0            999 V2000
    2.0198    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  4  2  0  0  0  0
  6  3  1  0  0  0  0
  7  4  1  0  0  0  0
  7  6  2  0  0  0  0
  8  5  1  0  0  0  0
  8  6  1  0  0  0  0
M  END
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3D MOL for HMDB0040148 (Trimethyloxazole)

HMDB0040148
     RDKit          3D
Trimethyloxazole
 17 17  0  0  0  0  0  0  0  0999 V2000
    3.0524   -0.4090    0.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5598   -0.2204    0.0943 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6135   -1.1745    0.0960 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6163   -0.6331    0.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9480   -1.2964   -0.0141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3886    0.7259   -0.0378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4610    1.7719   -0.1349 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9072    0.9136    0.0120 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3134   -1.1604    0.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4109   -0.7969   -0.8179 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4891    0.5834    0.3711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5545   -0.8918   -0.8664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8177   -2.3915   -0.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4391   -1.0857    0.9446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0161    1.6648   -1.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1498    1.6371    0.6999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9552    2.7630   -0.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  6  8  1  0
  8  2  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  5 12  1  0
  5 13  1  0
  5 14  1  0
  7 15  1  0
  7 16  1  0
  7 17  1  0
M  END
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3D SDF for HMDB0040148 (Trimethyloxazole)


  Mrv1652305271900312D          

  8  8  0  0  0  0            999 V2000
    2.0198    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  4  2  0  0  0  0
  6  3  1  0  0  0  0
  7  4  1  0  0  0  0
  7  6  2  0  0  0  0
  8  5  1  0  0  0  0
  8  6  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040148

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=NC(C)=C(C)O1

> <INCHI_IDENTIFIER>
InChI=1S/C6H9NO/c1-4-5(2)8-6(3)7-4/h1-3H3

> <INCHI_KEY>
ZRLDBDZSLLGDOX-UHFFFAOYSA-N

> <FORMULA>
C6H9NO

> <MOLECULAR_WEIGHT>
111.1418

> <EXACT_MASS>
111.068413915

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
12.629145129795692

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
trimethyl-1,3-oxazole

> <ALOGPS_LOGP>
1.70

> <JCHEM_LOGP>
0.36913342333333354

> <ALOGPS_LOGS>
-0.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
1.9387535064751789

> <JCHEM_POLAR_SURFACE_AREA>
26.03

> <JCHEM_REFRACTIVITY>
30.9493

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.44e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trimethyl-1,3-oxazole

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0040148 (Trimethyloxazole)

HMDB0040148
     RDKit          3D
Trimethyloxazole
 17 17  0  0  0  0  0  0  0  0999 V2000
    3.0524   -0.4090    0.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5598   -0.2204    0.0943 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6135   -1.1745    0.0960 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6163   -0.6331    0.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9480   -1.2964   -0.0141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3886    0.7259   -0.0378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4610    1.7719   -0.1349 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9072    0.9136    0.0120 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3134   -1.1604    0.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4109   -0.7969   -0.8179 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4891    0.5834    0.3711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5545   -0.8918   -0.8664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8177   -2.3915   -0.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4391   -1.0857    0.9446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0161    1.6648   -1.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1498    1.6371    0.6999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9552    2.7630   -0.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  6  8  1  0
  8  2  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  5 12  1  0
  5 13  1  0
  5 14  1  0
  7 15  1  0
  7 16  1  0
  7 17  1  0
M  END
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PDB for HMDB0040148 (Trimethyloxazole)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       3.770   1.651   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.615  -1.536   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       1.830  -0.290   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0      -0.186   1.175   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    5                                                            
CONECT    3    6                                                            
CONECT    4    1    5    7                                                  
CONECT    5    2    4    8                                                  
CONECT    6    3    7    8                                                  
CONECT    7    4    6                                                       
CONECT    8    5    6                                                       
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END
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3D PDB for HMDB0040148 (Trimethyloxazole)

COMPND    HMDB0040148
HETATM    1  C1  UNL     1       3.052  -0.409   0.171  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.560  -0.220   0.094  1.00  0.00           C  
HETATM    3  N1  UNL     1       0.614  -1.175   0.096  1.00  0.00           N  
HETATM    4  C3  UNL     1      -0.616  -0.633   0.015  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.948  -1.296  -0.014  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.389   0.726  -0.038  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.461   1.772  -0.135  1.00  0.00           C  
HETATM    8  O1  UNL     1       0.907   0.914   0.012  1.00  0.00           O  
HETATM    9  H1  UNL     1       3.313  -1.160   0.916  1.00  0.00           H  
HETATM   10  H2  UNL     1       3.411  -0.797  -0.818  1.00  0.00           H  
HETATM   11  H3  UNL     1       3.489   0.583   0.371  1.00  0.00           H  
HETATM   12  H4  UNL     1      -2.555  -0.892  -0.866  1.00  0.00           H  
HETATM   13  H5  UNL     1      -1.818  -2.392  -0.195  1.00  0.00           H  
HETATM   14  H6  UNL     1      -2.439  -1.086   0.945  1.00  0.00           H  
HETATM   15  H7  UNL     1      -2.016   1.665  -1.097  1.00  0.00           H  
HETATM   16  H8  UNL     1      -2.150   1.637   0.700  1.00  0.00           H  
HETATM   17  H9  UNL     1      -0.955   2.763  -0.157  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3    3    8
CONECT    3    4
CONECT    4    5    6    6
CONECT    5   12   13   14
CONECT    6    7    8
CONECT    7   15   16   17
END
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SMILES for HMDB0040148 (Trimethyloxazole)

CC1=NC(C)=C(C)O1
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INCHI for HMDB0040148 (Trimethyloxazole)

InChI=1S/C6H9NO/c1-4-5(2)8-6(3)7-4/h1-3H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
2,4,5-TrimethyloxazoleHMDB
Oxazole, 2,4,5-trimethylHMDB
Trimethyl-oxazoleHMDB
Chemical FormulaC6H9NO
Average Molecular Weight111.1418
Monoisotopic Molecular Weight111.068413915
IUPAC Nametrimethyl-1,3-oxazole
Traditional Nametrimethyl-1,3-oxazole
CAS Registry Number20662-84-4
SMILES
CC1=NC(C)=C(C)O1
InChI Identifier
InChI=1S/C6H9NO/c1-4-5(2)8-6(3)7-4/h1-3H3
InChI KeyZRLDBDZSLLGDOX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2,4,5-trisubstituted oxazoles. 2,4,5-Trisubstituted oxazoles are compounds containing an oxazole ring substituted at positions 2, 4 and 5 only. Oxazole is a five-membered aromatic heterocycle with one oxygen, one nitrogen, and three carbon atoms. Isomers include 1,2-oxazole and 1,3-oxazole.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassOxazoles
Direct Parent2,4,5-trisubstituted oxazoles
Alternative Parents
Substituents
  • 2,4,5-trisubstituted 1,3-oxazole
  • Heteroaromatic compound
  • Oxacycle
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Biological role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point133.00 to 134.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility2801 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.206 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility14.4 g/LALOGPS
logP1.7ALOGPS
logP0.37ChemAxon
logS-0.89ALOGPS
pKa (Strongest Basic)1.94ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.03 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity30.95 m³·mol⁻¹ChemAxon
Polarizability12.63 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+122.58131661259
DarkChem[M-H]-120.37931661259
DeepCCS[M+H]+132.14330932474
DeepCCS[M-H]-129.93530932474
DeepCCS[M-2H]-165.8630932474
DeepCCS[M+Na]+140.72530932474
AllCCS[M+H]+123.032859911
AllCCS[M+H-H2O]+118.232859911
AllCCS[M+NH4]+127.532859911
AllCCS[M+Na]+128.832859911
AllCCS[M-H]-121.632859911
AllCCS[M+Na-2H]-124.232859911
AllCCS[M+HCOO]-127.232859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.2.68 minutes32390414
Predicted by Siyang on May 30, 202212.3808 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.3 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid48.4 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1065.1 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid463.1 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid177.1 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid298.9 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid82.5 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid390.2 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid545.8 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)174.6 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid952.6 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid314.8 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1116.8 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid338.7 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid316.7 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate524.9 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA492.4 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water118.9 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TrimethyloxazoleCC1=NC(C)=C(C)O11173.5Standard polar33892256
TrimethyloxazoleCC1=NC(C)=C(C)O1819.0Standard non polar33892256
TrimethyloxazoleCC1=NC(C)=C(C)O1841.5Semi standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB019845
KNApSAcK IDNot Available
Chemspider ID28060
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound30215
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1051411
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Xi J, Huang TC, Ho CT: Characterization of volatile compounds from the reaction of 3-hydroxy-2-butanone and ammonium sulfide model system. J Agric Food Chem. 1999 Jan;47(1):245-8. [PubMed:10563879 ]
  2. Marchand S, Almy J, de Revel G: The cysteine reaction with diacetyl under wine-like conditions: proposed mechanisms for mixed origins of 2-methylthiazole, 2-methyl-3-thiazoline, 2-methylthiazolidine, and 2,4,5-trimethyloxazole. J Food Sci. 2011 Aug;76(6):C861-8. doi: 10.1111/j.1750-3841.2011.02261.x. Epub 2011 Jul 15. [PubMed:21762161 ]
  3. Marchand S, de Revel G, Bertrand A: Approaches to wine aroma: release of aroma compounds from reactions between cysteine and carbonyl compounds in wine. J Agric Food Chem. 2000 Oct;48(10):4890-5. [PubMed:11052750 ]
  4. Pripis-Nicolau L, de Revel G, Bertrand A, Maujean A: Formation of flavor components by the reaction of amino acid and carbonyl compounds in mild conditions. J Agric Food Chem. 2000 Sep;48(9):3761-6. [PubMed:10995267 ]
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