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Showing metabocard for Methyl acetate (HMDB0031523)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:43:49 UTC
Update Date2023-02-21 17:20:45 UTC
HMDB IDHMDB0031523
Secondary Accession Numbers
  • HMDB31523
Metabolite Identification
Common NameMethyl acetate
DescriptionMethyl acetate belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group). Methyl acetate is present in apple, grape, banana and other fruits. Methyl acetate is a flavouring ingredient and it is an ester that, in the laboratory, is synthesized from acetic acid and methanol in the presence of strong acids such as sulfuric acid in an esterification reaction. In the presence of strong bases such as sodium hydroxide or strong acids such as hydrochloric acid or sulfuric acid it is hydrolyzed back into methanol and acetic acid, especially at elevated temperature. Methyl acetate, also known as acetic acid methyl ester or methyl ethanoate, is a clear, flammable liquid with a characteristic, not unpleasant smell like certain glues or nail polish removers. Methyl acetate has characteristics very similar to its analog ethyl acetate. Methyl acetate is used as a solvent in glues, paints, and nail polish removers, in chemical reactions, and for extractions. Methyl acetate is a non-polar (lipophilic) to weakly polar (hydrophilic) aprotic solvent. Methyl acetate has a solubility of 25% in water at room temperature. At elevated temperature its solubility in water is much higher. Methyl acetate is not stable in the presence of strong aqueous bases or acids. The conversion of methyl acetate back into its components, by an acid, is a first-order reaction with respect to the ester. The reaction of methyl acetate and a base, for example sodium hydroxide, is a second-order reaction with respect to both reactants
Structure
Data?1677000045
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0031523 (Methyl acetate)

  Mrv1652303202019002D          

  5  4  0  0  0  0            999 V2000
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  3  2  0  0  0  0
  5  2  1  0  0  0  0
  5  3  1  0  0  0  0
M  END
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3D MOL for HMDB0031523 (Methyl acetate)

HMDB0031523
     RDKit          3D
Methyl acetate
 11 10  0  0  0  0  0  0  0  0999 V2000
    1.8789    0.1052    0.1296 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5378    0.2681    0.5263 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4772   -0.1667   -0.3082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8791    0.0052    0.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1495   -0.6941   -1.3968 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2013    0.9788   -0.4892 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5039    0.1590    1.0580 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0853   -0.8615   -0.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6045   -0.3477   -0.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0129    1.1070    0.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0841   -0.5532    1.0534 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  4  9  1  0
  4 10  1  0
  4 11  1  0
M  END
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3D SDF for HMDB0031523 (Methyl acetate)

  Mrv1652303202019002D          

  5  4  0  0  0  0            999 V2000
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  3  2  0  0  0  0
  5  2  1  0  0  0  0
  5  3  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031523

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C3H6O2/c1-3(4)5-2/h1-2H3

> <INCHI_KEY>
KXKVLQRXCPHEJC-UHFFFAOYSA-N

> <FORMULA>
C3H6O2

> <MOLECULAR_WEIGHT>
74.0785

> <EXACT_MASS>
74.036779436

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
7.361112535353955

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl acetate

> <ALOGPS_LOGP>
0.18

> <JCHEM_LOGP>
-0.07745165833333349

> <ALOGPS_LOGS>
0.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.985074750252889

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
17.4128

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.59e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl acetate

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0031523 (Methyl acetate)

HMDB0031523
     RDKit          3D
Methyl acetate
 11 10  0  0  0  0  0  0  0  0999 V2000
    1.8789    0.1052    0.1296 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5378    0.2681    0.5263 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4772   -0.1667   -0.3082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8791    0.0052    0.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1495   -0.6941   -1.3968 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2013    0.9788   -0.4892 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5039    0.1590    1.0580 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0853   -0.8615   -0.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6045   -0.3477   -0.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0129    1.1070    0.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0841   -0.5532    1.0534 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  4  9  1  0
  4 10  1  0
  4 11  1  0
M  END
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PDB for HMDB0031523 (Methyl acetate)

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    5                                                            
CONECT    3    1    4    5                                                  
CONECT    4    3                                                            
CONECT    5    2    3                                                       
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
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3D PDB for HMDB0031523 (Methyl acetate)

COMPND    HMDB0031523
HETATM    1  C1  UNL     1       1.879   0.105   0.130  1.00  0.00           C  
HETATM    2  O1  UNL     1       0.538   0.268   0.526  1.00  0.00           O  
HETATM    3  C2  UNL     1      -0.477  -0.167  -0.308  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.879   0.005   0.110  1.00  0.00           C  
HETATM    5  O2  UNL     1      -0.149  -0.694  -1.397  1.00  0.00           O  
HETATM    6  H1  UNL     1       2.201   0.979  -0.489  1.00  0.00           H  
HETATM    7  H2  UNL     1       2.504   0.159   1.058  1.00  0.00           H  
HETATM    8  H3  UNL     1       2.085  -0.862  -0.357  1.00  0.00           H  
HETATM    9  H4  UNL     1      -2.604  -0.348  -0.649  1.00  0.00           H  
HETATM   10  H5  UNL     1      -2.013   1.107   0.323  1.00  0.00           H  
HETATM   11  H6  UNL     1      -2.084  -0.553   1.053  1.00  0.00           H  
CONECT    1    2    6    7    8
CONECT    2    3
CONECT    3    4    5    5
CONECT    4    9   10   11
END
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SMILES for HMDB0031523 (Methyl acetate)

COC(C)=O
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INCHI for HMDB0031523 (Methyl acetate)

InChI=1S/C3H6O2/c1-3(4)5-2/h1-2H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC3H6O2
Average Molecular Weight74.0785
Monoisotopic Molecular Weight74.036779436
IUPAC Namemethyl acetate
Traditional Namemethyl acetate
CAS Registry Number79-20-9
SMILES
COC(C)=O
InChI Identifier
InChI=1S/C3H6O2/c1-3(4)5-2/h1-2H3
InChI KeyKXKVLQRXCPHEJC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methyl esters. These are organic compounds containing a carboxyl group that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=H or organyl group and R'=methyl group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acid derivatives
Direct ParentMethyl esters
Alternative Parents
Substituents
  • Methyl ester
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial applicationBiological role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-98.7 °CNot Available
Boiling Point535.70 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility243 mg/mL at 20 °CNot Available
LogP0.18Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
Abnormal Concentrations
Associated Disorders and Diseases
Disease References
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Autism
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Pervasive developmental disorder not otherwise specified
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Crohn's disease
  1. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Ulcerative colitis
  1. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008125
KNApSAcK IDC00048479
Chemspider ID6335
KEGG Compound IDC17530
BioCyc IDMETHYL-ACETATE
BiGG IDNot Available
Wikipedia LinkMethyl_acetate
METLIN IDNot Available
PubChem Compound6584
PDB IDNot Available
ChEBI ID77700
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1502751
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References