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Showing metabocard for Methyl phenylacetate (HMDB0032617)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:50:48 UTC
Update Date2023-02-21 17:22:30 UTC
HMDB IDHMDB0032617
Secondary Accession Numbers
  • HMDB32617
Metabolite Identification
Common NameMethyl phenylacetate
DescriptionMethyl phenylacetate, also known as fema 2733 or mephaneine, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Methyl phenylacetate is a sweet, almond, and floral tasting compound. Methyl phenylacetate is found, on average, in the highest concentration within corns. Methyl phenylacetate has also been detected, but not quantified, in several different foods, such as cocoa and cocoa products, coffee and coffee products, fruits, and pepper (c. frutescens). This could make methyl phenylacetate a potential biomarker for the consumption of these foods. Methyl phenylacetate has a strong odor similar to honey. It is a colorless liquid that is only slightly soluble in water, but soluble in most organic solvents. It is used in the flavor industry and in perfumes to impart honey scents. This compound also occurs in brandy, capsicum, coffee, honey, pepper, and some wine. Methyl phenyldiazoacetate, precursor to cyclopropanation agents, is prepared by treating methyl phenylacetate with p-acetamidobenzenesulfonyl azide in the presence of base. Methyl phenylacetate is an organic compound that is the methyl ester of phenylacetic acid, with the structural formula C6H5CH2COOCH3.
Structure
Data?1677000150
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0032617 (Methyl phenylacetate)

  Mrv1652305271900212D          

 11 11  0  0  0  0            999 V2000
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  8  5  2  0  0  0  0
  8  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  7  1  0  0  0  0
 10  9  2  0  0  0  0
 11  1  1  0  0  0  0
 11  9  1  0  0  0  0
M  END
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3D MOL for HMDB0032617 (Methyl phenylacetate)

HMDB0032617
     RDKit          3D
Methyl phenylacetate
 21 21  0  0  0  0  0  0  0  0999 V2000
   -3.5936    0.8167   -0.1408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5303    0.3409    0.6904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6994   -0.6594    0.2196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9266   -1.1196   -0.9304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5612   -1.1512    1.0845 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7146   -0.5673    0.5683 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8617    0.8299    0.5977 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0028    1.4465    0.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1002    0.7001   -0.3211 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9432   -0.6687   -0.3442 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7591   -1.3017    0.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9172    0.0371   -0.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4019    1.2716    0.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1706    1.6795   -0.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4703   -2.2579    1.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6916   -0.8258    2.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0273    1.4136    0.9746 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1121    2.5176    0.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9879    1.2129   -0.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7641   -1.3136   -0.7096 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6898   -2.4014    0.0603 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
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  5 15  1  0
  5 16  1  0
  7 17  1  0
  8 18  1  0
  9 19  1  0
 10 20  1  0
 11 21  1  0
M  END
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3D SDF for HMDB0032617 (Methyl phenylacetate)

  Mrv1652305271900212D          

 11 11  0  0  0  0            999 V2000
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  8  5  2  0  0  0  0
  8  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  7  1  0  0  0  0
 10  9  2  0  0  0  0
 11  1  1  0  0  0  0
 11  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032617

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)CC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O2/c1-11-9(10)7-8-5-3-2-4-6-8/h2-6H,7H2,1H3

> <INCHI_KEY>
CRZQGDNQQAALAY-UHFFFAOYSA-N

> <FORMULA>
C9H10O2

> <MOLECULAR_WEIGHT>
150.1745

> <EXACT_MASS>
150.068079564

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
15.997119171937396

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-phenylacetate

> <ALOGPS_LOGP>
2.03

> <JCHEM_LOGP>
1.756888161333333

> <ALOGPS_LOGS>
-2.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.077444074849475

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
42.1347

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.04e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl phenylacetate

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0032617 (Methyl phenylacetate)

HMDB0032617
     RDKit          3D
Methyl phenylacetate
 21 21  0  0  0  0  0  0  0  0999 V2000
   -3.5936    0.8167   -0.1408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5303    0.3409    0.6904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6994   -0.6594    0.2196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9266   -1.1196   -0.9304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5612   -1.1512    1.0845 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7146   -0.5673    0.5683 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8617    0.8299    0.5977 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0028    1.4465    0.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1002    0.7001   -0.3211 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9432   -0.6687   -0.3442 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7591   -1.3017    0.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9172    0.0371   -0.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4019    1.2716    0.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1706    1.6795   -0.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4703   -2.2579    1.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6916   -0.8258    2.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0273    1.4136    0.9746 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1121    2.5176    0.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9879    1.2129   -0.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7641   -1.3136   -0.7096 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6898   -2.4014    0.0603 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
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  5 15  1  0
  5 16  1  0
  7 17  1  0
  8 18  1  0
  9 19  1  0
 10 20  1  0
 11 21  1  0
M  END
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PDB for HMDB0032617 (Methyl phenylacetate)

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      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    8                                                       
CONECT    6    4    8                                                       
CONECT    7    8    9                                                       
CONECT    8    5    6    7                                                  
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    1    9                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0032617 (Methyl phenylacetate)

COMPND    HMDB0032617
HETATM    1  C1  UNL     1      -3.594   0.817  -0.141  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.530   0.341   0.690  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.699  -0.659   0.220  1.00  0.00           C  
HETATM    4  O2  UNL     1      -1.927  -1.120  -0.930  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.561  -1.151   1.085  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.715  -0.567   0.568  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.862   0.830   0.598  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.003   1.447   0.176  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.100   0.700  -0.321  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.943  -0.669  -0.344  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.759  -1.302   0.099  1.00  0.00           C  
HETATM   12  H1  UNL     1      -3.917   0.037  -0.845  1.00  0.00           H  
HETATM   13  H2  UNL     1      -4.402   1.272   0.460  1.00  0.00           H  
HETATM   14  H3  UNL     1      -3.171   1.680  -0.733  1.00  0.00           H  
HETATM   15  H4  UNL     1      -0.470  -2.258   1.055  1.00  0.00           H  
HETATM   16  H5  UNL     1      -0.692  -0.826   2.102  1.00  0.00           H  
HETATM   17  H6  UNL     1       0.027   1.414   0.975  1.00  0.00           H  
HETATM   18  H7  UNL     1       2.112   2.518   0.195  1.00  0.00           H  
HETATM   19  H8  UNL     1       3.988   1.213  -0.650  1.00  0.00           H  
HETATM   20  H9  UNL     1       3.764  -1.314  -0.710  1.00  0.00           H  
HETATM   21  H10 UNL     1       1.690  -2.401   0.060  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6   15   16
CONECT    6    7    7   11
CONECT    7    8   17
CONECT    8    9    9   18
CONECT    9   10   19
CONECT   10   11   11   20
CONECT   11   21
END
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SMILES for HMDB0032617 (Methyl phenylacetate)

COC(=O)CC1=CC=CC=C1
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INCHI for HMDB0032617 (Methyl phenylacetate)

InChI=1S/C9H10O2/c1-11-9(10)7-8-5-3-2-4-6-8/h2-6H,7H2,1H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
Methyl phenylacetic acidGenerator
FEMA 2733HMDB
MephaneineHMDB
Methyl alpha-toluateHMDB
Methyl ester OF phenylacetic acidHMDB
Methyl 2-phenylacetic acidGenerator
Methyl phenylacetateMeSH
Chemical FormulaC9H10O2
Average Molecular Weight150.1745
Monoisotopic Molecular Weight150.068079564
IUPAC Namemethyl 2-phenylacetate
Traditional Namemethyl phenylacetate
CAS Registry Number101-41-7
SMILES
COC(=O)CC1=CC=CC=C1
InChI Identifier
InChI=1S/C9H10O2/c1-11-9(10)7-8-5-3-2-4-6-8/h2-6H,7H2,1H3
InChI KeyCRZQGDNQQAALAY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • Methyl ester
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial application
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point215.00 to 217.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility2072 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.83Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
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 IDFDB010559
KNApSAcK IDC00051576
Chemspider ID7278
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethyl phenylacetate
METLIN IDNot Available
PubChem Compound7559
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1008431
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .