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Showing metabocard for Propyl acetate (HMDB0034237)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 19:02:28 UTC
Update Date2023-02-21 17:24:04 UTC
HMDB IDHMDB0034237
Secondary Accession Numbers
  • HMDB34237
Metabolite Identification
Common NamePropyl acetate
DescriptionPropyl acetate, also known as 1-acetoxypropane or propyl ethanoate, 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). It is formed by the esterification of acetic acid and 1-propanol (known as a condensation reaction), often via Fischer–Speier esterification, with sulfuric acid as a catalyst and water produced as a byproduct. This clear, colorless liquid is known by its characteristic odor of pears. Propyl acetate is a drug. Propyl acetate is a bitter, celery, and fruity tasting compound. It has been detected, but not quantified, in several different foods, such as muskmelons, figs, apples, pineapples, and cocoa beans. Due to this fact, it is commonly used in fragrances and as a flavor additive. Propyl acetate has been found to be associated with the diseases such as nonalcoholic fatty liver disease; also propyl acetate has been linked to the inborn metabolic disorders including celiac disease.
Structure
Data?1677000244
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0034237 (Propyl acetate)

  Mrv1652303202019022D          

  7  6  0  0  0  0            999 V2000
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    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  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
M  END
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3D MOL for HMDB0034237 (Propyl acetate)

HMDB0034237
     RDKit          3D
Propyl acetate
 17 16  0  0  0  0  0  0  0  0999 V2000
   -2.7388   -0.0336   -0.2253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2953   -0.3038    0.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4743    0.9210   -0.1927 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8846    0.7581    0.1176 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7139   -0.2086   -0.4156 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1514   -0.3343   -0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2149   -1.0109   -1.2479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1274   -0.7789   -0.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3835   -0.1243    0.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8602    0.9964   -0.6085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9682   -1.1890   -0.4363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1874   -0.5862    1.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8587    1.7700    0.4043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6576    1.1576   -1.2483 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3044   -0.9213    0.8670 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6680   -0.7888   -0.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6143    0.6768    0.1119 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
  4  5  1  0
  5  6  1  0
  5  7  2  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  2 12  1  0
  3 13  1  0
  3 14  1  0
  6 15  1  0
  6 16  1  0
  6 17  1  0
M  END
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3D SDF for HMDB0034237 (Propyl acetate)

  Mrv1652303202019022D          

  7  6  0  0  0  0            999 V2000
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    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  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034237

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCOC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H10O2/c1-3-4-7-5(2)6/h3-4H2,1-2H3

> <INCHI_KEY>
YKYONYBAUNKHLG-UHFFFAOYSA-N

> <FORMULA>
C5H10O2

> <MOLECULAR_WEIGHT>
102.1317

> <EXACT_MASS>
102.068079564

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
11.394024553590322

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
propyl acetate

> <ALOGPS_LOGP>
1.28

> <JCHEM_LOGP>
0.8018786913333336

> <ALOGPS_LOGS>
-0.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.993792003476465

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
26.6854

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.82e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
propyl acetate

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0034237 (Propyl acetate)

HMDB0034237
     RDKit          3D
Propyl acetate
 17 16  0  0  0  0  0  0  0  0999 V2000
   -2.7388   -0.0336   -0.2253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2953   -0.3038    0.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4743    0.9210   -0.1927 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8846    0.7581    0.1176 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7139   -0.2086   -0.4156 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1514   -0.3343   -0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2149   -1.0109   -1.2479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1274   -0.7789   -0.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3835   -0.1243    0.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8602    0.9964   -0.6085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9682   -1.1890   -0.4363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1874   -0.5862    1.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8587    1.7700    0.4043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6576    1.1576   -1.2483 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3044   -0.9213    0.8670 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6680   -0.7888   -0.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6143    0.6768    0.1119 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
  4  5  1  0
  5  6  1  0
  5  7  2  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  2 12  1  0
  3 13  1  0
  3 14  1  0
  6 15  1  0
  6 16  1  0
  6 17  1  0
M  END
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PDB for HMDB0034237 (Propyl 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      -0.357   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.644   2.104   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.311   2.104   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.977  -0.206   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for HMDB0034237 (Propyl acetate)

COMPND    HMDB0034237
HETATM    1  C1  UNL     1      -2.739  -0.034  -0.225  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.295  -0.304   0.142  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.474   0.921  -0.193  1.00  0.00           C  
HETATM    4  O1  UNL     1       0.885   0.758   0.118  1.00  0.00           O  
HETATM    5  C4  UNL     1       1.714  -0.209  -0.416  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.151  -0.334  -0.048  1.00  0.00           C  
HETATM    7  O2  UNL     1       1.215  -1.011  -1.248  1.00  0.00           O  
HETATM    8  H1  UNL     1      -3.127  -0.779  -0.954  1.00  0.00           H  
HETATM    9  H2  UNL     1      -3.383  -0.124   0.685  1.00  0.00           H  
HETATM   10  H3  UNL     1      -2.860   0.996  -0.608  1.00  0.00           H  
HETATM   11  H4  UNL     1      -0.968  -1.189  -0.436  1.00  0.00           H  
HETATM   12  H5  UNL     1      -1.187  -0.586   1.226  1.00  0.00           H  
HETATM   13  H6  UNL     1      -0.859   1.770   0.404  1.00  0.00           H  
HETATM   14  H7  UNL     1      -0.658   1.158  -1.248  1.00  0.00           H  
HETATM   15  H8  UNL     1       3.304  -0.921   0.867  1.00  0.00           H  
HETATM   16  H9  UNL     1       3.668  -0.789  -0.916  1.00  0.00           H  
HETATM   17  H10 UNL     1       3.614   0.677   0.112  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3   11   12
CONECT    3    4   13   14
CONECT    4    5
CONECT    5    6    7    7
CONECT    6   15   16   17
END
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SMILES for HMDB0034237 (Propyl acetate)

CCCOC(C)=O
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INCHI for HMDB0034237 (Propyl acetate)

InChI=1S/C5H10O2/c1-3-4-7-5(2)6/h3-4H2,1-2H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
1-AcetoxypropaneChEBI
N-Propyl acetateChEBI
Propyl ethanoateChEBI
N-Propyl acetic acidGenerator
Propyl ethanoic acidGenerator
Propyl acetic acidGenerator
1-Propyl acetateMeSH
Propyl acetate, ion (1-)MeSH
Acetic acid N-propyl esterHMDB
Acetic acid, N-propyl esterHMDB
Acetic acid, propyl esterHMDB
Acetic acid,propyl esterHMDB
N-Propyl ethanoateHMDB
Chemical FormulaC5H10O2
Average Molecular Weight102.1317
Monoisotopic Molecular Weight102.068079564
IUPAC Namepropyl acetate
Traditional Namepropyl acetate
CAS Registry Number109-60-4
SMILES
CCCOC(C)=O
InChI Identifier
InChI=1S/C5H10O2/c1-3-4-7-5(2)6/h3-4H2,1-2H3
InChI KeyYKYONYBAUNKHLG-UHFFFAOYSA-N
Chemical Taxonomy
Description 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).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acid derivatives
Direct ParentCarboxylic acid esters
Alternative Parents
Substituents
  • Carboxylic acid 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-93 °CNot Available
Boiling Point101.00 to 102.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility18.9 mg/mL at 20 °CNot Available
LogP1.24Not 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
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected and Quantified0-31201.543 nmol/g wet fecesChildren (1-13 years old)Not Specified
Treated celiac disease		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) non progressor details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) progressor details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Nonalcoholic fatty liver disease		 details
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 ]
Celiac disease
  1. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
Associated OMIM IDs
DrugBank IDDB01670
Phenol Explorer Compound IDNot Available
FooDB IDFDB012549
KNApSAcK IDC00035729
Chemspider ID7706
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPropyl_acetate
METLIN IDNot Available
PubChem Compound7997
PDB IDNot Available
ChEBI ID40116
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1033971
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .