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Showing metabocard for Methyl butyrate (HMDB0033890)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 18:39:50 UTC
Update Date2023-02-21 17:23:44 UTC
HMDB IDHMDB0033890
Secondary Accession Numbers
  • HMDB33890
Metabolite Identification
Common NameMethyl butyrate
DescriptionMethyl butyrate belongs to the class of organic compounds known as organic acid methyl esters. Organic acid methyl esters are compounds containing an organic acid that is esterified with a methyl group. They have the general structure RC(=O)OR', where R= aliphatic tail or organyl group and R'=methyl group. Methyl butyrate is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.
Structure
Data?1677000224
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0033890 (Methyl butyrate)

  Mrv1652305271900212D          

  7  6  0  0  0  0            999 V2000
   -3.0250    1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3105    1.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5961    1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8816    1.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1671    1.2964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5474    1.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8816    2.5339    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
  4  7  2  0  0  0  0
M  END
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3D MOL for HMDB0033890 (Methyl butyrate)

HMDB0033890
     RDKit          3D
Methyl butyrate
 17 16  0  0  0  0  0  0  0  0999 V2000
   -2.2166    0.6893   -0.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7056   -0.6638   -0.4518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4235   -1.0318    0.2335 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6816   -0.1023   -0.0847 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5528    0.8865   -0.8474 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9263   -0.3250    0.4826 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0466    0.4992    0.2463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4646    1.4142    0.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7476    1.1229   -0.9823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9973    0.6591    0.7161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5818   -0.7587   -1.5624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4729   -1.4089   -0.1651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1241   -2.0390   -0.1675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5425   -1.1386    1.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9992   -0.0717    0.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0645    1.3052    0.9857 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0055    0.9634   -0.7636 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  2  0
  4  6  1  0
  6  7  1  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
  7 15  1  0
  7 16  1  0
  7 17  1  0
M  END
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3D SDF for HMDB0033890 (Methyl butyrate)

  Mrv1652305271900212D          

  7  6  0  0  0  0            999 V2000
   -3.0250    1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3105    1.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5961    1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8816    1.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1671    1.2964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5474    1.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8816    2.5339    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
  4  7  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033890

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCC(=O)OC

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

> <INCHI_KEY>
UUIQMZJEGPQKFD-UHFFFAOYSA-N

> <FORMULA>
C5H10O2

> <MOLECULAR_WEIGHT>
102.1317

> <EXACT_MASS>
102.068079564

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
11.328013593526935

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl butanoate

> <ALOGPS_LOGP>
1.22

> <JCHEM_LOGP>
1.0676528536666665

> <ALOGPS_LOGS>
-0.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.023872450206271

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
26.640700000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.82e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl butyrate

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0033890 (Methyl butyrate)

HMDB0033890
     RDKit          3D
Methyl butyrate
 17 16  0  0  0  0  0  0  0  0999 V2000
   -2.2166    0.6893   -0.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7056   -0.6638   -0.4518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4235   -1.0318    0.2335 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6816   -0.1023   -0.0847 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5528    0.8865   -0.8474 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9263   -0.3250    0.4826 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0466    0.4992    0.2463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4646    1.4142    0.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7476    1.1229   -0.9823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9973    0.6591    0.7161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5818   -0.7587   -1.5624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4729   -1.4089   -0.1651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1241   -2.0390   -0.1675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5425   -1.1386    1.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9992   -0.0717    0.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0645    1.3052    0.9857 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0055    0.9634   -0.7636 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  2  0
  4  6  1  0
  6  7  1  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
  7 15  1  0
  7 16  1  0
  7 17  1  0
M  END
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PDB for HMDB0033890 (Methyl butyrate)

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      -5.647   2.420   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.313   3.190   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.979   2.420   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.646   3.190   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.312   2.420   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.022   3.190   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.646   4.730   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    4                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for HMDB0033890 (Methyl butyrate)

COMPND    HMDB0033890
HETATM    1  C1  UNL     1      -2.217   0.689  -0.098  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.706  -0.664  -0.452  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.423  -1.032   0.233  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.682  -0.102  -0.085  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.553   0.887  -0.847  1.00  0.00           O  
HETATM    6  O2  UNL     1       1.926  -0.325   0.483  1.00  0.00           O  
HETATM    7  C5  UNL     1       3.047   0.499   0.246  1.00  0.00           C  
HETATM    8  H1  UNL     1      -1.465   1.414   0.209  1.00  0.00           H  
HETATM    9  H2  UNL     1      -2.748   1.123  -0.982  1.00  0.00           H  
HETATM   10  H3  UNL     1      -2.997   0.659   0.716  1.00  0.00           H  
HETATM   11  H4  UNL     1      -1.582  -0.759  -1.562  1.00  0.00           H  
HETATM   12  H5  UNL     1      -2.473  -1.409  -0.165  1.00  0.00           H  
HETATM   13  H6  UNL     1      -0.124  -2.039  -0.167  1.00  0.00           H  
HETATM   14  H7  UNL     1      -0.542  -1.139   1.309  1.00  0.00           H  
HETATM   15  H8  UNL     1       3.999  -0.072   0.293  1.00  0.00           H  
HETATM   16  H9  UNL     1       3.064   1.305   0.986  1.00  0.00           H  
HETATM   17  H10 UNL     1       3.006   0.963  -0.764  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3   11   12
CONECT    3    4   13   14
CONECT    4    5    5    6
CONECT    6    7
CONECT    7   15   16   17
END
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SMILES for HMDB0033890 (Methyl butyrate)

CCCC(=O)OC
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INCHI for HMDB0033890 (Methyl butyrate)

InChI=1S/C5H10O2/c1-3-4-5(6)7-2/h3-4H2,1-2H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
Methyl butyric acidGenerator
Butanoic acid, methyl esterHMDB
Butyric acid, methyl esterHMDB
Methyl butanoateHMDB
Methyl ester OF butanoic acidHMDB
Methyl N-butanoateHMDB
Methyl N-butyrateHMDB
N-Butyric acid methyl esterHMDB
Methyl butanoic acidGenerator
Chemical FormulaC5H10O2
Average Molecular Weight102.1317
Monoisotopic Molecular Weight102.068079564
IUPAC Namemethyl butanoate
Traditional Namemethyl butyrate
CAS Registry Number623-42-7
SMILES
CCCC(=O)OC
InChI Identifier
InChI=1S/C5H10O2/c1-3-4-5(6)7-2/h3-4H2,1-2H3
InChI KeyUUIQMZJEGPQKFD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty acid methyl esters. Fatty acid methyl esters are compounds containing a fatty acid that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=fatty aliphatic tail or organyl group and R'=methyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentFatty acid methyl esters
Alternative Parents
Substituents
  • Fatty acid methyl ester
  • Methyl ester
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • 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
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-95 °CNot Available
Boiling Point102.00 to 103.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility15 mg/mL at 25 °CNot Available
LogP1.29Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
Abnormal Concentrations
Associated Disorders and Diseases
Disease References
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
  2. Walton C, Fowler DP, Turner C, Jia W, Whitehead RN, Griffiths L, Dawson C, Waring RH, Ramsden DB, Cole JA, Cauchi M, Bessant C, Hunter JO: Analysis of volatile organic compounds of bacterial origin in chronic gastrointestinal diseases. Inflamm Bowel Dis. 2013 Sep;19(10):2069-78. doi: 10.1097/MIB.0b013e31829a91f6. [PubMed:23867873 ]
  3. 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 ]
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 ]
Diarrhoea predominant irritable bowel syndrome
  1. Ahmed I, Greenwood R, Costello Bde L, Ratcliffe NM, Probert CS: An investigation of fecal volatile organic metabolites in irritable bowel syndrome. PLoS One. 2013;8(3):e58204. doi: 10.1371/journal.pone.0058204. Epub 2013 Mar 13. [PubMed:23516449 ]
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 ]
Crohn's disease
  1. Walton C, Fowler DP, Turner C, Jia W, Whitehead RN, Griffiths L, Dawson C, Waring RH, Ramsden DB, Cole JA, Cauchi M, Bessant C, Hunter JO: Analysis of volatile organic compounds of bacterial origin in chronic gastrointestinal diseases. Inflamm Bowel Dis. 2013 Sep;19(10):2069-78. doi: 10.1097/MIB.0b013e31829a91f6. [PubMed:23867873 ]
  2. 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 ]
Irritable bowel syndrome
  1. Walton C, Fowler DP, Turner C, Jia W, Whitehead RN, Griffiths L, Dawson C, Waring RH, Ramsden DB, Cole JA, Cauchi M, Bessant C, Hunter JO: Analysis of volatile organic compounds of bacterial origin in chronic gastrointestinal diseases. Inflamm Bowel Dis. 2013 Sep;19(10):2069-78. doi: 10.1097/MIB.0b013e31829a91f6. [PubMed:23867873 ]
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 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012084
KNApSAcK IDC00050481
Chemspider ID11680
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethyl butyrate
METLIN IDNot Available
PubChem Compound12180
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00029891
Good Scents IDrw1008721
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.