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Showing metabocard for 4-Butyl-gamma-butyrolactone (HMDB0035422)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:24:04 UTC
Update Date2023-02-21 17:24:48 UTC
HMDB IDHMDB0035422
Secondary Accession Numbers
  • HMDB35422
Metabolite Identification
Common Name4-Butyl-gamma-butyrolactone
Description4-Butyl-gamma-butyrolactone, also known as 4-octanolide or 5-butyldihydro-2(3H)-furanone, belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Thus, 4-butyl-gamma-butyrolactone is considered to be a fatty ester. 4-Butyl-gamma-butyrolactone is a sweet, coconut, and creamy tasting compound. 4-Butyl-gamma-butyrolactone is found, on average, in the highest concentration within pineapples (Ananas comosus) and bilberries (Vaccinium myrtillus). 4-Butyl-gamma-butyrolactone has also been detected, but not quantified in, several different foods, such as asparagus (Asparagus officinalis), tortilla chip, peaches (Prunus persica), blackberries (Rubus), and papayas (Carica papaya). This could make 4-butyl-gamma-butyrolactone a potential biomarker for the consumption of these foods. 4-Butyl-gamma-butyrolactone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 4-Butyl-gamma-butyrolactone.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0035422 (4-Butyl-gamma-butyrolactone)

  Mrv0541 02241218172D          

 10 10  0  0  0  0            999 V2000
   -0.3514    0.2160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0188   -0.2689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7639   -1.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0611   -1.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3160   -0.2689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1006   -0.0139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8034   -0.0139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4165   -0.5660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2011   -0.3110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8142   -0.8630    0.0000 C   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
  1  5  1  0  0  0  0
  5  6  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
M  END
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3D MOL for HMDB0035422 (4-Butyl-gamma-butyrolactone)

HMDB0035422
     RDKit          3D
4-Butyl-gamma-butyrolactone
 24 24  0  0  0  0  0  0  0  0999 V2000
    3.3999    0.8281    0.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0240    0.2769    0.8170 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5200   -0.4164   -0.4164 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1561   -1.0239   -0.2427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8951   -0.0006    0.1098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2188   -0.7292    0.2581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1941    0.3985   -0.0991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4580    1.0429   -1.2184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0029    1.6005   -2.2049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1163    0.9073   -0.9599 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3368    1.4287   -0.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0836   -0.0165    0.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8247    1.4289    1.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4143    1.1255    1.1403 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2067   -0.4518    1.6590 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2223   -1.2468   -0.6370 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5020    0.3190   -1.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1344   -1.4588   -1.2218 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1473   -1.8364    0.4945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7044    0.5194    1.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4009   -1.0969    1.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2958   -1.5239   -0.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1781    0.0171   -0.3833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2388    1.0740    0.7870 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
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10  5  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
M  END
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3D SDF for HMDB0035422 (4-Butyl-gamma-butyrolactone)

  Mrv0541 02241218172D          

 10 10  0  0  0  0            999 V2000
   -0.3514    0.2160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0188   -0.2689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7639   -1.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0611   -1.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3160   -0.2689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1006   -0.0139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8034   -0.0139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4165   -0.5660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2011   -0.3110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8142   -0.8630    0.0000 C   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
  1  5  1  0  0  0  0
  5  6  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035422

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC1CCC(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C8H14O2/c1-2-3-4-7-5-6-8(9)10-7/h7H,2-6H2,1H3

> <INCHI_KEY>
IPBFYZQJXZJBFQ-UHFFFAOYSA-N

> <FORMULA>
C8H14O2

> <MOLECULAR_WEIGHT>
142.1956

> <EXACT_MASS>
142.099379692

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
16.247355097445087

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-butyloxolan-2-one

> <ALOGPS_LOGP>
1.94

> <JCHEM_LOGP>
1.9777860553333335

> <ALOGPS_LOGS>
-1.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.0425524221035785

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
38.4529

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.96e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-butyloxolan-2-one

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0035422 (4-Butyl-gamma-butyrolactone)

HMDB0035422
     RDKit          3D
4-Butyl-gamma-butyrolactone
 24 24  0  0  0  0  0  0  0  0999 V2000
    3.3999    0.8281    0.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0240    0.2769    0.8170 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5200   -0.4164   -0.4164 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1561   -1.0239   -0.2427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8951   -0.0006    0.1098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2188   -0.7292    0.2581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1941    0.3985   -0.0991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4580    1.0429   -1.2184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0029    1.6005   -2.2049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1163    0.9073   -0.9599 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3368    1.4287   -0.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0836   -0.0165    0.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8247    1.4289    1.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4143    1.1255    1.1403 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2067   -0.4518    1.6590 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2223   -1.2468   -0.6370 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5020    0.3190   -1.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1344   -1.4588   -1.2218 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1473   -1.8364    0.4945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7044    0.5194    1.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4009   -1.0969    1.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2958   -1.5239   -0.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1781    0.0171   -0.3833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2388    1.0740    0.7870 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
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10  5  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
M  END
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PDB for HMDB0035422 (4-Butyl-gamma-butyrolactone)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -0.656   0.403   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.902  -0.502   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.426  -1.967   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.114  -1.967   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.590  -0.502   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.054  -0.026   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -3.366  -0.026   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.511  -1.057   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.975  -0.581   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.120  -1.611   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    1    6                                                  
CONECT    6    5                                                            
CONECT    7    2    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for HMDB0035422 (4-Butyl-gamma-butyrolactone)

COMPND    HMDB0035422
HETATM    1  C1  UNL     1       3.400   0.828   0.471  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.024   0.277   0.817  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.520  -0.416  -0.416  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.156  -1.024  -0.243  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.895  -0.001   0.110  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.219  -0.729   0.258  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.194   0.398  -0.099  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.458   1.043  -1.218  1.00  0.00           C  
HETATM    9  O1  UNL     1      -3.003   1.600  -2.205  1.00  0.00           O  
HETATM   10  O2  UNL     1      -1.116   0.907  -0.960  1.00  0.00           O  
HETATM   11  H1  UNL     1       3.337   1.429  -0.455  1.00  0.00           H  
HETATM   12  H2  UNL     1       4.084  -0.016   0.248  1.00  0.00           H  
HETATM   13  H3  UNL     1       3.825   1.429   1.297  1.00  0.00           H  
HETATM   14  H4  UNL     1       1.414   1.126   1.140  1.00  0.00           H  
HETATM   15  H5  UNL     1       2.207  -0.452   1.659  1.00  0.00           H  
HETATM   16  H6  UNL     1       2.222  -1.247  -0.637  1.00  0.00           H  
HETATM   17  H7  UNL     1       1.502   0.319  -1.232  1.00  0.00           H  
HETATM   18  H8  UNL     1      -0.134  -1.459  -1.222  1.00  0.00           H  
HETATM   19  H9  UNL     1       0.147  -1.836   0.495  1.00  0.00           H  
HETATM   20  H10 UNL     1      -0.704   0.519   1.049  1.00  0.00           H  
HETATM   21  H11 UNL     1      -2.401  -1.097   1.266  1.00  0.00           H  
HETATM   22  H12 UNL     1      -2.296  -1.524  -0.525  1.00  0.00           H  
HETATM   23  H13 UNL     1      -4.178   0.017  -0.383  1.00  0.00           H  
HETATM   24  H14 UNL     1      -3.239   1.074   0.787  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3   14   15
CONECT    3    4   16   17
CONECT    4    5   18   19
CONECT    5    6   10   20
CONECT    6    7   21   22
CONECT    7    8   23   24
CONECT    8    9    9   10
END
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SMILES for HMDB0035422 (4-Butyl-gamma-butyrolactone)

CCCCC1CCC(=O)O1
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INCHI for HMDB0035422 (4-Butyl-gamma-butyrolactone)

InChI=1S/C8H14O2/c1-2-3-4-7-5-6-8(9)10-7/h7H,2-6H2,1H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC8H14O2
Average Molecular Weight142.1956
Monoisotopic Molecular Weight142.099379692
IUPAC Name5-butyloxolan-2-one
Traditional Name5-butyloxolan-2-one
CAS Registry Number104-50-7
SMILES
CCCCC1CCC(=O)O1
InChI Identifier
InChI=1S/C8H14O2/c1-2-3-4-7-5-6-8(9)10-7/h7H,2-6H2,1H3
InChI KeyIPBFYZQJXZJBFQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassGamma butyrolactones
Direct ParentGamma butyrolactones
Alternative Parents
Substituents
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial applicationBiological role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point234.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0The Good Scents Company Information System
LogP1.432 (est)The Good Scents Company Information System
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 IDFDB014100
KNApSAcK IDNot Available
Chemspider ID7418
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7704
PDB IDNot Available
ChEBI ID145738
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1006542
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.. .