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Showing metabocard for Butyl acetoacetate (HMDB0040447)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:59:20 UTC
Update Date2023-02-21 17:28:17 UTC
HMDB IDHMDB0040447
Secondary Accession Numbers
  • HMDB40447
Metabolite Identification
Common NameButyl acetoacetate
DescriptionButyl acetoacetate belongs to the class of organic compounds known as beta-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C3 carbon atom. Butyl acetoacetate is a sweet, brandy, and fermented tasting compound. Based on a literature review very few articles have been published on Butyl acetoacetate.
Structure
Data?1677000497
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0040447 (Butyl acetoacetate)

  Mrv0541 05061311502D          

 11 10  0  0  0  0            999 V2000
   -6.1579    0.1964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4435   -0.2161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4435   -1.0411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7290    0.1964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0145   -0.2161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0145   -1.0411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3001    0.1964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5856   -0.2161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8711    0.1964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1567   -0.2161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4422    0.1964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  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
 10 11  1  0  0  0  0
M  END
Download

3D MOL for HMDB0040447 (Butyl acetoacetate)

HMDB0040447
     RDKit          3D
Butyl acetoacetate
 25 24  0  0  0  0  0  0  0  0999 V2000
    3.3606    1.4742   -0.6604 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5422    0.6443    0.3113 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1584   -0.6404   -0.4238 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3286   -1.5364    0.4652 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1356   -0.9733    0.9044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8786   -0.5144    0.0911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7254   -0.5973   -1.1359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1261    0.0658    0.7076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0722    0.5105   -0.3334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4848   -0.0182   -0.2975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7527    1.2824   -1.2165 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0517    2.1548   -0.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6675    2.0184   -1.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9224    0.7517   -1.3033 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1335    0.3919    1.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6025    1.1818    0.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6819   -0.3766   -1.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1084   -1.1536   -0.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9527   -1.7601    1.3689 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1977   -2.5307   -0.0360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5458   -0.7254    1.3514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8338    0.9448    1.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1730    0.5639   -0.9065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3809   -1.0836   -0.6755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8706   -0.0747    0.7451 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  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  2 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  8 21  1  0
  8 22  1  0
 10 23  1  0
 10 24  1  0
 10 25  1  0
M  END
Download

3D SDF for HMDB0040447 (Butyl acetoacetate)

  Mrv0541 05061311502D          

 11 10  0  0  0  0            999 V2000
   -6.1579    0.1964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4435   -0.2161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4435   -1.0411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7290    0.1964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0145   -0.2161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0145   -1.0411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3001    0.1964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5856   -0.2161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8711    0.1964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1567   -0.2161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4422    0.1964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  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
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040447

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCOC(=O)CC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H14O3/c1-3-4-5-11-8(10)6-7(2)9/h3-6H2,1-2H3

> <INCHI_KEY>
REIYHFWZISXFKU-UHFFFAOYSA-N

> <FORMULA>
C8H14O3

> <MOLECULAR_WEIGHT>
158.195

> <EXACT_MASS>
158.094294314

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
17.254911422796607

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
butyl 3-oxobutanoate

> <ALOGPS_LOGP>
1.12

> <JCHEM_LOGP>
1.4683013249999997

> <ALOGPS_LOGS>
-1.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.930989574027725

> <JCHEM_PKA_STRONGEST_BASIC>
-6.960046624046866

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
41.1816

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.88e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
butyl 3-oxobutanoate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0040447 (Butyl acetoacetate)

HMDB0040447
     RDKit          3D
Butyl acetoacetate
 25 24  0  0  0  0  0  0  0  0999 V2000
    3.3606    1.4742   -0.6604 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5422    0.6443    0.3113 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1584   -0.6404   -0.4238 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3286   -1.5364    0.4652 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1356   -0.9733    0.9044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8786   -0.5144    0.0911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7254   -0.5973   -1.1359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1261    0.0658    0.7076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0722    0.5105   -0.3334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4848   -0.0182   -0.2975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7527    1.2824   -1.2165 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0517    2.1548   -0.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6675    2.0184   -1.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9224    0.7517   -1.3033 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1335    0.3919    1.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6025    1.1818    0.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6819   -0.3766   -1.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1084   -1.1536   -0.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9527   -1.7601    1.3689 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1977   -2.5307   -0.0360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5458   -0.7254    1.3514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8338    0.9448    1.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1730    0.5639   -0.9065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3809   -1.0836   -0.6755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8706   -0.0747    0.7451 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  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  2 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  8 21  1  0
  8 22  1  0
 10 23  1  0
 10 24  1  0
 10 25  1  0
M  END
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PDB for HMDB0040447 (Butyl acetoacetate)

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0     -11.495   0.367   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -10.161  -0.403   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0     -10.161  -1.943   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -8.827   0.367   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.494  -0.403   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -7.494  -1.943   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -6.160   0.367   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -4.826  -0.403   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.493   0.367   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.159  -0.403   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.825   0.367   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END
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3D PDB for HMDB0040447 (Butyl acetoacetate)

COMPND    HMDB0040447
HETATM    1  C1  UNL     1       3.361   1.474  -0.660  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.542   0.644   0.311  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.158  -0.640  -0.424  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.329  -1.536   0.465  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.136  -0.973   0.904  1.00  0.00           O  
HETATM    6  C5  UNL     1      -0.879  -0.514   0.091  1.00  0.00           C  
HETATM    7  O2  UNL     1      -0.725  -0.597  -1.136  1.00  0.00           O  
HETATM    8  C6  UNL     1      -2.126   0.066   0.708  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.072   0.510  -0.333  1.00  0.00           C  
HETATM   10  C8  UNL     1      -4.485  -0.018  -0.297  1.00  0.00           C  
HETATM   11  O3  UNL     1      -2.753   1.282  -1.217  1.00  0.00           O  
HETATM   12  H1  UNL     1       4.052   2.155  -0.091  1.00  0.00           H  
HETATM   13  H2  UNL     1       2.668   2.018  -1.317  1.00  0.00           H  
HETATM   14  H3  UNL     1       3.922   0.752  -1.303  1.00  0.00           H  
HETATM   15  H4  UNL     1       3.133   0.392   1.186  1.00  0.00           H  
HETATM   16  H5  UNL     1       1.603   1.182   0.541  1.00  0.00           H  
HETATM   17  H6  UNL     1       1.682  -0.377  -1.374  1.00  0.00           H  
HETATM   18  H7  UNL     1       3.108  -1.154  -0.683  1.00  0.00           H  
HETATM   19  H8  UNL     1       1.953  -1.760   1.369  1.00  0.00           H  
HETATM   20  H9  UNL     1       1.198  -2.531  -0.036  1.00  0.00           H  
HETATM   21  H10 UNL     1      -2.546  -0.725   1.351  1.00  0.00           H  
HETATM   22  H11 UNL     1      -1.834   0.945   1.353  1.00  0.00           H  
HETATM   23  H12 UNL     1      -5.173   0.564  -0.906  1.00  0.00           H  
HETATM   24  H13 UNL     1      -4.381  -1.084  -0.675  1.00  0.00           H  
HETATM   25  H14 UNL     1      -4.871  -0.075   0.745  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3   15   16
CONECT    3    4   17   18
CONECT    4    5   19   20
CONECT    5    6
CONECT    6    7    7    8
CONECT    8    9   21   22
CONECT    9   10   11   11
CONECT   10   23   24   25
END
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SMILES for HMDB0040447 (Butyl acetoacetate)

CCCCOC(=O)CC(C)=O
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INCHI for HMDB0040447 (Butyl acetoacetate)

InChI=1S/C8H14O3/c1-3-4-5-11-8(10)6-7(2)9/h3-6H2,1-2H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
Butyl acetoacetic acidGenerator
Acetoacetic acid, butyl esterHMDB
Butanoic acid, 3-oxo-, butyl esterHMDB
Butyl 3-ketobutanoateHMDB
Butyl 3-ketobutyrateHMDB
Butyl 3-oxobutanoateHMDB
Butyl 3-oxobutyrateHMDB
Butylester kyseliny acetoctoveHMDB
FEMA 2176HMDB
Butyl 3-oxobutanoic acidGenerator
Chemical FormulaC8H14O3
Average Molecular Weight158.195
Monoisotopic Molecular Weight158.094294314
IUPAC Namebutyl 3-oxobutanoate
Traditional Namebutyl 3-oxobutanoate
CAS Registry Number591-60-6
SMILES
CCCCOC(=O)CC(C)=O
InChI Identifier
InChI=1S/C8H14O3/c1-3-4-5-11-8(10)6-7(2)9/h3-6H2,1-2H3
InChI KeyREIYHFWZISXFKU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as beta-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C3 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassBeta-keto acids and derivatives
Direct ParentBeta-keto acids and derivatives
Alternative Parents
Substituents
  • Fatty acid ester
  • Beta-keto acid
  • Fatty acyl
  • 1,3-dicarbonyl compound
  • Ketone
  • 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 DescriptorsNot Available
Ontology
Physiological effect
Organoleptic effect
Disposition
Source
ProcessNot Available
Role
Industrial applicationBiological role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-35.6 °CNot Available
Boiling Point100.00 to 103.00 °C. @ 16.00 mm HgThe Good Scents Company Information System
Water Solubility15080 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.386 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
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 IDFDB020199
KNApSAcK IDNot Available
Chemspider ID11088
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11576
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1013081
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.. .