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Showing NP-Card for Acetoin acetate (NP0047709)

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Record Information
Version2.0
Created at2022-03-17 20:44:39 UTC
Updated at2022-03-17 20:44:39 UTC
NP-MRD IDNP0047709
Secondary Accession NumbersNone
Natural Product Identification
Common NameAcetoin acetate
DescriptionAcetoin acetate, also known as fema 3526, belongs to the class of organic compounds known as alpha-acyloxy ketones. These are ketones that have an acyloxy substituent alpha to the carbonyl group. They have the general structure R4C(=O)OC(R2)(R3)C(R1)=O (R1=organyl, R4=H or organyl; R2,R3 = any atom). Acetoin acetate is an extremely weak basic (essentially neutral) compound (based on its pKa). Acetoin acetate is a sweet, buttery, and creamy tasting compound. Outside of the human body, Acetoin acetate has been detected, but not quantified in, a few different foods, such as alcoholic beverages, cocoa and cocoa products, and fruits. This could make acetoin acetate a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047709 (Acetoin acetate)


  Mrv0541 05061307182D          

  9  8  0  0  0  0            999 V2000
   -1.8414   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  4  1  0  0  0  0
  6  3  1  0  0  0  0
  7  4  2  0  0  0  0
  8  6  2  0  0  0  0
  9  5  1  0  0  0  0
  9  6  1  0  0  0  0
M  END
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3D MOL for NP0047709 (Acetoin acetate)

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3D SDF for NP0047709 (Acetoin acetate)

  Mrv0541 05061307182D          

  9  8  0  0  0  0            999 V2000
   -1.8414   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  4  1  0  0  0  0
  6  3  1  0  0  0  0
  7  4  2  0  0  0  0
  8  6  2  0  0  0  0
  9  5  1  0  0  0  0
  9  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047709

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O3/c1-4(7)5(2)9-6(3)8/h5H,1-3H3

> <INCHI_KEY>
ZKPTYCJWRHHBOW-UHFFFAOYSA-N

> <FORMULA>
C6H10O3

> <MOLECULAR_WEIGHT>
130.1418

> <EXACT_MASS>
130.062994186

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
13.02262303248077

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-oxobutan-2-yl acetate

> <ALOGPS_LOGP>
0.19

> <JCHEM_LOGP>
0.2989214150000003

> <ALOGPS_LOGS>
-0.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.633053544379347

> <JCHEM_PKA_STRONGEST_BASIC>
-6.965600783352245

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
31.542400000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.87e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-oxobutan-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0047709 (Acetoin acetate)
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PDB for NP0047709 (Acetoin acetate)
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      -3.437  -1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.770  -2.874   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.231  -0.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.104  -0.564   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.897  -1.334   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.104   0.976   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       1.897  -2.874   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.564  -0.564   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    5                                                            
CONECT    3    6                                                            
CONECT    4    1    5    7                                                  
CONECT    5    2    4    9                                                  
CONECT    6    3    8    9                                                  
CONECT    7    4                                                            
CONECT    8    6                                                            
CONECT    9    5    6                                                       
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END

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3D PDB for NP0047709 (Acetoin acetate)
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SMILES for NP0047709 (Acetoin acetate)
CC(OC(C)=O)C(C)=O
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INCHI for NP0047709 (Acetoin acetate)
InChI=1S/C6H10O3/c1-4(7)5(2)9-6(3)8/h5H,1-3H3
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Synonyms
ValueSource
Acetoin acetic acidGenerator
2-Acetoxy-3-butanoneHMDB
2-Butanon-3-ol, acetateHMDB
2-Ketobutan-3-yl acetateHMDB
3-(Acetyloxy)-2-butanoneHMDB
3-Acetoxy-2-butanoneHMDB
3-oxo-2-Butyl acetateHMDB
FEMA 3526HMDB
3-Oxobutan-2-yl acetic acidGenerator
Chemical FormulaC6H10O3
Average Mass130.1418 Da
Monoisotopic Mass130.06299 Da
IUPAC Name3-oxobutan-2-yl acetate
Traditional Name3-oxobutan-2-yl acetate
CAS Registry Number4906-24-5
SMILES
CC(OC(C)=O)C(C)=O
InChI Identifier
InChI=1S/C6H10O3/c1-4(7)5(2)9-6(3)8/h5H,1-3H3
InChI KeyZKPTYCJWRHHBOW-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Theobroma cacaoFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha-acyloxy ketones. These are ketones that have an acyloxy substituent alpha to the carbonyl group. They have the general structure R4C(=O)OC(R2)(R3)C(R1)=O (R1=organyl, R4=H or organyl; R2,R3 = any atom).
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentAlpha-acyloxy ketones  
Alternative Parents
Substituents
  • Alpha-acyloxy ketone
    • 

  • Ketone
    • 

  • Carboxylic acid ester
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.19ALOGPS
logP0.3ChemAxon
logS-0.35ALOGPS
pKa (Strongest Acidic)17.63ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity31.54 m³·mol⁻¹ChemAxon
Polarizability13.02 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0033698  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011808  
KNApSAcK IDNot Available
Chemspider ID454676  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound521246  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available