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Showing NP-Card for Acetoxyacetone (NP0047977)

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Record Information
Version2.0
Created at2022-03-17 20:49:01 UTC
Updated at2022-03-17 20:49:01 UTC
NP-MRD IDNP0047977
Secondary Accession NumbersNone
Natural Product Identification
Common NameAcetoxyacetone
DescriptionAcetoxyacetone, also known as acetol acetate or acetoxypropanone, 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). Acetoxyacetone is an extremely weak basic (essentially neutral) compound (based on its pKa). Acetoxyacetone is a buttery and fruity tasting compound. Outside of the human body, Acetoxyacetone has been detected, but not quantified in, pineapples. Acetoxyacetone is found in Coffea arabica. This could make acetoxyacetone a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047977 (Acetoxyacetone)


  Mrv0541 05061307502D          

  8  7  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
    1.7309   -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
   -1.1270   -0.3020    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
  4  3  1  0  0  0  0
  5  2  1  0  0  0  0
  6  4  2  0  0  0  0
  7  5  2  0  0  0  0
  8  3  1  0  0  0  0
  8  5  1  0  0  0  0
M  END
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3D MOL for NP0047977 (Acetoxyacetone)

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3D SDF for NP0047977 (Acetoxyacetone)

  Mrv0541 05061307502D          

  8  7  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
    1.7309   -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
   -1.1270   -0.3020    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
  4  3  1  0  0  0  0
  5  2  1  0  0  0  0
  6  4  2  0  0  0  0
  7  5  2  0  0  0  0
  8  3  1  0  0  0  0
  8  5  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047977

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C5H8O3/c1-4(6)3-8-5(2)7/h3H2,1-2H3

> <INCHI_KEY>
DBERHVIZRVGDFO-UHFFFAOYSA-N

> <FORMULA>
C5H8O3

> <MOLECULAR_WEIGHT>
116.1152

> <EXACT_MASS>
116.047344122

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
11.355232742665137

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-oxopropyl acetate

> <ALOGPS_LOGP>
-0.27

> <JCHEM_LOGP>
-0.2698428273333332

> <ALOGPS_LOGS>
0.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.511874819256313

> <JCHEM_PKA_STRONGEST_BASIC>
-6.95085678457926

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
27.048500000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.49e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-propanone, 1-(acetyloxy)-

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0047977 (Acetoxyacetone)
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PDB for NP0047977 (Acetoxyacetone)
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       3.231  -0.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.770  -1.334   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       1.897  -1.334   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.104   0.976   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       1.897  -2.874   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.564  -0.564   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    5                                                            
CONECT    3    4    8                                                       
CONECT    4    1    3    6                                                  
CONECT    5    2    7    8                                                  
CONECT    6    4                                                            
CONECT    7    5                                                            
CONECT    8    3    5                                                       
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END

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3D PDB for NP0047977 (Acetoxyacetone)
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SMILES for NP0047977 (Acetoxyacetone)
CC(=O)COC(C)=O
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INCHI for NP0047977 (Acetoxyacetone)
InChI=1S/C5H8O3/c1-4(6)3-8-5(2)7/h3H2,1-2H3
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Synonyms
ValueSource
1-(Acetyloxy)-2-propanoneHMDB
1-Acetoxy-2-propanoneHMDB
1-Acetoxy-propan-2-oneHMDB
1-AcetoxyacetoneHMDB
1-Acetyloxy-propan-2-oneHMDB
1-Hydroxy-2-propanone acetateHMDB
2-Oxopropyl acetateHMDB
2-Propanone, 1-hydroxy-, acetateHMDB
2-Propanone, 1-hydroxy-, acetate (8ci)HMDB
ACETIC ACID,(2-oxopropyl) ester acetonylacetATEHMDB
Acetol acetateHMDB
Acetonyl acetateHMDB
Acetoxy-2-propanoneHMDB
AcetoxypropanoneHMDB
Acetylmethyl acetateHMDB
O-AcetylacetolHMDB
2-Oxopropyl acetic acidGenerator
Chemical FormulaC5H8O3
Average Mass116.1152 Da
Monoisotopic Mass116.04734 Da
IUPAC Name2-oxopropyl acetate
Traditional Name2-propanone, 1-(acetyloxy)-
CAS Registry Number592-20-1
SMILES
CC(=O)COC(C)=O
InChI Identifier
InChI=1S/C5H8O3/c1-4(6)3-8-5(2)7/h3H2,1-2H3
InChI KeyDBERHVIZRVGDFO-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Ananas comosusFooDB
Coffea arabicaLOTUS Database
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
logP-0.27ALOGPS
logP-0.27ChemAxon
logS0.11ALOGPS
pKa (Strongest Acidic)17.51ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity27.05 m³·mol⁻¹ChemAxon
Polarizability11.36 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0034466  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012876  
KNApSAcK IDNot Available
Chemspider ID11105  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11593  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available