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Showing NP-Card for 2,4-Pentanedione (NP0047298)

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Record Information
Version2.0
Created at2022-03-17 20:37:51 UTC
Updated at2022-03-17 20:37:51 UTC
NP-MRD IDNP0047298
Secondary Accession NumbersNone
Natural Product Identification
Common Name2,4-Pentanedione
Description2,4-Pentanedione, also known as ACAC or acetylacetone, belongs to the class of organic compounds known as beta-diketones. These are organic compounds containing two keto groups separated by a single carbon atom. Thus, 2,4-pentanedione is considered to be an oxygenated hydrocarbon lipid molecule. 2,4-Pentanedione is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 2,4-Pentanedione has been detected, but not quantified in, evergreen blackberries and papaya. This could make 2,4-pentanedione a potential biomarker for the consumption of these foods. 2,4-Pentanedione is found in Pinus sylvestris . 2,4-Pentanedione was first documented in 2007 (PMID: 17944413). A beta-diketone that is pentane in which the hydrogens at positions 2 and 4 are replaced by oxo groups (PMID: 24445259) (PMID: 23340796) (PMID: 23449989) (PMID: 23331483).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047298 (2,4-Pentanedione)


  Mrv0541 05061306032D          

  7  6  0  0  0  0            999 V2000
   -1.9395   -0.5264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9395    0.2757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2158    0.6768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6604    0.6768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3041    0.2757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0264    0.6768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3013   -0.5264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
M  END
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3D MOL for NP0047298 (2,4-Pentanedione)

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3D SDF for NP0047298 (2,4-Pentanedione)

  Mrv0541 05061306032D          

  7  6  0  0  0  0            999 V2000
   -1.9395   -0.5264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9395    0.2757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2158    0.6768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6604    0.6768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3041    0.2757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0264    0.6768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3013   -0.5264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0047298

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C5H8O2/c1-4(6)3-5(2)7/h3H2,1-2H3

> <INCHI_KEY>
YRKCREAYFQTBPV-UHFFFAOYSA-N

> <FORMULA>
C5H8O2

> <MOLECULAR_WEIGHT>
100.1158

> <EXACT_MASS>
100.0524295

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
10.329231685781394

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
pentane-2,4-dione

> <ALOGPS_LOGP>
-0.20

> <JCHEM_LOGP>
0.32813377699999996

> <ALOGPS_LOGS>
0.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.505447220392284

> <JCHEM_PKA_STRONGEST_BASIC>
-7.12467028891513

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
26.090000000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.40e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetylacetone

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0047298 (2,4-Pentanedione)
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PDB for NP0047298 (2,4-Pentanedione)
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  O   UNK     0      -3.620  -0.983   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -3.620   0.515   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.269   1.263   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.966   1.263   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.168   0.515   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.516   1.263   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -6.162  -0.983   0.000  0.00  0.00           O+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                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END

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3D PDB for NP0047298 (2,4-Pentanedione)
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SMILES for NP0047298 (2,4-Pentanedione)
CC(=O)CC(C)=O
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INCHI for NP0047298 (2,4-Pentanedione)
InChI=1S/C5H8O2/c1-4(6)3-5(2)7/h3H2,1-2H3
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View in JSmol
Synonyms
ValueSource
2,4-DioxopentaneChEBI
2,4-PentadioneChEBI
ACACChEBI
AcetoacetoneChEBI
Acetyl 2-propanoneChEBI
CH3-CO-CH2-CO-CH3ChEBI
HacacChEBI
Pentan-2,4-dioneChEBI
AcetylacetoneKegg
2,4-PentandioneHMDB
4-Hydroxy-3-penten-2-oneHMDB
Acetyl acetoneHMDB
Acetyl-2-propanoneHMDB
Acetyl-acetoneHMDB
Benzil-related compound, 44HMDB
CH3COCH2COCH3HMDB
DiacetylmethaneHMDB
Pentane-2,4-dioneHMDB
PentanedioneHMDB
Pentanedione-2,4HMDB
Indium-111-acetylacetoneHMDB
2,4-PentanedioneChEBI
Chemical FormulaC5H8O2
Average Mass100.1158 Da
Monoisotopic Mass100.05243 Da
IUPAC Namepentane-2,4-dione
Traditional Nameacetylacetone
CAS Registry Number123-54-6
SMILES
CC(=O)CC(C)=O
InChI Identifier
InChI=1S/C5H8O2/c1-4(6)3-5(2)7/h3H2,1-2H3
InChI KeyYRKCREAYFQTBPV-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Carica papaya L.FooDB
Pinus sylvestrisPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as beta-diketones. These are organic compounds containing two keto groups separated by a single carbon atom.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentBeta-diketones  
Alternative Parents
Substituents
  • 1,3-diketone
    • 

  • Ketone
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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-0.2ALOGPS
logP0.33ChemAxon
logS0.15ALOGPS
pKa (Strongest Acidic)8.51ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity26.09 m³·mol⁻¹ChemAxon
Polarizability10.33 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031648  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008303  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC15499  
BioCyc IDCPD-8879  
BiGG IDNot Available
Wikipedia LinkAcetylacetone  
METLIN IDNot Available
PubChem Compound31261  
PDB IDNot Available
ChEBI ID14750  
Good Scents IDNot Available
References
General References
  1. Darwish ES, Fattah AM, Attaby FA, Al-Shayea ON: Synthesis and antimicrobial evaluation of some novel thiazole, pyridone, pyrazole, chromene, hydrazone derivatives bearing a biologically active sulfonamide moiety. Int J Mol Sci. 2014 Jan 17;15(1):1237-54. doi: 10.3390/ijms15011237. [PubMed:24445259  ] 
  2. Yuan XH, Liu LM, Ying WB: [Preparation and spectral analysis of Bi(4-x) La(x)Ti3O12 ferroelectric thin films by metal-organic deposition method]. Guang Pu Xue Yu Guang Pu Fen Xi. 2007 Jul;27(7):1355-8. [PubMed:17944413  ] 
  3. Li C, Wang S, Huang Y, Zheng B, Tian Z, Wen Y, Li F: Synthesis, characterization and electrochemiluminescent properties of cyclometalated platinum(II) complexes with substituted 2-phenylpyridine ligands. Dalton Trans. 2013 Mar 21;42(11):4059-67. doi: 10.1039/c2dt32466k. Epub 2013 Jan  23. [PubMed:23340796  ] 
  4. Rao Ch S, Subash Y E: The effect of chronic tobacco smoking and chewing on the lipid profile. J Clin Diagn Res. 2013 Jan;7(1):31-4. doi: 10.7860/JCDR/2012/5086.2663. Epub 2013 Jan 1. [PubMed:23449989  ] 
  5. Yao C, Xu X, Wang J, Shi L, Li L: Low-temperature, solution-processed hole selective layers for polymer solar cells. ACS Appl Mater Interfaces. 2013 Feb;5(3):1100-7. doi: 10.1021/am302878m. Epub 2013 Jan 31. [PubMed:23331483  ]