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Showing NP-Card for 5-Methyl-2,3-hexanedione (NP0047288)

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Record Information
Version1.0
Created at2022-03-17 20:37:41 UTC
Updated at2022-03-17 20:37:41 UTC
NP-MRD IDNP0047288
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-Methyl-2,3-hexanedione
Description5-Methyl-2,3-hexanedione, also known as acetyl isopentanoyl or acetyl isovaleryl, belongs to the class of organic compounds known as alpha-diketones. These are organic compounds containing two ketone groups on two adjacent carbon atoms. 5-Methyl-2,3-hexanedione is an extremely weak basic (essentially neutral) compound (based on its pKa). 5-Methyl-2,3-hexanedione is a sweet, brown, and butter tasting compound. Outside of the human body, 5-Methyl-2,3-hexanedione has been detected, but not quantified in, coffee and coffee products and potato. This could make 5-methyl-2,3-hexanedione a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047288 (5-Methyl-2,3-hexanedione)


  Mrv0541 05061306012D          

  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
   -1.1270    0.5230    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
    0.3020   -0.3020    0.0000 C   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    0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  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  1  0  0  0  0
  7  6  1  0  0  0  0
  8  6  2  0  0  0  0
  9  7  2  0  0  0  0
M  END
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3D MOL for NP0047288 (5-Methyl-2,3-hexanedione)

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3D SDF for NP0047288 (5-Methyl-2,3-hexanedione)

  Mrv0541 05061306012D          

  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
   -1.1270    0.5230    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
    0.3020   -0.3020    0.0000 C   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    0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  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  1  0  0  0  0
  7  6  1  0  0  0  0
  8  6  2  0  0  0  0
  9  7  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0047288

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H12O2/c1-5(2)4-7(9)6(3)8/h5H,4H2,1-3H3

> <INCHI_KEY>
PQCLJXVUAWLNSV-UHFFFAOYSA-N

> <FORMULA>
C7H12O2

> <MOLECULAR_WEIGHT>
128.169

> <EXACT_MASS>
128.083729628

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
14.008848962702036

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-methylhexane-2,3-dione

> <ALOGPS_LOGP>
1.27

> <JCHEM_LOGP>
1.8276230843333336

> <ALOGPS_LOGS>
-1.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.24916822844354

> <JCHEM_PKA_STRONGEST_BASIC>
-8.399121812593666

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
35.3173

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.61e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,3-hexanedione, 5-methyl-

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0047288 (5-Methyl-2,3-hexanedione)
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PDB for NP0047288 (5-Methyl-2,3-hexanedione)
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      -2.104   0.976   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      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.104  -0.564   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  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+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   0.976   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2    5                                                            
CONECT    3    6                                                            
CONECT    4    5    7                                                       
CONECT    5    1    2    4                                                  
CONECT    6    3    7    8                                                  
CONECT    7    4    6    9                                                  
CONECT    8    6                                                            
CONECT    9    7                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END

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3D PDB for NP0047288 (5-Methyl-2,3-hexanedione)
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SMILES for NP0047288 (5-Methyl-2,3-hexanedione)
CC(C)CC(=O)C(C)=O
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INCHI for NP0047288 (5-Methyl-2,3-hexanedione)
InChI=1S/C7H12O2/c1-5(2)4-7(9)6(3)8/h5H,4H2,1-3H3
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Synonyms
ValueSource
2-Methylhexa-4,5-dioneHMDB
5-Methylhexane-2,3-dioneHMDB
Acetyl isopentanoylHMDB
Acetyl isovalerylHMDB
AcetylisopentanoylHMDB
AcetylisovalerylHMDB
FEMA 3190HMDB
Isobutyl methyl diketoneHMDB
IsobutylmethylglyoxalHMDB
Chemical FormulaC7H12O2
Average Mass128.1690 Da
Monoisotopic Mass128.08373 Da
IUPAC Name5-methylhexane-2,3-dione
Traditional Name2,3-hexanedione, 5-methyl-
CAS Registry Number13706-86-0
SMILES
CC(C)CC(=O)C(C)=O
InChI Identifier
InChI=1S/C7H12O2/c1-5(2)4-7(9)6(3)8/h5H,4H2,1-3H3
InChI KeyPQCLJXVUAWLNSV-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Coffea arabica L.FooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephoraFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Solanum tuberosumFooDB
    • 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-diketones. These are organic compounds containing two ketone groups on two adjacent carbon atoms.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentAlpha-diketones  
Alternative Parents
Substituents
  • Alpha-diketone
    • 

  • 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
logP1.27ALOGPS
logP1.83ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)16.25ChemAxon
pKa (Strongest Basic)-8.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity35.32 m³·mol⁻¹ChemAxon
Polarizability14.01 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031593  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008223  
KNApSAcK IDNot Available
Chemspider ID24415  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound26204  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available