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Showing NP-Card for 2,5-hexanedione (NP0269136)

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Record Information
Version2.0
Created at2022-09-08 14:29:34 UTC
Updated at2022-09-08 14:29:34 UTC
NP-MRD IDNP0269136
Secondary Accession NumbersNone
Natural Product Identification
Common Name2,5-hexanedione
Description2,5-Hexanedione, also known as acetonyl acetone or 2,5-diketohexane, belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Thus, 2,5-hexanedione is considered to be an oxygenated hydrocarbon lipid molecule. 2,5-Hexanedione is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2,5-Hexanedione is a potentially toxic compound. 2,5-hexanedione is found in Pueraria montana and Vitis vinifera. 2,5-hexanedione was first documented in 1991 (PMID: 1781736). A diketone that is hexane substituted by oxo groups at positions 2 and 5 (PMID: 24634916) (PMID: 25549948).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0269136 (2,5-hexanedione)


  Mrv0541 09071422392D          

  8  7  0  0  0  0            999 V2000
    2.9684    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  1  1  0  0  0  0
  5  3  1  0  0  0  0
  6  2  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  6  2  0  0  0  0
M  END
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3D MOL for NP0269136 (2,5-hexanedione)

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3D SDF for NP0269136 (2,5-hexanedione)

  Mrv0541 09071422392D          

  8  7  0  0  0  0            999 V2000
    2.9684    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  1  1  0  0  0  0
  5  3  1  0  0  0  0
  6  2  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  6  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0269136

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O2/c1-5(7)3-4-6(2)8/h3-4H2,1-2H3

> <INCHI_KEY>
OJVAMHKKJGICOG-UHFFFAOYSA-N

> <FORMULA>
C6H10O2

> <MOLECULAR_WEIGHT>
114.1424

> <EXACT_MASS>
114.068079564

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
12.249687749431548

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
hexane-2,5-dione

> <ALOGPS_LOGP>
0.28

> <JCHEM_LOGP>
0.2607680779999997

> <ALOGPS_LOGS>
-0.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.605191998067234

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.73079897623495

> <JCHEM_PKA_STRONGEST_BASIC>
-6.979618557660593

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
30.6392

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.08e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,5-hexanedione

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0269136 (2,5-hexanedione)
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PDB for NP0269136 (2,5-hexanedione)
HEADER    PROTEIN                                 07-SEP-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-14         0                                  
HETATM    1  C   UNK     0       5.541   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.127   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.207  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.206   0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.207  -1.540   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.206   2.310   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2    6                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    1    3    7                                                  
CONECT    6    2    4    8                                                  
CONECT    7    5                                                            
CONECT    8    6                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END

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3D PDB for NP0269136 (2,5-hexanedione)
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SMILES for NP0269136 (2,5-hexanedione)
CC(=O)CCC(C)=O
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INCHI for NP0269136 (2,5-hexanedione)
InChI=1S/C6H10O2/c1-5(7)3-4-6(2)8/h3-4H2,1-2H3
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Synonyms
ValueSource
1,2-DiacetylethaneChEBI
2,5-DiketohexaneChEBI
2,5-HexadioneChEBI
Acetonyl acetoneChEBI
AcetonylacetoneChEBI
alpha,beta-DiacetylethaneChEBI
CH3COCH2CH2COCH3ChEBI
Hexane-2,5-dioneChEBI
NSC 7621ChEBI
a,b-DiacetylethaneGenerator
Α,β-diacetylethaneGenerator
alpha, beta-DiacetylethaneMeSH
DiacetonylMeSH
2,5-DioxohexaneMeSH
Acetone, acetonylMeSH
Chemical FormulaC6H10O2
Average Mass114.1424 Da
Monoisotopic Mass114.06808 Da
IUPAC Namehexane-2,5-dione
Traditional Name2,5-hexanedione
CAS Registry NumberNot Available
SMILES
CC(=O)CCC(C)=O
InChI Identifier
InChI=1S/C6H10O2/c1-5(7)3-4-6(2)8/h3-4H2,1-2H3
InChI KeyOJVAMHKKJGICOG-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Pueraria montanaLOTUS Database
Vitis viniferaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ketones. These are organic compounds  in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentKetones  
Alternative Parents
Substituents
  • 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
logP0.28ALOGPS
logP0.26ChemAxon
logS-0.35ALOGPS
pKa (Strongest Acidic)17.73ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity30.64 m³·mol⁻¹ChemAxon
Polarizability12.25 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDCPD-15521  
BiGG IDNot Available
Wikipedia LinkHexane-2,5-dione  
METLIN IDNot Available
PubChem Compound8035  
PDB IDNot Available
ChEBI ID85014  
Good Scents IDNot Available
References
General References
  1. Nakajima T, Elovaara E, Park SS, Gelboin HV, Vainio H: Immunochemical detection of cytochrome P450 isozymes induced in rat liver by n-hexane, 2-hexanone and acetonyl acetone. Arch Toxicol. 1991;65(7):542-7. doi: 10.1007/BF01973714. [PubMed:1781736  ] 
  2. Liu X, Song X, Zhang S, Wang M, Pan B: Non-hydroxyl radical mediated photochemical processes for dye degradation. Phys Chem Chem Phys. 2014 Apr 28;16(16):7571-7. doi: 10.1039/c3cp54765e. [PubMed:24634916  ] 
  3. Cheng X, Luo R, Wang G, Xu CJ, Feng X, Yang RH, Ding E, He YQ, Chuai M, Lee KK, Yang X: Effects of 2,5-hexanedione on angiogenesis and vasculogenesis in chick embryos. Reprod Toxicol. 2015 Jan;51:79-89. doi: 10.1016/j.reprotox.2014.12.006. Epub 2014  Dec 27. [PubMed:25549948  ] 
  4. LOTUS database [Link]