2-Oxohexane
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Basic Info
| Common Name | 2-Oxohexane(F03325) |
| 2D Structure | |
| Description | 2-Oxohexane is a volatile organic compound. 2-Oxohexane is occasionally found as a volatile component of normal human biofluids. 2-Oxohexane is an hexacarbon solvent; the neurotoxicity of hexacarbon solvents has become apparent and an extensive literature has already developed as a result of the clinical and epidemiological implications of the human disease. The main neurological disorders associated with chronic volatile substance are peripheral neuropathy, cerebellar disease, chronic encephalopathy and dementia. Apart from peripheral neuropathy, the clinical features are non-specific, evidence for solvent-related toxicity is in most cases circumstantial and there is no clear dose/response relationship. (A7698, A7699, A7700). |
| FRCD ID | F03325 |
| CAS Number | 591-78-6 |
| PubChem CID | 11583 |
| Formula | C6H12O |
| IUPAC Name | hexan-2-one |
| InChI Key | QQZOPKMRPOGIEB-UHFFFAOYSA-N |
| InChI | InChI=1S/C6H12O/c1-3-4-5-6(2)7/h3-5H2,1-2H3 |
| Canonical SMILES | CCCCC(=O)C |
| Isomeric SMILES | CCCCC(=O)C |
| Synonyms |
Butyl methyl ketone
2-HEXANONE
Hexan-2-one
591-78-6
2-Oxohexane
Propylacetone
Hexanone
Methyl butyl ketone
n-Butyl methyl ketone
Methyl N-butyl ketone
|
| Classifies |
Predicted: Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic oxygen compounds |
| Class | Organooxygen compounds |
| Subclass | Carbonyl compounds |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Ketones |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Ketone - Organic oxide - Hydrocarbon derivative - Aliphatic acyclic compound |
| Description | This compound 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. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 100.161 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 3 |
| Complexity | 57.2 |
| Monoisotopic Mass | 100.089 |
| Exact Mass | 100.089 |
| XLogP | 1.4 |
| Formal Charge | 0 |
| Heavy Atom Count | 7 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9919 |
| Human Intestinal Absorption | HIA+ | 0.9944 |
| Caco-2 Permeability | Caco2+ | 0.8707 |
| P-glycoprotein Substrate | Non-substrate | 0.7088 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8441 |
| Non-inhibitor | 0.9092 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8863 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.4324 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8442 |
| CYP450 2D6 Substrate | Non-substrate | 0.8464 |
| CYP450 3A4 Substrate | Non-substrate | 0.6425 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.6313 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9588 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9513 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9482 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9850 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8820 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8911 |
| Non-inhibitor | 0.8658 | |
| AMES Toxicity | Non AMES toxic | 0.9809 |
| Carcinogens | Carcinogens | 0.6610 |
| Fish Toxicity | Low FHMT | 0.6963 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.8365 |
| Honey Bee Toxicity | High HBT | 0.7367 |
| Biodegradation | Ready biodegradable | 0.9332 |
| Acute Oral Toxicity | III | 0.8155 |
| Carcinogenicity (Three-class) | Non-required | 0.7389 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -0.7238 | LogS |
| Caco-2 Permeability | 1.5864 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.5558 | LD50, mol/kg |
| Fish Toxicity | 2.5064 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -1.0254 | pIGC50, ug/L |
Targets
- General Function:
- Protein complex binding
- Specific Function:
- Catalyzes the phosphorylation of D-fructose 6-phosphate to fructose 1,6-bisphosphate by ATP, the first committing step of glycolysis.
- Gene Name:
- PFKP
- Uniprot ID:
- Q01813
- Molecular Weight:
- 85595.405 Da
- Mechanism of Action:
- 2-Hexanone and 2,5-hexanedione may inhibit sulfhydryl-dependent enzymes such as fructose-6-phosphate kinase, impairing energy metabolism and subsequently resulting in axon deterioration.
References
- Couri D, Milks M: Toxicity and metabolism of the neurotoxic hexacarbons n-hexane, 2-hexanone, and 2,5-hexanedione. Annu Rev Pharmacol Toxicol. 1982;22:145-66. [7044283 ]
- General Function:
- Metal ion binding
- Specific Function:
- Catalyzes the phosphorylation of D-fructose 6-phosphate to fructose 1,6-bisphosphate by ATP, the first committing step of glycolysis.
- Gene Name:
- PFKL
- Uniprot ID:
- P17858
- Molecular Weight:
- 85017.825 Da
- Mechanism of Action:
- 2-Hexanone and 2,5-hexanedione may inhibit sulfhydryl-dependent enzymes such as fructose-6-phosphate kinase, impairing energy metabolism and subsequently resulting in axon deterioration.
References
- Couri D, Milks M: Toxicity and metabolism of the neurotoxic hexacarbons n-hexane, 2-hexanone, and 2,5-hexanedione. Annu Rev Pharmacol Toxicol. 1982;22:145-66. [7044283 ]
- General Function:
- Protein c-terminus binding
- Specific Function:
- Catalyzes the phosphorylation of D-fructose 6-phosphate to fructose 1,6-bisphosphate by ATP, the first committing step of glycolysis.
- Gene Name:
- PFKM
- Uniprot ID:
- P08237
- Molecular Weight:
- 85181.925 Da
- Mechanism of Action:
- 2-Hexanone and 2,5-hexanedione may inhibit sulfhydryl-dependent enzymes such as fructose-6-phosphate kinase, impairing energy metabolism and subsequently resulting in axon deterioration.
References
- Couri D, Milks M: Toxicity and metabolism of the neurotoxic hexacarbons n-hexane, 2-hexanone, and 2,5-hexanedione. Annu Rev Pharmacol Toxicol. 1982;22:145-66. [7044283 ]
- General Function:
- Atp binding
- Specific Function:
- Catalyzes the reversible transfer of the terminal phosphate group between ATP and AMP. Plays an important role in cellular energy homeostasis and in adenine nucleotide metabolism. Adenylate kinase activity is critical for regulation of the phosphate utilization and the AMP de novo biosynthesis pathways. Plays a key role in hematopoiesis.
- Gene Name:
- AK2
- Uniprot ID:
- P54819
- Molecular Weight:
- 26477.44 Da
- Mechanism of Action:
- 2-Hexanone and 2,5-hexanedione may inhibit sulfhydryl-dependent enzymes such as adenylate kinases, impairing energy metabolism and subsequently resulting in axon deterioration.
References
- Graham DG: Neurotoxicants and the cytoskeleton. Curr Opin Neurol. 1999 Dec;12(6):733-7. [10676757 ]
- General Function:
- Nucleoside triphosphate adenylate kinase activity
- Specific Function:
- Involved in maintaining the homeostasis of cellular nucleotides by catalyzing the interconversion of nucleoside phosphates. Efficiently phosphorylates AMP and dAMP using ATP as phosphate donor, but phosphorylates only AMP when using GTP as phosphate donor. Also displays broad nucleoside diphosphate kinase activity.
- Gene Name:
- AK4
- Uniprot ID:
- P27144
- Molecular Weight:
- 25267.83 Da
- Mechanism of Action:
- 2-Hexanone and 2,5-hexanedione may inhibit sulfhydryl-dependent enzymes such as adenylate kinases, impairing energy metabolism and subsequently resulting in axon deterioration.
References
- Graham DG: Neurotoxicants and the cytoskeleton. Curr Opin Neurol. 1999 Dec;12(6):733-7. [10676757 ]
- General Function:
- Nucleoside diphosphate kinase activity
- Specific Function:
- Catalyzes the reversible transfer of the terminal phosphate group between ATP and AMP. Also displays broad nucleoside diphosphate kinase activity. Plays an important role in cellular energy homeostasis and in adenine nucleotide metabolism.
- Gene Name:
- AK1
- Uniprot ID:
- P00568
- Molecular Weight:
- 21634.725 Da
- Mechanism of Action:
- 2-Hexanone and 2,5-hexanedione may inhibit sulfhydryl-dependent enzymes such as adenylate kinases, impairing energy metabolism and subsequently resulting in axon deterioration.
References
- Graham DG: Neurotoxicants and the cytoskeleton. Curr Opin Neurol. 1999 Dec;12(6):733-7. [10676757 ]
- General Function:
- Nucleoside diphosphate kinase activity
- Specific Function:
- Nucleoside monophosphate (NMP) kinase that catalyzes the reversible transfer of the terminal phosphate group between nucleoside triphosphates and monophosphates. Active on AMP and dAMP with ATP as a donor. When GTP is used as phosphate donor, the enzyme phosphorylates AMP, CMP, and to a small extent dCMP. Also displays broad nucleoside diphosphate kinase activity.
- Gene Name:
- AK5
- Uniprot ID:
- Q9Y6K8
- Molecular Weight:
- 63332.385 Da
- Mechanism of Action:
- 2-Hexanone and 2,5-hexanedione may inhibit sulfhydryl-dependent enzymes such as adenylate kinases, impairing energy metabolism and subsequently resulting in axon deterioration.
References
- Graham DG: Neurotoxicants and the cytoskeleton. Curr Opin Neurol. 1999 Dec;12(6):733-7. [10676757 ]
- General Function:
- Atpase activity
- Specific Function:
- Broad-specificity nucleoside monophosphate (NMP) kinase that catalyzes the reversible transfer of the terminal phosphate group between nucleoside triphosphates and monophosphates. AMP and dAMP are the preferred substrates, but CMP and dCMP are also good substrates. IMP is phosphorylated to a much lesser extent. All nucleoside triphosphates ATP, GTP, UTP, CTP, dATP, dCTP, dGTP, and TTP are accepted as phosphate donors. CTP is the best phosphate donor, followed by UTP, ATP, GTP and dCTP. May have a role in nuclear energy homeostasis. Has also ATPase activity. May be involved in regulation of Cajal body (CB) formation.
- Gene Name:
- AK6
- Uniprot ID:
- Q9Y3D8
- Molecular Weight:
- 20061.315 Da
- Mechanism of Action:
- 2-Hexanone and 2,5-hexanedione may inhibit sulfhydryl-dependent enzymes such as adenylate kinases, impairing energy metabolism and subsequently resulting in axon deterioration.
References
- Graham DG: Neurotoxicants and the cytoskeleton. Curr Opin Neurol. 1999 Dec;12(6):733-7. [10676757 ]
- General Function:
- Ubiquitin protein ligase binding
- Specific Function:
- Reversibly catalyzes the transfer of phosphate between ATP and various phosphogens (e.g. creatine phosphate). Creatine kinase isoenzymes play a central role in energy transduction in tissues with large, fluctuating energy demands, such as skeletal muscle, heart, brain and spermatozoa.
- Gene Name:
- CKB
- Uniprot ID:
- P12277
- Molecular Weight:
- 42643.95 Da
- Mechanism of Action:
- 2-Hexanone and 2,5-hexanedione may inhibit sulfhydryl-dependent enzymes such as creatine kinases, impairing energy metabolism and subsequently resulting in axon deterioration.
References
- Graham DG: Neurotoxicants and the cytoskeleton. Curr Opin Neurol. 1999 Dec;12(6):733-7. [10676757 ]
- General Function:
- Creatine kinase activity
- Specific Function:
- Reversibly catalyzes the transfer of phosphate between ATP and various phosphogens (e.g. creatine phosphate). Creatine kinase isoenzymes play a central role in energy transduction in tissues with large, fluctuating energy demands, such as skeletal muscle, heart, brain and spermatozoa.
- Gene Name:
- CKM
- Uniprot ID:
- P06732
- Molecular Weight:
- 43100.91 Da
- Mechanism of Action:
- 2-Hexanone and 2,5-hexanedione may inhibit sulfhydryl-dependent enzymes such as creatine kinases, impairing energy metabolism and subsequently resulting in axon deterioration.
References
- Graham DG: Neurotoxicants and the cytoskeleton. Curr Opin Neurol. 1999 Dec;12(6):733-7. [10676757 ]
- General Function:
- Creatine kinase activity
- Specific Function:
- Reversibly catalyzes the transfer of phosphate between ATP and various phosphogens (e.g. creatine phosphate). Creatine kinase isoenzymes play a central role in energy transduction in tissues with large, fluctuating energy demands, such as skeletal muscle, heart, brain and spermatozoa.
- Gene Name:
- CKMT2
- Uniprot ID:
- P17540
- Molecular Weight:
- 47504.08 Da
- Mechanism of Action:
- 2-Hexanone and 2,5-hexanedione may inhibit sulfhydryl-dependent enzymes such as creatine kinases, impairing energy metabolism and subsequently resulting in axon deterioration.
References
- Graham DG: Neurotoxicants and the cytoskeleton. Curr Opin Neurol. 1999 Dec;12(6):733-7. [10676757 ]
- General Function:
- Creatine kinase activity
- Specific Function:
- Reversibly catalyzes the transfer of phosphate between ATP and various phosphogens (e.g. creatine phosphate). Creatine kinase isoenzymes play a central role in energy transduction in tissues with large, fluctuating energy demands, such as skeletal muscle, heart, brain and spermatozoa.
- Gene Name:
- CKMT1A
- Uniprot ID:
- P12532
- Molecular Weight:
- 47036.3 Da
- Mechanism of Action:
- 2-Hexanone and 2,5-hexanedione may inhibit sulfhydryl-dependent enzymes such as creatine kinases, impairing energy metabolism and subsequently resulting in axon deterioration.
References
- Graham DG: Neurotoxicants and the cytoskeleton. Curr Opin Neurol. 1999 Dec;12(6):733-7. [10676757 ]
- General Function:
- Nucleoside triphosphate adenylate kinase activity
- Specific Function:
- Involved in maintaining the homeostasis of cellular nucleotides by catalyzing the interconversion of nucleoside phosphates. Has GTP:AMP phosphotransferase and ITP:AMP phosphotransferase activities.
- Gene Name:
- AK3
- Uniprot ID:
- Q9UIJ7
- Molecular Weight:
- 25565.2 Da
- Mechanism of Action:
- 2-Hexanone and 2,5-hexanedione may inhibit sulfhydryl-dependent enzymes such as adenylate kinases, impairing energy metabolism and subsequently resulting in axon deterioration.
References
- Graham DG: Neurotoxicants and the cytoskeleton. Curr Opin Neurol. 1999 Dec;12(6):733-7. [10676757 ]
- General Function:
- Nadp binding
- Specific Function:
- May play an important role in regulating the switch between different pathways for energy production during spermiogenesis and in the spermatozoon. Required for sperm motility and male fertility (By similarity).
- Gene Name:
- GAPDHS
- Uniprot ID:
- O14556
- Molecular Weight:
- 44500.835 Da
- Mechanism of Action:
- 2-Hexanone and 2,5-hexanedione may inhibit sulfhydryl-dependent enzymes such as glyceraldehyde-3-phosphate dehydrogenase , impairing energy metabolism and subsequently resulting in axon deterioration.
References
- Couri D, Milks M: Toxicity and metabolism of the neurotoxic hexacarbons n-hexane, 2-hexanone, and 2,5-hexanedione. Annu Rev Pharmacol Toxicol. 1982;22:145-66. [7044283 ]
- General Function:
- Nucleoside diphosphate kinase activity
- Specific Function:
- Nucleoside monophosphate (NMP) kinase that catalyzes the reversible transfer of the terminal phosphate group between nucleoside triphosphates and monophosphates. Has highest activity toward AMP, and weaker activity toward dAMP, CMP and dCMP. Also displays broad nucleoside diphosphate kinase activity. Involved in maintaining ciliary structure and function.
- Gene Name:
- AK7
- Uniprot ID:
- Q96M32
- Molecular Weight:
- 82657.68 Da
- Mechanism of Action:
- 2-Hexanone and 2,5-hexanedione may inhibit sulfhydryl-dependent enzymes such as adenylate kinases, impairing energy metabolism and subsequently resulting in axon deterioration.
References
- Graham DG: Neurotoxicants and the cytoskeleton. Curr Opin Neurol. 1999 Dec;12(6):733-7. [10676757 ]
- General Function:
- Peptidyl-cysteine s-nitrosylase activity
- Specific Function:
- Has both glyceraldehyde-3-phosphate dehydrogenase and nitrosylase activities, thereby playing a role in glycolysis and nuclear functions, respectively. Participates in nuclear events including transcription, RNA transport, DNA replication and apoptosis. Nuclear functions are probably due to the nitrosylase activity that mediates cysteine S-nitrosylation of nuclear target proteins such as SIRT1, HDAC2 and PRKDC. Modulates the organization and assembly of the cytoskeleton. Facilitates the CHP1-dependent microtubule and membrane associations through its ability to stimulate the binding of CHP1 to microtubules (By similarity). Glyceraldehyde-3-phosphate dehydrogenase is a key enzyme in glycolysis that catalyzes the first step of the pathway by converting D-glyceraldehyde 3-phosphate (G3P) into 3-phospho-D-glyceroyl phosphate. Component of the GAIT (gamma interferon-activated inhibitor of translation) complex which mediates interferon-gamma-induced transcript-selective translation inhibition in inflammation processes. Upon interferon-gamma treatment assembles into the GAIT complex which binds to stem loop-containing GAIT elements in the 3'-UTR of diverse inflammatory mRNAs (such as ceruplasmin) and suppresses their translation.
- Gene Name:
- GAPDH
- Uniprot ID:
- P04406
- Molecular Weight:
- 36053.0 Da
- Mechanism of Action:
- 2-Hexanone and 2,5-hexanedione may inhibit sulfhydryl-dependent enzymes such as glyceraldehyde-3-phosphate dehydrogenase , impairing energy metabolism and subsequently resulting in axon deterioration.
References
- Couri D, Milks M: Toxicity and metabolism of the neurotoxic hexacarbons n-hexane, 2-hexanone, and 2,5-hexanedione. Annu Rev Pharmacol Toxicol. 1982;22:145-66. [7044283 ]