Succinylacetone
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Basic Info
| Common Name | Succinylacetone(F05386) |
| 2D Structure | |
| Description | Succinylacetone is a tyrosine metabolite It is a specific marker for Tyrosinemia type I. Type I tyrosinemia is an inherited metabolism disorder due to a shortage of the enzyme fumarylacetoacetate hydrolase that is needed to break down tyrosine. . (A3530). |
| FRCD ID | F05386 |
| CAS Number | 51568-18-4 |
| PubChem CID | 5312 |
| Formula | C7H10O4 |
| IUPAC Name | 4,6-dioxoheptanoic acid |
| InChI Key | WYEPBHZLDUPIOD-UHFFFAOYSA-N |
| InChI | InChI=1S/C7H10O4/c1-5(8)4-6(9)2-3-7(10)11/h2-4H2,1H3,(H,10,11) |
| Canonical SMILES | CC(=O)CC(=O)CCC(=O)O |
| Isomeric SMILES | CC(=O)CC(=O)CCC(=O)O |
| Synonyms |
WYEPBHZLDUPIOD-UHFFFAOYSA-N
Succinylacetone
4,6-DIOXOHEPTANOIC ACID
51568-18-4
succinyl acetone
Heptanoic acid, 4,6-dioxo-
NSC 174804
CCRIS 1387
CHEMBL222824
CHEBI:87897
|
| Classifies |
Animal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic acids and derivatives |
| Class | Keto acids and derivatives |
| Subclass | Medium-chain keto acids and derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Medium-chain keto acids and derivatives |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Medium-chain keto acid - Gamma-keto acid - 1,3-diketone - 1,3-dicarbonyl compound - Ketone - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 158.153 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 5 |
| Complexity | 183 |
| Monoisotopic Mass | 158.058 |
| Exact Mass | 158.058 |
| XLogP | -0.8 |
| Formal Charge | 0 |
| Heavy Atom Count | 11 |
| 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+ | 0.9589 |
| Human Intestinal Absorption | HIA+ | 0.9259 |
| Caco-2 Permeability | Caco2+ | 0.5301 |
| P-glycoprotein Substrate | Non-substrate | 0.6771 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9211 |
| Non-inhibitor | 0.8669 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9417 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8514 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8287 |
| CYP450 2D6 Substrate | Non-substrate | 0.8913 |
| CYP450 3A4 Substrate | Non-substrate | 0.6906 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.8151 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9540 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9620 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9601 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9212 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9886 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9237 |
| Non-inhibitor | 0.9483 | |
| AMES Toxicity | Non AMES toxic | 0.9661 |
| Carcinogens | Non-carcinogens | 0.7588 |
| Fish Toxicity | High FHMT | 0.6154 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.6922 |
| Honey Bee Toxicity | High HBT | 0.6424 |
| Biodegradation | Ready biodegradable | 0.9751 |
| Acute Oral Toxicity | III | 0.7913 |
| Carcinogenicity (Three-class) | Non-required | 0.6907 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -0.9656 | LogS |
| Caco-2 Permeability | 0.5909 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.8923 | LD50, mol/kg |
| Fish Toxicity | 1.8827 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.3544 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Inhibition of renal uptake of indium-111-DTPA-octreotide in vivo. | J Nucl Med | 1996 Aug | 8708781 |
Targets
- General Function:
- Peptidyl-proline dioxygenase activity
- Specific Function:
- Cellular oxygen sensor that catalyzes, under normoxic conditions, the post-translational formation of 4-hydroxyproline in hypoxia-inducible factor (HIF) alpha proteins. Hydroxylates a specific proline found in each of the oxygen-dependent degradation (ODD) domains (N-terminal, NODD, and C-terminal, CODD) of HIF1A. Also hydroxylates HIF2A. Has a preference for the CODD site for both HIF1A and HIF1B. Hydroxylated HIFs are then targeted for proteasomal degradation via the von Hippel-Lindau ubiquitination complex. Under hypoxic conditions, the hydroxylation reaction is attenuated allowing HIFs to escape degradation resulting in their translocation to the nucleus, heterodimerization with HIF1B, and increased expression of hypoxy-inducible genes. EGLN1 is the most important isozyme under normoxia and, through regulating the stability of HIF1, involved in various hypoxia-influenced processes such as angiogenesis in retinal and cardiac functionality. Target proteins are preferentially recognized via a LXXLAP motif.
- Gene Name:
- EGLN1
- Uniprot ID:
- Q9GZT9
- Molecular Weight:
- 46020.585 Da
References
- Mecinovic J, Loenarz C, Chowdhury R, Schofield CJ: 2-Oxoglutarate analogue inhibitors of prolyl hydroxylase domain 2. Bioorg Med Chem Lett. 2009 Nov 1;19(21):6192-5. doi: 10.1016/j.bmcl.2009.09.005. Epub 2009 Sep 6. [19775891 ]