Fumarin
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Basic Info
| Common Name | Fumarin(F04814) |
| 2D Structure | |
| Description | Fumarin is an anticoagulant and rodenticide derived from coumarin. (L1252) |
| FRCD ID | F04814 |
| CAS Number | 117-52-2 |
| PubChem CID | 8335 |
| Formula | C17H14O5 |
| IUPAC Name | 3-[1-(furan-2-yl)-3-oxobutyl]-2-hydroxychromen-4-one |
| InChI Key | VGVYRHYDNGFIGF-UHFFFAOYSA-N |
| InChI | InChI=1S/C17H14O5/c1-10(18)9-12(13-7-4-8-21-13)15-16(19)11-5-2-3-6-14(11)22-17(15)20/h2-8,12,20H,9H2,1H3 |
| Canonical SMILES | CC(=O)CC(C1=CC=CO1)C2=C(OC3=CC=CC=C3C2=O)O |
| Isomeric SMILES | CC(=O)CC(C1=CC=CO1)C2=C(OC3=CC=CC=C3C2=O)O |
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Phenylpropanoids and polyketides |
| Class | Coumarins and derivatives |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Coumarins and derivatives |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Chromone - Coumarin - Benzopyran - 1-benzopyran - Pyranone - Pyran - Benzenoid - Heteroaromatic compound - Furan - Vinylogous acid - Ketone - Oxacycle - Organoheterocyclic compound - Organic oxygen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Carbonyl group - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 298.294 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 4 |
| Complexity | 495 |
| Monoisotopic Mass | 298.084 |
| Exact Mass | 298.084 |
| XLogP | 1.8 |
| Formal Charge | 0 |
| Heavy Atom Count | 22 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 1 |
| 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+ | 0.9395 |
| Human Intestinal Absorption | HIA+ | 0.9538 |
| Caco-2 Permeability | Caco2+ | 0.6253 |
| P-glycoprotein Substrate | Non-substrate | 0.5056 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8867 |
| Non-inhibitor | 0.8514 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8577 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7967 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.6892 |
| CYP450 2D6 Substrate | Non-substrate | 0.6321 |
| CYP450 3A4 Substrate | Non-substrate | 0.6082 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.6037 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.8397 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9015 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.7311 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8084 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8125 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8688 |
| Non-inhibitor | 0.9702 | |
| AMES Toxicity | Non AMES toxic | 0.6152 |
| Carcinogens | Non-carcinogens | 0.9455 |
| Fish Toxicity | High FHMT | 0.9834 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9719 |
| Honey Bee Toxicity | High HBT | 0.6477 |
| Biodegradation | Not ready biodegradable | 0.8781 |
| Acute Oral Toxicity | I | 0.7706 |
| Carcinogenicity (Three-class) | Danger | 0.3923 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.9157 | LogS |
| Caco-2 Permeability | 0.7664 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 4.0456 | LD50, mol/kg |
| Fish Toxicity | -0.5318 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.9013 | pIGC50, ug/L |
Targets
- General Function:
- Vitamin-k-epoxide reductase (warfarin-sensitive) activity
- Specific Function:
- Involved in vitamin K metabolism. Catalytic subunit of the vitamin K epoxide reductase (VKOR) complex which reduces inactive vitamin K 2,3-epoxide to active vitamin K. Vitamin K is required for the gamma-carboxylation of various proteins, including clotting factors, and is required for normal blood coagulation, but also for normal bone development.
- Gene Name:
- VKORC1
- Uniprot ID:
- Q9BQB6
- Molecular Weight:
- 18234.3 Da
- Mechanism of Action:
- Fumarin inhibits the enzyme Vitamin K epoxide reductase. This enzyme is needed for the reconstitution of the vitamin K in its cycle from vitamin K-epoxide, and so fumarin steadily decreases the level of active vitamin K in the blood. Vitamin K is required for the synthesis of important substances including prothrombin, which is involved in blood clotting. This disruption becomes increasingly severe until the blood effectively loses any ability to clot. In addition, fumarin increases permeability of blood capillaries. The blood plasma and blood itself begins to leak from the blood vessels, causing internal bleeding leading to shock, loss of consciousness, and eventually death.
References
- Wikipedia. Brodifacoum. Last Updated 22 June 2009. : http://en.wikipedia.org/wiki/Brodifacoum