Imperatorin
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Basic Info
| Common Name | Imperatorin(F03913) |
| 2D Structure | |
| Description | Imperatorin is found in anise. Imperatorin is present in Aegle marmelos (bael fruit) and seeds of Pastinaca sativa (parsnip).Imperatorin is a furocoumarin and a phytochemical that has been isolated from Urena lobata L. (Malvaceae). It is biosynthesized from umbelliferone, a coumarin derivative. Imperatorin has been shown to exhibit anti-hypertrophic and anti-convulsant functions (A7784, A7785). Imperatorin belongs to the family of Furanocoumarins. These are polycyclic aromatic compounds containing a furan ring fused to a coumarin moeity. |
| FRCD ID | F03913 |
| CAS Number | 482-44-0 |
| PubChem CID | 10212 |
| Formula | C16H14O4 |
| IUPAC Name | 9-(3-methylbut-2-enoxy)furo[3,2-g]chromen-7-one |
| InChI Key | OLOOJGVNMBJLLR-UHFFFAOYSA-N |
| InChI | InChI=1S/C16H14O4/c1-10(2)5-7-19-16-14-12(6-8-18-14)9-11-3-4-13(17)20-15(11)16/h3-6,8-9H,7H2,1-2H3 |
| Canonical SMILES | CC(=CCOC1=C2C(=CC3=C1OC=C3)C=CC(=O)O2)C |
| Isomeric SMILES | CC(=CCOC1=C2C(=CC3=C1OC=C3)C=CC(=O)O2)C |
| Wikipedia | Imperatorin |
| Synonyms |
IMPERATORIN
482-44-0
Ammidin
Marmelosin
Pentosalen
8-Isoamylenoxypsoralen
8-Isopentenyloxypsoralene
Marmelide
NSC 402949
CCRIS 4346
|
| Classifies |
Plant Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Phenylpropanoids and polyketides |
| Class | Coumarins and derivatives |
| Subclass | Furanocoumarins |
| Intermediate Tree Nodes | Linear furanocoumarins |
| Direct Parent | Psoralens |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Psoralen - Benzopyran - 1-benzopyran - Benzofuran - Alkyl aryl ether - Pyranone - Benzenoid - Pyran - Heteroaromatic compound - Furan - Lactone - Ether - Oxacycle - Organoheterocyclic compound - Organic oxygen compound - Hydrocarbon derivative - Organic oxide - Organooxygen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 270.284 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 3 |
| Complexity | 436 |
| Monoisotopic Mass | 270.089 |
| Exact Mass | 270.089 |
| XLogP | 3.4 |
| Formal Charge | 0 |
| Heavy Atom Count | 20 |
| 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+ | 0.8298 |
| Human Intestinal Absorption | HIA+ | 0.9962 |
| Caco-2 Permeability | Caco2- | 0.5187 |
| P-glycoprotein Substrate | Substrate | 0.6670 |
| P-glycoprotein Inhibitor | Inhibitor | 0.8783 |
| Inhibitor | 0.7308 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7391 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7743 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8374 |
| CYP450 2D6 Substrate | Non-substrate | 0.8840 |
| CYP450 3A4 Substrate | Substrate | 0.5656 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.8503 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.7199 |
| CYP450 2D6 Inhibitor | Inhibitor | 0.7115 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.8977 |
| CYP450 3A4 Inhibitor | Inhibitor | 0.7497 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.9360 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9522 |
| Non-inhibitor | 0.8890 | |
| AMES Toxicity | AMES toxic | 0.9107 |
| Carcinogens | Non-carcinogens | 0.9385 |
| Fish Toxicity | High FHMT | 0.9951 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9919 |
| Honey Bee Toxicity | High HBT | 0.8870 |
| Biodegradation | Not ready biodegradable | 0.7509 |
| Acute Oral Toxicity | III | 0.6516 |
| Carcinogenicity (Three-class) | Non-required | 0.5712 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.1536 | LogS |
| Caco-2 Permeability | 0.8364 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.7972 | LD50, mol/kg |
| Fish Toxicity | -1.4952 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.6404 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Antiviral effect of compounds derived from Angelica archangelica L. on Herpessimplex virus-1 and Coxsackievirus B3 infections. | Food Chem Toxicol | 2017 Nov | 28487231 |
| Preliminary in vitro and in vivo evaluation of antidiabetic activity of Ducrosia anethifolia Boiss. and its linear furanocoumarins. | Biomed Res Int | 2014 | 24800231 |
| Larvicidal activity of Cnidium monnieri fruit coumarins and structurally related compounds against insecticide-susceptible and insecticide-resistant Culex pipiens pallens and Aedes aegypti. | Pest Manag Sci | 2012 Jul | 22389164 |
| Inducible nitric oxide synthase and cyclooxygenase-2 participate in anti-inflammatory activity of imperatorin from Glehnia littoralis. | J Agric Food Chem | 2012 Feb 22 | 22188242 |
| Constituents of Peucedanum zenkeri seeds and their antimicrobial effects. | Pharmazie | 2003 Aug | 12967040 |
Targets
- General Function:
- Protein tyrosine/serine/threonine phosphatase activity
- Specific Function:
- Shows activity both for tyrosine-protein phosphate and serine-protein phosphate, but displays a strong preference toward phosphotyrosines. Specifically dephosphorylates and inactivates ERK1 and ERK2.
- Gene Name:
- DUSP3
- Uniprot ID:
- P51452
- Molecular Weight:
- 20478.1 Da
References
- Liu D, Kong G, Chen QC, Wang G, Li J, Xu Y, lin T, Tian Y, Zhang X, Yao X, Feng G, Lu Z, Chen H: Fatty acids as natural specific inhibitors of the proto-oncogenic protein Shp2. Bioorg Med Chem Lett. 2011 Nov 15;21(22):6833-7. doi: 10.1016/j.bmcl.2011.09.023. Epub 2011 Sep 13. [21962577 ]
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
- Gene Name:
- CYP2C9
- Uniprot ID:
- P11712
- Molecular Weight:
- 55627.365 Da
References
- Girennavar B, Jayaprakasha GK, Patil BS: Potent inhibition of human cytochrome P450 3A4, 2D6, and 2C9 isoenzymes by grapefruit juice and its furocoumarins. J Food Sci. 2007 Oct;72(8):C417-21. [17995595 ]
- General Function:
- Vitamin d3 25-hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide (PubMed:11159812). Catalyzes 4-beta-hydroxylation of cholesterol. May catalyze 25-hydroxylation of cholesterol in vitro (PubMed:21576599).
- Gene Name:
- CYP3A4
- Uniprot ID:
- P08684
- Molecular Weight:
- 57342.67 Da
References
- Girennavar B, Jayaprakasha GK, Patil BS: Potent inhibition of human cytochrome P450 3A4, 2D6, and 2C9 isoenzymes by grapefruit juice and its furocoumarins. J Food Sci. 2007 Oct;72(8):C417-21. [17995595 ]
- General Function:
- Protein tyrosine phosphatase activity
- Specific Function:
- Protein phosphatase that acts preferentially on tyrosine-phosphorylated MAPK1. Plays a role in the regulation of T and B-lymphocyte development and signal transduction.
- Gene Name:
- PTPN7
- Uniprot ID:
- P35236
- Molecular Weight:
- 40528.965 Da
References
- Liu D, Kong G, Chen QC, Wang G, Li J, Xu Y, lin T, Tian Y, Zhang X, Yao X, Feng G, Lu Z, Chen H: Fatty acids as natural specific inhibitors of the proto-oncogenic protein Shp2. Bioorg Med Chem Lett. 2011 Nov 15;21(22):6833-7. doi: 10.1016/j.bmcl.2011.09.023. Epub 2011 Sep 13. [21962577 ]