Phellopterin
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Basic Info
| Common Name | Phellopterin(F03916) |
| 2D Structure | |
| Description | A naturally occurring furanocoumarin found in roots of Angelica dahurica and in Seseli elatum (L579). Furocoumarins, are phototoxic and photocarcinogenic. They intercalate DNA and photochemically induce mutations. Furocoumarins are botanical phytoalexins found to varying extents in a variety of vegetables and fruits, notably citrus fruits. The levels of furocoumarins present in our diets, while normally well below that causing evident acute phototoxicity, do cause pharmacologically relevant drug interactions. Some are particularly active against cytochrome P450s. For example, in humans, bergamottin and dihydroxybergamottin are responsible for the 'grapefruit juice effect', in which these furanocoumarins affect the metabolism of certain drugs. |
| FRCD ID | F03916 |
| CAS Number | 2543-94-4 |
| PubChem CID | 98608 |
| Formula | C17H16O5 |
| IUPAC Name | 4-methoxy-9-(3-methylbut-2-enoxy)furo[3,2-g]chromen-7-one |
| InChI Key | BMLZFLQMBMYVHG-UHFFFAOYSA-N |
| InChI | InChI=1S/C17H16O5/c1-10(2)6-8-21-17-15-12(7-9-20-15)14(19-3)11-4-5-13(18)22-16(11)17/h4-7,9H,8H2,1-3H3 |
| Canonical SMILES | CC(=CCOC1=C2C(=C(C3=C1OC(=O)C=C3)OC)C=CO2)C |
| Isomeric SMILES | CC(=CCOC1=C2C(=C(C3=C1OC(=O)C=C3)OC)C=CO2)C |
| Synonyms |
4-methoxy-9-(3-methylbut-2-enoxy)furo[3,2-g]chromen-7-one
Phellopterin
2543-94-4
MLS000574895
CHEBI:80887
SMR000156210
Phelloterin
7H-Furo(3,2-g)(1)benzopyran-7-one, 4-methoxy-9-((3-methyl-2-butenyl)oxy)-
7H-Furo[3,2-g][1]benzopyran-7-one, 4-methoxy-9-[(3-methyl-2-butenyl)oxy]-
NSC 152469
|
| 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 - Psoralens |
| Direct Parent | 5-methoxypsoralens |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | 5-methoxypsoralen - Benzopyran - 1-benzopyran - Benzofuran - Anisole - Alkyl aryl ether - Pyranone - Pyran - Benzenoid - Furan - Heteroaromatic compound - Lactone - Oxacycle - Ether - Organoheterocyclic compound - Organic oxygen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as 5-methoxypsoralens. These are psoralens containing a methoxy group attached at the C5 position of the psoralen group. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 300.31 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 4 |
| Complexity | 479 |
| Monoisotopic Mass | 300.1 |
| Exact Mass | 300.1 |
| XLogP | 3.8 |
| Formal Charge | 0 |
| Heavy Atom Count | 22 |
| 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+ | 0.6676 |
| Human Intestinal Absorption | HIA+ | 0.9925 |
| Caco-2 Permeability | Caco2+ | 0.5243 |
| P-glycoprotein Substrate | Substrate | 0.6639 |
| P-glycoprotein Inhibitor | Inhibitor | 0.9211 |
| Inhibitor | 0.8784 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7371 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7539 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8357 |
| CYP450 2D6 Substrate | Non-substrate | 0.8773 |
| CYP450 3A4 Substrate | Substrate | 0.6245 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.8169 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.5477 |
| CYP450 2D6 Inhibitor | Inhibitor | 0.6410 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.8984 |
| CYP450 3A4 Inhibitor | Inhibitor | 0.6951 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.8888 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9485 |
| Non-inhibitor | 0.9025 | |
| AMES Toxicity | AMES toxic | 0.8624 |
| Carcinogens | Non-carcinogens | 0.9346 |
| Fish Toxicity | High FHMT | 0.9915 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9962 |
| Honey Bee Toxicity | High HBT | 0.9020 |
| Biodegradation | Not ready biodegradable | 0.7874 |
| Acute Oral Toxicity | III | 0.5497 |
| Carcinogenicity (Three-class) | Non-required | 0.5570 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.1020 | LogS |
| Caco-2 Permeability | 1.0722 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 3.0767 | LD50, mol/kg |
| Fish Toxicity | -1.4359 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.8895 | pIGC50, ug/L |
Targets
- 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 homodimerization activity
- Specific Function:
- Catalyzes the rate-limiting step of the oxidative pentose-phosphate pathway, which represents a route for the dissimilation of carbohydrates besides glycolysis. The main function of this enzyme is to provide reducing power (NADPH) and pentose phosphates for fatty acid and nucleic acid synthesis.
- Gene Name:
- G6PD
- Uniprot ID:
- P11413
- Molecular Weight:
- 59256.31 Da
References
- Liu T, Lin Y, Wen X, Jorissen RN, Gilson MK: BindingDB: a web-accessible database of experimentally determined protein-ligand binding affinities. Nucleic Acids Res. 2007 Jan;35(Database issue):D198-201. Epub 2006 Dec 1. [17145705 ]