Bergamottin
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Basic Info
| Common Name | Bergamottin(F03911) |
| 2D Structure | |
| Description | Bergamottin is found in citrus. Bergamottin is a constituent of bergamot oil. Also from lemon oil and oils of other Citrus species and carrot (Daucus carota) Bergamottin is a natural furanocoumarin found principally in grapefruit juice. It is also found in the oil of bergamot, from which it was first isolated and from which its name is derived. To a lesser extent, bergamottin is also present in the essential oils of other citrus fruits. Along with the chemically related compound 6 ,7 -dihydroxybergamottin, it is believed to be responsible for the grapefruit juice effect in which the consumption of the juice affects the metabolism of a variety of pharmaceutical drugs. Bergamottin has been shown to exhibit anti-tumor function (A7783). |
| FRCD ID | F03911 |
| CAS Number | 7380-40-7 |
| PubChem CID | 7251175 |
| Formula | C21H22O4 |
| IUPAC Name | 4-[(2Z)-3,7-dimethylocta-2,6-dienoxy]furo[3,2-g]chromen-7-one |
| InChI Key | DBMJZOMNXBSRED-DHDCSXOGSA-N |
| InChI | InChI=1S/C21H22O4/c1-14(2)5-4-6-15(3)9-11-24-21-16-7-8-20(22)25-19(16)13-18-17(21)10-12-23-18/h5,7-10,12-13H,4,6,11H2,1-3H3/b15-9- |
| Canonical SMILES | CC(=CCCC(=CCOC1=C2C=CC(=O)OC2=CC3=C1C=CO3)C)C |
| Isomeric SMILES | CC(=CCC/C(=C\COC1=C2C=CC(=O)OC2=CC3=C1C=CO3)/C)C |
| Wikipedia | Bergamottin |
| Synonyms |
ST057234
4-[(2Z)-3,7-dimethylocta-2,6-dienoxy]furo[3,2-g]chromen-7-one
AC1OIEWE
Bergaptol geranyl ether
CHEMBL1571785
SCHEMBL14029418
ZINC12363891
AKOS024282615
NCGC00017345-02
NCGC00142519-01
|
| Classifies |
Plant Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Lipids and lipid-like molecules |
| Class | Prenol lipids |
| Subclass | Terpene lactones |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Terpene lactones |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Terpene lactone - Linear furanocoumarin - Furanocoumarin - Psoralen - Coumarin - Benzopyran - 1-benzopyran - Monoterpenoid - Aromatic monoterpenoid - Benzofuran - Alkyl aryl ether - Pyranone - Benzenoid - Pyran - Furan - Heteroaromatic compound - Lactone - Oxacycle - Organoheterocyclic compound - Ether - Organic oxygen compound - Hydrocarbon derivative - Organic oxide - Organooxygen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 338.403 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 6 |
| Complexity | 570 |
| Monoisotopic Mass | 338.152 |
| Exact Mass | 338.152 |
| XLogP | 5.6 |
| Formal Charge | 0 |
| Heavy Atom Count | 25 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 1 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.8845 |
| Human Intestinal Absorption | HIA+ | 0.9964 |
| Caco-2 Permeability | Caco2+ | 0.5379 |
| P-glycoprotein Substrate | Substrate | 0.7274 |
| P-glycoprotein Inhibitor | Inhibitor | 0.8241 |
| Inhibitor | 0.9514 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.6531 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7980 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8387 |
| CYP450 2D6 Substrate | Non-substrate | 0.8382 |
| CYP450 3A4 Substrate | Substrate | 0.6824 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.9107 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.8949 |
| CYP450 2D6 Inhibitor | Inhibitor | 0.8931 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.8994 |
| CYP450 3A4 Inhibitor | Inhibitor | 0.8123 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.8031 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.7136 |
| Non-inhibitor | 0.7040 | |
| AMES Toxicity | Non AMES toxic | 0.5000 |
| Carcinogens | Non-carcinogens | 0.9402 |
| Fish Toxicity | High FHMT | 0.9989 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9997 |
| Honey Bee Toxicity | High HBT | 0.8734 |
| Biodegradation | Not ready biodegradable | 0.8044 |
| Acute Oral Toxicity | III | 0.4952 |
| Carcinogenicity (Three-class) | Non-required | 0.6340 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -5.3210 | LogS |
| Caco-2 Permeability | 0.9140 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.8500 | LD50, mol/kg |
| Fish Toxicity | -0.9384 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.7805 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Components of foods inhibit a drug exporter, human multidrug and toxin extrusion transporter 1. | Biol Pharm Bull | 2014 | 24492725 |
| Major furocoumarins in grapefruit juice II: phototoxicity, photogenotoxicity, and inhibitory potency vs. cytochrome P450 3A4 activity. | Food Chem Toxicol | 2012 Mar | 22155270 |
| Identification of coumarins from lemon fruit (Citrus limon) as inhibitors of in vitro tumor promotion and superoxide and nitric oxide generation. | J Agric Food Chem | 1999 Aug | 10552623 |
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 ]