Methoxsalen
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Basic Info
| Common Name | Methoxsalen(F03912) |
| 2D Structure | |
| Description | Methoxsalen is only found in individuals that have used or taken this drug. It is a naturally occurring furocoumarin compound found in several species of plants, including Psoralea corylifolia. It is a photoactive substance that forms DNA adducts in the presence of ultraviolet A irradiation. After activation Methoxsalen binds preferentially to the guanine and cytosine moieties of DNA, leading to cross-linking of DNA, thus inhibiting DNA synthesis and function. |
| FRCD ID | F03912 |
| CAS Number | 298-81-7 |
| PubChem CID | 4114 |
| Formula | C12H8O4 |
| IUPAC Name | 9-methoxyfuro[3,2-g]chromen-7-one |
| InChI Key | QXKHYNVANLEOEG-UHFFFAOYSA-N |
| InChI | InChI=1S/C12H8O4/c1-14-12-10-8(4-5-15-10)6-7-2-3-9(13)16-11(7)12/h2-6H,1H3 |
| Canonical SMILES | COC1=C2C(=CC3=C1OC=C3)C=CC(=O)O2 |
| Isomeric SMILES | COC1=C2C(=CC3=C1OC=C3)C=CC(=O)O2 |
| Wikipedia | Methoxsalen |
| Synonyms |
methoxsalen
8-Methoxypsoralen
XANTHOTOXIN
298-81-7
Meladinine
Ammoidin
Oxsoralen
Meloxine
Oxypsoralen
Xanthotoxine
|
| 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 | 8-methoxypsoralens |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | 8-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 8-methoxypsoralens. These are psoralens containing a methoxy group attached at the C8 position of the psoralen group. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 216.192 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 1 |
| Complexity | 325 |
| Monoisotopic Mass | 216.042 |
| Exact Mass | 216.042 |
| XLogP | 1.9 |
| Formal Charge | 0 |
| Heavy Atom Count | 16 |
| 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+ | 0.9211 |
| Human Intestinal Absorption | HIA+ | 0.9921 |
| Caco-2 Permeability | Caco2+ | 0.6185 |
| P-glycoprotein Substrate | Non-substrate | 0.5518 |
| P-glycoprotein Inhibitor | Inhibitor | 0.5000 |
| Inhibitor | 0.5468 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8178 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6431 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7921 |
| CYP450 2D6 Substrate | Non-substrate | 0.9116 |
| CYP450 3A4 Substrate | Non-substrate | 0.6236 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.9629 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.5968 |
| CYP450 2D6 Inhibitor | Inhibitor | 0.8932 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.9316 |
| CYP450 3A4 Inhibitor | Inhibitor | 0.7740 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.7381 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9563 |
| Non-inhibitor | 0.9638 | |
| AMES Toxicity | AMES toxic | 0.8860 |
| Carcinogens | Non-carcinogens | 0.9552 |
| Fish Toxicity | High FHMT | 0.9401 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9849 |
| Honey Bee Toxicity | High HBT | 0.8252 |
| Biodegradation | Not ready biodegradable | 0.7255 |
| Acute Oral Toxicity | III | 0.7930 |
| Carcinogenicity (Three-class) | Warning | 0.5533 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.5238 | LogS |
| Caco-2 Permeability | 0.8187 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.4054 | LD50, mol/kg |
| Fish Toxicity | -0.1047 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.5977 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Expression analysis of two P450 monooxygenase genes of the tobacco cutworm moth (Spodoptera litura) at different developmental stages and in response to plant allelochemicals. | J Chem Ecol | 2015 Jan | 25547988 |
| Preliminary in vitro and in vivo evaluation of antidiabetic activity of Ducrosia anethifolia Boiss. and its linear furanocoumarins. | Biomed Res Int | 2014 | 24800231 |
| Inhibition of cytochrome P450 2A participating in coumarin 7-hydroxylation in pigliver microsomes. | J Vet Pharmacol Ther | 2011 Oct | 21244437 |
| In vitro biotransformation and investigation of metabolic enzymes possiblyresponsible for the metabolism of bisdesoxyolaquindox in the liver fractions ofrats, chicken, and pigs. | Toxicology | 2011 Jan 11 | 20955753 |
| Isolation and identification of insecticidal components from Citrus aurantium fruit peel extract. | J Agric Food Chem | 2008 Jul 23 | 18578532 |
| Apiaceous vegetable constituents inhibit human cytochrome P-450 1A2 (hCYP1A2) activity and hCYP1A2-mediated mutagenicity of aflatoxin B1. | Food Chem Toxicol | 2006 Sep | 16762476 |
| Phytotoxins from the leaves of Ruta graveolens. | J Agric Food Chem | 2004 Jun 2 | 15161195 |
| Carbaryl induces CYP1A1 gene expression in HepG2 and HaCaT cells but is not aligand of the human hepatic Ah receptor. | Toxicol Appl Pharmacol | 1997 May | 9169082 |
| Photosensitized decontamination of blood with the silicon phthalocyanine Pc 4: noactivation of the human immunodeficiency virus promoter. | Photochem Photobiol | 1997 Mar | 9077132 |
| Isolation and identification of antimicrobial furocoumarins from parsley. | J Food Prot | 1997 Jan | 10465045 |
| Medical UV exposures and HIV activation. | Photochem Photobiol | 1996 Aug | 8760563 |
| Treatment of psoriasis with psoralens and ultraviolet A. A double-blind comparison of 8-methoxypsoralen and 5-methoxypsoralen. | Photodermatol Photoimmunol Photomed | 1994 Oct | 7880762 |
| Activation of the human immunodeficiency virus promoter by UVA radiation incombination with psoralens or angelicins. | Photochem Photobiol | 1993 Aug | 8415914 |
| Spectral effects in activation of the human immunodeficiency virus promoter bypsoralens plus ultraviolet A treatment. | Photodermatol Photoimmunol Photomed | 1992-1993 Dec | 1343228 |
| Antioxidant enzyme level response to prooxidant allelochemicals in larvae of the southern armyworm moth, Spodoptera eridania. | Free Radic Res Commun | 1990 | 2161387 |
| Use of the occlusive patch to evaluate the photosensitive properties of chemicals in guinea-pigs. | Food Chem Toxicol | 1985 Jul | 4029836 |
| Long-term risks of psoralen and UV-A therapy for psoriasis. | Arch Dermatol | 1983 May | 6342539 |
| Isolation and identification of xanthotoxin (8-methoxypsoralen) and bergapten (5-methoxypsoralen) from celery infected with Sclerotinia sclerotiorum. | Appl Microbiol | 1972 May | 5031558 |
Targets
- General Function:
- Serine hydrolase activity
- Specific Function:
- Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
- Gene Name:
- ACHE
- Uniprot ID:
- P22303
- Molecular Weight:
- 67795.525 Da
References
- Kang SY, Lee KY, Sung SH, Park MJ, Kim YC: Coumarins isolated from Angelica gigas inhibit acetylcholinesterase: structure-activity relationships. J Nat Prod. 2001 May;64(5):683-5. [11374978 ]
- General Function:
- Serotonin binding
- Specific Function:
- Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
- Gene Name:
- MAOA
- Uniprot ID:
- P21397
- Molecular Weight:
- 59681.27 Da
References
- Santana L, Uriarte E, Gonzalez-Diaz H, Zagotto G, Soto-Otero R, Mendez-Alvarez E: A QSAR model for in silico screening of MAO-A inhibitors. Prediction, synthesis, and biological assay of novel coumarins. J Med Chem. 2006 Feb 9;49(3):1149-56. [16451079 ]
- 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 ]