Acridine
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Basic Info
| Common Name | Acridine(F03770) |
| 2D Structure | |
| Description | Acridine is one of over 100 different polycyclic aromatic hydrocarbons (PAHs). PAHs are chemicals that are formed during the incomplete burning organic substances, such as fossil fuels. They are usually found as a mixture containing two or more of these compounds. (L10) |
| FRCD ID | F03770 |
| CAS Number | 260-94-6 |
| PubChem CID | 9215 |
| Formula | C13H9N |
| IUPAC Name | acridine |
| InChI Key | DZBUGLKDJFMEHC-UHFFFAOYSA-N |
| InChI | InChI=1S/C13H9N/c1-3-7-12-10(5-1)9-11-6-2-4-8-13(11)14-12/h1-9H |
| Canonical SMILES | C1=CC=C2C(=C1)C=C3C=CC=CC3=N2 |
| Isomeric SMILES | C1=CC=C2C(=C1)C=C3C=CC=CC3=N2 |
| Wikipedia | Acridine |
| Synonyms |
9-Azaanthracene
Akridin [Czech]
ACRIDINE
260-94-6
2,3-Benzoquinoline
Acrydine
10-Azaanthracene
Akridin
Dibenzo[b,e]pyridine
2,3,5,6-Dibenzopyridine
|
| Classifies |
Pollutant
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Quinolines and derivatives |
| Subclass | Benzoquinolines |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Acridines |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Acridine - Benzenoid - Pyridine - Heteroaromatic compound - Azacycle - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Organonitrogen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as acridines. These are organic compounds containing the acridine moiety, a linear tricyclic heterocycle which consists of two benzene rings joined by a pyridine ring. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 179.222 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 0 |
| Complexity | 181 |
| Monoisotopic Mass | 179.073 |
| Exact Mass | 179.073 |
| XLogP | 3.4 |
| Formal Charge | 0 |
| Heavy Atom Count | 14 |
| 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+ | 0.9866 |
| Human Intestinal Absorption | HIA+ | 0.9961 |
| Caco-2 Permeability | Caco2+ | 0.7659 |
| P-glycoprotein Substrate | Non-substrate | 0.7617 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9517 |
| Non-inhibitor | 0.9754 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7613 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.6206 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8313 |
| CYP450 2D6 Substrate | Non-substrate | 0.8351 |
| CYP450 3A4 Substrate | Non-substrate | 0.7555 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.9188 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.5260 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.5667 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.8774 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8837 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.6283 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9575 |
| Non-inhibitor | 0.8709 | |
| AMES Toxicity | AMES toxic | 0.9107 |
| Carcinogens | Non-carcinogens | 0.9312 |
| Fish Toxicity | High FHMT | 0.5681 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.8189 |
| Honey Bee Toxicity | High HBT | 0.5608 |
| Biodegradation | Not ready biodegradable | 0.8030 |
| Acute Oral Toxicity | III | 0.6050 |
| Carcinogenicity (Three-class) | Non-required | 0.6901 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.8427 | LogS |
| Caco-2 Permeability | 1.7335 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.2813 | LD50, mol/kg |
| Fish Toxicity | 1.7656 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.2758 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Methylparaben induces malformations and alterations on apoptosis, oxidant-antioxidant status, ccnd1 and myca expressions in zebrafish embryos. | J Biochem Mol Toxicol | 2018 Mar | 29360218 |
| Sardine oil loaded vanillic acid grafted chitosan microparticles, a new functional food ingredient: attenuates myocardial oxidative stress and apoptosis in cardiomyoblast cell lines (H9c2). | Cell Stress Chaperones | 2018 Mar | 28766116 |
| In vitro effects of two major phenolic compounds from the family Lamiaceae plants on the human gastric carcinoma cells. | Toxicol Ind Health | 2018 Aug | 29848188 |
| Assessment of sulforaphane-induced protective mechanisms against cadmium toxicity in human mesenchymal stem cells. | Environ Sci Pollut Res Int | 2018 Apr | 29383641 |
| The apoptotic effects of <i>Brucea javanica</i> fruit extract against HT29 cells associated with p53 upregulation and inhibition of NF-κB translocation. | Drug Des Devel Ther | 2018 | 29636600 |
| Using Vital Dyes to Trace Uptake of dsRNA by Green Peach Aphid Allows Effective Assessment of Target Gene Knockdown. | Int J Mol Sci | 2017 Jan 3 | 28054949 |
| Interaction of silver and gold nanoparticles in mammalian cancer: as real topical bullet for wound healing- A comparative study. | In Vitro Cell Dev Biol Anim | 2017 Aug | 28462492 |
| In vitro assessment of the genotoxic and cytotoxic effects of boiled juice (tucupi) from Manihot esculenta Crantz roots. | Genet Mol Res | 2016 Oct 5 | 27808379 |
| Combined effects of low levels of palmitate on toxicity of ZnO nanoparticles to THP-1 macrophages. | Environ Toxicol Pharmacol | 2016 Dec | 27770658 |
| [Disinfectants - bacterial cells interactions in the view of hygiene and public health]. | Postepy Hig Med Dosw (Online) | 2015 Sep 20 | 26400890 |
| Isolation of a flavonoid, apigenin 7-O-glucoside, from Mentha longifolia (L.)Hudson subspecies longifolia and its genotoxic potency. | Toxicol Ind Health | 2015 Sep | 23377117 |
| Sterigmatocystin-induced oxidative DNA damage in human liver-derived cell line through lysosomal damage. | Toxicol In Vitro | 2015 Feb | 25176419 |
| Structure of the tripartite multidrug efflux pump AcrAB-TolC suggests an alternative assembly mode. | Mol Cells | 2015 | 26013259 |
| Comparative genotoxicity of nanosilver in human liver HepG2 and colon Caco2 cells evaluated by fluorescent microscopy of cytochalasin B-blocked micronucleus formation. | J Appl Toxicol | 2014 Nov | 24909674 |
| In vitro cytotoxicity assessment of imidazolium ionic liquids: biological effects in fish Channel Catfish Ovary (CCO) cell line. | Ecotoxicol Environ Saf | 2013 Jun | 23561264 |
| Ochratoxin-induced toxicity, oxidative stress and apoptosis ameliorated by quercetin--modulation by Nrf2. | Food Chem Toxicol | 2013 Dec | 23994659 |
| Inhibitory effects of neem seed oil and its extract on various direct acting and activation-dependant mutagens-induced bacterial mutagenesis. | Pharm Biol | 2013 Dec | 23998188 |
| A preliminary experimental study on the cardiac toxicity of glutamate and the role of α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor in rats. | Chin Med J (Engl) | 2013 Apr | 23557566 |
| The influence of dietary β-glucan, PAMP exposure and Aeromonas salmonicida on apoptosis modulation in common carp (Cyprinus carpio). | Fish Shellfish Immunol | 2012 Oct | 23198291 |
| Persistent, toxin-antitoxin system-independent, tetracycline resistance-encoding plasmid from a dairy Enterococcus faecium isolate. | Appl Environ Microbiol | 2011 Oct | 21784909 |
Targets
- General Function:
- Transcription regulatory region dna binding
- Specific Function:
- Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues. Regulates the circadian clock by inhibiting the basal and circadian expression of the core circadian component PER1. Inhibits PER1 by repressing the CLOCK-ARNTL/BMAL1 heterodimer mediated transcriptional activation of PER1.
- Gene Name:
- AHR
- Uniprot ID:
- P35869
- Molecular Weight:
- 96146.705 Da
- Mechanism of Action:
- Many PAH's induce the expression of cytochrome P450 enzymes, especially CYP1A1, CYP1A2, and CYP1B1, by binding to the aryl hydrocarbon receptor or glycine N-methyltransferase protein. These enzymes metabolize PAH's into their toxic intermediates. The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis.
References
- Uno S, Dragin N, Miller ML, Dalton TP, Gonzalez FJ, Nebert DW: Basal and inducible CYP1 mRNA quantitation and protein localization throughout the mouse gastrointestinal tract. Free Radic Biol Med. 2008 Feb 15;44(4):570-83. Epub 2007 Nov 12. [17997381 ]
- General Function:
- Glycine n-methyltransferase activity
- Specific Function:
- Catalyzes the methylation of glycine by using S-adenosylmethionine (AdoMet) to form N-methylglycine (sarcosine) with the concomitant production of S-adenosylhomocysteine (AdoHcy). Possible crucial role in the regulation of tissue concentration of AdoMet and of metabolism of methionine.
- Gene Name:
- GNMT
- Uniprot ID:
- Q14749
- Molecular Weight:
- 32742.0 Da
- Mechanism of Action:
- Many PAH's induce the expression of cytochrome P450 enzymes, especially CYP1A1, CYP1A2, and CYP1B1, by binding to the aryl hydrocarbon receptor or glycine N-methyltransferase protein. These enzymes metabolize PAH's into their toxic intermediates. The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis.
References
- Uno S, Dragin N, Miller ML, Dalton TP, Gonzalez FJ, Nebert DW: Basal and inducible CYP1 mRNA quantitation and protein localization throughout the mouse gastrointestinal tract. Free Radic Biol Med. 2008 Feb 15;44(4):570-83. Epub 2007 Nov 12. [17997381 ]