Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C19H18O8 |
| Molecular Weight | 374.3414 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC(=O)C1=C(O)C(C)=C(OC(=O)C2=C(O)C(C=O)=C(O)C=C2C)C=C1C
InChI
InChIKey=YLOYKYXNDHOHHT-UHFFFAOYSA-N
InChI=1S/C19H18O8/c1-8-5-12(21)11(7-20)17(23)15(8)19(25)27-13-6-9(2)14(18(24)26-4)16(22)10(13)3/h5-7,21-23H,1-4H3
| Molecular Formula | C19H18O8 |
| Molecular Weight | 374.3414 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Atranorin is the main compound of the lichen Cladina kalbii Ahti, which grows in the arid regions of northeastern Brazil. Atranorin possesses anticancer activity, experiments in vitro and in vivo have shown, that it may inhibit lung cancer cell motility and tumorigenesis by affecting AP-1, Wnt, and STAT signaling and suppressing RhoGTPase activity. In addition, experiments on animal have revealed, that Atranorin might be an important tool in the management and/or treatment of inflammatory disorders.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: map04310 |
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Target ID: P63000 Gene ID: 5879.0 Gene Symbol: RAC1 Target Organism: Homo sapiens (Human) |
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Target ID: P60953 Gene ID: 998.0 Gene Symbol: CDC42 Target Organism: Homo sapiens (Human) |
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Target ID: map04630 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Lichen secondary metabolites are responsible for induction of apoptosis in HT-29 and A2780 human cancer cell lines. | 2012-04 |
|
| Antimalarial drug interactions of compounds isolated from Kigelia africana (Bignoniaceae) and their synergism with artemether, against the multidrug-resistant W2mef Plasmodium falciparum strain. | 2012-02 |
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| In vitro antiplasmodial activity and cytotoxicity of crude extracts and compounds from the stem bark of Kigelia africana (Lam.) Benth (Bignoniaceae). | 2011-06 |
|
| Antinociceptive activity of atranorin in mice orofacial nociception tests. | 2010-12-09 |
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| Determination of Teloschistes flavicans (sw) norm anti-inflammatory activity. | 2010-07 |
|
| Light screening in lichen cortices can be quantified by chlorophyll fluorescence techniques for both reflecting and absorbing pigments. | 2010-04 |
|
| Antimycobacterial activity of lichen substances. | 2010-04 |
|
| Lichen metabolites modulate hydrogen peroxide and nitric oxide in mouse macrophages. | 2009-12-05 |
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| Phytochemical investigation of the Australian lichens Ramalina glaucescens and Xanthoria parietina. | 2009-07 |
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| Biologically active components of a Papua New Guinea analgesic and anti-inflammatory lichen preparation. | 2009-07 |
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| Characterization of a non-reducing polyketide synthase gene from lichen Dirinaria applanata. | 2009-04 |
|
| Is a low content in atranol/chloroatranol safe in oak moss-sensitized individuals? | 2009-02 |
|
| Chemical constituents of the lichen, Candelaria concolor: a complete NMR and chemical degradative investigation. | 2009 |
|
| Light might regulate divergently depside and depsidone accumulation in the lichen Parmotrema hypotropum by affecting thallus temperature and water potential. | 2008-10-07 |
|
| Purification, physicochemical properties, thermal analysis and antinociceptive effect of atranorin extracted from Cladina kalbii. | 2008-10 |
|
| Quantitative determination of secondary metabolites in Cladina stellaris and other lichens by micellar electrokinetic chromatography. | 2008-02-22 |
|
| Antimicrobial activity of extracts of the lichen Parmelia sulcata and its salazinic acid constituent. | 2007-10-05 |
|
| Ozone reactivity and free radical scavenging behavior of phenolic secondary metabolites in lichens exposed to chronic oxidant air pollution from Mexico City. | 2007-08 |
|
| Lupane triterpenoids from Acacia mellifera with cytotoxic activity. | 2007-05-15 |
|
| Beta-orcinol metabolites from the lichen Hypotrachyna revoluta. | 2007-05-12 |
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| Metabolites from the Lichen Ochrolechia parella growing under two different heliotropic conditions. | 2007-02 |
|
| Lichen substances affect metal adsorption in Hypogymnia physodes. | 2007-01 |
|
| Antimicrobial activity of extracts of chemical races of the lichen Pseudevernia furfuracea and their physodic acid, chloroatranorin, atranorin, and olivetoric acid constituents. | 2006-09-23 |
|
| A study of the genetic variability of Rhizoplaca chrysoleuca using DNA sequences and secondary metabolic substances. | 2006-06-28 |
|
| Comparison of elicitation potential of chloroatranol and atranol--2 allergens in oak moss absolute. | 2006-04 |
|
| Chemistry of the lichen Hypogymnia physodes transplanted to an industrial region. | 2005-12 |
|
| Solubilization of poorly soluble lichen metabolites for biological testing on cell lines. | 2005-04 |
|
| Antifungal constituents from the Chinese moss Homalia trichomanoides. | 2005-01 |
|
| The antimicrobial activity of extracts of the lichen Cladonia foliacea and its (-)-usnic acid, atranorin, and fumarprotocetraric acid constituents. | 2004-07-10 |
|
| A study of lipid secretion from the lichen symbionts, ascomycetous fungus Myelochroa leucotyliza and green alga Trebouxia sp. | 2004-06 |
|
| Identification of crystalline material found in the thallus of the lichen, Myelochroa leucotyliza. | 2004-06 |
|
| Culture studies and secondary compounds of six Ramalina species. | 2004-05 |
|
| Contact allergy to oak moss: search for sensitizing molecules using combined bioassay-guided chemical fractionation, GC-MS, and structure-activity relationship analysis. | 2003-11 |
|
| Identification and quantitation of allelochemicals from the lichen Lethariella canariensis: phytotoxicity and antioxidative activity. | 2003-09 |
|
| Enzymatic production of atranorin: a component of the oak moss absolute by immobilized lichen cells. | 2003-04 |
|
| Production of phenolics by immobilized cells of the lichen Pseudevernia furfuracea: the role of epiphytic bacteria. | 2001-06 |
|
| Antimycobacterial activity of lichen metabolites in vitro. | 1998-04 |
|
| Depsides and depsidones as inhibitors of HIV-1 integrase: discovery of novel inhibitors through 3D database searching. | 1997-03-14 |
Patents
Sample Use Guides
Xenograft mouse model: atranorin (10 mg/kg) mixed with 20% DMSO every 3 days by intraperitoneal injection for 2 weeks.
Anti-inflammatory study: acute hind paw edema was induced in male rats by injecting 0.1 mL of carrageenan into the subplantar region of the right hind paw. Atranorin (ATR) (50, 100, and 200 mg/kg, p.o.) was administered to three different groups, while two other groups served as negative and positive controls and received vehicle (0.9% saline with two drops of 0.2% Tween 80, a solvent for ATR) and standard drug (aspirin, 300 mg/kg, p.o.), respectively. ATR and aspirin were administered 1 h prior to the injection of carrageenan.
Route of Administration:
Other
The inhibitory activity of atranorin (5 μg/mL) in additional lung cancer cell lines was examined by performing invasion assays in H460, H1650, H1975, and LLC cells. Atranorin treatment significantly decreased the number of invaded H460, H1650, H1975, and LLC cells. Quantitative analysis showed that atranorin inhibited invasion by 50%, 24%, 30%, and 80% in H460, H1650, H1975, and LLC cells, respectively, compared with vehicle-treated cells.
| Substance Class |
Chemical
Created
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450U2VJ2VG
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| Record Status |
Validated (UNII)
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C026304
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Atranorin
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