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 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28811522 |
|||
Target ID: P63000 Gene ID: 5879.0 Gene Symbol: RAC1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/28811522 |
|||
Target ID: P60953 Gene ID: 998.0 Gene Symbol: CDC42 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/28811522 |
|||
Target ID: map04630 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28811522 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Antimycobacterial activity of lichen metabolites in vitro. | 1998 Apr |
|
Production of phenolics by immobilized cells of the lichen Pseudevernia furfuracea: the role of epiphytic bacteria. | 2001 Jun |
|
Contact allergy to oak moss: search for sensitizing molecules using combined bioassay-guided chemical fractionation, GC-MS, and structure-activity relationship analysis. | 2003 Nov |
|
Identification of crystalline material found in the thallus of the lichen, Myelochroa leucotyliza. | 2004 Jun |
|
The antimicrobial activity of extracts of the lichen Cladonia foliacea and its (-)-usnic acid, atranorin, and fumarprotocetraric acid constituents. | 2004 Mar-Apr |
|
A study of the genetic variability of Rhizoplaca chrysoleuca using DNA sequences and secondary metabolic substances. | 2006 Jan-Feb |
|
Antimicrobial activity of extracts of chemical races of the lichen Pseudevernia furfuracea and their physodic acid, chloroatranorin, atranorin, and olivetoric acid constituents. | 2006 Jul-Aug |
|
Light might regulate divergently depside and depsidone accumulation in the lichen Parmotrema hypotropum by affecting thallus temperature and water potential. | 2008 Jul-Aug |
|
Biologically active components of a Papua New Guinea analgesic and anti-inflammatory lichen preparation. | 2009 Jul |
|
Light screening in lichen cortices can be quantified by chlorophyll fluorescence techniques for both reflecting and absorbing pigments. | 2010 Apr |
|
Antimalarial drug interactions of compounds isolated from Kigelia africana (Bignoniaceae) and their synergism with artemether, against the multidrug-resistant W2mef Plasmodium falciparum strain. | 2012 Feb |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28811522
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
by
admin
on
Edited
Fri Dec 15 18:35:51 GMT 2023
by
admin
on
Fri Dec 15 18:35:51 GMT 2023
|
Record UNII |
450U2VJ2VG
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Systematic Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
207-527-7
Created by
admin on Fri Dec 15 18:35:51 GMT 2023 , Edited by admin on Fri Dec 15 18:35:51 GMT 2023
|
PRIMARY | |||
|
479-20-9
Created by
admin on Fri Dec 15 18:35:51 GMT 2023 , Edited by admin on Fri Dec 15 18:35:51 GMT 2023
|
PRIMARY | |||
|
249980
Created by
admin on Fri Dec 15 18:35:51 GMT 2023 , Edited by admin on Fri Dec 15 18:35:51 GMT 2023
|
PRIMARY | |||
|
DTXSID10197319
Created by
admin on Fri Dec 15 18:35:51 GMT 2023 , Edited by admin on Fri Dec 15 18:35:51 GMT 2023
|
PRIMARY | |||
|
450U2VJ2VG
Created by
admin on Fri Dec 15 18:35:51 GMT 2023 , Edited by admin on Fri Dec 15 18:35:51 GMT 2023
|
PRIMARY | |||
|
C026304
Created by
admin on Fri Dec 15 18:35:51 GMT 2023 , Edited by admin on Fri Dec 15 18:35:51 GMT 2023
|
PRIMARY | |||
|
Atranorin
Created by
admin on Fri Dec 15 18:35:51 GMT 2023 , Edited by admin on Fri Dec 15 18:35:51 GMT 2023
|
PRIMARY | |||
|
68066
Created by
admin on Fri Dec 15 18:35:51 GMT 2023 , Edited by admin on Fri Dec 15 18:35:51 GMT 2023
|
PRIMARY | |||
|
m2130
Created by
admin on Fri Dec 15 18:35:51 GMT 2023 , Edited by admin on Fri Dec 15 18:35:51 GMT 2023
|
PRIMARY | Merck Index | ||
|
685591
Created by
admin on Fri Dec 15 18:35:51 GMT 2023 , Edited by admin on Fri Dec 15 18:35:51 GMT 2023
|
PRIMARY |