U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of ATRANORIN

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

HIDE SMILES / InChI

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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P60953
Gene ID: 998.0
Gene Symbol: CDC42
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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
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 Fri Dec 15 18:35:51 GMT 2023
Edited
by admin
on Fri Dec 15 18:35:51 GMT 2023
Record UNII
450U2VJ2VG
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ATRANORIN
MI  
Common Name English
ATRANORIN [MI]
Common Name English
NSC-685591
Code English
3-HYDROXY-4-(METHOXYCARBONYL)-2,5-DIMETHYLPHENYL 3-FORMYL-2,4-DIHYDROXY-6-METHYLBENZOATE
Systematic Name English
ATRANORIC ACID
Common Name English
NSC-249980
Code English
3-FORMYL-2,4-DIHYDROXY-6-METHYLBENZOIC ACID 3-HYDROXY-4-(METHOXYCARBONYL)-2,5-DIMETHYLPHENYL ESTER
Systematic Name English
Code System Code Type Description
ECHA (EC/EINECS)
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
CAS
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
NSC
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
EPA CompTox
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
FDA UNII
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
MESH
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
WIKIPEDIA
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
PUBCHEM
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
MERCK INDEX
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
NSC
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