Atranorin

Details

• Internal ID: 36f09359-f1d6-40fb-894d-f420a4337cf6
• Taxonomy: Phenylpropanoids and polyketides > Depsides and depsidones
• IUPAC Name: (3-hydroxy-4-methoxycarbonyl-2,5-dimethylphenyl) 3-formyl-2,4-dihydroxy-6-methylbenzoate
• SMILES (Canonical): CC1=CC(=C(C(=C1C(=O)OC2=C(C(=C(C(=C2)C)C(=O)OC)O)C)O)C=O)O
• SMILES (Isomeric): CC1=CC(=C(C(=C1C(=O)OC2=C(C(=C(C(=C2)C)C(=O)OC)O)C)O)C=O)O
• InChI: 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
• InChI Key: YLOYKYXNDHOHHT-UHFFFAOYSA-N
• Popularity: 452 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₈O₈
• Molecular Weight: 374.30 g/mol
• Exact Mass: 374.10016753 g/mol
• Topological Polar Surface Area (TPSA): 130.00 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 2.55
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• 479-20-9
• Atranoric acid
• Atranorine
• Parmelin
• Usnarin
• Antranoric acid
• Parmelin acid
• Usnarin acid
• 3-Hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl 3-formyl-2,4-dihydroxy-6-methylbenzoate
• NSC 249980
• NSC 685591
• NSC-685591
• EINECS 207-527-7
• UNII-450U2VJ2VG
• 450U2VJ2VG
• CHEMBL173395
• Benzoic acid,3-formyl-2,4-dihydroxy-6-methyl-,3-hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl ester
• C19H18O8
• NSC685591
• NSC-249980
• 3-formyl-2,4-dihydroxy-6-methylbenzoic acid 3-hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl ester
• Benzoic acid, 3-formyl-2,4-dihydroxy-6-methyl-, 3-hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl ester
• Isophthalaldehydic acid, 2,4-dihydroxy-6-methyl-, 4-ester with methyl 3,6-dimethyl-beta-resorcylate
• Benzoic acid,4-dihydroxy-6-methyl-, 3-hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl ester
• Isophthalaldehydic acid,4-dihydroxy-6-methyl-, 4-ester with methyl 3,6-dimethyl-.beta.-resorcylate
• Spectrum_000143
• SpecPlus_000239
• ATRANORIN [MI]
• Spectrum2_001749
• Spectrum3_001716
• Spectrum4_001700
• Spectrum5_000380
• (3-hydroxy-4-methoxycarbonyl-2,5-dimethylphenyl) 3-formyl-2,4-dihydroxy-6-methylbenzoate
• BSPBio_003332
• KBioGR_002000
• KBioSS_000623
• SPECTRUM200034
• DivK1c_006335
• SPBio_001858
• SCHEMBL1370191
• KBio1_001279
• KBio2_000623
• KBio2_003191
• KBio2_005759
• KBio3_002552
• DTXSID10197319
• CHEBI:144119
• YLOYKYXNDHOHHT-UHFFFAOYSA-N
• HY-N2907
• NSC87512
• BDBM50056919
• CCG-38801
• MFCD00016597
• NSC-87512
• NSC249980
• AKOS024319117
• SDCCGMLS-0066426.P001
• NCGC00095465-01
• NCGC00095465-02
• LS-37485
• MS-26044
• CS-0023502
• FT-0769622
• SR-05000002629
• SR-05000002629-1
• Q27258788
• (3-hydroxy-4-methoxycarbonyl-2,5-dimethyl-phenyl) 3-formyl-2,4-dihydroxy-6-methyl-benzoate
• 3-Hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl 3-formyl-2,4-dihydroxy-6-methylbenzoate #
• Methyl 4-(3-formyl-2,4-dihydroxy-6-methyl-benzoyloxy)-2-hydroxy- 3,6-dimethyl-benzoate
• Isophthalaldehydic acid, 2,4-dihydroxy-6-methyl-, 4-ester with methyl 3,6-dimethyl-.beta.-resorcylate
• methyl 1-(3-formyl-2,4-dihydroxy-6-methylphenylcarbonyloxy)-3-hydroxy-2,5-dimethyl-4-benzenecarboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9450	94.50%
Caco-2	+	0.7169	71.69%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8663	86.63%
OATP2B1 inhibitior	-	0.7104	71.04%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	-	0.5698	56.98%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.6613	66.13%
P-glycoprotein inhibitior	-	0.7465	74.65%
P-glycoprotein substrate	-	0.7971	79.71%
CYP3A4 substrate	+	0.5067	50.67%
CYP2C9 substrate	-	0.7974	79.74%
CYP2D6 substrate	-	0.8693	86.93%
CYP3A4 inhibition	-	0.8310	83.10%
CYP2C9 inhibition	-	0.7343	73.43%
CYP2C19 inhibition	-	0.8817	88.17%
CYP2D6 inhibition	-	0.8907	89.07%
CYP1A2 inhibition	-	0.6138	61.38%
CYP2C8 inhibition	+	0.6007	60.07%
CYP inhibitory promiscuity	-	0.6980	69.80%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7156	71.56%
Carcinogenicity (trinary)	Non-required	0.7193	71.93%
Eye corrosion	-	0.9856	98.56%
Eye irritation	-	0.4793	47.93%
Skin irritation	-	0.8241	82.41%
Skin corrosion	-	0.9491	94.91%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3749	37.49%
Micronuclear	+	0.6800	68.00%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	-	0.9583	95.83%
Respiratory toxicity	-	0.6556	65.56%
Reproductive toxicity	+	0.6059	60.59%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.6949	69.49%
Acute Oral Toxicity (c)	II	0.6323	63.23%
Estrogen receptor binding	+	0.8390	83.90%
Androgen receptor binding	+	0.6681	66.81%
Thyroid receptor binding	-	0.5515	55.15%
Glucocorticoid receptor binding	+	0.6466	64.66%
Aromatase binding	+	0.5457	54.57%
PPAR gamma	+	0.6798	67.98%
Honey bee toxicity	-	0.8733	87.33%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9878	98.78%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL340	P08684	Cytochrome P450 3A4	12589.3 nM; 12589.3 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	98.64%	98.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.27%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.05%	94.00%
CHEMBL3194	P02766	Transthyretin	87.89%	90.71%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.50%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.19%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	85.71%	94.73%
CHEMBL2581	P07339	Cathepsin D	85.56%	98.95%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.30%	96.90%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.69%	96.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.50%	96.95%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	80.55%	94.42%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.00%	89.00%

Plants that contains it

• Acacia saligna
• Ajuga decumbens
• Astragalus pectinatus
• Cinchona calisaya
• Coffea pseudozanguebariae
• Fleischmannia hymenophylla
• Garcinia atroviridis
• Gentiana purpurea
• Helleborus niger
• Pilosella officinarum
• Roystonea regia
• Solanum tomentosum
• Stellera chamaejasme
• Sterculia urens

Cross-Links

• PubChem: 68066
• NPASS: NPC149618
• ChEMBL: CHEMBL173395