Lecanoric Acid

Details

• Internal ID: c2b6537d-9e68-41cd-9369-b098851f0682
• Taxonomy: Phenylpropanoids and polyketides > Depsides and depsidones
• IUPAC Name: 4-(2,4-dihydroxy-6-methylbenzoyl)oxy-2-hydroxy-6-methylbenzoic acid
• SMILES (Canonical): CC1=CC(=CC(=C1C(=O)OC2=CC(=C(C(=C2)C)C(=O)O)O)O)O
• SMILES (Isomeric): CC1=CC(=CC(=C1C(=O)OC2=CC(=C(C(=C2)C)C(=O)O)O)O)O
• InChI: InChI=1S/C16H14O7/c1-7-3-9(17)5-11(18)14(7)16(22)23-10-4-8(2)13(15(20)21)12(19)6-10/h3-6,17-19H,1-2H3,(H,20,21)
• InChI Key: HEMSJKZDHNSSEW-UHFFFAOYSA-N
• Popularity: 209 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₄O₇
• Molecular Weight: 318.28 g/mol
• Exact Mass: 318.07395278 g/mol
• Topological Polar Surface Area (TPSA): 124.00 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 2.34
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

• 480-56-8
• Lecanoricacid
• o-orsellinate depside
• Orsellinate depside
• NSC 249981
• BRN 2172778
• D0M65TKS0F
• CHEBI:15871
• 4-(2,4-dihydroxy-6-methylbenzoyl)oxy-2-hydroxy-6-methylbenzoic acid
• NSC-249981
• 2,4-Dihydroxy-6-methylbenzoic acid 4-carboxy-3-hydroxy-5-methylphenyl ester
• Benzoic acid, 2,4-dihydroxy-6-methyl-, 4-carboxy-3-hydroxy-5-methylphenyl ester
• 4-10-00-01527 (Beilstein Handbook Reference)
• beta-Resorcylic acid, 6-methyl-, 4-(6-methyl-beta-resorcylate)
• 4-(2,4-dihydroxy-6-methylbenzoyloxy)-2-hydroxy-6-methylbenzoic acid
• 4-((2,4-Dihydroxy-6-methylbenzoyl)oxy)-2-hydroxy-6-methylbenzoic acid
• beta-Resorcylic acid, 6-methyl-, 4-(6-methyl-beta-resorcylate) (7CI,8CI); NSC 249981
• Spectrum_000499
• starbld0009608
• SpecPlus_000150
• Spectrum2_000211
• Spectrum3_000162
• Spectrum4_001485
• Spectrum5_000189
• UNII-D0M65TKS0F
• BSPBio_001623
• KBioGR_002089
• KBioSS_000979
• SPECTRUM200070
• MLS000563107
• DivK1c_006246
• SPBio_000221
• SCHEMBL3797774
• CHEMBL1451874
• KBio1_001190
• KBio2_000979
• KBio2_003547
• KBio2_006115
• KBio3_001123
• DTXSID60197384
• HY-N3394
• CCG-38414
• LMPK13080001
• NSC249981
• AKOS015916261
• SDCCGMLS-0066390.P001
• NCGC00095468-01
• NCGC00095468-02
• NCGC00095468-03
• AC-20266
• SMR001215955
• LS-143448
• CS-0024095
• C02868
• SR-01000841840
• SR-01000841840-2
• BRD-K77578964-001-02-8
• Q27098274
• .beta.-Resorcylic acid, 4-(6-methyl-.beta.-resorcylate)
• .beta.-Resorcylic acid, 6-methyl-, 4-(6-methyl-.beta.-resorcylate)
• -Resorcylic acid, 6-methyl-, 4-(6-methyl--resorcylate) (7CI,8CI); NSC 249981
• Benzoic acid,4-dihydroxy-6-methyl-, 4-carboxy-3-hydroxy-5-methylphenyl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9494	94.94%
Caco-2	+	0.7318	73.18%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.9053	90.53%
OATP2B1 inhibitior	-	0.5623	56.23%
OATP1B1 inhibitior	+	0.9640	96.40%
OATP1B3 inhibitior	-	0.2296	22.96%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8522	85.22%
P-glycoprotein inhibitior	-	0.8982	89.82%
P-glycoprotein substrate	-	0.9702	97.02%
CYP3A4 substrate	-	0.5814	58.14%
CYP2C9 substrate	-	0.6130	61.30%
CYP2D6 substrate	-	0.9089	90.89%
CYP3A4 inhibition	-	0.8087	80.87%
CYP2C9 inhibition	+	0.6786	67.86%
CYP2C19 inhibition	-	0.7626	76.26%
CYP2D6 inhibition	-	0.8939	89.39%
CYP1A2 inhibition	-	0.6485	64.85%
CYP2C8 inhibition	-	0.6769	67.69%
CYP inhibitory promiscuity	-	0.6513	65.13%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7456	74.56%
Carcinogenicity (trinary)	Non-required	0.7688	76.88%
Eye corrosion	-	0.9873	98.73%
Eye irritation	+	0.8352	83.52%
Skin irritation	-	0.7597	75.97%
Skin corrosion	-	0.8862	88.62%
Ames mutagenesis	-	0.7154	71.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4596	45.96%
Micronuclear	+	0.7200	72.00%
Hepatotoxicity	+	0.6000	60.00%
skin sensitisation	-	0.8942	89.42%
Respiratory toxicity	-	0.6444	64.44%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.5884	58.84%
Acute Oral Toxicity (c)	III	0.6121	61.21%
Estrogen receptor binding	+	0.8514	85.14%
Androgen receptor binding	+	0.5928	59.28%
Thyroid receptor binding	-	0.5849	58.49%
Glucocorticoid receptor binding	+	0.5748	57.48%
Aromatase binding	+	0.6966	69.66%
PPAR gamma	+	0.6196	61.96%
Honey bee toxicity	-	0.7720	77.20%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9939	99.39%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	15848.9 nM; 3981.1 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	28183.8 nM	Potency	via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	39810.7 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	12589.3 nM; 12589.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	39810.7 nM	Potency	via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	39810.7 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3194	P02766	Transthyretin	91.66%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.54%	99.15%
CHEMBL4208	P20618	Proteasome component C5	89.65%	90.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.33%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.00%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.25%	96.09%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	84.42%	94.42%
CHEMBL3401	O75469	Pregnane X receptor	84.39%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.10%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.84%	99.17%
CHEMBL2581	P07339	Cathepsin D	83.77%	98.95%
CHEMBL1929	P47989	Xanthine dehydrogenase	82.24%	96.12%
CHEMBL1913	P09619	Platelet-derived growth factor receptor beta	81.66%	95.70%

Plants that contains it

• Acacia saligna
• Astragalus pectinatus
• Celosia argentea
• Coffea pseudozanguebariae
• Conioselinum anthriscoides
• Fleischmannia hymenophylla
• Garcinia atroviridis
• Gentiana purpurea
• Pilosella officinarum
• Roystonea regia
• Solanum tomentosum
• Sterculia urens

Cross-Links

• PubChem: 99613
• NPASS: NPC105648
• ChEMBL: CHEMBL1451874
• LOTUS: LTS0032151
• wikiData: Q27098274