leptosphaerin B

Details

• Internal ID: e5ce2b55-df09-4bd2-bb77-efaad57939e5
• Taxonomy: Organoheterocyclic compounds > Isobenzofurans
• IUPAC Name: (6R,7S)-3-(2,6-dihydroxyphenyl)-7-hydroxy-6-methyl-6,7-dihydro-5H-2-benzofuran-4-one
• SMILES (Canonical): CC1CC(=O)C2=C(OC=C2C1O)C3=C(C=CC=C3O)O
• SMILES (Isomeric): C[C@@H]1CC(=O)C2=C(OC=C2[C@H]1O)C3=C(C=CC=C3O)O
• InChI: InChI=1S/C15H14O5/c1-7-5-11(18)12-8(14(7)19)6-20-15(12)13-9(16)3-2-4-10(13)17/h2-4,6-7,14,16-17,19H,5H2,1H3/t7-,14+/m1/s1
• InChI Key: ONTQFVIAKQPTQW-UOWDBTKRSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₄O₅
• Molecular Weight: 274.27 g/mol
• Exact Mass: 274.08412354 g/mol
• Topological Polar Surface Area (TPSA): 90.90 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 2.61
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

• RefChem:152855
• (6R,7S)-3-(2,6-dihydroxyphenyl)-7-hydroxy-6-methyl-6,7-dihydro-5H-2-benzofuran-4-one
• CHEMBL1095144
• SCHEMBL29906147
• CHEBI:215012
• (6R,7S)-3-(2,6-dihydroxyphenyl)-7-hydroxy-6-methyl-6,7-dihydro-5H-2-benzouran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9921	99.21%
Caco-2	+	0.6510	65.10%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7132	71.32%
OATP2B1 inhibitior	-	0.7065	70.65%
OATP1B1 inhibitior	+	0.9223	92.23%
OATP1B3 inhibitior	+	0.8199	81.99%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.8575	85.75%
P-glycoprotein inhibitior	-	0.8771	87.71%
P-glycoprotein substrate	-	0.8027	80.27%
CYP3A4 substrate	+	0.5421	54.21%
CYP2C9 substrate	+	0.7806	78.06%
CYP2D6 substrate	-	0.7971	79.71%
CYP3A4 inhibition	-	0.5779	57.79%
CYP2C9 inhibition	+	0.7662	76.62%
CYP2C19 inhibition	+	0.7244	72.44%
CYP2D6 inhibition	-	0.8926	89.26%
CYP1A2 inhibition	+	0.8596	85.96%
CYP2C8 inhibition	-	0.7735	77.35%
CYP inhibitory promiscuity	+	0.7095	70.95%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.4687	46.87%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.4843	48.43%
Skin irritation	-	0.6414	64.14%
Skin corrosion	-	0.9259	92.59%
Ames mutagenesis	+	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7848	78.48%
Micronuclear	+	0.7800	78.00%
Hepatotoxicity	+	0.7658	76.58%
skin sensitisation	-	0.8064	80.64%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.4735	47.35%
Acute Oral Toxicity (c)	III	0.4906	49.06%
Estrogen receptor binding	+	0.6587	65.87%
Androgen receptor binding	+	0.6304	63.04%
Thyroid receptor binding	+	0.5921	59.21%
Glucocorticoid receptor binding	+	0.9036	90.36%
Aromatase binding	-	0.4906	49.06%
PPAR gamma	+	0.7754	77.54%
Honey bee toxicity	-	0.9263	92.63%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9746	97.46%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.22%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.26%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.35%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.25%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.80%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.92%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.61%	96.09%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.87%	93.56%
CHEMBL3401	O75469	Pregnane X receptor	82.49%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.41%	97.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.77%	90.71%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 46831107
• LOTUS: LTS0008234
• wikiData: Q77562268