eriosemaone A

Details

• Internal ID: c1a113e1-bf47-40a2-96b6-6e61dea5a56f
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > 6-prenylated flavans > 6-prenylated flavanones
• IUPAC Name: (2S)-2-(2,4-dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-6-(3-methylbut-2-enyl)-2,3-dihydropyrano[2,3-h]chromen-4-one
• SMILES (Canonical): CC(=CCC1=C(C2=C(C3=C1OC(C=C3)(C)C)OC(CC2=O)C4=C(C=C(C=C4)O)O)O)C
• SMILES (Isomeric): CC(=CCC1=C(C2=C(C3=C1OC(C=C3)(C)C)O[C@@H](CC2=O)C4=C(C=C(C=C4)O)O)O)C
• InChI: InChI=1S/C25H26O6/c1-13(2)5-7-16-22(29)21-19(28)12-20(15-8-6-14(26)11-18(15)27)30-24(21)17-9-10-25(3,4)31-23(16)17/h5-6,8-11,20,26-27,29H,7,12H2,1-4H3/t20-/m0/s1
• InChI Key: WUVGXZKCQBMDDK-FQEVSTJZSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₆O₆
• Molecular Weight: 422.50 g/mol
• Exact Mass: 422.17293854 g/mol
• Topological Polar Surface Area (TPSA): 96.20 Ų
• XlogP: 5.20
• Atomic LogP (AlogP): 5.20
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• CHEMBL550385
• (2S)-2-(2,4-Dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2,3-dihydro-4H,8H-pyrano[2,3-f]chromen-4-one
• (2S)-2-(2,4-dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-6-(3-methylbut-2-enyl)-2,3-dihydropyrano[2,3-h]chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9841	98.41%
Caco-2	-	0.5855	58.55%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7617	76.17%
OATP2B1 inhibitior	-	0.7208	72.08%
OATP1B1 inhibitior	+	0.8004	80.04%
OATP1B3 inhibitior	+	0.9347	93.47%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9370	93.70%
P-glycoprotein inhibitior	+	0.6618	66.18%
P-glycoprotein substrate	+	0.6499	64.99%
CYP3A4 substrate	+	0.6706	67.06%
CYP2C9 substrate	-	0.7981	79.81%
CYP2D6 substrate	-	0.8063	80.63%
CYP3A4 inhibition	-	0.7463	74.63%
CYP2C9 inhibition	+	0.8193	81.93%
CYP2C19 inhibition	+	0.8273	82.73%
CYP2D6 inhibition	-	0.8386	83.86%
CYP1A2 inhibition	-	0.5051	50.51%
CYP2C8 inhibition	+	0.5695	56.95%
CYP inhibitory promiscuity	+	0.8359	83.59%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6351	63.51%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.5507	55.07%
Skin irritation	-	0.7340	73.40%
Skin corrosion	-	0.9223	92.23%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6955	69.55%
Micronuclear	-	0.5641	56.41%
Hepatotoxicity	+	0.5676	56.76%
skin sensitisation	-	0.7584	75.84%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.7190	71.90%
Acute Oral Toxicity (c)	III	0.4634	46.34%
Estrogen receptor binding	+	0.9236	92.36%
Androgen receptor binding	+	0.7839	78.39%
Thyroid receptor binding	+	0.6661	66.61%
Glucocorticoid receptor binding	+	0.8779	87.79%
Aromatase binding	+	0.6766	67.66%
PPAR gamma	+	0.8746	87.46%
Honey bee toxicity	-	0.7578	75.78%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9865	98.65%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.68%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.50%	94.45%
CHEMBL2581	P07339	Cathepsin D	97.54%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.11%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.13%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.02%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.04%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.39%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.93%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.89%	95.56%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	87.33%	80.00%
CHEMBL1929	P47989	Xanthine dehydrogenase	87.06%	96.12%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.82%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.80%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	84.57%	91.19%
CHEMBL3401	O75469	Pregnane X receptor	84.55%	94.73%
CHEMBL236	P41143	Delta opioid receptor	84.35%	99.35%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.24%	91.07%
CHEMBL4208	P20618	Proteasome component C5	84.14%	90.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.10%	99.15%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	82.93%	85.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.59%	100.00%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	81.81%	83.10%
CHEMBL1951	P21397	Monoamine oxidase A	81.68%	91.49%
CHEMBL2535	P11166	Glucose transporter	81.15%	98.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.71%	97.09%
CHEMBL240	Q12809	HERG	80.38%	89.76%

Plants that contains it

• Eriosema chinense
• Eriosema tuberosum
• Euchresta horsfieldii
• Flemingia macrophylla

Cross-Links

• PubChem: 11742973
• NPASS: NPC214774
• LOTUS: LTS0249714
• wikiData: Q104400783