(2S)-euchrenone a7

Details

• Internal ID: f6b9a86d-5558-4ffa-90a7-42a6d89762d5
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > 8-prenylated flavans > 8-prenylated flavanones
• IUPAC Name: (2S)-2-(2,4-dihydroxyphenyl)-7-hydroxy-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC(=CCC1=C(C=CC2=C1OC(CC2=O)C3=C(C=C(C=C3)O)O)O)C
• SMILES (Isomeric): CC(=CCC1=C(C=CC2=C1O[C@@H](CC2=O)C3=C(C=C(C=C3)O)O)O)C
• InChI: InChI=1S/C20H20O5/c1-11(2)3-5-14-16(22)8-7-15-18(24)10-19(25-20(14)15)13-6-4-12(21)9-17(13)23/h3-4,6-9,19,21-23H,5,10H2,1-2H3/t19-/m0/s1
• InChI Key: JJOUBYOHNYJCOU-IBGZPJMESA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₀O₅
• Molecular Weight: 340.40 g/mol
• Exact Mass: 340.13107373 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 4.02
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• CHEMBL457686
• D09OPA
• JJOUBYOHNYJCOU-IBGZPJMESA-N
• BDBM50251006

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9838	98.38%
Caco-2	+	0.7684	76.84%
Blood Brain Barrier	-	0.5629	56.29%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7746	77.46%
OATP2B1 inhibitior	-	0.5823	58.23%
OATP1B1 inhibitior	+	0.8630	86.30%
OATP1B3 inhibitior	+	0.9575	95.75%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.5620	56.20%
P-glycoprotein inhibitior	-	0.6601	66.01%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.5912	59.12%
CYP2C9 substrate	-	0.8006	80.06%
CYP2D6 substrate	-	0.7235	72.35%
CYP3A4 inhibition	+	0.6075	60.75%
CYP2C9 inhibition	+	0.9007	90.07%
CYP2C19 inhibition	+	0.8993	89.93%
CYP2D6 inhibition	-	0.5927	59.27%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	-	0.6666	66.66%
CYP inhibitory promiscuity	+	0.9271	92.71%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6821	68.21%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.5328	53.28%
Skin irritation	-	0.7351	73.51%
Skin corrosion	-	0.9166	91.66%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5827	58.27%
Micronuclear	+	0.5259	52.59%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.7491	74.91%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.6225	62.25%
Acute Oral Toxicity (c)	III	0.4391	43.91%
Estrogen receptor binding	+	0.8446	84.46%
Androgen receptor binding	+	0.8249	82.49%
Thyroid receptor binding	+	0.6412	64.12%
Glucocorticoid receptor binding	+	0.7360	73.60%
Aromatase binding	-	0.5371	53.71%
PPAR gamma	+	0.8121	81.21%
Honey bee toxicity	-	0.8062	80.62%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9894	98.94%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1978	P11511	Cytochrome P450 19A1	3400 nM	IC50	PMID: 11678652

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.47%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.87%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	97.06%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.62%	95.56%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	91.19%	93.40%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.87%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.70%	86.33%
CHEMBL1929	P47989	Xanthine dehydrogenase	90.36%	96.12%
CHEMBL3401	O75469	Pregnane X receptor	88.99%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.85%	89.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.91%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.37%	95.89%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.64%	99.15%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.56%	100.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.00%	99.17%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	83.00%	85.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.28%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.93%	99.23%
CHEMBL236	P41143	Delta opioid receptor	81.05%	99.35%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.94%	97.09%

Plants that contains it

• Artocarpus altilis
• Asimina parviflora
• Atraphaxis spinosa
• Baccharis neglecta
• Broussonetia papyrifera
• Centaurea cuneifolia subsp. cuneifolia
• Chondrodendron tomentosum
• Clerodendrum bungei
• Diospyros ebenum
• Embelia parviflora
• Embelia schimperi
• Ephedra sinica
• Epilobium hirsutum
• Erysimum leptophyllum
• Erythrina melanacantha
• Esenbeckia leiocarpa
• Euchresta horsfieldii
• Euphorbia jolkinii
• Faramea multiflora
• Gymnocalycium schickendantzii
• Haplophyllum obtusifolium
• Helichrysum tenuifolium
• Hypericum styphelioides
• Linnaea chinensis
• Lythrum salicaria
• Monsonia senegalensis
• Myrica rubra
• Onopordum acanthium
• Pancratium sickenbergeri
• Pinalia anomala
• Piper regnellii
• Plathymenia reticulata
• Pteridium esculentum
• Simarouba glauca
• Sophora flavescens
• Stenocereus laevigatus
• Syzygium polycephaloides
• Varronia leucocephala
• Vellozia nanuzae
• Vernonanthura fagifolia

Cross-Links

• PubChem: 44593508
• NPASS: NPC91560
• ChEMBL: CHEMBL457686
• LOTUS: LTS0246356
• wikiData: Q105129794