(3S)-5-hydroxy-3-[4-hydroxy-2-methoxy-5-(2-methylbut-3-en-2-yl)phenyl]-7-methoxy-2,3-dihydrochromen-4-one

Details

• Internal ID: 17b15f0f-9ee5-497f-988d-217dac4c3173
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > O-methylated isoflavonoids > 7-O-methylated isoflavonoids
• IUPAC Name: (3S)-5-hydroxy-3-[4-hydroxy-2-methoxy-5-(2-methylbut-3-en-2-yl)phenyl]-7-methoxy-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC(C)(C=C)C1=C(C=C(C(=C1)C2COC3=CC(=CC(=C3C2=O)O)OC)OC)O
• SMILES (Isomeric): CC(C)(C=C)C1=C(C=C(C(=C1)[C@H]2COC3=CC(=CC(=C3C2=O)O)OC)OC)O
• InChI: InChI=1S/C22H24O6/c1-6-22(2,3)15-9-13(18(27-5)10-16(15)23)14-11-28-19-8-12(26-4)7-17(24)20(19)21(14)25/h6-10,14,23-24H,1,11H2,2-5H3/t14-/m1/s1
• InChI Key: IVDADZLYWFNWFZ-CQSZACIVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₄O₆
• Molecular Weight: 384.40 g/mol
• Exact Mass: 384.15728848 g/mol
• Topological Polar Surface Area (TPSA): 85.20 Ų
• XlogP: 4.80
• Atomic LogP (AlogP): 3.94
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9854	98.54%
Caco-2	+	0.7700	77.00%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8618	86.18%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8935	89.35%
OATP1B3 inhibitior	+	0.9147	91.47%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.5731	57.31%
P-glycoprotein inhibitior	-	0.4582	45.82%
P-glycoprotein substrate	-	0.7504	75.04%
CYP3A4 substrate	+	0.6165	61.65%
CYP2C9 substrate	-	0.7979	79.79%
CYP2D6 substrate	-	0.8326	83.26%
CYP3A4 inhibition	+	0.6812	68.12%
CYP2C9 inhibition	+	0.7213	72.13%
CYP2C19 inhibition	+	0.9260	92.60%
CYP2D6 inhibition	-	0.7794	77.94%
CYP1A2 inhibition	+	0.8072	80.72%
CYP2C8 inhibition	+	0.5873	58.73%
CYP inhibitory promiscuity	+	0.7585	75.85%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9313	93.13%
Carcinogenicity (trinary)	Non-required	0.6412	64.12%
Eye corrosion	-	0.9865	98.65%
Eye irritation	-	0.5334	53.34%
Skin irritation	-	0.8121	81.21%
Skin corrosion	-	0.9536	95.36%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6521	65.21%
Micronuclear	+	0.6300	63.00%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.8546	85.46%
Respiratory toxicity	-	0.6333	63.33%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	+	0.5402	54.02%
Acute Oral Toxicity (c)	III	0.4988	49.88%
Estrogen receptor binding	+	0.7014	70.14%
Androgen receptor binding	+	0.7854	78.54%
Thyroid receptor binding	+	0.6877	68.77%
Glucocorticoid receptor binding	+	0.6860	68.60%
Aromatase binding	-	0.5896	58.96%
PPAR gamma	+	0.6219	62.19%
Honey bee toxicity	-	0.7760	77.60%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9876	98.76%

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	99.22%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.38%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.37%	85.14%
CHEMBL2581	P07339	Cathepsin D	94.35%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.95%	86.33%
CHEMBL240	Q12809	HERG	89.36%	89.76%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.34%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.21%	94.45%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	89.07%	97.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.68%	89.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	88.42%	91.07%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.26%	99.17%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	87.84%	93.40%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.27%	94.00%
CHEMBL340	P08684	Cytochrome P450 3A4	87.19%	91.19%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.54%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.07%	92.94%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.57%	99.23%
CHEMBL4208	P20618	Proteasome component C5	84.33%	90.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.43%	92.62%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.74%	99.15%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.06%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.84%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	81.06%	94.73%

Plants that contains it

• Sophora koreensis

Cross-Links

• PubChem: 162931701
• LOTUS: LTS0014489
• wikiData: Q105120981