(3S)-3-[2,4-Dihydroxy-3-(3-methyl-2-buten-1-yl)phenyl]-2,3-dihydro-5-hydroxy-7-methoxy-6-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one

Details

• Internal ID: b0062337-c0c1-481c-9944-2f90dd3c964d
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavans > Isoflavanones > 3-prenylated isoflavanones
• IUPAC Name: (3S)-3-[2,4-dihydroxy-3-(3-methylbut-2-enyl)phenyl]-5-hydroxy-7-methoxy-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC(=CCC1=C(C=CC(=C1O)C2COC3=CC(=C(C(=C3C2=O)O)CC=C(C)C)OC)O)C
• SMILES (Isomeric): CC(=CCC1=C(C=CC(=C1O)[C@H]2COC3=CC(=C(C(=C3C2=O)O)CC=C(C)C)OC)O)C
• InChI: InChI=1S/C26H30O6/c1-14(2)6-8-17-20(27)11-10-16(24(17)28)19-13-32-22-12-21(31-5)18(9-7-15(3)4)25(29)23(22)26(19)30/h6-7,10-12,19,27-29H,8-9,13H2,1-5H3/t19-/m1/s1
• InChI Key: OWVFKLIUBOKWCT-LJQANCHMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₀O₆
• Molecular Weight: 438.50 g/mol
• Exact Mass: 438.20423867 g/mol
• Topological Polar Surface Area (TPSA): 96.20 Ų
• XlogP: 6.40
• Atomic LogP (AlogP): 5.19
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

• (3S)-3-[2,4-Dihydroxy-3-(3-methyl-2-buten-1-yl)phenyl]-2,3-dihydro-5-hydroxy-7-methoxy-6-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one
• 152511-45-0

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9739	97.39%
Caco-2	+	0.4912	49.12%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7651	76.51%
OATP2B1 inhibitior	-	0.8603	86.03%
OATP1B1 inhibitior	+	0.9254	92.54%
OATP1B3 inhibitior	+	0.8986	89.86%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9348	93.48%
P-glycoprotein inhibitior	+	0.7389	73.89%
P-glycoprotein substrate	-	0.6577	65.77%
CYP3A4 substrate	+	0.5897	58.97%
CYP2C9 substrate	+	0.5973	59.73%
CYP2D6 substrate	-	0.7963	79.63%
CYP3A4 inhibition	-	0.6805	68.05%
CYP2C9 inhibition	+	0.8632	86.32%
CYP2C19 inhibition	+	0.8982	89.82%
CYP2D6 inhibition	+	0.5249	52.49%
CYP1A2 inhibition	+	0.9338	93.38%
CYP2C8 inhibition	+	0.5704	57.04%
CYP inhibitory promiscuity	+	0.9300	93.00%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7589	75.89%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.7751	77.51%
Skin irritation	-	0.8018	80.18%
Skin corrosion	-	0.9513	95.13%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6293	62.93%
Micronuclear	-	0.5300	53.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.8424	84.24%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.7015	70.15%
Acute Oral Toxicity (c)	III	0.6060	60.60%
Estrogen receptor binding	+	0.9072	90.72%
Androgen receptor binding	+	0.8261	82.61%
Thyroid receptor binding	+	0.5973	59.73%
Glucocorticoid receptor binding	+	0.7729	77.29%
Aromatase binding	-	0.5430	54.30%
PPAR gamma	+	0.8554	85.54%
Honey bee toxicity	-	0.7968	79.68%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9899	98.99%

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	99.70%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.87%	94.45%
CHEMBL2581	P07339	Cathepsin D	95.60%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.12%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.35%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.56%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.07%	89.00%
CHEMBL240	Q12809	HERG	90.92%	89.76%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.19%	95.56%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	89.03%	95.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.21%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.02%	100.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	87.14%	93.99%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.48%	99.17%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.33%	92.62%
CHEMBL340	P08684	Cytochrome P450 3A4	85.09%	91.19%
CHEMBL3401	O75469	Pregnane X receptor	83.70%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.61%	99.15%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.54%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.62%	99.23%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.00%	90.71%
CHEMBL1929	P47989	Xanthine dehydrogenase	80.95%	96.12%

Plants that contains it

• Glycyrrhiza uralensis

Cross-Links

• PubChem: 154496831
• LOTUS: LTS0270926
• wikiData: Q105202317