2-[3,4-Dihydroxy-5-(3-methylbut-2-enyl)phenyl]-5-hydroxy-8,8-dimethyl-6-(3-methylbut-2-enyl)-2,3-dihydropyrano[2,3-h]chromen-4-one

Details

• Internal ID: dfe2e307-7ddd-40a0-8470-8a20a57ecafd
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > 6-prenylated flavans > 6-prenylated flavanones
• IUPAC Name: 2-[3,4-dihydroxy-5-(3-methylbut-2-enyl)phenyl]-5-hydroxy-8,8-dimethyl-6-(3-methylbut-2-enyl)-2,3-dihydropyrano[2,3-h]chromen-4-one
• SMILES (Canonical): CC(=CCC1=C(C(=CC(=C1)C2CC(=O)C3=C(O2)C4=C(C(=C3O)CC=C(C)C)OC(C=C4)(C)C)O)O)C
• SMILES (Isomeric): CC(=CCC1=C(C(=CC(=C1)C2CC(=O)C3=C(O2)C4=C(C(=C3O)CC=C(C)C)OC(C=C4)(C)C)O)O)C
• InChI: InChI=1S/C30H34O6/c1-16(2)7-9-18-13-19(14-23(32)26(18)33)24-15-22(31)25-27(34)20(10-8-17(3)4)28-21(29(25)35-24)11-12-30(5,6)36-28/h7-8,11-14,24,32-34H,9-10,15H2,1-6H3
• InChI Key: ZXOMCEYZUCIRAM-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₃₄O₆
• Molecular Weight: 490.60 g/mol
• Exact Mass: 490.23553880 g/mol
• Topological Polar Surface Area (TPSA): 96.20 Ų
• XlogP: 7.20
• Atomic LogP (AlogP): 6.71
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9791	97.91%
Caco-2	-	0.7372	73.72%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7707	77.07%
OATP2B1 inhibitior	-	0.8602	86.02%
OATP1B1 inhibitior	+	0.8179	81.79%
OATP1B3 inhibitior	+	0.9629	96.29%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9451	94.51%
P-glycoprotein inhibitior	+	0.7512	75.12%
P-glycoprotein substrate	-	0.5716	57.16%
CYP3A4 substrate	+	0.6440	64.40%
CYP2C9 substrate	-	0.7983	79.83%
CYP2D6 substrate	-	0.8139	81.39%
CYP3A4 inhibition	-	0.9071	90.71%
CYP2C9 inhibition	+	0.7915	79.15%
CYP2C19 inhibition	+	0.8218	82.18%
CYP2D6 inhibition	-	0.8733	87.33%
CYP1A2 inhibition	-	0.8240	82.40%
CYP2C8 inhibition	+	0.5321	53.21%
CYP inhibitory promiscuity	+	0.5579	55.79%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6341	63.41%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.8333	83.33%
Skin irritation	-	0.7304	73.04%
Skin corrosion	-	0.9181	91.81%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8196	81.96%
Micronuclear	-	0.5341	53.41%
Hepatotoxicity	-	0.5199	51.99%
skin sensitisation	-	0.7619	76.19%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.6915	69.15%
Acute Oral Toxicity (c)	III	0.5298	52.98%
Estrogen receptor binding	+	0.9117	91.17%
Androgen receptor binding	+	0.7158	71.58%
Thyroid receptor binding	+	0.6673	66.73%
Glucocorticoid receptor binding	+	0.8834	88.34%
Aromatase binding	+	0.7557	75.57%
PPAR gamma	+	0.7850	78.50%
Honey bee toxicity	-	0.7730	77.30%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
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	99.92%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.49%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.33%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.87%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	92.86%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.69%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	92.66%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.37%	97.09%
CHEMBL2581	P07339	Cathepsin D	90.48%	98.95%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	90.27%	80.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.39%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	86.27%	94.73%
CHEMBL4208	P20618	Proteasome component C5	86.04%	90.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.89%	90.71%
CHEMBL3038469	P24941	CDK2/Cyclin A	84.66%	91.38%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.14%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.58%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.55%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.37%	92.62%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	83.31%	95.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.14%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.72%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	82.32%	91.19%

Plants that contains it

• Amorpha fruticosa

Cross-Links

• PubChem: 14187656
• LOTUS: LTS0149338
• wikiData: Q105385653