2-[3,4-Dihydroxy-2,5-bis(3-methylbut-2-enyl)phenyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one

Details

• Internal ID: 23f6e255-4a3e-480e-a6de-f98ed28dc256
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > 2-prenylated flavans > 2-prenylated flavanones
• IUPAC Name: 2-[3,4-dihydroxy-2,5-bis(3-methylbut-2-enyl)phenyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC(=CCC1=CC(=C(C(=C1O)O)CC=C(C)C)C2CC(=O)C3=C(C=C(C=C3O2)O)O)C
• SMILES (Isomeric): CC(=CCC1=CC(=C(C(=C1O)O)CC=C(C)C)C2CC(=O)C3=C(C=C(C=C3O2)O)O)C
• InChI: InChI=1S/C25H28O6/c1-13(2)5-7-15-9-18(17(8-6-14(3)4)25(30)24(15)29)21-12-20(28)23-19(27)10-16(26)11-22(23)31-21/h5-6,9-11,21,26-27,29-30H,7-8,12H2,1-4H3
• InChI Key: BVHLNRAYBCPKOY-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₈O₆
• Molecular Weight: 424.50 g/mol
• Exact Mass: 424.18858861 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: 5.90
• Atomic LogP (AlogP): 5.23
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

• 176046-04-1
• ( inverted exclamation markA)-Sigmoidin A
• 2-[3,4-dihydroxy-2,5-bis(3-methylbut-2-enyl)phenyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one
• MEGxp0_000008
• HY-N8649
• LMPK12140398
• AKOS040762347
• FS-7735
• CS-0148818

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9613	96.13%
Caco-2	-	0.5196	51.96%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6736	67.36%
OATP2B1 inhibitior	-	0.5700	57.00%
OATP1B1 inhibitior	+	0.8539	85.39%
OATP1B3 inhibitior	+	0.9684	96.84%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8855	88.55%
P-glycoprotein inhibitior	-	0.4780	47.80%
P-glycoprotein substrate	-	0.7602	76.02%
CYP3A4 substrate	+	0.5810	58.10%
CYP2C9 substrate	-	0.7979	79.79%
CYP2D6 substrate	-	0.8017	80.17%
CYP3A4 inhibition	-	0.8332	83.32%
CYP2C9 inhibition	+	0.6612	66.12%
CYP2C19 inhibition	+	0.6993	69.93%
CYP2D6 inhibition	-	0.7223	72.23%
CYP1A2 inhibition	+	0.6474	64.74%
CYP2C8 inhibition	-	0.5696	56.96%
CYP inhibitory promiscuity	+	0.6801	68.01%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7173	71.73%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.7074	70.74%
Skin irritation	-	0.7481	74.81%
Skin corrosion	-	0.9300	93.00%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7087	70.87%
Micronuclear	-	0.5200	52.00%
Hepatotoxicity	+	0.5428	54.28%
skin sensitisation	-	0.7792	77.92%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	+	0.5877	58.77%
Acute Oral Toxicity (c)	III	0.4620	46.20%
Estrogen receptor binding	+	0.8836	88.36%
Androgen receptor binding	+	0.6862	68.62%
Thyroid receptor binding	+	0.5806	58.06%
Glucocorticoid receptor binding	+	0.8187	81.87%
Aromatase binding	-	0.5175	51.75%
PPAR gamma	+	0.8521	85.21%
Honey bee toxicity	-	0.7751	77.51%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9931	99.31%

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	99.63%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.69%	98.95%
CHEMBL1929	P47989	Xanthine dehydrogenase	95.26%	96.12%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.04%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.26%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	90.19%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.07%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.03%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.42%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.35%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.65%	86.33%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	85.67%	89.34%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.19%	100.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.17%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.67%	99.17%
CHEMBL4208	P20618	Proteasome component C5	84.12%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.60%	95.89%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	82.90%	93.40%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.11%	92.62%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	80.61%	83.10%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.56%	94.80%

Plants that contains it

• Antiaris toxicaria
• Erythrina abyssinica
• Erythrina sigmoidea

Cross-Links

• PubChem: 4303225
• LOTUS: LTS0039156
• wikiData: Q104946568