(3S)-5,7-dihydroxy-3-[4-hydroxy-2-methoxy-3-(3-methylbut-2-enyl)phenyl]-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one

Details

• Internal ID: 81e3ed9d-bb78-4aef-9806-6d758213c14f
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavans > Isoflavanones > 3-prenylated isoflavanones
• IUPAC Name: (3S)-5,7-dihydroxy-3-[4-hydroxy-2-methoxy-3-(3-methylbut-2-enyl)phenyl]-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC(=CCC1=C(C=CC(=C1OC)C2COC3=C(C2=O)C(=C(C(=C3)O)CC=C(C)C)O)O)C
• SMILES (Isomeric): CC(=CCC1=C(C=CC(=C1OC)[C@H]2COC3=C(C2=O)C(=C(C(=C3)O)CC=C(C)C)O)O)C
• InChI: InChI=1S/C26H30O6/c1-14(2)6-8-17-21(28)12-22-23(24(17)29)25(30)19(13-32-22)16-10-11-20(27)18(26(16)31-5)9-7-15(3)4/h6-7,10-12,19,27-29H,8-9,13H2,1-5H3/t19-/m1/s1
• InChI Key: ARNVYCOTFWJTBS-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

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9860	98.60%
Caco-2	+	0.5739	57.39%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7651	76.51%
OATP2B1 inhibitior	-	0.8609	86.09%
OATP1B1 inhibitior	+	0.9146	91.46%
OATP1B3 inhibitior	+	0.8322	83.22%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9386	93.86%
P-glycoprotein inhibitior	+	0.7638	76.38%
P-glycoprotein substrate	-	0.6586	65.86%
CYP3A4 substrate	+	0.5972	59.72%
CYP2C9 substrate	+	0.5973	59.73%
CYP2D6 substrate	-	0.7963	79.63%
CYP3A4 inhibition	-	0.6732	67.32%
CYP2C9 inhibition	+	0.8400	84.00%
CYP2C19 inhibition	+	0.8963	89.63%
CYP2D6 inhibition	-	0.6342	63.42%
CYP1A2 inhibition	+	0.9215	92.15%
CYP2C8 inhibition	+	0.5134	51.34%
CYP inhibitory promiscuity	+	0.9174	91.74%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7643	76.43%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.7219	72.19%
Skin irritation	-	0.8072	80.72%
Skin corrosion	-	0.9557	95.57%
Ames mutagenesis	+	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4586	45.86%
Micronuclear	-	0.5200	52.00%
Hepatotoxicity	-	0.5608	56.08%
skin sensitisation	-	0.8184	81.84%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.8371	83.71%
Acute Oral Toxicity (c)	III	0.6981	69.81%
Estrogen receptor binding	+	0.9398	93.98%
Androgen receptor binding	+	0.8253	82.53%
Thyroid receptor binding	+	0.6476	64.76%
Glucocorticoid receptor binding	+	0.8783	87.83%
Aromatase binding	+	0.5687	56.87%
PPAR gamma	+	0.8280	82.80%
Honey bee toxicity	-	0.8536	85.36%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9889	98.89%

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	99.88%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.73%	94.45%
CHEMBL2581	P07339	Cathepsin D	95.51%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.13%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.18%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.16%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.15%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.13%	95.56%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	90.93%	92.68%
CHEMBL1951	P21397	Monoamine oxidase A	89.95%	91.49%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.31%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.18%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.95%	92.62%
CHEMBL3401	O75469	Pregnane X receptor	87.57%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.76%	96.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	85.52%	93.99%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.39%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.07%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	84.59%	91.19%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.51%	99.17%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.38%	93.40%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.35%	94.80%
CHEMBL2535	P11166	Glucose transporter	80.05%	98.75%

Plants that contains it

• Campylotropis hirtella
• Sophora chrysophylla
• Sophora koreensis
• Sophora tomentosa

Cross-Links

• PubChem: 92469183
• LOTUS: LTS0022307
• wikiData: Q104917449