4-[(2S)-7-hydroxy-6-methoxy-8-(3-methylbut-2-enyl)-3,4-dihydro-2H-chromen-2-yl]-3-(3-methylbut-2-enyl)benzene-1,2-diol

Details

• Internal ID: ba21c9f3-35ac-4928-b089-b437acebe4b0
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > 2-prenylated flavans
• IUPAC Name: 4-[(2S)-7-hydroxy-6-methoxy-8-(3-methylbut-2-enyl)-3,4-dihydro-2H-chromen-2-yl]-3-(3-methylbut-2-enyl)benzene-1,2-diol
• SMILES (Canonical): CC(=CCC1=C(C=CC(=C1O)O)C2CCC3=CC(=C(C(=C3O2)CC=C(C)C)O)OC)C
• SMILES (Isomeric): CC(=CCC1=C(C=CC(=C1O)O)[C@@H]2CCC3=CC(=C(C(=C3O2)CC=C(C)C)O)OC)C
• InChI: InChI=1S/C26H32O5/c1-15(2)6-9-19-18(11-12-21(27)24(19)28)22-13-8-17-14-23(30-5)25(29)20(26(17)31-22)10-7-16(3)4/h6-7,11-12,14,22,27-29H,8-10,13H2,1-5H3/t22-/m0/s1
• InChI Key: VPRXRGLNLDGXIE-QFIPXVFZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₂O₅
• Molecular Weight: 424.50 g/mol
• Exact Mass: 424.22497412 g/mol
• Topological Polar Surface Area (TPSA): 79.20 Ų
• XlogP: 6.60
• Atomic LogP (AlogP): 5.90
• H-Bond Acceptor: 5
• 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	+	0.9557	95.57%
Caco-2	+	0.6017	60.17%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7792	77.92%
OATP2B1 inhibitior	-	0.8606	86.06%
OATP1B1 inhibitior	+	0.8904	89.04%
OATP1B3 inhibitior	+	0.9460	94.60%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.8494	84.94%
P-glycoprotein inhibitior	+	0.7299	72.99%
P-glycoprotein substrate	-	0.5560	55.60%
CYP3A4 substrate	+	0.6029	60.29%
CYP2C9 substrate	-	0.6063	60.63%
CYP2D6 substrate	+	0.4455	44.55%
CYP3A4 inhibition	-	0.9169	91.69%
CYP2C9 inhibition	+	0.5288	52.88%
CYP2C19 inhibition	+	0.7108	71.08%
CYP2D6 inhibition	-	0.7055	70.55%
CYP1A2 inhibition	+	0.6573	65.73%
CYP2C8 inhibition	+	0.7009	70.09%
CYP inhibitory promiscuity	+	0.6353	63.53%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7283	72.83%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.8103	81.03%
Skin irritation	-	0.7883	78.83%
Skin corrosion	-	0.9364	93.64%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7960	79.60%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.8253	82.53%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.8590	85.90%
Acute Oral Toxicity (c)	III	0.4874	48.74%
Estrogen receptor binding	+	0.8795	87.95%
Androgen receptor binding	+	0.6925	69.25%
Thyroid receptor binding	+	0.6413	64.13%
Glucocorticoid receptor binding	+	0.7476	74.76%
Aromatase binding	+	0.5721	57.21%
PPAR gamma	+	0.8039	80.39%
Honey bee toxicity	-	0.8189	81.89%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9776	97.76%

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	99.56%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.55%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	94.14%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	93.80%	92.94%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	93.11%	98.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.96%	94.45%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	91.24%	92.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.22%	86.33%
CHEMBL3192	Q9BY41	Histone deacetylase 8	90.10%	93.99%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.44%	99.17%
CHEMBL1951	P21397	Monoamine oxidase A	88.09%	91.49%
CHEMBL2581	P07339	Cathepsin D	86.25%	98.95%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.15%	89.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.01%	97.09%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	85.94%	91.79%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.28%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.04%	95.56%
CHEMBL2535	P11166	Glucose transporter	84.73%	98.75%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	83.75%	91.03%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	83.74%	93.40%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.65%	100.00%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	82.41%	94.03%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.62%	99.15%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	80.49%	95.78%

Plants that contains it

• Dendrolobium lanceolatum

Cross-Links

• PubChem: 11743107
• LOTUS: LTS0018627
• wikiData: Q105290962