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

Details

• Internal ID: de106145-e349-4dd4-afce-865855011fb1
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > 3-prenylated flavans > 3-prenylated flavanones
• IUPAC Name: (2S)-5,7-dihydroxy-2-[3-[(2R)-2-hydroxy-3-methylbut-3-enyl]-4-methoxy-5-(3-methylbut-2-enyl)phenyl]-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC(=CCC1=C(C(=CC(=C1)C2CC(=O)C3=C(C=C(C=C3O2)O)O)CC(C(=C)C)O)OC)C
• SMILES (Isomeric): CC(=CCC1=C(C(=CC(=C1)[C@@H]2CC(=O)C3=C(C=C(C=C3O2)O)O)C[C@H](C(=C)C)O)OC)C
• InChI: InChI=1S/C26H30O6/c1-14(2)6-7-16-8-17(9-18(26(16)31-5)10-20(28)15(3)4)23-13-22(30)25-21(29)11-19(27)12-24(25)32-23/h6,8-9,11-12,20,23,27-29H,3,7,10,13H2,1-2,4-5H3/t20-,23+/m1/s1
• InChI Key: KYRSZRIRTFGZQS-OFNKIYASSA-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: 5.50
• Atomic LogP (AlogP): 4.80
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9788	97.88%
Caco-2	+	0.5575	55.75%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6834	68.34%
OATP2B1 inhibitior	-	0.8610	86.10%
OATP1B1 inhibitior	+	0.8996	89.96%
OATP1B3 inhibitior	+	0.9173	91.73%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9044	90.44%
P-glycoprotein inhibitior	+	0.6355	63.55%
P-glycoprotein substrate	-	0.6702	67.02%
CYP3A4 substrate	+	0.6312	63.12%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7812	78.12%
CYP3A4 inhibition	+	0.6285	62.85%
CYP2C9 inhibition	+	0.6334	63.34%
CYP2C19 inhibition	+	0.7824	78.24%
CYP2D6 inhibition	-	0.5941	59.41%
CYP1A2 inhibition	+	0.7069	70.69%
CYP2C8 inhibition	+	0.4633	46.33%
CYP inhibitory promiscuity	+	0.8304	83.04%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.7338	73.38%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.8204	82.04%
Skin irritation	-	0.7707	77.07%
Skin corrosion	-	0.9397	93.97%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3913	39.13%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	+	0.5556	55.56%
skin sensitisation	-	0.8006	80.06%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.5645	56.45%
Acute Oral Toxicity (c)	III	0.4247	42.47%
Estrogen receptor binding	+	0.8622	86.22%
Androgen receptor binding	-	0.5204	52.04%
Thyroid receptor binding	+	0.5930	59.30%
Glucocorticoid receptor binding	+	0.8838	88.38%
Aromatase binding	-	0.4933	49.33%
PPAR gamma	+	0.7837	78.37%
Honey bee toxicity	-	0.5640	56.40%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9921	99.21%

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	99.62%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	98.85%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.33%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.50%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.39%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.90%	98.95%
CHEMBL1929	P47989	Xanthine dehydrogenase	95.49%	96.12%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	94.91%	92.68%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.60%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.17%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.28%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.03%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.45%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.95%	99.23%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.85%	92.62%
CHEMBL3401	O75469	Pregnane X receptor	86.47%	94.73%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.60%	96.95%
CHEMBL4208	P20618	Proteasome component C5	84.96%	90.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.05%	100.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.35%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.24%	95.89%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.73%	91.07%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.49%	95.89%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.04%	99.15%
CHEMBL340	P08684	Cytochrome P450 3A4	80.44%	91.19%
CHEMBL2535	P11166	Glucose transporter	80.43%	98.75%

Plants that contains it

• Erythrina addisoniae

Cross-Links

• PubChem: 162852553
• LOTUS: LTS0000288
• wikiData: Q105147898