(2S)-6-(gamma,gamma-dimethylallyl)-5,3'-dihydroxy-4'-methoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone

Details

• Internal ID: 1bf43f63-f07f-4178-a2e3-d7c1a3309017
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > 6-prenylated flavans > 6-prenylated flavanones
• IUPAC Name: (2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-8,8-dimethyl-6-(3-methylbut-2-enyl)-2,3-dihydropyrano[2,3-h]chromen-4-one
• SMILES (Canonical): CC(=CCC1=C(C2=C(C3=C1OC(C=C3)(C)C)OC(CC2=O)C4=CC(=C(C=C4)OC)O)O)C
• SMILES (Isomeric): CC(=CCC1=C(C2=C(C3=C1OC(C=C3)(C)C)O[C@@H](CC2=O)C4=CC(=C(C=C4)OC)O)O)C
• InChI: InChI=1S/C26H28O6/c1-14(2)6-8-16-23(29)22-19(28)13-21(15-7-9-20(30-5)18(27)12-15)31-25(22)17-10-11-26(3,4)32-24(16)17/h6-7,9-12,21,27,29H,8,13H2,1-5H3/t21-/m0/s1
• InChI Key: RGXSRPKLOMKRQU-NRFANRHFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₈O₆
• Molecular Weight: 436.50 g/mol
• Exact Mass: 436.18858861 g/mol
• Topological Polar Surface Area (TPSA): 85.20 Ų
• XlogP: 5.60
• Atomic LogP (AlogP): 5.51
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• CHEBI:65681
• (2S)-6-(gamma,gamma-dimethylallyl)-5,3'-dihydroxy-4'-methoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone
• (2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2,3-dihydro-4H,8H-pyrano[2,3-f]chromen-4-one
• BDBM50241688
• Q27134164
• (2S)-6-(3-Methyl-2-butenyl)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-8,8-dimethyl-2,3-dihydro-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one
• (2S)-6-(gamma,gamma-dimethylallyl)-5-3''-dihydroxy-4''-methoxy-6'''',6''''dimethylpyran[2'''',3''''7,8]flavanone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9861	98.61%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7324	73.24%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8516	85.16%
OATP1B3 inhibitior	+	0.8647	86.47%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9538	95.38%
P-glycoprotein inhibitior	+	0.7973	79.73%
P-glycoprotein substrate	-	0.5126	51.26%
CYP3A4 substrate	+	0.6658	66.58%
CYP2C9 substrate	-	0.7981	79.81%
CYP2D6 substrate	-	0.8063	80.63%
CYP3A4 inhibition	-	0.8249	82.49%
CYP2C9 inhibition	+	0.7404	74.04%
CYP2C19 inhibition	+	0.8803	88.03%
CYP2D6 inhibition	-	0.6879	68.79%
CYP1A2 inhibition	-	0.6982	69.82%
CYP2C8 inhibition	+	0.6028	60.28%
CYP inhibitory promiscuity	+	0.7673	76.73%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6182	61.82%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.7686	76.86%
Skin irritation	-	0.7665	76.65%
Skin corrosion	-	0.9399	93.99%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7534	75.34%
Micronuclear	-	0.5141	51.41%
Hepatotoxicity	-	0.6272	62.72%
skin sensitisation	-	0.8189	81.89%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.6663	66.63%
Acute Oral Toxicity (c)	III	0.5050	50.50%
Estrogen receptor binding	+	0.9247	92.47%
Androgen receptor binding	+	0.6861	68.61%
Thyroid receptor binding	+	0.7002	70.02%
Glucocorticoid receptor binding	+	0.8608	86.08%
Aromatase binding	+	0.6271	62.71%
PPAR gamma	+	0.8272	82.72%
Honey bee toxicity	-	0.7092	70.92%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9755	97.55%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1869	P11926	Ornithine decarboxylase	2100 nM	IC50	PMID: 10075742

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.76%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	99.21%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.70%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.59%	85.14%
CHEMBL1951	P21397	Monoamine oxidase A	95.64%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.68%	89.00%
CHEMBL2581	P07339	Cathepsin D	92.56%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.20%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.19%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.28%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.33%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.08%	95.56%
CHEMBL4208	P20618	Proteasome component C5	86.69%	90.00%
CHEMBL340	P08684	Cytochrome P450 3A4	86.48%	91.19%
CHEMBL2535	P11166	Glucose transporter	85.44%	98.75%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.23%	92.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.04%	94.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	83.31%	89.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.29%	91.07%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.22%	90.71%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.88%	95.71%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	80.14%	80.00%

Plants that contains it

• Achillea cretica
• Ageratina riparia
• Cordia americana
• Deguelia urucu
• Glycosmis lanceolata
• Pedicularis semitorta
• Scopolia japonica

Cross-Links

• PubChem: 44559037
• NPASS: NPC192686
• ChEMBL: CHEMBL451703