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

Details

• Internal ID: 793129fa-4c4b-4e0a-853f-b757b6d6716f
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > 6-prenylated flavans > 6-prenylated flavanones
• IUPAC Name: (2S)-2-(3,4-dimethoxyphenyl)-5-hydroxy-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)OC)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)OC)O)C
• InChI: InChI=1S/C27H30O6/c1-15(2)7-9-17-24(29)23-19(28)14-21(16-8-10-20(30-5)22(13-16)31-6)32-26(23)18-11-12-27(3,4)33-25(17)18/h7-8,10-13,21,29H,9,14H2,1-6H3/t21-/m0/s1
• InChI Key: FUBFEZXQVKEAMQ-NRFANRHFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₆
• Molecular Weight: 450.50 g/mol
• Exact Mass: 450.20423867 g/mol
• Topological Polar Surface Area (TPSA): 74.20 Ų
• XlogP: 5.90
• Atomic LogP (AlogP): 5.81
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

• CHEBI:65680
• (2S)-6-(gamma,gamma-dimethylallyl)-5-hydroxy-3',4'-dimethoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone
• (2S)-2-(3,4-dimethoxyphenyl)-5-hydroxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2,3-dihydro-4H,8H-pyrano[2,3-f]chromen-4-one
• BDBM50241687
• Q27134163
• (2S)-6-(3-Methyl-2-butenyl)-5-hydroxy-2-(3,4-dimethoxyphenyl)-8,8-dimethyl-2,3-dihydro-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one
• (2S)-6-(gamma,gamma-dimethylallyl)-5-hydroxy-3'',4''-dimethoxy-6'''',6''''-dimethylpyran[2'''',3'''':7,8]flavanone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9903	99.03%
Caco-2	+	0.5311	53.11%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7512	75.12%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8356	83.56%
OATP1B3 inhibitior	+	0.8864	88.64%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9668	96.68%
P-glycoprotein inhibitior	+	0.8931	89.31%
P-glycoprotein substrate	+	0.5412	54.12%
CYP3A4 substrate	+	0.6678	66.78%
CYP2C9 substrate	-	0.7981	79.81%
CYP2D6 substrate	-	0.8063	80.63%
CYP3A4 inhibition	-	0.6862	68.62%
CYP2C9 inhibition	+	0.6289	62.89%
CYP2C19 inhibition	+	0.8759	87.59%
CYP2D6 inhibition	-	0.7637	76.37%
CYP1A2 inhibition	-	0.7352	73.52%
CYP2C8 inhibition	+	0.5763	57.63%
CYP inhibitory promiscuity	+	0.7252	72.52%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6260	62.60%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.7877	78.77%
Skin irritation	-	0.7583	75.83%
Skin corrosion	-	0.9445	94.45%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7737	77.37%
Micronuclear	-	0.5641	56.41%
Hepatotoxicity	-	0.5647	56.47%
skin sensitisation	-	0.8118	81.18%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.6764	67.64%
Acute Oral Toxicity (c)	III	0.5282	52.82%
Estrogen receptor binding	+	0.9226	92.26%
Androgen receptor binding	+	0.6634	66.34%
Thyroid receptor binding	+	0.7356	73.56%
Glucocorticoid receptor binding	+	0.8635	86.35%
Aromatase binding	+	0.6155	61.55%
PPAR gamma	+	0.8328	83.28%
Honey bee toxicity	-	0.7157	71.57%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.9741	97.41%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1869	P11926	Ornithine decarboxylase	2200 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	99.68%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.27%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	99.01%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.67%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.82%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.64%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.02%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.62%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.06%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.40%	99.17%
CHEMBL2535	P11166	Glucose transporter	88.22%	98.75%
CHEMBL4208	P20618	Proteasome component C5	87.45%	90.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	86.99%	89.50%
CHEMBL340	P08684	Cytochrome P450 3A4	84.95%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.62%	95.56%
CHEMBL5555	O00767	Acyl-CoA desaturase	82.33%	97.50%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	81.99%	83.10%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.91%	92.94%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.54%	91.07%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.87%	90.71%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.77%	92.62%

Plants that contains it

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

Cross-Links

• PubChem: 44559036
• NPASS: NPC284820
• ChEMBL: CHEMBL455606