(2S)-6-(Gamma,Gamma-Dimethylallyl)-3',4'-Dimethoxy-6'',6''-Dimethylpyran[2'',3'':7,8]Flavanone

Details

• Internal ID: fa66c202-0c89-4383-82e2-140f16d32e16
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > 6-prenylated flavans > 6-prenylated flavanones
• IUPAC Name: (2S)-2-(3,4-dimethoxyphenyl)-8,8-dimethyl-6-(3-methylbut-2-enyl)-2,3-dihydropyrano[2,3-h]chromen-4-one
• SMILES (Canonical): CC(=CCC1=CC2=C(C3=C1OC(C=C3)(C)C)OC(CC2=O)C4=CC(=C(C=C4)OC)OC)C
• SMILES (Isomeric): CC(=CCC1=CC2=C(C3=C1OC(C=C3)(C)C)O[C@@H](CC2=O)C4=CC(=C(C=C4)OC)OC)C
• InChI: InChI=1S/C27H30O5/c1-16(2)7-8-18-13-20-21(28)15-23(17-9-10-22(29-5)24(14-17)30-6)31-26(20)19-11-12-27(3,4)32-25(18)19/h7,9-14,23H,8,15H2,1-6H3/t23-/m0/s1
• InChI Key: KJBZFWLVOZNDBN-QHCPKHFHSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₅
• Molecular Weight: 434.50 g/mol
• Exact Mass: 434.20932405 g/mol
• Topological Polar Surface Area (TPSA): 54.00 Ų
• XlogP: 5.70
• Atomic LogP (AlogP): 6.10
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 5

Synonyms

• (2S)-6-(gamma,gamma-dimethylallyl)-3',4'-dimethoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone
• (2S)-2-(3,4-dimethoxyphenyl)-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2,3-dihydro-4H,8H-pyrano[2,3-f]chromen-4-one
• (2S)-2-(3,4-dimethoxyphenyl)-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2,3-dihydro-4H,8H-pyrano(2,3-f)chromen-4-one
• (2S)-6-(Gamma,Gamma-Dimethylallyl)-3',4'-Dimethoxy-6'',6''-Dimethylpyran(2'',3'':7,8)Flavanone
• RefChem:68964
• GlyTouCan:G99236CR
• G99236CR
• (2S)-2-(3,4-dimethoxyphenyl)-8,8-dimethyl-6-(3-methylbut-2-enyl)-2,3-dihydropyrano(2,3-h)chromen-4-one
• CHEMBL516860
• BDBM50241693
• Q27134166
• (2S)-6-(gamma,gamma-dimethylallyl)-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	+	0.9957	99.57%
Caco-2	+	0.6115	61.15%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7362	73.62%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8766	87.66%
OATP1B3 inhibitior	+	0.9256	92.56%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9795	97.95%
P-glycoprotein inhibitior	+	0.9547	95.47%
P-glycoprotein substrate	+	0.5843	58.43%
CYP3A4 substrate	+	0.6552	65.52%
CYP2C9 substrate	-	0.8027	80.27%
CYP2D6 substrate	-	0.7486	74.86%
CYP3A4 inhibition	+	0.7049	70.49%
CYP2C9 inhibition	-	0.6240	62.40%
CYP2C19 inhibition	+	0.8998	89.98%
CYP2D6 inhibition	-	0.8033	80.33%
CYP1A2 inhibition	-	0.6722	67.22%
CYP2C8 inhibition	+	0.4664	46.64%
CYP inhibitory promiscuity	+	0.8572	85.72%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6005	60.05%
Eye corrosion	-	0.9877	98.77%
Eye irritation	-	0.8814	88.14%
Skin irritation	-	0.7810	78.10%
Skin corrosion	-	0.9594	95.94%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8620	86.20%
Micronuclear	-	0.5641	56.41%
Hepatotoxicity	-	0.5650	56.50%
skin sensitisation	-	0.7562	75.62%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.7056	70.56%
Estrogen receptor binding	+	0.9180	91.80%
Androgen receptor binding	+	0.6190	61.90%
Thyroid receptor binding	+	0.7623	76.23%
Glucocorticoid receptor binding	+	0.8429	84.29%
Aromatase binding	-	0.5455	54.55%
PPAR gamma	+	0.8101	81.01%
Honey bee toxicity	-	0.7101	71.01%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.7052	70.52%
Fish aquatic toxicity	+	0.9780	97.80%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1869	P11926	Ornithine decarboxylase	2300 nM	IC50	PMID: 10075742

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.56%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.00%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.61%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.27%	94.45%
CHEMBL2581	P07339	Cathepsin D	93.66%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.46%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.03%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.77%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.67%	89.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	88.29%	89.50%
CHEMBL2535	P11166	Glucose transporter	87.64%	98.75%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.31%	92.94%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.40%	92.62%
CHEMBL4208	P20618	Proteasome component C5	85.30%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.00%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.99%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	84.67%	91.19%
CHEMBL3922	P50579	Methionine aminopeptidase 2	84.06%	97.28%
CHEMBL221	P23219	Cyclooxygenase-1	83.33%	90.17%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.32%	91.07%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.40%	95.71%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	80.24%	92.38%

Plants that contains it

• Deguelia urucu

Cross-Links

• PubChem: 44559078
• NPASS: NPC40033
• ChEMBL: CHEMBL516860