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

Details

• Internal ID: 1a66bad1-7727-4ef3-b6c8-eb981671d756
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > 6-prenylated flavans > 6-prenylated flavanones
• IUPAC Name: (2S)-5-hydroxy-2-(4-hydroxy-3-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)O)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)O)OC)O)C
• InChI: InChI=1S/C26H28O6/c1-14(2)6-8-16-23(29)22-19(28)13-20(15-7-9-18(27)21(12-15)30-5)31-25(22)17-10-11-26(3,4)32-24(16)17/h6-7,9-12,20,27,29H,8,13H2,1-5H3/t20-/m0/s1
• InChI Key: KCZWDIXZSAGPCD-FQEVSTJZSA-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:65682
• (2S)-6-(gamma,gamma-dimethylallyl)-5,4'-dihydroxy-3'-methoxy-6'',6''-dimethylpyran[2'',3'':7,8]flavanone
• (2S)-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-2,3-dihydro-4H,8H-pyrano[2,3-f]chromen-4-one
• BDBM50241692
• Q27134165
• (2S)-6-(3-Methyl-2-butenyl)-5-hydroxy-2-(3-methoxy-4-hydroxyphenyl)-8,8-dimethyl-2,3-dihydro-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one
• (2S)-6-(gamma,gamma-dimethylallyl)-5,4''-dihydroxy-3''-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	-	0.6008	60.08%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7324	73.24%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8423	84.23%
OATP1B3 inhibitior	+	0.8647	86.47%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9122	91.22%
P-glycoprotein inhibitior	+	0.7481	74.81%
P-glycoprotein substrate	-	0.5458	54.58%
CYP3A4 substrate	+	0.6565	65.65%
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	+	0.5891	58.91%
CYP inhibitory promiscuity	+	0.7673	76.73%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6182	61.82%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.6805	68.05%
Skin irritation	-	0.7665	76.65%
Skin corrosion	-	0.9399	93.99%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6469	64.69%
Micronuclear	-	0.5141	51.41%
Hepatotoxicity	-	0.5772	57.72%
skin sensitisation	-	0.8189	81.89%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.7030	70.30%
Acute Oral Toxicity (c)	III	0.5050	50.50%
Estrogen receptor binding	+	0.9237	92.37%
Androgen receptor binding	+	0.6806	68.06%
Thyroid receptor binding	+	0.7036	70.36%
Glucocorticoid receptor binding	+	0.8826	88.26%
Aromatase binding	+	0.6699	66.99%
PPAR gamma	+	0.8449	84.49%
Honey bee toxicity	-	0.7184	71.84%
Biodegradation	-	0.8750	87.50%
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	1100 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	99.92%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	99.25%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.88%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.66%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.83%	89.00%
CHEMBL2581	P07339	Cathepsin D	92.57%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.82%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.71%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.78%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.39%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.64%	95.56%
CHEMBL4208	P20618	Proteasome component C5	88.47%	90.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.78%	99.15%
CHEMBL340	P08684	Cytochrome P450 3A4	86.31%	91.19%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.20%	92.62%
CHEMBL2535	P11166	Glucose transporter	85.47%	98.75%
CHEMBL1951	P21397	Monoamine oxidase A	84.11%	91.49%
CHEMBL2413	P32246	C-C chemokine receptor type 1	83.15%	89.50%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	82.77%	80.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.59%	90.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.10%	94.00%

Plants that contains it

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

Cross-Links

• PubChem: 44559077
• NPASS: NPC119209
• ChEMBL: CHEMBL464609