4'-[(6-O-beta-D-Glucopyranosyl-beta-D-glucopyranosyl)oxy]-2'-hydroxy-3',6'-dimethoxy-alpha,beta-dihydrochalcone

Details

• Internal ID: 46f5f30e-7716-4e63-b73f-3ab919ab3b8f
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides
• IUPAC Name: 1-[2-hydroxy-3,6-dimethoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyphenyl]-3-phenylpropan-1-one
• SMILES (Canonical): COC1=CC(=C(C(=C1C(=O)CCC2=CC=CC=C2)O)OC)OC3C(C(C(C(O3)COC4C(C(C(C(O4)CO)O)O)O)O)O)O
• SMILES (Isomeric): COC1=CC(=C(C(=C1C(=O)CCC2=CC=CC=C2)O)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)O
• InChI: InChI=1S/C29H38O15/c1-39-15-10-16(27(40-2)22(34)19(15)14(31)9-8-13-6-4-3-5-7-13)42-29-26(38)24(36)21(33)18(44-29)12-41-28-25(37)23(35)20(32)17(11-30)43-28/h3-7,10,17-18,20-21,23-26,28-30,32-38H,8-9,11-12H2,1-2H3/t17-,18-,20-,21-,23+,24+,25-,26-,28-,29-/m1/s1
• InChI Key: HIBKUVNPLDZFLK-YHRQVHEKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₈O₁₅
• Molecular Weight: 626.60 g/mol
• Exact Mass: 626.22107050 g/mol
• Topological Polar Surface Area (TPSA): 234.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -1.77
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 12

Synonyms

• 4'-[(6-O-beta-D-Glucopyranosyl-beta-D-glucopyranosyl)oxy]-2'-hydroxy-3',6'-dimethoxy-alpha,beta-dihydrochalcone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8372	83.72%
Caco-2	-	0.8778	87.78%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7483	74.83%
OATP2B1 inhibitior	-	0.8611	86.11%
OATP1B1 inhibitior	+	0.7774	77.74%
OATP1B3 inhibitior	+	0.9552	95.52%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.8425	84.25%
P-glycoprotein inhibitior	-	0.5335	53.35%
P-glycoprotein substrate	-	0.6141	61.41%
CYP3A4 substrate	+	0.6194	61.94%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8400	84.00%
CYP3A4 inhibition	-	0.9373	93.73%
CYP2C9 inhibition	-	0.7657	76.57%
CYP2C19 inhibition	-	0.8870	88.70%
CYP2D6 inhibition	-	0.9314	93.14%
CYP1A2 inhibition	-	0.8944	89.44%
CYP2C8 inhibition	+	0.7743	77.43%
CYP inhibitory promiscuity	-	0.8198	81.98%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.7302	73.02%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9314	93.14%
Skin irritation	-	0.8524	85.24%
Skin corrosion	-	0.9607	96.07%
Ames mutagenesis	-	0.6270	62.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.8052	80.52%
Micronuclear	-	0.6467	64.67%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.9049	90.49%
Respiratory toxicity	-	0.6333	63.33%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	-	0.7000	70.00%
Nephrotoxicity	-	0.8804	88.04%
Acute Oral Toxicity (c)	III	0.8115	81.15%
Estrogen receptor binding	+	0.8402	84.02%
Androgen receptor binding	-	0.5970	59.70%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6177	61.77%
Aromatase binding	+	0.5375	53.75%
PPAR gamma	+	0.6856	68.56%
Honey bee toxicity	-	0.8217	82.17%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6504	65.04%
Fish aquatic toxicity	-	0.5000	50.00%

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	98.81%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.65%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.36%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.01%	99.17%
CHEMBL2581	P07339	Cathepsin D	93.08%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.51%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	91.01%	94.73%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	90.35%	95.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.03%	96.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.54%	94.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.95%	95.89%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.34%	94.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.09%	89.00%

Plants that contains it

• Commiphora kua
• Eucalyptus staigeriana
• Ipomopsis polycladon
• Merwilla dracomontana
• Mitrephora diversifolia
• Persicaria decipiens
• Selenicereus ocamponis
• Tamarix aphylla
• Xanthosoma sagittifolium

Cross-Links

• PubChem: 10699171
• NPASS: NPC150546
• LOTUS: LTS0118451
• wikiData: Q105028738