3-[(2S,3S,4S,5R,6S)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-(3,5-dihydroxy-4-methoxyphenyl)-5,7-dihydroxychromen-4-one

Details

• Internal ID: a1e78b04-b4f6-4be2-af07-09a205a2ef73
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 3-[(2S,3S,4S,5R,6S)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-(3,5-dihydroxy-4-methoxyphenyl)-5,7-dihydroxychromen-4-one
• SMILES (Canonical): COC1=C(C=C(C=C1O)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)CO)OC5C(C(C(C(O5)CO)O)O)O)O)O)O
• SMILES (Isomeric): COC1=C(C=C(C=C1O)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O[C@H]4[C@H]([C@@H]([C@H]([C@@H](O4)CO)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)CO)O)O)O)O)O)O
• InChI: InChI=1S/C28H32O18/c1-41-24-11(33)2-8(3-12(24)34)23-26(18(36)16-10(32)4-9(31)5-13(16)42-23)46-28-22(40)20(38)25(15(7-30)44-28)45-27-21(39)19(37)17(35)14(6-29)43-27/h2-5,14-15,17,19-22,25,27-35,37-40H,6-7H2,1H3/t14-,15-,17-,19+,20-,21+,22-,25-,27-,28-/m0/s1
• InChI Key: ZBZXUVASLIBHBO-UWFZOVOLSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₂O₁₈
• Molecular Weight: 656.50 g/mol
• Exact Mass: 656.15886417 g/mol
• Topological Polar Surface Area (TPSA): 295.00 Ų
• XlogP: -1.80
• Atomic LogP (AlogP): -2.71
• H-Bond Acceptor: 18
• H-Bond Donor: 11
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5457	54.57%
Caco-2	-	0.9118	91.18%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.5961	59.61%
OATP2B1 inhibitior	-	0.5758	57.58%
OATP1B1 inhibitior	+	0.8763	87.63%
OATP1B3 inhibitior	+	0.9786	97.86%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.6197	61.97%
P-glycoprotein inhibitior	-	0.5328	53.28%
P-glycoprotein substrate	-	0.5978	59.78%
CYP3A4 substrate	+	0.6480	64.80%
CYP2C9 substrate	-	0.8485	84.85%
CYP2D6 substrate	-	0.8501	85.01%
CYP3A4 inhibition	-	0.9437	94.37%
CYP2C9 inhibition	-	0.9060	90.60%
CYP2C19 inhibition	-	0.8926	89.26%
CYP2D6 inhibition	-	0.9515	95.15%
CYP1A2 inhibition	-	0.9150	91.50%
CYP2C8 inhibition	+	0.7085	70.85%
CYP inhibitory promiscuity	-	0.7142	71.42%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6642	66.42%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9092	90.92%
Skin irritation	-	0.8320	83.20%
Skin corrosion	-	0.9606	96.06%
Ames mutagenesis	+	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7406	74.06%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.9324	93.24%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.8516	85.16%
Acute Oral Toxicity (c)	III	0.6678	66.78%
Estrogen receptor binding	+	0.8488	84.88%
Androgen receptor binding	+	0.5903	59.03%
Thyroid receptor binding	+	0.5400	54.00%
Glucocorticoid receptor binding	+	0.5596	55.96%
Aromatase binding	+	0.5993	59.93%
PPAR gamma	+	0.6945	69.45%
Honey bee toxicity	-	0.7049	70.49%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.6698	66.98%

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	99.41%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.78%	89.00%
CHEMBL2581	P07339	Cathepsin D	95.37%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.21%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.85%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	91.41%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.29%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.21%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.97%	86.33%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	85.92%	95.64%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.30%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.62%	94.45%
CHEMBL4208	P20618	Proteasome component C5	81.16%	90.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.41%	96.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.02%	86.92%

Plants that contains it

• Vitex negundo

Cross-Links

• PubChem: 163051067
• LOTUS: LTS0098143
• wikiData: Q105370923