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

Details

• Internal ID: fce1b481-7785-40e0-9042-727213d9c683
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 3-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxychromen-4-one
• SMILES (Canonical): COC1=C(C(=C2C(=C1)OC(=C(C2=O)OC3C(C(C(C(O3)CO)OC4C(C(C(C(O4)CO)O)O)O)O)O)C5=CC(=C(C=C5)O)O)O)OC
• SMILES (Isomeric): COC1=C(C(=C2C(=C1)OC(=C(C2=O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)C5=CC(=C(C=C5)O)O)O)OC
• InChI: InChI=1S/C29H34O18/c1-41-13-6-12-16(18(35)25(13)42-2)19(36)27(24(43-12)9-3-4-10(32)11(33)5-9)47-29-23(40)21(38)26(15(8-31)45-29)46-28-22(39)20(37)17(34)14(7-30)44-28/h3-6,14-15,17,20-23,26,28-35,37-40H,7-8H2,1-2H3/t14-,15-,17-,20+,21-,22-,23-,26-,28+,29+/m1/s1
• InChI Key: GGRCKRIFVXKFAC-WTNAIJNVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₄O₁₈
• Molecular Weight: 670.60 g/mol
• Exact Mass: 670.17451423 g/mol
• Topological Polar Surface Area (TPSA): 284.00 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -2.40
• H-Bond Acceptor: 18
• H-Bond Donor: 10
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5623	56.23%
Caco-2	-	0.9097	90.97%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.5984	59.84%
OATP2B1 inhibitior	-	0.7161	71.61%
OATP1B1 inhibitior	+	0.9232	92.32%
OATP1B3 inhibitior	+	0.9748	97.48%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.5472	54.72%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	-	0.5463	54.63%
CYP3A4 substrate	+	0.6621	66.21%
CYP2C9 substrate	-	0.8415	84.15%
CYP2D6 substrate	-	0.8515	85.15%
CYP3A4 inhibition	-	0.9284	92.84%
CYP2C9 inhibition	-	0.9208	92.08%
CYP2C19 inhibition	-	0.9124	91.24%
CYP2D6 inhibition	-	0.9531	95.31%
CYP1A2 inhibition	-	0.9232	92.32%
CYP2C8 inhibition	+	0.8141	81.41%
CYP inhibitory promiscuity	-	0.7113	71.13%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7032	70.32%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9098	90.98%
Skin irritation	-	0.8442	84.42%
Skin corrosion	-	0.9614	96.14%
Ames mutagenesis	+	0.5036	50.36%
Human Ether-a-go-go-Related Gene inhibition	+	0.6747	67.47%
Micronuclear	+	0.6633	66.33%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.9340	93.40%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.9628	96.28%
Acute Oral Toxicity (c)	III	0.7041	70.41%
Estrogen receptor binding	+	0.8320	83.20%
Androgen receptor binding	+	0.6476	64.76%
Thyroid receptor binding	+	0.5268	52.68%
Glucocorticoid receptor binding	+	0.5834	58.34%
Aromatase binding	+	0.5880	58.80%
PPAR gamma	+	0.7103	71.03%
Honey bee toxicity	-	0.6645	66.45%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.7167	71.67%

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	99.66%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.52%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.80%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.80%	94.00%
CHEMBL2581	P07339	Cathepsin D	94.45%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.57%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.31%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.84%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.27%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	88.25%	94.73%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	87.77%	95.64%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.64%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.68%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.03%	96.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.90%	86.92%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.99%	95.89%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.64%	95.83%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	80.50%	80.78%

Plants that contains it

• Ipomopsis aggregata

Cross-Links

• PubChem: 163051542
• LOTUS: LTS0208570
• wikiData: Q105008291