2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-3-[(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]oxychromen-4-one

Details

• Internal ID: 48312752-5485-4d4c-8284-29f6bbbd2898
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-3-[(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]oxychromen-4-one
• SMILES (Canonical): COC1=CC(=CC(=C1O)O)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)COC5C(C(C(C(O5)CO)O)O)O)O)O)O
• SMILES (Isomeric): COC1=CC(=CC(=C1O)O)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[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O)O
• InChI: InChI=1S/C28H32O18/c1-41-13-3-8(2-11(32)17(13)33)25-26(20(36)16-10(31)4-9(30)5-12(16)43-25)46-28-24(40)22(38)19(35)15(45-28)7-42-27-23(39)21(37)18(34)14(6-29)44-27/h2-5,14-15,18-19,21-24,27-35,37-40H,6-7H2,1H3/t14-,15-,18-,19-,21+,22+,23-,24-,27-,28+/m1/s1
• InChI Key: JUNGQERXHWTHAD-GNDQXLCUSA-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	-	0.9196	91.96%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.5961	59.61%
OATP2B1 inhibitior	-	0.5774	57.74%
OATP1B1 inhibitior	+	0.8581	85.81%
OATP1B3 inhibitior	+	0.9786	97.86%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.5751	57.51%
P-glycoprotein inhibitior	-	0.5227	52.27%
P-glycoprotein substrate	+	0.5497	54.97%
CYP3A4 substrate	+	0.6450	64.50%
CYP2C9 substrate	-	0.8415	84.15%
CYP2D6 substrate	-	0.8515	85.15%
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	+	0.8289	82.89%
CYP inhibitory promiscuity	-	0.7142	71.42%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6642	66.42%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9115	91.15%
Skin irritation	-	0.8320	83.20%
Skin corrosion	-	0.9606	96.06%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4538	45.38%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.9324	93.24%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.7424	74.24%
Acute Oral Toxicity (c)	III	0.6678	66.78%
Estrogen receptor binding	+	0.8507	85.07%
Androgen receptor binding	+	0.5677	56.77%
Thyroid receptor binding	-	0.4879	48.79%
Glucocorticoid receptor binding	+	0.5791	57.91%
Aromatase binding	+	0.6168	61.68%
PPAR gamma	+	0.7506	75.06%
Honey bee toxicity	-	0.7781	77.81%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6149	61.49%
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	99.55%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.61%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.47%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.57%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.30%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.54%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.17%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.23%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	91.39%	94.73%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	89.62%	95.64%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.76%	95.56%
CHEMBL3194	P02766	Transthyretin	88.27%	90.71%
CHEMBL2424	Q04760	Glyoxalase I	85.69%	91.67%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.74%	96.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.95%	86.92%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.75%	92.62%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.43%	99.15%
CHEMBL2002	P12268	Inosine-5'-monophosphate dehydrogenase 2	81.76%	98.21%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.35%	97.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.12%	97.36%

Plants that contains it

• Afrocarpus gracilior
• Agave xylonacantha
• Anthemis cretica
• Antiphiona pinnatisecta
• Calophyllum inophyllum
• Lycopodium japonicum
• Maackia tashiroi
• Monoon cupulare
• Thelypteris esquirolii
• Turnera diffusa

Cross-Links

• PubChem: 102401707
• NPASS: NPC286667
• LOTUS: LTS0274846
• wikiData: Q105135325