5-Hydroxy-2-(4-methoxyphenyl)-7-[3,4,5-trihydroxy-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]oxan-2-yl]oxychromen-4-one

Details

• Internal ID: 1801bed5-2eb7-40b2-a32b-f0fd13c463eb
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 5-hydroxy-2-(4-methoxyphenyl)-7-[3,4,5-trihydroxy-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=CC(=C4C(=C3)OC(=CC4=O)C5=CC=C(C=C5)OC)O)O)O)O)O)O)O
• SMILES (Isomeric): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=CC(=C4C(=C3)OC(=CC4=O)C5=CC=C(C=C5)OC)O)O)O)O)O)O)O
• InChI: InChI=1S/C28H32O14/c1-11-21(31)23(33)25(35)27(39-11)38-10-19-22(32)24(34)26(36)28(42-19)40-14-7-15(29)20-16(30)9-17(41-18(20)8-14)12-3-5-13(37-2)6-4-12/h3-9,11,19,21-29,31-36H,10H2,1-2H3
• InChI Key: YFVGIJBUXMQFOF-UHFFFAOYSA-N
• Popularity: 10 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₂O₁₄
• Molecular Weight: 592.50 g/mol
• Exact Mass: 592.17920569 g/mol
• Topological Polar Surface Area (TPSA): 214.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -0.80
• H-Bond Acceptor: 14
• H-Bond Donor: 7
• Rotatable Bonds: 7

Synonyms

• 5-hydroxy-2-(4-methoxyphenyl)-7-[3,4,5-trihydroxy-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]oxan-2-yl]oxychromen-4-one
• Buddleoside;Linarine
• CHEMBL601333
• SCHEMBL7169195
• AKOS000507432
• AKOS021983167
• FT-0686654
• 4H-1-Benzopyran-4-one, 7-((2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)-oxy)-5-hydroxy-2-(4-methoxyphenyl)-
• 4H-1-Benzopyran-4-one, 7-[[2-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyranosyl]-oxy]-5-hydroxy-2-(4-methoxyphenyl)-
• 5-hydroxy-2-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl 6-O-(6-deoxyhexopyranosyl)hexopyranoside
• 5-hydroxy-2-(4-methoxyphenyl)-7-[3,4,5-trihydroxy-6-[(3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl)oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5129	51.29%
Caco-2	-	0.8708	87.08%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7197	71.97%
OATP2B1 inhibitior	-	0.7078	70.78%
OATP1B1 inhibitior	+	0.9086	90.86%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8473	84.73%
P-glycoprotein inhibitior	-	0.8194	81.94%
P-glycoprotein substrate	+	0.6260	62.60%
CYP3A4 substrate	+	0.5696	56.96%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8527	85.27%
CYP3A4 inhibition	-	0.8625	86.25%
CYP2C9 inhibition	-	0.9259	92.59%
CYP2C19 inhibition	-	0.9289	92.89%
CYP2D6 inhibition	-	0.9201	92.01%
CYP1A2 inhibition	-	0.9339	93.39%
CYP2C8 inhibition	+	0.6812	68.12%
CYP inhibitory promiscuity	-	0.6937	69.37%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6511	65.11%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.9288	92.88%
Skin irritation	-	0.8266	82.66%
Skin corrosion	-	0.9635	96.35%
Ames mutagenesis	-	0.5764	57.64%
Human Ether-a-go-go-Related Gene inhibition	+	0.8049	80.49%
Micronuclear	+	0.7192	71.92%
Hepatotoxicity	-	0.8500	85.00%
skin sensitisation	-	0.9465	94.65%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.6625	66.25%
Nephrotoxicity	-	0.9375	93.75%
Acute Oral Toxicity (c)	III	0.7286	72.86%
Estrogen receptor binding	+	0.7835	78.35%
Androgen receptor binding	+	0.5903	59.03%
Thyroid receptor binding	+	0.5488	54.88%
Glucocorticoid receptor binding	+	0.6033	60.33%
Aromatase binding	+	0.5321	53.21%
PPAR gamma	+	0.7064	70.64%
Honey bee toxicity	-	0.7773	77.73%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.8051	80.51%

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	99.63%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.98%	91.49%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.70%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.31%	85.14%
CHEMBL2581	P07339	Cathepsin D	96.44%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	94.88%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.57%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.13%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	90.82%	94.73%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.75%	97.36%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.33%	95.56%
CHEMBL1907	P15144	Aminopeptidase N	90.03%	93.31%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.95%	86.92%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.75%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.82%	97.09%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	85.32%	81.11%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.27%	95.89%
CHEMBL3194	P02766	Transthyretin	84.18%	90.71%
CHEMBL4208	P20618	Proteasome component C5	84.15%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.26%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.41%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.23%	90.71%

Plants that contains it

• Anaphalis sinica
• Bombax ceiba
• Buddleja officinalis
• Buddleja scordioides
• Cephalotaxus fortunei
• Chrysanthemum indicum
• Chrysanthemum naktongense
• Cirsium japonicum
• Cirsium japonicum var. maackii
• Citrus japonica
• Clinopodium nepeta subsp. spruneri
• Fagopyrum acutatum
• Hedysarum setigerum
• Hyssopus officinalis
• Isatis tinctoria
• Linaria vulgaris
• Mentha arvensis
• Ophryosporus heptanthus
• Scutellaria caucasica
• Silene firma
• Teucridium parvifolium
• Thalictrum simplex
• Valeriana ajanensis subsp. fasciculata

Cross-Links

• PubChem: 5480901
• NPASS: NPC22062
• ChEMBL: CHEMBL601333
• LOTUS: LTS0103484
• wikiData: Q105347820