7-[(6-O-alpha-L-Rhamnopyranosyl-beta-D-glucopyranosyl)oxy]-4',5,6-trihydroxyflavone

Details

• Internal ID: 72d0c21c-d7e9-4ee4-a97d-184f693b85a0
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 5,6-dihydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-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=C(C(=C4C(=C3)OC(=CC4=O)C5=CC=C(C=C5)O)O)O)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=C(C(=C4C(=C3)OC(=CC4=O)C5=CC=C(C=C5)O)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C27H30O15/c1-9-18(30)22(34)24(36)26(39-9)38-8-16-20(32)23(35)25(37)27(42-16)41-15-7-14-17(21(33)19(15)31)12(29)6-13(40-14)10-2-4-11(28)5-3-10/h2-7,9,16,18,20,22-28,30-37H,8H2,1H3/t9-,16+,18-,20+,22+,23-,24+,25+,26+,27+/m0/s1
• InChI Key: CMAUMDKYDZZLTH-CATNFWIESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₅
• Molecular Weight: 594.50 g/mol
• Exact Mass: 594.15847025 g/mol
• Topological Polar Surface Area (TPSA): 245.00 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): -1.39
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5564	55.64%
Caco-2	-	0.9090	90.90%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7477	74.77%
OATP2B1 inhibitior	-	0.5622	56.22%
OATP1B1 inhibitior	+	0.6844	68.44%
OATP1B3 inhibitior	+	0.9216	92.16%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.6901	69.01%
P-glycoprotein inhibitior	-	0.7752	77.52%
P-glycoprotein substrate	+	0.5647	56.47%
CYP3A4 substrate	+	0.6084	60.84%
CYP2C9 substrate	-	0.7038	70.38%
CYP2D6 substrate	-	0.8611	86.11%
CYP3A4 inhibition	-	0.9249	92.49%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9545	95.45%
CYP1A2 inhibition	-	0.8673	86.73%
CYP2C8 inhibition	+	0.7684	76.84%
CYP inhibitory promiscuity	-	0.6787	67.87%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6741	67.41%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.9145	91.45%
Skin irritation	-	0.8089	80.89%
Skin corrosion	-	0.9595	95.95%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6784	67.84%
Micronuclear	+	0.7192	71.92%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.9325	93.25%
Respiratory toxicity	-	0.6667	66.67%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.9347	93.47%
Acute Oral Toxicity (c)	III	0.5971	59.71%
Estrogen receptor binding	+	0.7371	73.71%
Androgen receptor binding	+	0.6452	64.52%
Thyroid receptor binding	+	0.5256	52.56%
Glucocorticoid receptor binding	+	0.5886	58.86%
Aromatase binding	+	0.5787	57.87%
PPAR gamma	+	0.7382	73.82%
Honey bee toxicity	-	0.7139	71.39%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5949	59.49%
Fish aquatic toxicity	+	0.8993	89.93%

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	99.03%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.62%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.26%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.62%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.82%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.57%	85.14%
CHEMBL1951	P21397	Monoamine oxidase A	91.60%	91.49%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	91.46%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	91.30%	94.73%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	89.80%	95.78%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.78%	86.92%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	89.02%	95.64%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.26%	99.17%
CHEMBL3194	P02766	Transthyretin	86.30%	90.71%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	86.12%	96.21%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.93%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.89%	95.89%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.55%	96.09%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	85.51%	83.57%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.44%	97.36%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.02%	95.56%

Plants that contains it

• Millingtonia hortensis
• Oroxylum indicum
• Teucridium parvifolium

Cross-Links

• PubChem: 5321203
• NPASS: NPC152156
• LOTUS: LTS0182254
• wikiData: Q104964264