5,7,4'-Trihydroxyflavone-3-yl 2-O-(alpha-L-rhamnopyranosyl)-6-O-[2-O-(3-methoxy-4-hydroxy-trans-cinnamoyl)-alpha-L-rhamnopyranosyl]-beta-D-galactopyranoside

Details

• Internal ID: db50b3c7-df08-42ab-9a14-8ef501555644
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: [(2R,3R,4R,5R,6S)-2-[[(2R,3R,4S,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-3,4-dihydroxy-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]methoxy]-4,5-dihydroxy-6-methyloxan-3-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC=C(C=C5)O)COC6C(C(C(C(O6)C)O)O)OC(=O)C=CC7=CC(=C(C=C7)O)OC)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@H]([C@H](O[C@H]2OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC=C(C=C5)O)CO[C@H]6[C@@H]([C@@H]([C@H]([C@@H](O6)C)O)O)OC(=O)/C=C/C7=CC(=C(C=C7)O)OC)O)O)O)O)O
• InChI: InChI=1S/C43H48O22/c1-16-29(49)33(53)36(56)41(59-16)65-40-35(55)31(51)26(15-58-42-39(34(54)30(50)17(2)60-42)63-27(48)11-5-18-4-10-22(46)24(12-18)57-3)62-43(40)64-38-32(52)28-23(47)13-21(45)14-25(28)61-37(38)19-6-8-20(44)9-7-19/h4-14,16-17,26,29-31,33-36,39-47,49-51,53-56H,15H2,1-3H3/b11-5+/t16-,17-,26+,29-,30-,31-,33+,34+,35-,36+,39+,40+,41-,42+,43-/m0/s1
• InChI Key: OYMFGCWYYJYUKC-VYEJHIHYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₄₈O₂₂
• Molecular Weight: 916.80 g/mol
• Exact Mass: 916.26372315 g/mol
• Topological Polar Surface Area (TPSA): 340.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): -0.56
• H-Bond Acceptor: 22
• H-Bond Donor: 11
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5530	55.30%
Caco-2	-	0.8823	88.23%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.5729	57.29%
OATP2B1 inhibitior	-	0.7103	71.03%
OATP1B1 inhibitior	+	0.8549	85.49%
OATP1B3 inhibitior	+	0.9478	94.78%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7708	77.08%
P-glycoprotein inhibitior	+	0.6801	68.01%
P-glycoprotein substrate	+	0.7163	71.63%
CYP3A4 substrate	+	0.7056	70.56%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8718	87.18%
CYP3A4 inhibition	-	0.9007	90.07%
CYP2C9 inhibition	-	0.8872	88.72%
CYP2C19 inhibition	-	0.9236	92.36%
CYP2D6 inhibition	-	0.9301	93.01%
CYP1A2 inhibition	-	0.9344	93.44%
CYP2C8 inhibition	+	0.8975	89.75%
CYP inhibitory promiscuity	-	0.7459	74.59%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6348	63.48%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9052	90.52%
Skin irritation	-	0.8375	83.75%
Skin corrosion	-	0.9543	95.43%
Ames mutagenesis	-	0.6165	61.65%
Human Ether-a-go-go-Related Gene inhibition	+	0.6433	64.33%
Micronuclear	+	0.7092	70.92%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.9161	91.61%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.9811	98.11%
Acute Oral Toxicity (c)	III	0.5848	58.48%
Estrogen receptor binding	+	0.7893	78.93%
Androgen receptor binding	+	0.6388	63.88%
Thyroid receptor binding	+	0.5372	53.72%
Glucocorticoid receptor binding	+	0.6842	68.42%
Aromatase binding	+	0.5872	58.72%
PPAR gamma	+	0.7485	74.85%
Honey bee toxicity	-	0.6835	68.35%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9530	95.30%

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	99.83%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	99.20%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.81%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	97.70%	91.49%
CHEMBL3194	P02766	Transthyretin	95.96%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.78%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.75%	96.09%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	94.63%	95.64%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.86%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.26%	95.56%
CHEMBL2581	P07339	Cathepsin D	92.03%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	91.04%	94.73%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	88.76%	80.78%
CHEMBL3714130	P46095	G-protein coupled receptor 6	88.04%	97.36%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.48%	95.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.41%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.58%	94.45%
CHEMBL4208	P20618	Proteasome component C5	85.51%	90.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.05%	99.15%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.71%	95.89%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	82.41%	95.78%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.91%	89.62%
CHEMBL242	Q92731	Estrogen receptor beta	81.31%	98.35%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	80.31%	91.71%

Plants that contains it

• Albizia altissima
• Artocarpus altilis
• Centaurea solstitialis
• Cosmos diversifolius
• Cryptocarya oblata
• Curcuma caesia
• Erythrina pallida
• Eucalyptus radiata subsp. radiata
• Inga velutina
• Lactuca serriola
• Lagochilus leiacanthus
• Ocimum africanum
• Onobrychis viciifolia
• Phelline lucida
• Piptostigma fugax
• Rhododendron mucronatum
• Strychnos tricalysioides
• Trichodesma incanum
• Urochloa eminii
• Xanthorrhoea resinosa

Cross-Links

• PubChem: 101781229
• NPASS: NPC312368