Oxytroflavoside A

Details

• Internal ID: 7b489bf7-da89-4a2f-b532-70d0441edb74
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: (3S)-5-[[(2R,3R,4S,5R,6S)-3,4-dihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxochromen-3-yl]oxy-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]methoxy]-3-hydroxy-3-methyl-5-oxopentanoic acid
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=C(OC4=CC(=CC(=C4C3=O)O)OC)C5=CC=C(C=C5)O)COC(=O)CC(C)(CC(=O)O)O)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)OC)C5=CC=C(C=C5)O)COC(=O)C[C@](C)(CC(=O)O)O)O)O)O)O)O
• InChI: InChI=1S/C34H40O19/c1-13-23(40)26(43)28(45)32(49-13)53-31-27(44)24(41)19(12-48-21(39)11-34(2,46)10-20(37)38)51-33(31)52-30-25(42)22-17(36)8-16(47-3)9-18(22)50-29(30)14-4-6-15(35)7-5-14/h4-9,13,19,23-24,26-28,31-33,35-36,40-41,43-46H,10-12H2,1-3H3,(H,37,38)/t13-,19+,23-,24-,26+,27-,28+,31+,32-,33-,34-/m0/s1
• InChI Key: YZKBUFGSRKWUHK-PEKSDXLZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₄₀O₁₉
• Molecular Weight: 752.70 g/mol
• Exact Mass: 752.21637904 g/mol
• Topological Polar Surface Area (TPSA): 298.00 Ų
• XlogP: -1.00
• Atomic LogP (AlogP): -0.92
• H-Bond Acceptor: 18
• H-Bond Donor: 9
• Rotatable Bonds: 12

Synonyms

• CHEMBL2071417
• AKOS040735899
• 3-[2-O-alpha-L-Rhamnopyranosyl-6-O-[(S)-3,5-dihydroxy-3-methyl-5-oxopentanoyl]-beta-D-galactopyranosyloxy]-4',5-dihydroxy-7-methoxyflavone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6402	64.02%
Caco-2	-	0.8951	89.51%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.5965	59.65%
OATP2B1 inhibitior	-	0.5751	57.51%
OATP1B1 inhibitior	+	0.8510	85.10%
OATP1B3 inhibitior	+	0.9263	92.63%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.7870	78.70%
P-glycoprotein inhibitior	+	0.6472	64.72%
P-glycoprotein substrate	+	0.6346	63.46%
CYP3A4 substrate	+	0.6991	69.91%
CYP2C9 substrate	-	0.6425	64.25%
CYP2D6 substrate	-	0.8720	87.20%
CYP3A4 inhibition	-	0.8520	85.20%
CYP2C9 inhibition	-	0.9479	94.79%
CYP2C19 inhibition	-	0.9394	93.94%
CYP2D6 inhibition	-	0.9392	93.92%
CYP1A2 inhibition	-	0.8684	86.84%
CYP2C8 inhibition	+	0.8123	81.23%
CYP inhibitory promiscuity	-	0.9490	94.90%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6153	61.53%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9164	91.64%
Skin irritation	-	0.8283	82.83%
Skin corrosion	-	0.9489	94.89%
Ames mutagenesis	-	0.5137	51.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.7205	72.05%
Micronuclear	+	0.5900	59.00%
Hepatotoxicity	-	0.5926	59.26%
skin sensitisation	-	0.9217	92.17%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.9760	97.60%
Acute Oral Toxicity (c)	III	0.5667	56.67%
Estrogen receptor binding	+	0.8300	83.00%
Androgen receptor binding	+	0.6795	67.95%
Thyroid receptor binding	+	0.5216	52.16%
Glucocorticoid receptor binding	+	0.7096	70.96%
Aromatase binding	+	0.6354	63.54%
PPAR gamma	+	0.7215	72.15%
Honey bee toxicity	-	0.7270	72.70%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9628	96.28%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.76%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.57%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.05%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.03%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.19%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	94.96%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.90%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.00%	96.09%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	93.94%	95.64%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.81%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	93.40%	94.73%
CHEMBL3714130	P46095	G-protein coupled receptor 6	93.39%	97.36%
CHEMBL1951	P21397	Monoamine oxidase A	93.29%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.15%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.58%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	81.02%	92.50%

Plants that contains it

• Abies alba
• Abies pinsapo subsp. marocana
• Ampelocera edentula
• Angelica acutiloba
• Arnica mollis
• Brassica carinata
• Bryonia alba
• Carpha glomerata
• Croton gratissimus
• Cyanostegia angustifolia
• Dactylorhiza viridis
• Diplopterygium glaucum
• Eucalyptus resinifera
• Euphrasia nana
• Eurycoma harmandiana
• Ixeris japonica
• Lysimachia fordiana
• Orthosiphon aristatus
• Oxytropis falcata
• Pterolobium hexapetalum
• Ranunculus asiaticus
• Remirea maritima
• Sinapis alba
• Solanum lanceolatum
• Viburnum erubescens
• Wikstroemia indica
• Xanthorhiza simplicissima

Cross-Links

• PubChem: 60200065
• NPASS: NPC209550
• LOTUS: LTS0195426
• wikiData: Q105369289