3-[(2R,3S,4R,5R)-3,4-dihydroxy-5-[(1S)-1-hydroxyethyl]oxolan-2-yl]oxy-7-[(2S,3S,4R,5S)-5-[(1R)-1-[(2R,3S,4R,5R)-3,4-dihydroxy-5-[(1S)-1-hydroxyethyl]oxolan-2-yl]oxyethyl]-3,4-dihydroxyoxolan-2-yl]-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one

Details

• Internal ID: 0d086fd4-7633-4646-847c-eb9451e7ab0c
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 3-[(2R,3S,4R,5R)-3,4-dihydroxy-5-[(1S)-1-hydroxyethyl]oxolan-2-yl]oxy-7-[(2S,3S,4R,5S)-5-[(1R)-1-[(2R,3S,4R,5R)-3,4-dihydroxy-5-[(1S)-1-hydroxyethyl]oxolan-2-yl]oxyethyl]-3,4-dihydroxyoxolan-2-yl]-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one
• SMILES (Canonical): CC(C1C(C(C(O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)C4C(C(C(O4)C(C)OC5C(C(C(O5)C(C)O)O)O)O)O)C6=CC=C(C=C6)O)O)O)O
• SMILES (Isomeric): C[C@@H]([C@@H]1[C@@H]([C@@H]([C@H](O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)[C@H]4[C@H]([C@H]([C@H](O4)[C@@H](C)O[C@H]5[C@H]([C@H]([C@H](O5)[C@H](C)O)O)O)O)O)C6=CC=C(C=C6)O)O)O)O
• InChI: InChI=1S/C33H40O17/c1-10(34)26-22(41)24(43)32(48-26)45-12(3)28-20(39)21(40)29(47-28)14-8-16(37)18-17(9-14)46-30(13-4-6-15(36)7-5-13)31(19(18)38)50-33-25(44)23(42)27(49-33)11(2)35/h4-12,20-29,32-37,39-44H,1-3H3/t10-,11-,12+,20+,21-,22+,23+,24-,25-,26+,27+,28+,29-,32+,33+/m0/s1
• InChI Key: BRVZZNMAPDHDTF-JCXBLXGPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₀O₁₇
• Molecular Weight: 708.70 g/mol
• Exact Mass: 708.22654980 g/mol
• Topological Polar Surface Area (TPSA): 275.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): -1.53
• H-Bond Acceptor: 17
• H-Bond Donor: 10
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8717	87.17%
Caco-2	-	0.8941	89.41%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7444	74.44%
OATP2B1 inhibitior	+	0.5716	57.16%
OATP1B1 inhibitior	+	0.9031	90.31%
OATP1B3 inhibitior	-	0.2410	24.10%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.7897	78.97%
P-glycoprotein inhibitior	-	0.4421	44.21%
P-glycoprotein substrate	-	0.5220	52.20%
CYP3A4 substrate	+	0.6731	67.31%
CYP2C9 substrate	-	0.6986	69.86%
CYP2D6 substrate	-	0.8600	86.00%
CYP3A4 inhibition	-	0.5571	55.71%
CYP2C9 inhibition	-	0.8428	84.28%
CYP2C19 inhibition	-	0.6928	69.28%
CYP2D6 inhibition	-	0.8846	88.46%
CYP1A2 inhibition	-	0.5526	55.26%
CYP2C8 inhibition	+	0.7906	79.06%
CYP inhibitory promiscuity	+	0.6444	64.44%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4118	41.18%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9043	90.43%
Skin irritation	-	0.7490	74.90%
Skin corrosion	-	0.9559	95.59%
Ames mutagenesis	-	0.5237	52.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.7386	73.86%
Micronuclear	+	0.8800	88.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.8793	87.93%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.5939	59.39%
Acute Oral Toxicity (c)	III	0.4184	41.84%
Estrogen receptor binding	+	0.7709	77.09%
Androgen receptor binding	+	0.7076	70.76%
Thyroid receptor binding	+	0.5500	55.00%
Glucocorticoid receptor binding	+	0.5902	59.02%
Aromatase binding	+	0.5231	52.31%
PPAR gamma	+	0.6937	69.37%
Honey bee toxicity	-	0.7452	74.52%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7150	71.50%
Fish aquatic toxicity	+	0.9700	97.00%

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	99.54%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.28%	91.11%
CHEMBL2581	P07339	Cathepsin D	99.10%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.71%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	94.20%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	93.91%	94.73%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	92.66%	95.64%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.51%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.47%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.40%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.37%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.63%	94.45%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.93%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.66%	99.17%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	82.74%	95.78%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.68%	95.89%
CHEMBL2535	P11166	Glucose transporter	82.59%	98.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.48%	99.23%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	81.86%	93.10%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	81.31%	97.53%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.10%	97.09%

Plants that contains it

• Macroptilium atropurpureum

Cross-Links

• PubChem: 162962254
• LOTUS: LTS0266449
• wikiData: Q104945047