3-[3-[3,4-Dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]oxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one

Details

• Internal ID: 8596367e-5b44-4c8e-9ea7-f245a5700c9a
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 3-[3-[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]oxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC=C(C=C5)O)OC6C(C(CO6)(CO)O)O)O)O)O)O)O
• SMILES (Isomeric): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC=C(C=C5)O)OC6C(C(CO6)(CO)O)O)O)O)O)O)O
• InChI: InChI=1S/C32H38O19/c1-11-19(37)22(40)24(42)29(47-11)45-8-17-20(38)23(41)27(51-31-28(43)32(44,9-33)10-46-31)30(49-17)50-26-21(39)18-15(36)6-14(35)7-16(18)48-25(26)12-2-4-13(34)5-3-12/h2-7,11,17,19-20,22-24,27-31,33-38,40-44H,8-10H2,1H3
• InChI Key: PXDYLXHBUIPSMK-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₃₈O₁₉
• Molecular Weight: 726.60 g/mol
• Exact Mass: 726.20072898 g/mol
• Topological Polar Surface Area (TPSA): 304.00 Ų
• XlogP: -2.20
• Atomic LogP (AlogP): -2.93
• H-Bond Acceptor: 19
• H-Bond Donor: 11
• Rotatable Bonds: 9

Synonyms

• NSC641259
• 3-[3-[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]oxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• Kaempferol 3-(2G-apiosylrobinobioside)
• kaempferol 3-O-(apiofuranosyl-(1/'/'/'-2/'/')-rhamnopyranosyl-(1/'/'/'/'-6/'/'))-galactopyranoside
• Kaempferol-3-O-[.beta.-D-apiofuranosyl(1-2)-.alpha.-rhamno pyranosyl(1-6)]-.beta.-D-galactopyranoside
• CHEMBL2004567
• CHEBI:191719
• NSC-641259
• NCI60_013918
• 3-[3-[3,4-dihydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl]oxy-4,5-dihydroxy-6-[(3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl)oxymethyl]tetrahydropyran-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6822	68.22%
Caco-2	-	0.9109	91.09%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6873	68.73%
OATP2B1 inhibitior	-	0.8504	85.04%
OATP1B1 inhibitior	+	0.8748	87.48%
OATP1B3 inhibitior	+	0.9553	95.53%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8499	84.99%
P-glycoprotein inhibitior	-	0.4875	48.75%
P-glycoprotein substrate	+	0.6834	68.34%
CYP3A4 substrate	+	0.7043	70.43%
CYP2C9 substrate	-	0.8407	84.07%
CYP2D6 substrate	-	0.8650	86.50%
CYP3A4 inhibition	-	0.8804	88.04%
CYP2C9 inhibition	-	0.9020	90.20%
CYP2C19 inhibition	-	0.8493	84.93%
CYP2D6 inhibition	-	0.9267	92.67%
CYP1A2 inhibition	-	0.8913	89.13%
CYP2C8 inhibition	+	0.8186	81.86%
CYP inhibitory promiscuity	-	0.7619	76.19%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5384	53.84%
Eye corrosion	-	0.9929	99.29%
Eye irritation	-	0.9135	91.35%
Skin irritation	-	0.8152	81.52%
Skin corrosion	-	0.9478	94.78%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7522	75.22%
Micronuclear	+	0.6633	66.33%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.8842	88.42%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.8441	84.41%
Acute Oral Toxicity (c)	III	0.6434	64.34%
Estrogen receptor binding	+	0.8117	81.17%
Androgen receptor binding	+	0.6573	65.73%
Thyroid receptor binding	+	0.5211	52.11%
Glucocorticoid receptor binding	+	0.5693	56.93%
Aromatase binding	+	0.6424	64.24%
PPAR gamma	+	0.7302	73.02%
Honey bee toxicity	-	0.7140	71.40%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5750	57.50%
Fish aquatic toxicity	+	0.7925	79.25%

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	99.72%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	98.65%	89.00%
CHEMBL2581	P07339	Cathepsin D	97.36%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.83%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	96.29%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.96%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.74%	95.56%
CHEMBL226	P30542	Adenosine A1 receptor	93.05%	95.93%
CHEMBL1937	Q92769	Histone deacetylase 2	91.33%	94.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.01%	97.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	89.50%	97.36%
CHEMBL3401	O75469	Pregnane X receptor	89.19%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.37%	94.45%
CHEMBL242	Q92731	Estrogen receptor beta	87.10%	98.35%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.93%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.41%	96.09%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.65%	95.83%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.61%	86.92%
CHEMBL6175	Q9H3R0	Lysine-specific demethylase 4C	84.34%	96.69%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.98%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.69%	95.89%
CHEMBL4208	P20618	Proteasome component C5	83.58%	90.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.57%	99.15%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	83.27%	93.10%
CHEMBL4530	P00488	Coagulation factor XIII	82.56%	96.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.22%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.86%	92.94%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	80.63%	80.33%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.52%	94.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.35%	99.17%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	80.13%	95.64%

Plants that contains it

• Monnina sylvatica
• Solidago altissima

Cross-Links

• PubChem: 5465152
• LOTUS: LTS0252420
• wikiData: Q105216131