Rhamnocitrin 3-apiosyl-(1->2)-glucoside

Details

• Internal ID: 467b932d-a69d-4360-92c5-b998219eefe0
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 3-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxychromen-4-one
• SMILES (Canonical): COC1=CC(=C2C(=C1)OC(=C(C2=O)OC3C(C(C(C(O3)CO)O)O)OC4C(C(CO4)(CO)O)O)C5=CC=C(C=C5)O)O
• SMILES (Isomeric): COC1=CC(=C2C(=C1)OC(=C(C2=O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O[C@H]4[C@@H]([C@](CO4)(CO)O)O)C5=CC=C(C=C5)O)O
• InChI: InChI=1S/C27H30O15/c1-37-13-6-14(31)17-15(7-13)39-21(11-2-4-12(30)5-3-11)22(19(17)33)41-25-23(20(34)18(32)16(8-28)40-25)42-26-24(35)27(36,9-29)10-38-26/h2-7,16,18,20,23-26,28-32,34-36H,8-10H2,1H3/t16-,18-,20+,23-,24+,25+,26+,27-/m1/s1
• InChI Key: YNTOLJZMFPWELF-OGBUFVBUSA-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): 234.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): -1.48
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 8

Synonyms

• Rhamnocitrin 3-O-|A-D-apiofuranosyl(1 inverted exclamation marku2)-|A-D-glucopyranoside
• Rhamnocitrin 3-apiosyl-(1->2)-glucoside
• HY-N10645
• AKOS040763631
• FS-8256
• Rhamnocitrin 3-apiosyl-(1???2)-glucoside
• CS-0621382

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6754	67.54%
Caco-2	-	0.9020	90.20%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6254	62.54%
OATP2B1 inhibitior	-	0.5701	57.01%
OATP1B1 inhibitior	+	0.8937	89.37%
OATP1B3 inhibitior	+	0.9655	96.55%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9122	91.22%
P-glycoprotein inhibitior	+	0.5750	57.50%
P-glycoprotein substrate	+	0.5097	50.97%
CYP3A4 substrate	+	0.6941	69.41%
CYP2C9 substrate	-	0.8407	84.07%
CYP2D6 substrate	-	0.8539	85.39%
CYP3A4 inhibition	-	0.8418	84.18%
CYP2C9 inhibition	-	0.8860	88.60%
CYP2C19 inhibition	-	0.8296	82.96%
CYP2D6 inhibition	-	0.9113	91.13%
CYP1A2 inhibition	-	0.9060	90.60%
CYP2C8 inhibition	+	0.7481	74.81%
CYP inhibitory promiscuity	-	0.7811	78.11%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5250	52.50%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9051	90.51%
Skin irritation	-	0.8131	81.31%
Skin corrosion	-	0.9457	94.57%
Ames mutagenesis	+	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6465	64.65%
Micronuclear	+	0.6733	67.33%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.8821	88.21%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.7713	77.13%
Acute Oral Toxicity (c)	III	0.6985	69.85%
Estrogen receptor binding	+	0.8088	80.88%
Androgen receptor binding	+	0.7401	74.01%
Thyroid receptor binding	+	0.5725	57.25%
Glucocorticoid receptor binding	+	0.6212	62.12%
Aromatase binding	+	0.6658	66.58%
PPAR gamma	+	0.7384	73.84%
Honey bee toxicity	-	0.7367	73.67%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.6644	66.44%

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	99.68%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.49%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.58%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.19%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.71%	95.56%
CHEMBL2581	P07339	Cathepsin D	95.65%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.72%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	93.83%	95.93%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.32%	85.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.17%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.99%	96.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.08%	86.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.85%	86.33%
CHEMBL4208	P20618	Proteasome component C5	86.80%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.25%	95.89%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.07%	94.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.89%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	84.87%	94.73%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.50%	95.89%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.06%	95.83%
CHEMBL3922	P50579	Methionine aminopeptidase 2	83.88%	97.28%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.61%	92.94%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.50%	99.17%
CHEMBL242	Q92731	Estrogen receptor beta	83.41%	98.35%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.21%	97.14%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	81.04%	95.53%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.29%	97.36%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.27%	96.00%

Plants that contains it

• Phyllolobium chinense

Cross-Links

• PubChem: 10416064
• LOTUS: LTS0241976
• wikiData: Q105351104