Rhc-irh

Details

• Internal ID: c673622b-b8b3-428e-83a8-e4f441b07270
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 3-[(2S,3R,4S,5R,6R)-6-[[(2R,3R,4S,5R,6S)-3,4-dihydroxy-6-methyl-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(OC(C(C2O)O)OCC3C(C(C(C(O3)OC4=C(OC5=CC(=CC(=C5C4=O)O)OC)C6=CC=C(C=C6)O)O)O)O)C)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2[C@@H](O[C@H]([C@@H]([C@@H]2O)O)OC[C@@H]3[C@@H]([C@@H]([C@H]([C@@H](O3)OC4=C(OC5=CC(=CC(=C5C4=O)O)OC)C6=CC=C(C=C6)O)O)O)O)C)O)O)O
• InChI: InChI=1S/C34H42O19/c1-11-20(37)23(40)26(43)33(48-11)52-29-12(2)49-32(28(45)25(29)42)47-10-18-21(38)24(41)27(44)34(51-18)53-31-22(39)19-16(36)8-15(46-3)9-17(19)50-30(31)13-4-6-14(35)7-5-13/h4-9,11-12,18,20-21,23-29,32-38,40-45H,10H2,1-3H3/t11-,12-,18+,20-,21-,23+,24-,25-,26+,27+,28+,29-,32+,33-,34-/m0/s1
• InChI Key: CGNAHCOLJLGPEQ-PAODLKMBSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₄₂O₁₉
• Molecular Weight: 754.70 g/mol
• Exact Mass: 754.23202911 g/mol
• Topological Polar Surface Area (TPSA): 293.00 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): -2.24
• H-Bond Acceptor: 19
• H-Bond Donor: 10
• Rotatable Bonds: 9

Synonyms

• 73519-10-5
• 3-[(2S,3R,4S,5R,6R)-6-[[(2R,3R,4S,5R,6S)-3,4-dihydroxy-6-methyl-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxychromen-4-one
• Rhamnocitrin 3-O-isorhamninoside
• DTXSID80994291
• 3-((O-6-Deoxy-alpha-L-mannopyranosyl-(1-4)-O-6-deoxy-alpha-L-mannopyranosyl-(1-6)-beta-D-galactopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one
• 4H-1-Benzopyran-4-one, 3-((O-6-deoxy-alpha-L-mannopyranosyl-(1-4)-O-6-deoxy-alpha-L-mannopyranosyl-(1-6)-beta-D-galactopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-
• 5-Hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxo-4H-1-benzopyran-3-yl 6-deoxyhexopyranosyl-(1->4)-6-deoxyhexopyranosyl-(1->6)hexopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4796	47.96%
Caco-2	-	0.8906	89.06%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6680	66.80%
OATP2B1 inhibitior	-	0.5751	57.51%
OATP1B1 inhibitior	+	0.8789	87.89%
OATP1B3 inhibitior	+	0.9137	91.37%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.4500	45.00%
P-glycoprotein inhibitior	+	0.6028	60.28%
P-glycoprotein substrate	+	0.6222	62.22%
CYP3A4 substrate	+	0.6528	65.28%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8527	85.27%
CYP3A4 inhibition	-	0.9310	93.10%
CYP2C9 inhibition	-	0.9351	93.51%
CYP2C19 inhibition	-	0.9301	93.01%
CYP2D6 inhibition	-	0.9356	93.56%
CYP1A2 inhibition	-	0.9113	91.13%
CYP2C8 inhibition	+	0.7773	77.73%
CYP inhibitory promiscuity	-	0.6965	69.65%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6809	68.09%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9053	90.53%
Skin irritation	-	0.8382	83.82%
Skin corrosion	-	0.9635	96.35%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4274	42.74%
Micronuclear	+	0.7192	71.92%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.9454	94.54%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	-	0.6625	66.25%
Nephrotoxicity	-	0.9112	91.12%
Acute Oral Toxicity (c)	III	0.6850	68.50%
Estrogen receptor binding	+	0.7845	78.45%
Androgen receptor binding	+	0.6490	64.90%
Thyroid receptor binding	+	0.5531	55.31%
Glucocorticoid receptor binding	+	0.6625	66.25%
Aromatase binding	+	0.5756	57.56%
PPAR gamma	+	0.7284	72.84%
Honey bee toxicity	-	0.7402	74.02%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.8533	85.33%

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	99.50%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.26%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.08%	94.00%
CHEMBL2581	P07339	Cathepsin D	96.59%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.21%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	95.19%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.40%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.18%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	92.50%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.63%	96.09%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	90.82%	95.64%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.51%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.37%	95.56%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.94%	97.36%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.83%	95.89%
CHEMBL4208	P20618	Proteasome component C5	84.76%	90.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.19%	97.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.92%	86.92%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.11%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.22%	99.23%

Plants that contains it

• Rhamnus formosana

Cross-Links

• PubChem: 5491232
• LOTUS: LTS0152815
• wikiData: Q82985184