Rhodalidin

Details

• Internal ID: 622ea62d-cbba-47a8-ba19-4cc703d3803d
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-8-O-glycosides
• IUPAC Name: 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-8-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxychromen-4-one
• SMILES (Canonical): C1C(C(C(C(O1)OC2=C(C=C(C3=C2OC(=C(C3=O)OC4C(C(C(C(O4)CO)O)O)O)C5=CC=C(C=C5)O)O)O)O)O)O
• SMILES (Isomeric): C1[C@H]([C@@H]([C@H]([C@@H](O1)OC2=C(C=C(C3=C2OC(=C(C3=O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)C5=CC=C(C=C5)O)O)O)O)O)O
• InChI: InChI=1S/C26H28O16/c27-6-13-16(33)18(35)20(37)26(39-13)42-24-17(34)14-10(29)5-11(30)22(41-25-19(36)15(32)12(31)7-38-25)23(14)40-21(24)8-1-3-9(28)4-2-8/h1-5,12-13,15-16,18-20,25-33,35-37H,6-7H2/t12-,13-,15+,16-,18+,19-,20-,25+,26+/m1/s1
• InChI Key: KAMNGBDKYCAJCF-BPCHNOSOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₈O₁₆
• Molecular Weight: 596.50 g/mol
• Exact Mass: 596.13773480 g/mol
• Topological Polar Surface Area (TPSA): 266.00 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): -2.43
• H-Bond Acceptor: 16
• H-Bond Donor: 10
• Rotatable Bonds: 6

Synonyms

• UNII-B3O599Q1UA
• B3O599Q1UA
• 94696-37-4
• 4H-1-Benzopyran-4-one, 3-(beta-D-glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(beta-D-xylopyranosyloxy)-
• DTXSID401346053
• Q27274316
• 4H-1-BENZOPYRAN-4-ONE, 3-(.BETA.-D-GLUCOPYRANOSYLOXY)-5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-8-(.BETA.-D-XYLOPYRANOSYLOXY)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5110	51.10%
Caco-2	-	0.9158	91.58%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.4988	49.88%
OATP2B1 inhibitior	-	0.5540	55.40%
OATP1B1 inhibitior	+	0.9021	90.21%
OATP1B3 inhibitior	+	0.9174	91.74%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.6598	65.98%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	-	0.6541	65.41%
CYP3A4 substrate	+	0.6269	62.69%
CYP2C9 substrate	-	0.6762	67.62%
CYP2D6 substrate	-	0.8575	85.75%
CYP3A4 inhibition	-	0.9373	93.73%
CYP2C9 inhibition	-	0.9644	96.44%
CYP2C19 inhibition	-	0.9395	93.95%
CYP2D6 inhibition	-	0.9332	93.32%
CYP1A2 inhibition	-	0.9304	93.04%
CYP2C8 inhibition	+	0.6574	65.74%
CYP inhibitory promiscuity	-	0.8779	87.79%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6882	68.82%
Eye corrosion	-	0.9940	99.40%
Eye irritation	-	0.8667	86.67%
Skin irritation	-	0.8205	82.05%
Skin corrosion	-	0.9667	96.67%
Ames mutagenesis	+	0.6246	62.46%
Human Ether-a-go-go-Related Gene inhibition	+	0.7165	71.65%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.6797	67.97%
skin sensitisation	-	0.9071	90.71%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.8814	88.14%
Acute Oral Toxicity (c)	III	0.4508	45.08%
Estrogen receptor binding	+	0.7748	77.48%
Androgen receptor binding	+	0.6906	69.06%
Thyroid receptor binding	-	0.5290	52.90%
Glucocorticoid receptor binding	-	0.4657	46.57%
Aromatase binding	+	0.5639	56.39%
PPAR gamma	+	0.6568	65.68%
Honey bee toxicity	-	0.6996	69.96%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6850	68.50%
Fish aquatic toxicity	+	0.7253	72.53%

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	99.69%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.23%	89.00%
CHEMBL2581	P07339	Cathepsin D	94.82%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.74%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.63%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.33%	97.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.82%	99.15%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	86.56%	95.64%
CHEMBL3401	O75469	Pregnane X receptor	85.30%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.79%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.43%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.30%	96.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.57%	86.92%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.21%	95.83%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	82.51%	95.78%
CHEMBL242	Q92731	Estrogen receptor beta	82.43%	98.35%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	82.34%	80.33%
CHEMBL220	P22303	Acetylcholinesterase	82.22%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.08%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.83%	90.71%

Plants that contains it

• Phedimus kamtschaticus
• Rhodiola rosea

Cross-Links

• PubChem: 13577326
• LOTUS: LTS0201420
• wikiData: Q27274316