Rhodiosin

Details

• Internal ID: 0ef2c0e7-d408-4e9b-991f-44dfeecef5c7
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 7-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,5,8-trihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=C(C3=C(C(=C2)O)C(=O)C(=C(O3)C4=CC=C(C=C4)O)O)O)O)OC5C(C(C(C(O5)CO)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(C3=C(C(=C2)O)C(=O)C(=C(O3)C4=CC=C(C=C4)O)O)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O
• InChI: InChI=1S/C27H30O16/c1-8-15(31)25(43-26-21(37)19(35)16(32)13(7-28)41-26)22(38)27(39-8)40-12-6-11(30)14-18(34)20(36)23(42-24(14)17(12)33)9-2-4-10(29)5-3-9/h2-6,8,13,15-16,19,21-22,25-33,35-38H,7H2,1H3/t8-,13+,15-,16+,19-,21+,22+,25+,26-,27-/m0/s1
• InChI Key: WXBBQBYCUTXTJQ-ULMXTSOFSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₆
• Molecular Weight: 610.50 g/mol
• Exact Mass: 610.15338487 g/mol
• Topological Polar Surface Area (TPSA): 266.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -1.69
• H-Bond Acceptor: 16
• H-Bond Donor: 10
• Rotatable Bonds: 6

Synonyms

• 86831-54-1
• BFG0D2RH6Z
• Rhodiosin; Herbacetin-7-O-glucorhamnoside
• 7-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,5,8-trihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• UNII-BFG0D2RH6Z
• DTXSID801318608
• HY-N2425
• MFCD00238673
• AKOS040756489
• 4H-1-Benzopyran-4-one, 7-((6-deoxy-3-o-beta-D-glucopyranosyl-alpha-L-mannopyranosyl)oxy)-3,5,8-trihydroxy-2-(4-hydroxyphenyl)-
• AC-34297
• MS-30699
• CS-0022638
• A916115
• Q27274642
• herbacetin 7-O-(3''-O-beta-D-glucopyranosyl-alpha-L-rhamnopyranoside)
• 4H-1-BENZOPYRAN-4-ONE, 7-((6-DEOXY-3-O-.BETA.-D-GLUCOPYRANOSYL-.ALPHA.-L-MANNOPYRANOSYL)OXY)-3,5,8-TRIHYDROXY-2-(4-HYDROXYPHENYL)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4777	47.77%
Caco-2	-	0.9091	90.91%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6881	68.81%
OATP2B1 inhibitior	-	0.5643	56.43%
OATP1B1 inhibitior	+	0.8740	87.40%
OATP1B3 inhibitior	+	0.9552	95.52%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.8771	87.71%
P-glycoprotein inhibitior	-	0.6301	63.01%
P-glycoprotein substrate	+	0.5132	51.32%
CYP3A4 substrate	+	0.6453	64.53%
CYP2C9 substrate	-	0.6986	69.86%
CYP2D6 substrate	-	0.8617	86.17%
CYP3A4 inhibition	-	0.9358	93.58%
CYP2C9 inhibition	-	0.9271	92.71%
CYP2C19 inhibition	-	0.9330	93.30%
CYP2D6 inhibition	-	0.9643	96.43%
CYP1A2 inhibition	-	0.8830	88.30%
CYP2C8 inhibition	+	0.7458	74.58%
CYP inhibitory promiscuity	-	0.7188	71.88%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7023	70.23%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.9095	90.95%
Skin irritation	-	0.8192	81.92%
Skin corrosion	-	0.9626	96.26%
Ames mutagenesis	+	0.5572	55.72%
Human Ether-a-go-go-Related Gene inhibition	+	0.7037	70.37%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.9312	93.12%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.8302	83.02%
Acute Oral Toxicity (c)	III	0.5734	57.34%
Estrogen receptor binding	+	0.7840	78.40%
Androgen receptor binding	+	0.6157	61.57%
Thyroid receptor binding	+	0.5573	55.73%
Glucocorticoid receptor binding	+	0.5718	57.18%
Aromatase binding	+	0.6041	60.41%
PPAR gamma	+	0.7322	73.22%
Honey bee toxicity	-	0.7165	71.65%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.8289	82.89%

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	99.64%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.52%	89.00%
CHEMBL2581	P07339	Cathepsin D	97.26%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.00%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.91%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	94.54%	91.49%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	91.47%	95.64%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.51%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	89.33%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.55%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.50%	86.92%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.96%	95.89%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	86.41%	95.78%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	86.07%	96.21%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.51%	97.36%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.65%	96.09%
CHEMBL3194	P02766	Transthyretin	84.56%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.81%	94.45%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.05%	99.15%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.98%	90.71%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.73%	92.94%

Plants that contains it

• Rhodiola crenulata
• Rhodiola rosea

Cross-Links

• PubChem: 76959646
• LOTUS: LTS0239710
• wikiData: Q27274642