Rhodiolgin

Details

• Internal ID: 6cccdd21-9ef5-4b86-98ce-0c8e6488f161
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-3,5,8-trihydroxy-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-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)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)O)O
• InChI: InChI=1S/C21H20O12/c1-6-13(25)16(28)18(30)21(31-6)32-11-5-10(24)12-15(27)17(29)19(33-20(12)14(11)26)7-2-3-8(22)9(23)4-7/h2-6,13,16,18,21-26,28-30H,1H3/t6-,13-,16+,18+,21-/m0/s1
• InChI Key: NEUWGQOEDGCMSK-NNURTEGNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₁₂
• Molecular Weight: 464.40 g/mol
• Exact Mass: 464.09547607 g/mol
• Topological Polar Surface Area (TPSA): 207.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 0.19
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 3

Synonyms

• 94696-39-6
• Gossypetin-7-o-L-rhamnopyranoside
• UNII-K1E4B8S1S7
• K1E4B8S1S7
• 4H-1-Benzopyran-4-one, 7-((6-deoxy-alpha-L-mannopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-3,5,8-trihydroxy-
• DTXSID901345862
• Q27281817
• 2-(3,4-Dihydroxyphenyl)-3,5,8-trihydroxy-7-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one
• 2-(3,4-dihydroxyphenyl)-3,5,8-trihydroxy-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
• 4H-1-BENZOPYRAN-4-ONE, 7-((6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)OXY)-2-(3,4-DIHYDROXYPHENYL)-3,5,8-TRIHYDROXY-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8357	83.57%
Caco-2	-	0.8637	86.37%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7163	71.63%
OATP2B1 inhibitior	+	0.5989	59.89%
OATP1B1 inhibitior	+	0.9356	93.56%
OATP1B3 inhibitior	+	0.9188	91.88%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.7227	72.27%
P-glycoprotein inhibitior	-	0.6870	68.70%
P-glycoprotein substrate	-	0.6582	65.82%
CYP3A4 substrate	+	0.6031	60.31%
CYP2C9 substrate	-	0.7038	70.38%
CYP2D6 substrate	-	0.8611	86.11%
CYP3A4 inhibition	-	0.7109	71.09%
CYP2C9 inhibition	-	0.8538	85.38%
CYP2C19 inhibition	-	0.8339	83.39%
CYP2D6 inhibition	-	0.9547	95.47%
CYP1A2 inhibition	-	0.5306	53.06%
CYP2C8 inhibition	+	0.7725	77.25%
CYP inhibitory promiscuity	-	0.5648	56.48%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6170	61.70%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.8506	85.06%
Skin irritation	-	0.6220	62.20%
Skin corrosion	-	0.9360	93.60%
Ames mutagenesis	+	0.6526	65.26%
Human Ether-a-go-go-Related Gene inhibition	-	0.4429	44.29%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.8874	88.74%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.8278	82.78%
Acute Oral Toxicity (c)	III	0.5184	51.84%
Estrogen receptor binding	+	0.7288	72.88%
Androgen receptor binding	+	0.6286	62.86%
Thyroid receptor binding	+	0.5404	54.04%
Glucocorticoid receptor binding	+	0.6872	68.72%
Aromatase binding	+	0.5240	52.40%
PPAR gamma	+	0.7221	72.21%
Honey bee toxicity	-	0.7823	78.23%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5251	52.51%
Fish aquatic toxicity	+	0.9457	94.57%

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%
CHEMBL1951	P21397	Monoamine oxidase A	98.46%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.70%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.66%	86.33%
CHEMBL2581	P07339	Cathepsin D	95.57%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.01%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.20%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.33%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	88.63%	94.73%
CHEMBL3714130	P46095	G-protein coupled receptor 6	88.59%	97.36%
CHEMBL3194	P02766	Transthyretin	87.60%	90.71%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.94%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.12%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.27%	92.94%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.37%	99.23%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	83.15%	95.78%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	83.03%	93.65%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.99%	99.17%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	82.77%	95.64%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	81.50%	83.00%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	80.86%	80.78%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.08%	96.09%

Plants that contains it

• Rhodiola quadrifida
• Rhodiola rosea

Cross-Links

• PubChem: 91827018
• LOTUS: LTS0097703
• wikiData: Q27281817