Peonidin 3-O-rutinoside

Details

• Internal ID: f1656ff3-0298-4f05-a3fd-b901fe43a6cf
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Anthocyanins > Anthocyanidin-3-O-glycosides
• IUPAC Name: (2R,3R,4R,5R,6S)-2-[[(2R,3S,4S,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)chromenylium-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-methyloxane-3,4,5-triol
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=CC4=C(C=C(C=C4[O+]=C3C5=CC(=C(C=C5)O)OC)O)O)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=CC4=C(C=C(C=C4[O+]=C3C5=CC(=C(C=C5)O)OC)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C28H32O15/c1-10-20(32)22(34)24(36)27(40-10)39-9-19-21(33)23(35)25(37)28(43-19)42-18-8-13-15(31)6-12(29)7-16(13)41-26(18)11-3-4-14(30)17(5-11)38-2/h3-8,10,19-25,27-28,32-37H,9H2,1-2H3,(H2-,29,30,31)/p+1/t10-,19+,20-,21+,22+,23-,24+,25+,27+,28+/m0/s1
• InChI Key: ONQVTPMFYSRRLL-HUJUZFAXSA-O
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₃O₁₅+
• Molecular Weight: 609.60 g/mol
• Exact Mass: 609.18194534 g/mol
• Topological Polar Surface Area (TPSA): 229.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.46
• H-Bond Acceptor: 14
• H-Bond Donor: 9
• Rotatable Bonds: 7

Synonyms

• DTXSID201341469
• 3-[(6-O-alpha-L-Rhamnopyranosyl-beta-D-glucopyranosyl)oxy]-4',5,7-trihydroxy-3'-methoxyflavylium

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8034	80.34%
Caco-2	-	0.9174	91.74%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.5196	51.96%
OATP2B1 inhibitior	-	0.5788	57.88%
OATP1B1 inhibitior	+	0.8926	89.26%
OATP1B3 inhibitior	+	0.9528	95.28%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7077	70.77%
P-glycoprotein inhibitior	-	0.6150	61.50%
P-glycoprotein substrate	-	0.5283	52.83%
CYP3A4 substrate	+	0.6206	62.06%
CYP2C9 substrate	-	0.8109	81.09%
CYP2D6 substrate	-	0.8088	80.88%
CYP3A4 inhibition	-	0.9289	92.89%
CYP2C9 inhibition	-	0.8786	87.86%
CYP2C19 inhibition	-	0.8242	82.42%
CYP2D6 inhibition	-	0.8823	88.23%
CYP1A2 inhibition	-	0.8687	86.87%
CYP2C8 inhibition	+	0.8264	82.64%
CYP inhibitory promiscuity	-	0.6898	68.98%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6451	64.51%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.9112	91.12%
Skin irritation	-	0.8253	82.53%
Skin corrosion	-	0.9515	95.15%
Ames mutagenesis	-	0.5791	57.91%
Human Ether-a-go-go-Related Gene inhibition	-	0.3648	36.48%
Micronuclear	+	0.7318	73.18%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.9334	93.34%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	-	0.6375	63.75%
Nephrotoxicity	-	0.8897	88.97%
Acute Oral Toxicity (c)	III	0.6716	67.16%
Estrogen receptor binding	+	0.7868	78.68%
Androgen receptor binding	-	0.5406	54.06%
Thyroid receptor binding	+	0.5678	56.78%
Glucocorticoid receptor binding	+	0.6177	61.77%
Aromatase binding	+	0.6324	63.24%
PPAR gamma	+	0.7121	71.21%
Honey bee toxicity	-	0.7944	79.44%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5649	56.49%
Fish aquatic toxicity	+	0.7953	79.53%

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	99.15%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.38%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.39%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.37%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.91%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	93.58%	91.49%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	93.05%	89.62%
CHEMBL3714130	P46095	G-protein coupled receptor 6	92.85%	97.36%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.55%	99.15%
CHEMBL241	Q14432	Phosphodiesterase 3A	92.35%	92.94%
CHEMBL2581	P07339	Cathepsin D	91.29%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.74%	99.17%
CHEMBL4355	O14976	Serine/threonine-protein kinase GAK	87.13%	89.32%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.64%	96.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.28%	86.92%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	83.81%	95.78%
CHEMBL1907	P15144	Aminopeptidase N	83.60%	93.31%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.17%	95.56%
CHEMBL3438	Q05513	Protein kinase C zeta	81.74%	88.48%
CHEMBL3194	P02766	Transthyretin	81.06%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.95%	95.89%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.88%	95.83%
CHEMBL3401	O75469	Pregnane X receptor	80.86%	94.73%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.59%	92.62%

Plants that contains it

• Aconitum violaceum
• Aronia melanocarpa
• Codonopsis pilosula
• Delphinium shawurense
• Fagraea gracilipes
• Garcinia xipshuanbannaensis
• Gutierrezia microcephala
• Helichrysum graveolens
• Iryanthera paraensis
• Lathyrus nissolia
• Leonurus persicus
• Magnolia sieboldii
• Peltogyne floribunda
• Prunus avium
• Prunus cerasus
• Ratibida mexicana
• Ribes nigrum
• Rubus idaeus

Cross-Links

• PubChem: 90470732
• NPASS: NPC140454
• LOTUS: LTS0143796
• wikiData: Q104667386