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

Details

• Internal ID: 9077c138-6a47-47ff-90a4-01ccf8d52e90
• 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-3,5-dimethoxyphenyl)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)OC)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)OC)O)OC)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C29H34O16/c1-10-20(32)23(35)25(37)28(42-10)41-9-19-22(34)24(36)26(38)29(45-19)44-18-8-13-14(31)6-12(30)7-15(13)43-27(18)11-4-16(39-2)21(33)17(5-11)40-3/h4-8,10,19-20,22-26,28-29,32,34-38H,9H2,1-3H3,(H2-,30,31,33)/p+1/t10-,19+,20-,22+,23+,24-,25+,26+,28+,29+/m0/s1
• InChI Key: YCDMGCUGMVVWAB-FCYARAGISA-O
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₅O₁₆+
• Molecular Weight: 639.60 g/mol
• Exact Mass: 639.19251002 g/mol
• Topological Polar Surface Area (TPSA): 238.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.45
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8042	80.42%
Caco-2	-	0.9050	90.50%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.4955	49.55%
OATP2B1 inhibitior	-	0.7192	71.92%
OATP1B1 inhibitior	+	0.8557	85.57%
OATP1B3 inhibitior	+	0.9315	93.15%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.6662	66.62%
P-glycoprotein inhibitior	-	0.5210	52.10%
P-glycoprotein substrate	+	0.5320	53.20%
CYP3A4 substrate	+	0.6253	62.53%
CYP2C9 substrate	-	0.8109	81.09%
CYP2D6 substrate	-	0.8088	80.88%
CYP3A4 inhibition	-	0.9643	96.43%
CYP2C9 inhibition	-	0.9064	90.64%
CYP2C19 inhibition	-	0.8689	86.89%
CYP2D6 inhibition	-	0.8989	89.89%
CYP1A2 inhibition	-	0.8827	88.27%
CYP2C8 inhibition	+	0.7787	77.87%
CYP inhibitory promiscuity	-	0.7208	72.08%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6300	63.00%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9075	90.75%
Skin irritation	-	0.8362	83.62%
Skin corrosion	-	0.9559	95.59%
Ames mutagenesis	-	0.6091	60.91%
Human Ether-a-go-go-Related Gene inhibition	+	0.7400	74.00%
Micronuclear	+	0.7018	70.18%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.9360	93.60%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	-	0.6500	65.00%
Nephrotoxicity	-	0.9272	92.72%
Acute Oral Toxicity (c)	III	0.6671	66.71%
Estrogen receptor binding	+	0.8212	82.12%
Androgen receptor binding	-	0.5547	55.47%
Thyroid receptor binding	+	0.5876	58.76%
Glucocorticoid receptor binding	+	0.6340	63.40%
Aromatase binding	+	0.6132	61.32%
PPAR gamma	+	0.7178	71.78%
Honey bee toxicity	-	0.7824	78.24%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6349	63.49%
Fish aquatic toxicity	+	0.8030	80.30%

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	99.29%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.20%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.29%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.55%	89.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	94.48%	92.94%
CHEMBL3714130	P46095	G-protein coupled receptor 6	94.06%	97.36%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.99%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	92.85%	91.49%
CHEMBL2581	P07339	Cathepsin D	90.48%	98.95%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.24%	89.62%
CHEMBL4355	O14976	Serine/threonine-protein kinase GAK	89.20%	89.32%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.84%	99.17%
CHEMBL1937	Q92769	Histone deacetylase 2	87.62%	94.75%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.36%	96.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.18%	99.15%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.38%	92.62%
CHEMBL3401	O75469	Pregnane X receptor	83.68%	94.73%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	82.61%	92.38%
CHEMBL3194	P02766	Transthyretin	82.10%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.50%	95.56%
CHEMBL4208	P20618	Proteasome component C5	80.11%	90.00%

Plants that contains it

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

Cross-Links

• PubChem: 101942241
• NPASS: NPC33908