2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1-benzopyran-1-ium-3-yl 6-O-[(2Z)-3-(4-hydroxyphenyl)prop-2-enoyl]-beta-D-glucopyranoside

Details

• Internal ID: a40a124e-a62d-4968-aa7c-815b88efd352
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Anthocyanidin 3-O-p-coumaroyl glycosides > Anthocyanidin 3-O-6-p-coumaroyl glycosides
• IUPAC Name: [(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (Z)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): C1=CC(=CC=C1C=CC(=O)OCC2C(C(C(C(O2)OC3=CC4=C(C=C(C=C4[O+]=C3C5=CC(=C(C=C5)O)O)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1/C=C\C(=O)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)O)O)O)O)O)O)O
• InChI: InChI=1S/C30H26O13/c31-16-5-1-14(2-6-16)3-8-25(36)40-13-24-26(37)27(38)28(39)30(43-24)42-23-12-18-20(34)10-17(32)11-22(18)41-29(23)15-4-7-19(33)21(35)9-15/h1-12,24,26-28,30,37-39H,13H2,(H4-,31,32,33,34,35,36)/p+1/t24-,26-,27+,28-,30-/m1/s1
• InChI Key: QAOBEOXFSUJDJL-SHPGVJHPSA-O
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₂₇O₁₃+
• Molecular Weight: 595.50 g/mol
• Exact Mass: 595.14516591 g/mol
• Topological Polar Surface Area (TPSA): 208.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): 2.35
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

• cyanidin 3-O-(6-O-cis-4-coumaroyl-beta-D-glucoside)
• cyanidin 3-O-(6-O-cis-p-coumaroyl-beta-D-glucoside)
• cyanidin 3-O-(6-O-(Z)-p-coumaroyl-beta-D-glucoside)
• cyanidin 3-O-{6-O-[(Z)-4-coumaroyl]-beta-D-glucoside}
• 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1-benzopyran-1-ium-3-yl 6-O-[(2Z)-3-(4-hydroxyphenyl)prop-2-enoyl]-beta-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6081	60.81%
Caco-2	-	0.9056	90.56%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.5034	50.34%
OATP2B1 inhibitior	-	0.5553	55.53%
OATP1B1 inhibitior	+	0.8900	89.00%
OATP1B3 inhibitior	+	0.9109	91.09%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.6964	69.64%
P-glycoprotein inhibitior	+	0.6077	60.77%
P-glycoprotein substrate	-	0.6985	69.85%
CYP3A4 substrate	+	0.6542	65.42%
CYP2C9 substrate	-	0.8047	80.47%
CYP2D6 substrate	-	0.8627	86.27%
CYP3A4 inhibition	-	0.9155	91.55%
CYP2C9 inhibition	-	0.8860	88.60%
CYP2C19 inhibition	-	0.8437	84.37%
CYP2D6 inhibition	-	0.9003	90.03%
CYP1A2 inhibition	-	0.8809	88.09%
CYP2C8 inhibition	+	0.8873	88.73%
CYP inhibitory promiscuity	-	0.6741	67.41%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6544	65.44%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.8974	89.74%
Skin irritation	-	0.7820	78.20%
Skin corrosion	-	0.9575	95.75%
Ames mutagenesis	-	0.5637	56.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.3866	38.66%
Micronuclear	+	0.7392	73.92%
Hepatotoxicity	-	0.8571	85.71%
skin sensitisation	-	0.8703	87.03%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.8744	87.44%
Acute Oral Toxicity (c)	III	0.4355	43.55%
Estrogen receptor binding	+	0.7779	77.79%
Androgen receptor binding	+	0.7757	77.57%
Thyroid receptor binding	+	0.5351	53.51%
Glucocorticoid receptor binding	+	0.6510	65.10%
Aromatase binding	+	0.5555	55.55%
PPAR gamma	+	0.6834	68.34%
Honey bee toxicity	-	0.7165	71.65%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5655	56.55%
Fish aquatic toxicity	+	0.9544	95.44%

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	99.38%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.68%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.30%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.35%	86.33%
CHEMBL3194	P02766	Transthyretin	95.82%	90.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.49%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.68%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.10%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.44%	99.15%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.81%	89.62%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	85.76%	95.78%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.59%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.18%	95.56%
CHEMBL2581	P07339	Cathepsin D	85.06%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.80%	94.45%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.39%	86.92%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	83.00%	91.71%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.93%	95.50%
CHEMBL3401	O75469	Pregnane X receptor	81.45%	94.73%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	81.31%	80.78%
CHEMBL1937	Q92769	Histone deacetylase 2	81.06%	94.75%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.03%	95.83%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	80.87%	83.00%

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: 118797966
• NPASS: NPC259293