5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromenium-3-yl 6-O-[(2Z)-3-(4-hydroxyphenyl)prop-2-enoyl]-beta-D-glucopyranoside

Details

• Internal ID: 5fcdb178-f1c7-409a-bd42-7956c2d58682
• 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-[5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromenylium-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)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)O
• InChI: InChI=1S/C30H26O14/c31-15-4-1-13(2-5-15)3-6-24(36)41-12-23-26(38)27(39)28(40)30(44-23)43-22-11-17-18(33)9-16(32)10-21(17)42-29(22)14-7-19(34)25(37)20(35)8-14/h1-11,23,26-28,30,38-40H,12H2,(H5-,31,32,33,34,35,36,37)/p+1/t23-,26-,27+,28-,30-/m1/s1
• InChI Key: DHTPVCYNNWQRMN-LHRGPQAGSA-O
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₂₇O₁₄+
• Molecular Weight: 611.50 g/mol
• Exact Mass: 611.14008053 g/mol
• Topological Polar Surface Area (TPSA): 228.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): 2.06
• H-Bond Acceptor: 13
• H-Bond Donor: 9
• Rotatable Bonds: 7

Synonyms

• DTXSID801030109
• delfinidin 3-O-(6-O-(Z)-4-coumaroyl-beta-D-glucoside)
• delfinidin 3-O-(6-O-(Z)-p-coumaroyl-beta-D-glucoside)
• delphinidin 3-O-(6-O-(Z)-4-coumaroyl-beta-D-glucoside)
• 5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromenium-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	-	0.9085	90.85%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.5034	50.34%
OATP2B1 inhibitior	-	0.5550	55.50%
OATP1B1 inhibitior	+	0.8508	85.08%
OATP1B3 inhibitior	+	0.9109	91.09%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.7345	73.45%
P-glycoprotein inhibitior	+	0.6268	62.68%
P-glycoprotein substrate	-	0.6622	66.22%
CYP3A4 substrate	+	0.6483	64.83%
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	+	0.8849	88.49%
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	-	0.8968	89.68%
Skin irritation	-	0.7820	78.20%
Skin corrosion	-	0.9575	95.75%
Ames mutagenesis	-	0.5837	58.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.6557	65.57%
Micronuclear	+	0.7392	73.92%
Hepatotoxicity	-	0.8324	83.24%
skin sensitisation	-	0.8703	87.03%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.9337	93.37%
Acute Oral Toxicity (c)	III	0.4355	43.55%
Estrogen receptor binding	+	0.7935	79.35%
Androgen receptor binding	+	0.7717	77.17%
Thyroid receptor binding	+	0.5463	54.63%
Glucocorticoid receptor binding	+	0.6782	67.82%
Aromatase binding	+	0.5605	56.05%
PPAR gamma	+	0.7039	70.39%
Honey bee toxicity	-	0.7687	76.87%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
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	99.61%	91.11%
CHEMBL3194	P02766	Transthyretin	97.42%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.41%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	97.21%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.80%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.96%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.74%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.44%	99.17%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	91.20%	89.62%
CHEMBL1937	Q92769	Histone deacetylase 2	87.63%	94.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.98%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.09%	97.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.05%	99.15%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	85.85%	95.64%
CHEMBL3401	O75469	Pregnane X receptor	85.25%	94.73%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	83.61%	91.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.39%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.98%	94.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.69%	95.50%
CHEMBL2581	P07339	Cathepsin D	80.86%	98.95%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	80.56%	83.00%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	80.51%	95.78%

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: 72193639
• NPASS: NPC119866