[(2S,3S,4S,5R,6S)-6-[(2S,3S,4S,5S,6S)-2-[2-(3,4-dihydroxyphenyl)-7-hydroxy-5-[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromenylium-3-yl]oxy-6-[[(E)-3-[4-[(2S,3R,4S,5S,6R)-6-[[(E)-3-(3,5-dihydroxyphenyl)prop-2-enoyl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-3-hydroxyphenyl]prop-2-enoyl]oxymethyl]-4,5-dihydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl 3-(3,4-dihydroxyphenyl)prop-2-enoate

Details

• Internal ID: f9650344-46d5-4d98-9605-a74a722ad129
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Anthocyanidin 3-O-p-coumaroyl glycosides > Anthocyanidin 3-O-6-p-coumaroyl glycosides
• IUPAC Name: [(2S,3S,4S,5R,6S)-6-[(2S,3S,4S,5S,6S)-2-[2-(3,4-dihydroxyphenyl)-7-hydroxy-5-[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromenylium-3-yl]oxy-6-[[(E)-3-[4-[(2S,3R,4S,5S,6R)-6-[[(E)-3-(3,5-dihydroxyphenyl)prop-2-enoyl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-3-hydroxyphenyl]prop-2-enoyl]oxymethyl]-4,5-dihydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl 3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): C1=CC(=C(C=C1C=CC(=O)OCC2C(C(C(C(O2)OC3C(C(C(OC3OC4=C([O+]=C5C=C(C=C(C5=C4)OC6C(C(C(C(O6)CO)O)O)O)O)C7=CC(=C(C=C7)O)O)COC(=O)C=CC8=CC(=C(C=C8)OC9C(C(C(C(O9)COC(=O)C=CC1=CC(=CC(=C1)O)O)O)O)O)O)O)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C=CC(=O)OC[C@H]2[C@H]([C@@H]([C@H]([C@@H](O2)O[C@H]3[C@H]([C@@H]([C@@H](O[C@H]3OC4=C([O+]=C5C=C(C=C(C5=C4)O[C@H]6[C@@H]([C@H]([C@@H]([C@@H](O6)CO)O)O)O)O)C7=CC(=C(C=C7)O)O)COC(=O)/C=C/C8=CC(=C(C=C8)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)COC(=O)/C=C/C1=CC(=CC(=C1)O)O)O)O)O)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C66H68O35/c67-22-43-50(79)54(83)58(87)64(97-43)95-41-20-32(70)19-40-33(41)21-42(61(93-40)29-6-8-35(72)37(74)17-29)96-66-62(101-65-60(89)56(85)52(81)45(99-65)24-90-47(76)10-3-26-1-7-34(71)36(73)15-26)57(86)53(82)46(100-66)25-92-48(77)11-4-27-2-9-39(38(75)16-27)94-63-59(88)55(84)51(80)44(98-63)23-91-49(78)12-5-28-13-30(68)18-31(69)14-28/h1-21,43-46,50-60,62-67,79-89H,22-25H2,(H7-,68,69,70,71,72,73,74,75,76)/p+1/b11-4+,12-5+/t43-,44+,45-,46-,50+,51+,52+,53+,54-,55-,56-,57-,58+,59+,60+,62-,63+,64+,65-,66+/m0/s1
• InChI Key: KSAPUZOIPBGBPL-QSHSICIMSA-O
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆₆H₆₉O₃₅+
• Molecular Weight: 1422.20 g/mol
• Exact Mass: 1421.3619389 g/mol
• Topological Polar Surface Area (TPSA): 558.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -1.82
• H-Bond Acceptor: 34
• H-Bond Donor: 20
• Rotatable Bonds: 22

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7695	76.95%
Caco-2	-	0.8572	85.72%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.9000	90.00%
Subcellular localzation	Nucleus	0.4984	49.84%
OATP2B1 inhibitior	-	0.8630	86.30%
OATP1B1 inhibitior	+	0.8910	89.10%
OATP1B3 inhibitior	+	0.9736	97.36%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.9557	95.57%
P-glycoprotein inhibitior	+	0.7417	74.17%
P-glycoprotein substrate	-	0.5249	52.49%
CYP3A4 substrate	+	0.6869	68.69%
CYP2C9 substrate	-	0.8045	80.45%
CYP2D6 substrate	-	0.8622	86.22%
CYP3A4 inhibition	-	0.9408	94.08%
CYP2C9 inhibition	-	0.8977	89.77%
CYP2C19 inhibition	-	0.8553	85.53%
CYP2D6 inhibition	-	0.9269	92.69%
CYP1A2 inhibition	-	0.9141	91.41%
CYP2C8 inhibition	+	0.8562	85.62%
CYP inhibitory promiscuity	-	0.8246	82.46%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6709	67.09%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.8963	89.63%
Skin irritation	-	0.8257	82.57%
Skin corrosion	-	0.9534	95.34%
Ames mutagenesis	+	0.5463	54.63%
Human Ether-a-go-go-Related Gene inhibition	+	0.7794	77.94%
Micronuclear	+	0.6633	66.33%
Hepatotoxicity	-	0.8662	86.62%
skin sensitisation	-	0.8765	87.65%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.8213	82.13%
Acute Oral Toxicity (c)	IV	0.3956	39.56%
Estrogen receptor binding	+	0.6555	65.55%
Androgen receptor binding	+	0.7258	72.58%
Thyroid receptor binding	+	0.6706	67.06%
Glucocorticoid receptor binding	+	0.7217	72.17%
Aromatase binding	+	0.6456	64.56%
PPAR gamma	+	0.7902	79.02%
Honey bee toxicity	-	0.6489	64.89%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5755	57.55%
Fish aquatic toxicity	+	0.9324	93.24%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.52%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.98%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.97%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.14%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.10%	86.33%
CHEMBL3194	P02766	Transthyretin	95.36%	90.71%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	92.19%	83.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.57%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.99%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.59%	86.92%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.08%	99.15%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.48%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	87.46%	95.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.57%	95.56%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	86.13%	96.38%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.08%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	85.94%	94.73%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	84.05%	80.78%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	83.90%	95.78%
CHEMBL2581	P07339	Cathepsin D	83.40%	98.95%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.19%	95.83%
CHEMBL1937	Q92769	Histone deacetylase 2	83.08%	94.75%
CHEMBL3922	P50579	Methionine aminopeptidase 2	81.97%	97.28%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.91%	94.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.82%	92.94%
CHEMBL5255	O00206	Toll-like receptor 4	81.35%	92.50%

Plants that contains it

• Ipomoea asarifolia

Cross-Links

• PubChem: 163192049
• LOTUS: LTS0143345
• wikiData: Q105145328