[(2S,3S,4R,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-4,5-dihydroxy-6-[[(E)-3-[3-hydroxy-4-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-[3-(4-hydroxyphenyl)prop-2-enoyloxymethyl]oxan-2-yl]oxyphenyl]prop-2-enoyl]oxymethyl]oxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl 3-(4-hydroxyphenyl)prop-2-enoate

Details

• Internal ID: fe5b8118-0e2d-4a94-8b6a-2e7768acf92a
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Anthocyanidin 3-O-p-coumaroyl glycosides > Anthocyanidin 3-O-6-p-coumaroyl glycosides
• IUPAC Name: [(2S,3S,4R,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-4,5-dihydroxy-6-[[(E)-3-[3-hydroxy-4-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-[3-(4-hydroxyphenyl)prop-2-enoyloxymethyl]oxan-2-yl]oxyphenyl]prop-2-enoyl]oxymethyl]oxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl 3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): C1=CC(=CC=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=C(C=C1)O)O)O)O)O)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=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=CC1=CC=C(C=C1)O)O)O)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C66H68O33/c67-24-43-50(77)54(81)58(85)64(95-43)93-41-22-34(70)21-40-35(41)23-42(61(91-40)31-9-14-36(71)37(72)20-31)94-66-62(99-65-60(87)56(83)52(79)45(97-65)26-89-48(75)17-7-29-3-12-33(69)13-4-29)57(84)53(80)46(98-66)27-90-49(76)18-8-30-5-15-39(38(73)19-30)92-63-59(86)55(82)51(78)44(96-63)25-88-47(74)16-6-28-1-10-32(68)11-2-28/h1-23,43-46,50-60,62-67,77-87H,24-27H2,(H5-,68,69,70,71,72,73,74,75)/p+1/b18-8+/t43-,44+,45-,46-,50+,51+,52+,53+,54-,55+,56+,57-,58+,59+,60+,62-,63+,64+,65-,66+/m0/s1
• InChI Key: DESIAOCLZCPBTI-OCXMSFNHSA-O
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆₆H₆₉O₃₃+
• Molecular Weight: 1390.20 g/mol
• Exact Mass: 1389.3721096 g/mol
• Topological Polar Surface Area (TPSA): 518.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -1.23
• H-Bond Acceptor: 32
• H-Bond Donor: 18
• 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	-	0.8575	85.75%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Nucleus	0.4984	49.84%
OATP2B1 inhibitior	-	0.8630	86.30%
OATP1B1 inhibitior	+	0.8804	88.04%
OATP1B3 inhibitior	+	0.9736	97.36%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.9472	94.72%
P-glycoprotein inhibitior	+	0.7416	74.16%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6930	69.30%
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	+	0.8733	87.33%
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	-	0.8965	89.65%
Skin irritation	-	0.8257	82.57%
Skin corrosion	-	0.9534	95.34%
Ames mutagenesis	+	0.5263	52.63%
Human Ether-a-go-go-Related Gene inhibition	+	0.7707	77.07%
Micronuclear	+	0.6633	66.33%
Hepatotoxicity	-	0.8787	87.87%
skin sensitisation	-	0.8765	87.65%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.8368	83.68%
Acute Oral Toxicity (c)	IV	0.3956	39.56%
Estrogen receptor binding	+	0.6713	67.13%
Androgen receptor binding	+	0.7326	73.26%
Thyroid receptor binding	+	0.6675	66.75%
Glucocorticoid receptor binding	+	0.7088	70.88%
Aromatase binding	+	0.6239	62.39%
PPAR gamma	+	0.7888	78.88%
Honey bee toxicity	-	0.6487	64.87%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5555	55.55%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.16%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.05%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.55%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.80%	86.33%
CHEMBL3194	P02766	Transthyretin	95.87%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.89%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.49%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.40%	96.09%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	91.62%	83.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.41%	99.15%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	88.34%	95.78%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.83%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.80%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.72%	94.45%
CHEMBL1937	Q92769	Histone deacetylase 2	84.34%	94.75%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	83.92%	97.31%
CHEMBL3401	O75469	Pregnane X receptor	83.34%	94.73%
CHEMBL226	P30542	Adenosine A1 receptor	83.06%	95.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.54%	95.56%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.52%	97.28%
CHEMBL2581	P07339	Cathepsin D	82.16%	98.95%
CHEMBL5255	O00206	Toll-like receptor 4	81.70%	92.50%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	81.68%	80.78%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.79%	95.89%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.40%	89.62%

Plants that contains it

• Ipomoea asarifolia

Cross-Links

• PubChem: 163191964
• LOTUS: LTS0190644
• wikiData: Q104977479