[(2S,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-6-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 4-hydroxybenzoate

Details

• Internal ID: 9a95bc60-c14d-4214-82d7-746198225fc7
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides
• IUPAC Name: [(2S,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-6-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 4-hydroxybenzoate
• SMILES (Canonical): C1=CC(=CC=C1C(=O)OC2C(C(C(OC2C3=C(C4=C(C=C3O)OC(=CC4=O)C5=CC(=C(C=C5)O)O)O)CO)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C(=O)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2C3=C(C4=C(C=C3O)OC(=CC4=O)C5=CC(=C(C=C5)O)O)O)CO)O)O)O
• InChI: InChI=1S/C28H24O13/c29-10-20-23(35)25(37)27(41-28(38)11-1-4-13(30)5-2-11)26(40-20)22-17(34)9-19-21(24(22)36)16(33)8-18(39-19)12-3-6-14(31)15(32)7-12/h1-9,20,23,25-27,29-32,34-37H,10H2/t20-,23-,25+,26+,27-/m1/s1
• InChI Key: CMHUXCFQCMZVCA-ZXZUCKGRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₂₄O₁₃
• Molecular Weight: 568.50 g/mol
• Exact Mass: 568.12169082 g/mol
• Topological Polar Surface Area (TPSA): 224.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.37
• H-Bond Acceptor: 13
• H-Bond Donor: 8
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6249	62.49%
Caco-2	-	0.9293	92.93%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.5589	55.89%
OATP2B1 inhibitior	-	0.5454	54.54%
OATP1B1 inhibitior	+	0.8108	81.08%
OATP1B3 inhibitior	+	0.9680	96.80%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.5592	55.92%
P-glycoprotein inhibitior	+	0.5893	58.93%
P-glycoprotein substrate	-	0.6433	64.33%
CYP3A4 substrate	+	0.6528	65.28%
CYP2C9 substrate	-	0.6039	60.39%
CYP2D6 substrate	-	0.8590	85.90%
CYP3A4 inhibition	-	0.9184	91.84%
CYP2C9 inhibition	-	0.9174	91.74%
CYP2C19 inhibition	-	0.9299	92.99%
CYP2D6 inhibition	-	0.9641	96.41%
CYP1A2 inhibition	-	0.9320	93.20%
CYP2C8 inhibition	+	0.8710	87.10%
CYP inhibitory promiscuity	-	0.8782	87.82%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7263	72.63%
Eye corrosion	-	0.9928	99.28%
Eye irritation	-	0.8772	87.72%
Skin irritation	-	0.8274	82.74%
Skin corrosion	-	0.9638	96.38%
Ames mutagenesis	-	0.5764	57.64%
Human Ether-a-go-go-Related Gene inhibition	+	0.7231	72.31%
Micronuclear	+	0.6633	66.33%
Hepatotoxicity	-	0.6446	64.46%
skin sensitisation	-	0.9201	92.01%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.9188	91.88%
Acute Oral Toxicity (c)	IV	0.4205	42.05%
Estrogen receptor binding	+	0.7764	77.64%
Androgen receptor binding	+	0.8096	80.96%
Thyroid receptor binding	+	0.5229	52.29%
Glucocorticoid receptor binding	+	0.5933	59.33%
Aromatase binding	-	0.5668	56.68%
PPAR gamma	+	0.6707	67.07%
Honey bee toxicity	-	0.6997	69.97%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.8695	86.95%

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	99.58%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.39%	91.49%
CHEMBL2581	P07339	Cathepsin D	97.92%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.15%	89.00%
CHEMBL3194	P02766	Transthyretin	94.57%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.69%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.17%	94.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.54%	96.21%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.25%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.02%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.94%	97.09%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	87.47%	95.64%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.57%	99.15%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	86.38%	95.78%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	85.10%	83.57%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	84.17%	89.23%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.29%	95.83%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	83.22%	83.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.91%	97.28%
CHEMBL3232685	O00257	E3 SUMO-protein ligase CBX4	81.86%	93.00%
CHEMBL3401	O75469	Pregnane X receptor	81.85%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.26%	95.89%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	80.33%	97.53%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	80.05%	91.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.03%	99.23%

Plants that contains it

• Gentiana asclepiadea

Cross-Links

• PubChem: 162849368
• LOTUS: LTS0251029
• wikiData: Q104964562