5-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-1-benzopyran-7-yl O-beta-D-glucopyranuronosyl-(1-->3)-O-2-O-[(2E)-3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propen-1-yl]-beta-D-glucopyranuronosyl-(1-->2)-beta-D-glucopyranosiduronic acid

Details

• Internal ID: c41bfba3-d178-4d20-9748-561a0855aaa3
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glucuronides > Flavonoid-7-O-glucuronides
• IUPAC Name: (2S,3S,4S,5R,6R)-6-[(2S,3S,4S,5R,6R)-2-carboxy-6-[(2S,3R,4S,5S,6S)-6-carboxy-4,5-dihydroxy-2-[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-7-yl]oxyoxan-3-yl]oxy-3-hydroxy-5-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxyoxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC(=O)OC2C(C(C(OC2OC3C(C(C(OC3OC4=CC(=C5C(=C4)OC(=CC5=O)C6=CC(=C(C=C6)O)OC)O)C(=O)O)O)O)C(=O)O)O)OC7C(C(C(C(O7)C(=O)O)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C/C(=O)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2O[C@@H]3[C@H]([C@@H]([C@H](O[C@H]3OC4=CC(=C5C(=C4)OC(=CC5=O)C6=CC(=C(C=C6)O)OC)O)C(=O)O)O)O)C(=O)O)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)C(=O)O)O)O)O)O
• InChI: InChI=1S/C44H44O27/c1-62-22-9-14(3-6-17(22)45)4-8-25(49)66-38-33(67-42-31(54)27(50)28(51)34(68-42)39(56)57)32(55)36(41(60)61)70-44(38)71-37-30(53)29(52)35(40(58)59)69-43(37)64-16-11-19(47)26-20(48)13-21(65-24(26)12-16)15-5-7-18(46)23(10-15)63-2/h3-13,27-38,42-47,50-55H,1-2H3,(H,56,57)(H,58,59)(H,60,61)/b8-4+/t27-,28-,29-,30-,31+,32-,33-,34-,35-,36-,37+,38+,42+,43+,44-/m0/s1
• InChI Key: RZPZIPTUBXCPJX-MTVAWGJLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₄H₄₄O₂₇
• Molecular Weight: 1004.80 g/mol
• Exact Mass: 1004.20699612 g/mol
• Topological Polar Surface Area (TPSA): 420.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): -2.04
• H-Bond Acceptor: 24
• H-Bond Donor: 12
• Rotatable Bonds: 15

Synonyms

• 380468-63-3
• 5-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-1-benzopyran-7-yl O-beta-D-glucopyranuronosyl-(1-->3)-O-2-O-[(2E)-3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propen-1-yl]-beta-D-glucopyranuronosyl-(1-->2)-beta-D-glucopyranosiduronic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8106	81.06%
Caco-2	-	0.8702	87.02%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.5840	58.40%
OATP2B1 inhibitior	-	0.5714	57.14%
OATP1B1 inhibitior	+	0.9060	90.60%
OATP1B3 inhibitior	+	0.9668	96.68%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.7165	71.65%
P-glycoprotein inhibitior	+	0.7330	73.30%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6841	68.41%
CYP2C9 substrate	-	0.8144	81.44%
CYP2D6 substrate	-	0.8689	86.89%
CYP3A4 inhibition	-	0.6028	60.28%
CYP2C9 inhibition	-	0.7718	77.18%
CYP2C19 inhibition	-	0.7734	77.34%
CYP2D6 inhibition	-	0.9142	91.42%
CYP1A2 inhibition	-	0.8686	86.86%
CYP2C8 inhibition	+	0.8962	89.62%
CYP inhibitory promiscuity	-	0.5946	59.46%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4625	46.25%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.8998	89.98%
Skin irritation	-	0.7170	71.70%
Skin corrosion	-	0.9313	93.13%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6870	68.70%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	-	0.7782	77.82%
skin sensitisation	-	0.8836	88.36%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.9537	95.37%
Acute Oral Toxicity (c)	III	0.4448	44.48%
Estrogen receptor binding	+	0.7566	75.66%
Androgen receptor binding	+	0.7247	72.47%
Thyroid receptor binding	+	0.5734	57.34%
Glucocorticoid receptor binding	+	0.6226	62.26%
Aromatase binding	+	0.5577	55.77%
PPAR gamma	+	0.7306	73.06%
Honey bee toxicity	-	0.6471	64.71%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9746	97.46%

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	99.37%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.37%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	98.19%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.63%	86.33%
CHEMBL3194	P02766	Transthyretin	97.51%	90.71%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.39%	85.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	94.93%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.87%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.00%	96.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	91.50%	95.50%
CHEMBL3714130	P46095	G-protein coupled receptor 6	89.87%	97.36%
CHEMBL2581	P07339	Cathepsin D	89.28%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.98%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.48%	99.17%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	86.66%	81.11%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.37%	90.71%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	85.11%	95.78%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.88%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.68%	94.45%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	84.12%	91.71%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	84.06%	94.08%
CHEMBL3401	O75469	Pregnane X receptor	82.48%	94.73%
CHEMBL1287628	Q9Y5S8	NADPH oxidase 1	82.10%	95.48%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.57%	99.23%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.48%	97.14%
CHEMBL3438	Q05513	Protein kinase C zeta	80.32%	88.48%

Plants that contains it

• Medicago sativa
• Medicago truncatula

Cross-Links

• PubChem: 163190564
• LOTUS: LTS0006423
• wikiData: Q105248532