(2S,3S,4S,5R,6S)-6-[5,6-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-methoxy-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid

Details

• Internal ID: 28aa997e-ce72-4a8f-9022-740a95bb375f
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glucuronides > Flavonoid-3-O-glucuronides
• IUPAC Name: (2S,3S,4S,5R,6S)-6-[5,6-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-methoxy-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• SMILES (Canonical): COC1=C(C=C(C=C1)C2=C(C(=O)C3=C(C(=C(C=C3O2)OC)O)O)OC4C(C(C(C(O4)C(=O)O)O)O)O)O
• SMILES (Isomeric): COC1=C(C=C(C=C1)C2=C(C(=O)C3=C(C(=C(C=C3O2)OC)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)C(=O)O)O)O)O)O
• InChI: InChI=1S/C23H22O14/c1-33-9-4-3-7(5-8(9)24)19-20(36-23-18(30)16(28)17(29)21(37-23)22(31)32)15(27)12-10(35-19)6-11(34-2)13(25)14(12)26/h3-6,16-18,21,23-26,28-30H,1-2H3,(H,31,32)/t16-,17-,18+,21-,23+/m0/s1
• InChI Key: TTZIHUKKIDPTQT-USFRMQJTSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₂O₁₄
• Molecular Weight: 522.40 g/mol
• Exact Mass: 522.10095537 g/mol
• Topological Polar Surface Area (TPSA): 222.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): -0.14
• H-Bond Acceptor: 13
• H-Bond Donor: 7
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7123	71.23%
Caco-2	-	0.8698	86.98%
Blood Brain Barrier	-	0.9250	92.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6622	66.22%
OATP2B1 inhibitior	-	0.5493	54.93%
OATP1B1 inhibitior	+	0.9411	94.11%
OATP1B3 inhibitior	+	0.9589	95.89%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.8321	83.21%
P-glycoprotein inhibitior	-	0.4392	43.92%
P-glycoprotein substrate	-	0.6832	68.32%
CYP3A4 substrate	+	0.6239	62.39%
CYP2C9 substrate	-	0.8232	82.32%
CYP2D6 substrate	-	0.8719	87.19%
CYP3A4 inhibition	-	0.7521	75.21%
CYP2C9 inhibition	-	0.8958	89.58%
CYP2C19 inhibition	-	0.8909	89.09%
CYP2D6 inhibition	-	0.9307	93.07%
CYP1A2 inhibition	-	0.8108	81.08%
CYP2C8 inhibition	+	0.9105	91.05%
CYP inhibitory promiscuity	-	0.7569	75.69%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6217	62.17%
Eye corrosion	-	0.9873	98.73%
Eye irritation	-	0.8623	86.23%
Skin irritation	-	0.7288	72.88%
Skin corrosion	-	0.9334	93.34%
Ames mutagenesis	-	0.5664	56.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.3927	39.27%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	-	0.6464	64.64%
skin sensitisation	-	0.9298	92.98%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.9471	94.71%
Acute Oral Toxicity (c)	III	0.5086	50.86%
Estrogen receptor binding	+	0.7079	70.79%
Androgen receptor binding	+	0.6800	68.00%
Thyroid receptor binding	-	0.5178	51.78%
Glucocorticoid receptor binding	+	0.6626	66.26%
Aromatase binding	-	0.6128	61.28%
PPAR gamma	+	0.5810	58.10%
Honey bee toxicity	-	0.7882	78.82%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9387	93.87%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.17%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.14%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.32%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.26%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.02%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.53%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.03%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.02%	99.17%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	92.93%	95.64%
CHEMBL1951	P21397	Monoamine oxidase A	92.66%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.70%	95.56%
CHEMBL3194	P02766	Transthyretin	88.46%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.20%	94.45%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.05%	90.71%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.51%	95.50%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.69%	99.15%
CHEMBL1255126	O15151	Protein Mdm4	83.65%	90.20%
CHEMBL3401	O75469	Pregnane X receptor	83.41%	94.73%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	81.52%	95.78%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.44%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.35%	92.62%

Plants that contains it

• Spinacia oleracea

Cross-Links

• PubChem: 10896639
• LOTUS: LTS0003539
• wikiData: Q105264584