(2Z)-6-hydroxy-2-[(4-hydroxyphenyl)methylidene]-7-methyl-4-[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-1-benzofuran-3-one

Details

• Internal ID: 15924c0c-1bbe-463b-8690-9810ac77d08d
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Aurone O-glycosides
• IUPAC Name: (2Z)-6-hydroxy-2-[(4-hydroxyphenyl)methylidene]-7-methyl-4-[(2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-1-benzofuran-3-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=C3C(=C(C(=C2)O)C)OC(=CC4=CC=C(C=C4)O)C3=O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@H]([C@@H]([C@@H]([C@H](O1)OC2=C3C(=C(C(=C2)O)C)O/C(=C\C4=CC=C(C=C4)O)/C3=O)O)O)O
• InChI: InChI=1S/C22H22O9/c1-9-13(24)8-14(31-22-20(28)19(27)17(25)10(2)29-22)16-18(26)15(30-21(9)16)7-11-3-5-12(23)6-4-11/h3-8,10,17,19-20,22-25,27-28H,1-2H3/b15-7-/t10-,17+,19-,20-,22+/m0/s1
• InChI Key: QHCYSTGSLGXKMF-XGAWWKFWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₂O₉
• Molecular Weight: 430.40 g/mol
• Exact Mass: 430.12638228 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.23
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9278	92.78%
Caco-2	-	0.7327	73.27%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6879	68.79%
OATP2B1 inhibitior	+	0.5755	57.55%
OATP1B1 inhibitior	+	0.8944	89.44%
OATP1B3 inhibitior	+	0.9038	90.38%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.8127	81.27%
P-glycoprotein inhibitior	-	0.5861	58.61%
P-glycoprotein substrate	-	0.8306	83.06%
CYP3A4 substrate	+	0.6013	60.13%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8455	84.55%
CYP3A4 inhibition	+	0.6309	63.09%
CYP2C9 inhibition	-	0.6997	69.97%
CYP2C19 inhibition	+	0.6973	69.73%
CYP2D6 inhibition	-	0.7889	78.89%
CYP1A2 inhibition	+	0.5436	54.36%
CYP2C8 inhibition	+	0.6469	64.69%
CYP inhibitory promiscuity	+	0.8271	82.71%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Danger	0.5238	52.38%
Eye corrosion	-	0.9873	98.73%
Eye irritation	-	0.8620	86.20%
Skin irritation	-	0.6798	67.98%
Skin corrosion	-	0.9420	94.20%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	-	0.5840	58.40%
skin sensitisation	-	0.6882	68.82%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.7350	73.50%
Acute Oral Toxicity (c)	II	0.3932	39.32%
Estrogen receptor binding	+	0.7678	76.78%
Androgen receptor binding	+	0.5804	58.04%
Thyroid receptor binding	+	0.5337	53.37%
Glucocorticoid receptor binding	+	0.7219	72.19%
Aromatase binding	+	0.5371	53.71%
PPAR gamma	+	0.6801	68.01%
Honey bee toxicity	-	0.7675	76.75%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9875	98.75%

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	99.77%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.53%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	98.01%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.07%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	95.15%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.78%	86.33%
CHEMBL2581	P07339	Cathepsin D	94.50%	98.95%
CHEMBL3714130	P46095	G-protein coupled receptor 6	92.84%	97.36%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.03%	99.17%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	87.84%	90.93%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.58%	95.89%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	87.17%	93.40%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.65%	99.23%
CHEMBL3194	P02766	Transthyretin	85.66%	90.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.80%	94.00%
CHEMBL3038469	P24941	CDK2/Cyclin A	83.21%	91.38%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	82.67%	93.10%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.64%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.79%	90.71%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	81.75%	95.78%
CHEMBL2535	P11166	Glucose transporter	81.04%	98.75%

Plants that contains it

• Pterocarpus marsupium

Cross-Links

• PubChem: 163191195
• LOTUS: LTS0258487
• wikiData: Q105220858