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

Details

• Internal ID: 1865cabe-6060-4b2c-a8b3-84fc45da3970
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Aurone O-glycosides
• IUPAC Name: (2Z)-2-[(4-hydroxyphenyl)methylidene]-7-methyl-6-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-1-benzofuran-3-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=C(C3=C(C=C2)C(=O)C(=CC4=CC=C(C=C4)O)O3)C)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)OC2=C(C3=C(C=C2)C(=O)/C(=C/C4=CC=C(C=C4)O)/O3)C)O)O)O
• InChI: InChI=1S/C22H22O8/c1-10-15(30-22-20(27)19(26)17(24)11(2)28-22)8-7-14-18(25)16(29-21(10)14)9-12-3-5-13(23)6-4-12/h3-9,11,17,19-20,22-24,26-27H,1-2H3/b16-9-/t11-,17-,19+,20+,22+/m0/s1
• InChI Key: QAHBZNNBXKMITG-DADZJWIHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₂O₈
• Molecular Weight: 414.40 g/mol
• Exact Mass: 414.13146766 g/mol
• Topological Polar Surface Area (TPSA): 126.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.52
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• 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	-	0.7709	77.09%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6879	68.79%
OATP2B1 inhibitior	-	0.5649	56.49%
OATP1B1 inhibitior	+	0.8813	88.13%
OATP1B3 inhibitior	+	0.9038	90.38%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.8747	87.47%
P-glycoprotein inhibitior	-	0.5820	58.20%
P-glycoprotein substrate	-	0.7579	75.79%
CYP3A4 substrate	+	0.6027	60.27%
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	+	0.5774	57.74%
CYP inhibitory promiscuity	+	0.8271	82.71%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Danger	0.5238	52.38%
Eye corrosion	-	0.9873	98.73%
Eye irritation	-	0.9395	93.95%
Skin irritation	-	0.6798	67.98%
Skin corrosion	-	0.9420	94.20%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5278	52.78%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	-	0.5914	59.14%
skin sensitisation	-	0.6882	68.82%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.4917	49.17%
Acute Oral Toxicity (c)	II	0.3932	39.32%
Estrogen receptor binding	+	0.7606	76.06%
Androgen receptor binding	+	0.6244	62.44%
Thyroid receptor binding	+	0.6046	60.46%
Glucocorticoid receptor binding	+	0.7421	74.21%
Aromatase binding	+	0.5302	53.02%
PPAR gamma	+	0.7101	71.01%
Honey bee toxicity	-	0.7561	75.61%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
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	99.95%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.01%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.45%	89.00%
CHEMBL2581	P07339	Cathepsin D	95.85%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.30%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.93%	86.33%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.59%	97.36%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.52%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	88.03%	94.73%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	86.88%	90.93%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.85%	90.71%
CHEMBL2039	P27338	Monoamine oxidase B	84.38%	92.51%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.77%	96.00%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	83.32%	93.10%
CHEMBL242	Q92731	Estrogen receptor beta	83.06%	98.35%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.90%	99.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.72%	100.00%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.67%	91.71%
CHEMBL3038469	P24941	CDK2/Cyclin A	82.65%	91.38%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.64%	95.89%
CHEMBL3194	P02766	Transthyretin	82.46%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.31%	95.89%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	81.25%	95.78%

Plants that contains it

• Pterocarpus marsupium

Cross-Links

• PubChem: 163186773
• LOTUS: LTS0244802
• wikiData: Q105217391