5-hydroxy-2-[2-hydroxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-7-methoxychromen-4-one

Details

• Internal ID: f7622841-45bb-46e3-a30c-293704fb5ed0
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 7-O-methylated flavonoids
• IUPAC Name: 5-hydroxy-2-[2-hydroxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-7-methoxychromen-4-one
• SMILES (Canonical): COC1=CC(=C2C(=C1)OC(=CC2=O)C3=C(C=CC=C3OC4C(C(C(C(O4)CO)O)O)O)O)O
• SMILES (Isomeric): COC1=CC(=C2C(=C1)OC(=CC2=O)C3=C(C=CC=C3O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O
• InChI: InChI=1S/C22H22O11/c1-30-9-5-11(25)17-12(26)7-15(31-14(17)6-9)18-10(24)3-2-4-13(18)32-22-21(29)20(28)19(27)16(8-23)33-22/h2-7,16,19-25,27-29H,8H2,1H3/t16-,19-,20+,21-,22-/m1/s1
• InChI Key: OPGQTTVBIMRHFD-RECXWPGBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₂O₁₁
• Molecular Weight: 462.40 g/mol
• Exact Mass: 462.11621151 g/mol
• Topological Polar Surface Area (TPSA): 175.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 0.06
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4855	48.55%
Caco-2	-	0.8467	84.67%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6190	61.90%
OATP2B1 inhibitior	+	0.5914	59.14%
OATP1B1 inhibitior	+	0.8962	89.62%
OATP1B3 inhibitior	+	0.9740	97.40%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.6478	64.78%
P-glycoprotein inhibitior	-	0.6581	65.81%
P-glycoprotein substrate	-	0.6455	64.55%
CYP3A4 substrate	+	0.6082	60.82%
CYP2C9 substrate	-	0.8485	84.85%
CYP2D6 substrate	-	0.8501	85.01%
CYP3A4 inhibition	-	0.9108	91.08%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9173	91.73%
CYP2D6 inhibition	-	0.9514	95.14%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.5950	59.50%
CYP inhibitory promiscuity	-	0.7292	72.92%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6890	68.90%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.8997	89.97%
Skin irritation	-	0.8153	81.53%
Skin corrosion	-	0.9600	96.00%
Ames mutagenesis	+	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4633	46.33%
Micronuclear	+	0.6633	66.33%
Hepatotoxicity	-	0.8625	86.25%
skin sensitisation	-	0.9373	93.73%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.6613	66.13%
Acute Oral Toxicity (c)	III	0.6624	66.24%
Estrogen receptor binding	+	0.6820	68.20%
Androgen receptor binding	+	0.6450	64.50%
Thyroid receptor binding	+	0.5182	51.82%
Glucocorticoid receptor binding	+	0.6628	66.28%
Aromatase binding	+	0.5816	58.16%
PPAR gamma	+	0.6329	63.29%
Honey bee toxicity	-	0.7985	79.85%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.7079	70.79%

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	99.35%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.65%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.61%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.59%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.48%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.70%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.38%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	91.78%	94.73%
CHEMBL220	P22303	Acetylcholinesterase	91.25%	94.45%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.25%	96.21%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.11%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.33%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.38%	97.09%
CHEMBL3194	P02766	Transthyretin	85.98%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.59%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.50%	95.89%
CHEMBL2535	P11166	Glucose transporter	84.32%	98.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.74%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.53%	94.45%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.75%	95.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.37%	96.00%

Plants that contains it

• Andrographis alata
• Andrographis stenophylla

Cross-Links

• PubChem: 101262883
• LOTUS: LTS0228270
• wikiData: Q105196186