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

Details

• Internal ID: 57454cf2-59d5-498d-ba4c-3f1b7adfa111
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 7-O-methylated flavonoids
• IUPAC Name: 5-hydroxy-7-methoxy-2-[2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one
• SMILES (Canonical): COC1=CC(=C2C(=C1)OC(=CC2=O)C3=CC=CC=C3OC4C(C(C(C(O4)CO)O)O)O)O
• SMILES (Isomeric): COC1=CC(=C2C(=C1)OC(=CC2=O)C3=CC=CC=C3O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
• InChI: InChI=1S/C22H22O10/c1-29-10-6-12(24)18-13(25)8-15(30-16(18)7-10)11-4-2-3-5-14(11)31-22-21(28)20(27)19(26)17(9-23)32-22/h2-8,17,19-24,26-28H,9H2,1H3/t17-,19-,20+,21-,22-/m1/s1
• InChI Key: NCWUWWMZUSHZKJ-MIUGBVLSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₂O₁₀
• Molecular Weight: 446.40 g/mol
• Exact Mass: 446.12129689 g/mol
• Topological Polar Surface Area (TPSA): 155.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 0.35
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• 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	-	0.8036	80.36%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6190	61.90%
OATP2B1 inhibitior	-	0.5518	55.18%
OATP1B1 inhibitior	+	0.8843	88.43%
OATP1B3 inhibitior	+	0.9740	97.40%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.5070	50.70%
P-glycoprotein inhibitior	-	0.5792	57.92%
P-glycoprotein substrate	-	0.6078	60.78%
CYP3A4 substrate	+	0.6086	60.86%
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	+	0.5891	58.91%
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	-	0.9226	92.26%
Skin irritation	-	0.8153	81.53%
Skin corrosion	-	0.9600	96.00%
Ames mutagenesis	+	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4489	44.89%
Micronuclear	+	0.6633	66.33%
Hepatotoxicity	-	0.8875	88.75%
skin sensitisation	-	0.9373	93.73%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.6321	63.21%
Acute Oral Toxicity (c)	III	0.6624	66.24%
Estrogen receptor binding	+	0.7050	70.50%
Androgen receptor binding	+	0.6948	69.48%
Thyroid receptor binding	-	0.4948	49.48%
Glucocorticoid receptor binding	+	0.6295	62.95%
Aromatase binding	+	0.5865	58.65%
PPAR gamma	+	0.6775	67.75%
Honey bee toxicity	-	0.7403	74.03%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
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	99.39%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.38%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.32%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.98%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.59%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.99%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.23%	99.15%
CHEMBL1951	P21397	Monoamine oxidase A	90.15%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.59%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.48%	86.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	88.19%	96.21%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.79%	99.17%
CHEMBL2535	P11166	Glucose transporter	86.14%	98.75%
CHEMBL3401	O75469	Pregnane X receptor	85.78%	94.73%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.57%	95.83%
CHEMBL3194	P02766	Transthyretin	83.81%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.42%	99.23%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.29%	95.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.98%	96.00%
CHEMBL4208	P20618	Proteasome component C5	81.54%	90.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.52%	97.09%

Plants that contains it

• Andrographis echioides
• Andrographis lineata
• Andrographis rothii
• Andrographis stenophylla

Cross-Links

• PubChem: 9496891
• LOTUS: LTS0015671
• wikiData: Q105177426