Azalein

Details

• Internal ID: ad618c4f-37e8-4a62-9b07-df0ce7f1d9a2
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-7-hydroxy-5-methoxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=C(OC3=C(C2=O)C(=CC(=C3)O)OC)C4=CC(=C(C=C4)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(OC3=C(C2=O)C(=CC(=C3)O)OC)C4=CC(=C(C=C4)O)O)O)O)O
• InChI: InChI=1S/C22H22O11/c1-8-16(26)18(28)19(29)22(31-8)33-21-17(27)15-13(30-2)6-10(23)7-14(15)32-20(21)9-3-4-11(24)12(25)5-9/h3-8,16,18-19,22-26,28-29H,1-2H3/t8-,16-,18+,19+,22-/m0/s1
• InChI Key: FYSMTINDJSASRR-UFGFRKJLSA-N
• Popularity: 3 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: 0.60
• Atomic LogP (AlogP): 0.79
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

• 2-(3,4-dihydroxyphenyl)-7-hydroxy-5-methoxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
• 29028-02-2
• FE4X3MSR8A
• Q413011
• Flavone, 3,3',4',7-tetrahydroxy-5-methoxy-, 3-rhamnoside
• 3-((6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)OXY)-2-(3,4-DIHYDROXYPHENYL)-7-HYDROXY-5-METHOXY-4H-1-BENZOPYRAN-4-ONE
• 4H-1-BENZOPYRAN-4-ONE, 3-((6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)OXY)-2-(3,4-DIHYDROXYPHENYL)-7-HYDROXY-5-METHOXY-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7980	79.80%
Caco-2	-	0.7921	79.21%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6676	66.76%
OATP2B1 inhibitior	+	0.5824	58.24%
OATP1B1 inhibitior	+	0.9515	95.15%
OATP1B3 inhibitior	+	0.9220	92.20%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.6467	64.67%
P-glycoprotein inhibitior	+	0.5794	57.94%
P-glycoprotein substrate	-	0.6062	60.62%
CYP3A4 substrate	+	0.6246	62.46%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8374	83.74%
CYP3A4 inhibition	-	0.6056	60.56%
CYP2C9 inhibition	-	0.9236	92.36%
CYP2C19 inhibition	-	0.8201	82.01%
CYP2D6 inhibition	-	0.8906	89.06%
CYP1A2 inhibition	-	0.7268	72.68%
CYP2C8 inhibition	+	0.8775	87.75%
CYP inhibitory promiscuity	-	0.5508	55.08%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6071	60.71%
Eye corrosion	-	0.9840	98.40%
Eye irritation	-	0.7801	78.01%
Skin irritation	-	0.6906	69.06%
Skin corrosion	-	0.9434	94.34%
Ames mutagenesis	+	0.5663	56.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.5939	59.39%
Micronuclear	+	0.9200	92.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.9206	92.06%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.8156	81.56%
Acute Oral Toxicity (c)	III	0.4825	48.25%
Estrogen receptor binding	+	0.7188	71.88%
Androgen receptor binding	+	0.7101	71.01%
Thyroid receptor binding	-	0.5289	52.89%
Glucocorticoid receptor binding	+	0.7545	75.45%
Aromatase binding	-	0.5094	50.94%
PPAR gamma	+	0.7047	70.47%
Honey bee toxicity	-	0.7492	74.92%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5651	56.51%
Fish aquatic toxicity	+	0.9150	91.50%

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	99.45%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.49%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.86%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	95.22%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.02%	86.33%
CHEMBL2581	P07339	Cathepsin D	94.37%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.16%	85.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.66%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.23%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.14%	96.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.02%	90.71%
CHEMBL3194	P02766	Transthyretin	87.85%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.90%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	85.80%	94.73%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.51%	97.36%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	83.70%	95.78%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	83.07%	80.78%
CHEMBL2535	P11166	Glucose transporter	82.87%	98.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.69%	99.23%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.35%	92.94%
CHEMBL4208	P20618	Proteasome component C5	81.93%	90.00%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	81.70%	94.03%

Plants that contains it

• Carya illinoinensis
• Rhododendron mucronatum

Cross-Links

• PubChem: 5321320
• NPASS: NPC201443
• LOTUS: LTS0029994
• wikiData: Q413011