Acetylicariin

Details

• Internal ID: 0d53ba94-f9ec-4b88-a088-96c0a8fcbc6d
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: [(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-4-oxo-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-7-yl]oxyoxan-3-yl] acetate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=C(OC3=C(C2=O)C=CC(=C3CC=C(C)C)OC4C(C(C(C(O4)CO)O)O)OC(=O)C)C5=CC=C(C=C5)OC)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(=C3CC=C(C)C)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)OC(=O)C)C5=CC=C(C=C5)OC)O)O)O
• InChI: InChI=1S/C35H42O15/c1-15(2)6-11-20-22(47-35-33(46-17(4)37)28(42)26(40)23(14-36)48-35)13-12-21-25(39)32(50-34-29(43)27(41)24(38)16(3)45-34)30(49-31(20)21)18-7-9-19(44-5)10-8-18/h6-10,12-13,16,23-24,26-29,33-36,38,40-43H,11,14H2,1-5H3/t16-,23+,24-,26+,27+,28-,29+,33+,34-,35+/m0/s1
• InChI Key: XJZJMIAIABVNFV-OBTUXVMGSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₄₂O₁₅
• Molecular Weight: 702.70 g/mol
• Exact Mass: 702.25237063 g/mol
• Topological Polar Surface Area (TPSA): 220.00 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 0.93
• H-Bond Acceptor: 15
• H-Bond Donor: 6
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8242	82.42%
Caco-2	-	0.9027	90.27%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6175	61.75%
OATP2B1 inhibitior	+	0.5651	56.51%
OATP1B1 inhibitior	+	0.8688	86.88%
OATP1B3 inhibitior	+	0.9464	94.64%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9696	96.96%
P-glycoprotein inhibitior	+	0.7332	73.32%
P-glycoprotein substrate	+	0.5555	55.55%
CYP3A4 substrate	+	0.6803	68.03%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8605	86.05%
CYP3A4 inhibition	-	0.9063	90.63%
CYP2C9 inhibition	-	0.6987	69.87%
CYP2C19 inhibition	-	0.7320	73.20%
CYP2D6 inhibition	-	0.8512	85.12%
CYP1A2 inhibition	-	0.7660	76.60%
CYP2C8 inhibition	+	0.6682	66.82%
CYP inhibitory promiscuity	-	0.6968	69.68%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7262	72.62%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9155	91.55%
Skin irritation	-	0.8067	80.67%
Skin corrosion	-	0.9464	94.64%
Ames mutagenesis	+	0.5246	52.46%
Human Ether-a-go-go-Related Gene inhibition	+	0.7048	70.48%
Micronuclear	+	0.5133	51.33%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.8731	87.31%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.8220	82.20%
Acute Oral Toxicity (c)	III	0.6090	60.90%
Estrogen receptor binding	+	0.7799	77.99%
Androgen receptor binding	+	0.6760	67.60%
Thyroid receptor binding	+	0.5294	52.94%
Glucocorticoid receptor binding	+	0.7121	71.21%
Aromatase binding	+	0.5440	54.40%
PPAR gamma	+	0.6984	69.84%
Honey bee toxicity	-	0.7220	72.20%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	+	0.9762	97.62%

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	99.15%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.94%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	95.27%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.27%	89.00%
CHEMBL2581	P07339	Cathepsin D	93.03%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.29%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.21%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.96%	96.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.72%	86.92%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.69%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.33%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.67%	85.14%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	88.99%	83.57%
CHEMBL3401	O75469	Pregnane X receptor	88.47%	94.73%
CHEMBL3714130	P46095	G-protein coupled receptor 6	88.38%	97.36%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.36%	96.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.52%	95.50%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	82.37%	81.11%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.63%	92.62%
CHEMBL4208	P20618	Proteasome component C5	80.63%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.58%	95.89%

Plants that contains it

• Epimedium brevicornu
• Epimedium grandiflorum
• Epimedium koreanum
• Epimedium pubescens
• Epimedium sagittatum
• Epimedium sempervirens
• Epimedium wushanense

Cross-Links

• PubChem: 101396841
• NPASS: NPC240735