Sagittatoside A

Details

• Internal ID: 86d469a3-6c1a-41f6-b865-acce1dfa6374
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 3-[(2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=C(OC3=C(C(=CC(=C3C2=O)O)O)CC=C(C)C)C4=CC=C(C=C4)OC)OC5C(C(C(C(O5)CO)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(OC3=C(C(=CC(=C3C2=O)O)O)CC=C(C)C)C4=CC=C(C=C4)OC)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O
• InChI: InChI=1S/C33H40O15/c1-13(2)5-10-17-18(35)11-19(36)21-24(39)30(28(46-29(17)21)15-6-8-16(43-4)9-7-15)47-33-31(26(41)22(37)14(3)44-33)48-32-27(42)25(40)23(38)20(12-34)45-32/h5-9,11,14,20,22-23,25-27,31-38,40-42H,10,12H2,1-4H3/t14-,20+,22-,23+,25-,26+,27+,31+,32-,33-/m0/s1
• InChI Key: COHHGQPQHHUMDG-WVQJJEIESA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₀O₁₅
• Molecular Weight: 676.70 g/mol
• Exact Mass: 676.23672056 g/mol
• Topological Polar Surface Area (TPSA): 234.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 0.42
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 9

Synonyms

• 118525-35-2
• Icariin-A
• 3-[(2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one
• SCHEMBL4982932
• HY-N0873
• CS-3690
• MS-31069

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8585	85.85%
Caco-2	-	0.9212	92.12%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6495	64.95%
OATP2B1 inhibitior	-	0.7145	71.45%
OATP1B1 inhibitior	+	0.8825	88.25%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9107	91.07%
P-glycoprotein inhibitior	-	0.4369	43.69%
P-glycoprotein substrate	+	0.5283	52.83%
CYP3A4 substrate	+	0.6694	66.94%
CYP2C9 substrate	-	0.8387	83.87%
CYP2D6 substrate	-	0.8462	84.62%
CYP3A4 inhibition	-	0.9306	93.06%
CYP2C9 inhibition	-	0.7318	73.18%
CYP2C19 inhibition	-	0.6575	65.75%
CYP2D6 inhibition	-	0.8183	81.83%
CYP1A2 inhibition	-	0.7072	70.72%
CYP2C8 inhibition	+	0.6681	66.81%
CYP inhibitory promiscuity	-	0.5487	54.87%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7378	73.78%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.9191	91.91%
Skin irritation	-	0.8008	80.08%
Skin corrosion	-	0.9495	94.95%
Ames mutagenesis	-	0.5228	52.28%
Human Ether-a-go-go-Related Gene inhibition	+	0.7096	70.96%
Micronuclear	+	0.5033	50.33%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.8766	87.66%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.8954	89.54%
Acute Oral Toxicity (c)	III	0.6326	63.26%
Estrogen receptor binding	+	0.8571	85.71%
Androgen receptor binding	+	0.7014	70.14%
Thyroid receptor binding	+	0.5727	57.27%
Glucocorticoid receptor binding	+	0.6932	69.32%
Aromatase binding	+	0.6242	62.42%
PPAR gamma	+	0.7112	71.12%
Honey bee toxicity	-	0.6900	69.00%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9668	96.68%

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	99.90%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.68%	91.49%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.00%	94.00%
CHEMBL2581	P07339	Cathepsin D	95.03%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	94.51%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.25%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.15%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.03%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.45%	99.15%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.63%	86.92%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.28%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.10%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.62%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.54%	94.45%
CHEMBL3714130	P46095	G-protein coupled receptor 6	89.11%	97.36%
CHEMBL4208	P20618	Proteasome component C5	83.75%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.14%	95.89%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.03%	95.50%

Plants that contains it

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

Cross-Links

• PubChem: 13916054
• NPASS: NPC304787
• LOTUS: LTS0266237
• wikiData: Q104393867