Icariin

Details

• Internal ID: 6245b1a3-a128-4a32-9553-b9f84a42d4de
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-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(=C3CC=C(C)C)OC4C(C(C(C(O4)CO)O)O)O)O)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)O)O)C5=CC=C(C=C5)OC)O)O)O
• InChI: InChI=1S/C33H40O15/c1-13(2)5-10-17-19(45-33-28(42)26(40)23(37)20(12-34)46-33)11-18(35)21-24(38)31(48-32-27(41)25(39)22(36)14(3)44-32)29(47-30(17)21)15-6-8-16(43-4)9-7-15/h5-9,11,14,20,22-23,25-28,32-37,39-42H,10,12H2,1-4H3/t14-,20+,22-,23+,25+,26-,27+,28+,32-,33+/m0/s1
• InChI Key: TZJALUIVHRYQQB-XLRXWWTNSA-N
• Popularity: 865 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: 1.70
• Atomic LogP (AlogP): 0.07
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 9

Synonyms

• 489-32-7
• Ieariline
• CHEBI:78420
• VNM47R2QSQ
• Epimedii herba icariin
• DTXSID00964133
• 3-((6-Deoxymannopyranosyl)oxy)-7-(glucopyranosyloxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one
• 5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
• 5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-7-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-3-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxychromen-4-one
• RefChem:147596
• DTXCID301391843
• 610-440-0
• 5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one
• MFCD00210516
• Icariine
• C33H40O15
• 3-[(6-deoxy-alpha-L-mannopyranosyl)oxy]-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-7-yl beta-D-glucopyranoside
• SMR000466309
• UNII-VNM47R2QSQ
• -Anhydroicaritin
• Icariin (Standard)
• Spectrum2_001695
• Spectrum3_001130
• Spectrum4_001975
• Spectrum5_000933
• Icariin, analytical standard
• BSPBio_002599
• KBioGR_002475
• MLS000759413
• MLS001424083
• MLS006011789
• SCHEMBL312615
• SPECTRUM1505257
• SPBio_001650
• CHEMBL553204
• orb1304925
• Icariin, >=94% (HPLC)
• SCHEMBL30140586
• GTPL13728
• HY-N0014R
• KBio3_002099
• HMS2051J13
• HMS2235I20
• 3-[(6-Deoxy-alpha-L-mannopyranosyl)oxy]-7-(beta-D-glucopyranosyloxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one
• BCP18807
• EPIMEDII HERBA ICARIIN [MI]
• EX-A6783
• HY-N0014
• MSK40107
• BBL010487
• BDBM50027363
• CCG-38780
• STK801622
• AKOS005614005
• CCG-100955
• CS-3675
• DB12052
• MI08119
• NC00205
• SDCCGMLS-0066754.P001
• NCGC00178583-01
• 4H-1-Benzopyran-4-one, 3-((6-deoxy-alpha-L-mannopyranosyl)oxy)-7-(beta-D-glucopyranosyloxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-butenyl)-
• 5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-chromen-4-one
• VS-02526
• NS00014970
• C17555
• AB00639912-06
• 489I327
• A827628
• SR-01000759346
• Q5985057
• SR-01000759346-4
• BRD-K65639003-001-02-5
• BRD-K65639003-001-05-8
• BRD-K65639003-001-09-0
• 4'-O-methyl-8-gamma,gamma-dimethylallylkaempferol-3-rhamnoside-7-glucoside
• 3-[(6-Deoxy-?-L-mannopyranosyl)oxy]-7-?-D-glucopyranosyloxy-5-hydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one
• 4H-1-BENZOPYRAN-4-ONE, 3-((6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)OXY)-7-(.BETA.-D-GLUCOPYRANOSYLOXY)-5-HYDROXY-2-(4-METHOXYPHENYL)-8-(3-METHYL-2-BUTEN-1-YL)-
• 5-Hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-7-(((2S,4S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-3-(((3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one
• 5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-4H-chromen-4-one
• 5-HYDROXY-2-(4-METHOXYPHENYL)-8-(3-METHYLBUT-2-EN-1-YL)-7-{[3,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)OXAN-2-YL]OXY}-3-[(3,4,5-TRIHYDROXY-6-METHYLOXAN-2-YL)OXY]-4H-CHROMEN-4-ONE

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8585	85.85%
Caco-2	-	0.9373	93.73%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6495	64.95%
OATP2B1 inhibitior	-	0.5758	57.58%
OATP1B1 inhibitior	+	0.8807	88.07%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8472	84.72%
P-glycoprotein inhibitior	+	0.6382	63.82%
P-glycoprotein substrate	-	0.5343	53.43%
CYP3A4 substrate	+	0.6488	64.88%
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	+	0.6611	66.11%
CYP inhibitory promiscuity	-	0.5487	54.87%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7378	73.78%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.9079	90.79%
Skin irritation	-	0.8008	80.08%
Skin corrosion	-	0.9495	94.95%
Ames mutagenesis	+	0.5172	51.72%
Human Ether-a-go-go-Related Gene inhibition	+	0.7132	71.32%
Micronuclear	+	0.5033	50.33%
Hepatotoxicity	-	0.5448	54.48%
skin sensitisation	-	0.8766	87.66%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.7847	78.47%
Acute Oral Toxicity (c)	III	0.6326	63.26%
Estrogen receptor binding	+	0.7985	79.85%
Androgen receptor binding	+	0.6487	64.87%
Thyroid receptor binding	+	0.5382	53.82%
Glucocorticoid receptor binding	+	0.6406	64.06%
Aromatase binding	+	0.5685	56.85%
PPAR gamma	+	0.6904	69.04%
Honey bee toxicity	-	0.7280	72.80%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.9668	96.68%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1827	O76074	Phosphodiesterase 5A	5900 nM	IC50	PMID: 18778098

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.85%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.60%	94.00%
CHEMBL2581	P07339	Cathepsin D	95.52%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.66%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.92%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.88%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	93.43%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.16%	85.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.11%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.46%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.81%	96.00%
CHEMBL1951	P21397	Monoamine oxidase A	90.32%	91.49%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.23%	86.92%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.47%	94.45%
CHEMBL4208	P20618	Proteasome component C5	82.49%	90.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.33%	97.36%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.00%	92.94%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.46%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.15%	96.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.05%	96.95%

Plants that contains it

• Acer carpinifolium
• Campanula medium
• Cleistopholis staudtii
• Dipteryx odorata
• Distephanus anisochaetoides
• Echinacea pallida
• Epimedium acuminatum
• Epimedium brevicornu
• Epimedium diphyllum
• Epimedium grandiflorum
• Epimedium hunanense
• Epimedium koreanum
• Epimedium pubescens
• Epimedium sagittatum
• Epimedium sempervirens
• Epimedium sutchuenense
• Epimedium wushanense
• Eriocoma robusta
• Galium rubioides
• Helichrysum lepidissimum
• Helleborus multifidus
• Hopea utilis
• Hypericum revolutum
• Leuzea centauroides
• Litsea salicifolia
• Mesembryanthemum expansum
• Osmorhiza aristata
• Psychotria serpens
• Pycnandra acuminata
• Succisa pratensis
• Vancouveria hexandra

Cross-Links

• PubChem: 5318997
• NPASS: NPC5319
• ChEMBL: CHEMBL553204
• LOTUS: LTS0085291
• wikiData: Q5985057