Icaritin

Details

• Internal ID: 37d1f8e0-5c7b-4025-a719-6d00cdbe64fe
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones > 8-prenylated flavones
• IUPAC Name: 3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one
• SMILES (Canonical): CC(=CCC1=C2C(=C(C=C1O)O)C(=O)C(=C(O2)C3=CC=C(C=C3)OC)O)C
• SMILES (Isomeric): CC(=CCC1=C2C(=C(C=C1O)O)C(=O)C(=C(O2)C3=CC=C(C=C3)OC)O)C
• InChI: InChI=1S/C21H20O6/c1-11(2)4-9-14-15(22)10-16(23)17-18(24)19(25)20(27-21(14)17)12-5-7-13(26-3)8-6-12/h4-8,10,22-23,25H,9H2,1-3H3
• InChI Key: TUUXBSASAQJECY-UHFFFAOYSA-N
• Popularity: 211 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₆
• Molecular Weight: 368.40 g/mol
• Exact Mass: 368.12598835 g/mol
• Topological Polar Surface Area (TPSA): 96.20 Ų
• XlogP: 4.80
• Atomic LogP (AlogP): 4.09
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• 118525-40-9
• 3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one
• UNII-UFE666UELY
• UFE666UELY
• CHEMBL498485
• SGN162
• SGN-162
• 3,5,7-Trihydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one
• 4H-1-benzopyran-4-one, 3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-buten-1-yl)-
• Cycloicaritin
• Icartin
• Icaritin(Anhydroicaritin)
• D0L0BX
• ICARITIN [WHO-DD]
• MLS006010055
• BIDD:ER0021
• SCHEMBL4223542
• Icaritin, >=98% (HPLC)
• DTXSID00152154
• TUUXBSASAQJECY-UHFFFAOYSA-N
• BCP32968
• HY-N0678
• BDBM50272527
• MFCD22422519
• s9080
• AKOS015896858
• CCG-268265
• CS-3679
• DB12672
• NCGC00345813-01
• NCGC00345813-04
• AC-33950
• AS-55987
• SMR004701218
• FT-0670266
• I0974
• Q27291061
• 4'-methoxy-3,5,7trihydroxy-8-3,3-dimethylallylflavone
• 3-hydroxy-7-o-beta-glucose-8-prenyl-4''-methoxy Chrysin
• 3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one
• 3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-4h-chromen-4-one
• 4H-1-Benzopyran-4-one, 3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-butenyl)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9853	98.53%
Caco-2	+	0.5510	55.10%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5455	54.55%
OATP2B1 inhibitior	-	0.5605	56.05%
OATP1B1 inhibitior	+	0.9026	90.26%
OATP1B3 inhibitior	+	0.8673	86.73%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8192	81.92%
P-glycoprotein inhibitior	+	0.7043	70.43%
P-glycoprotein substrate	-	0.7362	73.62%
CYP3A4 substrate	+	0.5692	56.92%
CYP2C9 substrate	-	0.5929	59.29%
CYP2D6 substrate	-	0.8145	81.45%
CYP3A4 inhibition	-	0.6679	66.79%
CYP2C9 inhibition	+	0.8700	87.00%
CYP2C19 inhibition	+	0.9318	93.18%
CYP2D6 inhibition	+	0.5347	53.47%
CYP1A2 inhibition	+	0.7798	77.98%
CYP2C8 inhibition	+	0.6091	60.91%
CYP inhibitory promiscuity	+	0.9269	92.69%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6873	68.73%
Eye corrosion	-	0.9874	98.74%
Eye irritation	-	0.5252	52.52%
Skin irritation	-	0.7629	76.29%
Skin corrosion	-	0.9459	94.59%
Ames mutagenesis	+	0.5763	57.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.5271	52.71%
Micronuclear	+	0.5500	55.00%
Hepatotoxicity	-	0.6073	60.73%
skin sensitisation	-	0.8260	82.60%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.8038	80.38%
Acute Oral Toxicity (c)	III	0.6590	65.90%
Estrogen receptor binding	+	0.9310	93.10%
Androgen receptor binding	+	0.8610	86.10%
Thyroid receptor binding	+	0.7141	71.41%
Glucocorticoid receptor binding	+	0.8941	89.41%
Aromatase binding	+	0.7980	79.80%
PPAR gamma	+	0.9073	90.73%
Honey bee toxicity	-	0.8499	84.99%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9866	98.66%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1827	O76074	Phosphodiesterase 5A	2200 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	99.76%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.24%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.03%	94.00%
CHEMBL2581	P07339	Cathepsin D	94.93%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	94.50%	91.49%
CHEMBL3401	O75469	Pregnane X receptor	93.79%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.42%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.81%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.91%	95.56%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	89.87%	85.30%
CHEMBL1929	P47989	Xanthine dehydrogenase	89.35%	96.12%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.27%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.87%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.97%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.26%	85.14%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.13%	95.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.28%	96.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.56%	95.89%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.34%	91.71%
CHEMBL4208	P20618	Proteasome component C5	82.13%	90.00%

Plants that contains it

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

Cross-Links

• PubChem: 5318980
• NPASS: NPC273538
• ChEMBL: CHEMBL498485
• LOTUS: LTS0035253
• wikiData: Q27291061