Compound Summary
Icariin
Compound Information
Icariin
Compound Name: | Icariin |
Compound CID: | 5318997 |
Synonyms: | Icariin 489-32-7 Ieariline UNII-VNM47R2QSQ 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 More... |
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 |
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 |
InChIKey: | TZJALUIVHRYQQB-XLRXWWTNSA-N |
Canonical Smiles: | 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 |
Isomeric Smiles: | 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 |
Molecular Weight: | 676.7 |
Molecular Formula: | C33H40O15 |
Compound Structure
2D Structure:
3D Structure:
Computed Properties
Icariin
Molecular Weight: | 676.7 |
Molecular Formula: | C33H40O15 |
Hydrogen Bond Donor Count: | 8 |
Hydrogen Bond Acceptor Count: | 15 |
Rotatable Bond Count: | 9 |
Heavy Atom Count: | 48 |
Complexity: | 1170 |
Synonyms
Icariin
| Icariin | Icariin |
|---|---|
Icariin |
489-32-7 |
Ieariline |
UNII-VNM47R2QSQ |
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 |
CHEBI:78420 |
MFCD00210516 |
VNM47R2QSQ |
Icariine |
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 |
Horny goat weed |
Icariin; |
Epimedium Extract |
3-((6-Deoxymannopyranosyl)oxy)-7-(glucopyranosyloxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one |
Epimedii herba icariin |
Spectrum2_001695 |
Spectrum3_001130 |
Spectrum4_001975 |
Spectrum5_000933 |
Icariin, analytical standard |
BSPBio_002599 |
KBioGR_002475 |
MLS000759413 |
MLS001424083 |
MLS006011789 |
SCHEMBL312615 |
SPECTRUM1505257 |
SPBio_001650 |
AMBZ0238 |
CHEMBL553204 |
Icariin, >=94% (HPLC) |
KBio3_002099 |
DTXSID00964133 |
HMS2051J13 |
HMS2235I20 |
BCP18807 |
HY-N0014 |
ZINC3960893 |
BBL010487 |
BDBM50027363 |
CCG-38780 |
STK801622 |
AKOS005614005 |
AM85785 |
CCG-100955 |
CS-3675 |
DB12052 |
MCULE-2932284439 |
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)oxan-2-yloxy-3-(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yloxychromen-4-one |
VS-02526 |
N1705 |
C17555 |
AB00639912-06 |
489I327 |
A827628 |
SR-01000759346 |
Q-100549 |
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" |
3,5-dihydroxy-4\\-methoxy-6\\\\,6\\\\-dimethyl-4\\\\,5\\\\-dihydropyrano2\\\\,3\\\\:7,8-flavone |
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 |
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-yloxy}-3-{(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yloxy}-4H-chromen-4-one |
5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-7-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-3-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)-4H-chromen-4-one |
7-(Hexopyranosyloxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-1-benzopyran-3-yl 6-deoxyhexopyranoside |
Experimental Data
Icariin
| Species | Dose | Unit | Control(Avg days) | Treatment(Avg days) | Avg/Med Lifespan Change(%) | Control(Max days) | Treatment(Max days) | Max Lifespan Change(%) | Significant | Strain | Gender | PubMed | Avg/Med Lifespan Change tab |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Caenorhabditis elegans | 15.000000000000000 | umol/L | 8.470000000000000 | Unclear | N2 | 33683565 | |||||||
| Caenorhabditis elegans | 45.000000000000000 | umol/L | 20.700000000000000 | S | N2 | 22216122 | Active | ||||||
| Caenorhabditis elegans | 75.000000000000000 | umol/L | 8.460000000000000 | NS | N2 | 33683565 | Inactive | ||||||
| Caenorhabditis elegans | 45.000000000000000 | umol/L | 24.000000000000000 | S | N2 | 33683565 | Active | ||||||
| Mus musculus | 0.020000000000000 | % | 702.000000000000000 | 758.000000000000000 | 8.000000000000000 | 898.000000000000000 | 953.000000000000000 | 6.000000000000000 | NS | C57BL/6J | MALES | 26145038 | Inactive |
Experimental Data Visualization
Icariin
Statistics Data
Icariin
| Species | Avg/Med Lifespan Change(%) | Max Lifespan Change(%) | Count Reference | Count Data point |
|---|---|---|---|---|
| Caenorhabditis elegans | 24.000000000000000 | 2 | 4 | |
| Mus musculus | 8.000000000000000 | 6.000000000000000 | 1 | 1 |
Statistics Data Visualization
Icariin
