Details of the Drug

General Information of Drug (ID: DMOJQGT)

Drug Name
ICARIIN
Synonyms
Icariin; 489-32-7; Ieariline; UNII-VNM47R2QSQ; CHEBI:78420; VNM47R2QSQ; Icariine; 3-((6-Deoxymannopyranosyl)oxy)-7-(glucopyranosyloxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one; Icarin; 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; 4H-1-Benzopyran-4-one, 3-((6-deoxy-alpha-L-mannopyranosyl)oxy)-7-(be
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 3 Molecular Weight (mw) 676.7
Logarithm of the Partition Coefficient (xlogp) 1.7
Rotatable Bond Count (rotbonds) 9
Hydrogen Bond Donor Count (hbonddonor) 8
Hydrogen Bond Acceptor Count (hbondacc) 15
Chemical Identifiers
Formula
C33H40O15
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
Canonical 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
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
Cross-matching ID
PubChem CID
5318997
ChEBI ID
CHEBI:78420
CAS Number
489-32-7
DrugBank ID
DB12052
TTD ID
D05OQG

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Phosphodiesterase 5A (PDE5A) TTJ0IQB PDE5A_HUMAN Inhibitor [1]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Bone morphogenetic protein 2 (BMP2) OT23T37S BMP2_HUMAN Gene/Protein Processing [2]
Caspase-1 (CASP1) OTZ3YQFU CASP1_HUMAN Protein Interaction/Cellular Processes [3]
cGMP-specific 3',5'-cyclic phosphodiesterase (PDE5A) OTT8Q1AP PDE5A_HUMAN Gene/Protein Processing [4]
Interleukin-1 beta (IL1B) OT0DWXXB IL1B_HUMAN Gene/Protein Processing [3]
NACHT, LRR and PYD domains-containing protein 3 (NLRP3) OTZM6MHU NLRP3_HUMAN Gene/Protein Processing [3]
NAD-dependent protein deacetylase sirtuin-1 (SIRT1) OTAYZMOY SIR1_HUMAN Gene/Protein Processing [5]
Nitric oxide synthase 3 (NOS3) OTLDT7NR NOS3_HUMAN Gene/Protein Processing [6]
Progesterone receptor (PGR) OT0FZ3QE PRGR_HUMAN Gene/Protein Processing [7]
Solute carrier organic anion transporter family member 1B3 (SLCO1B3) OTOM3BUH SO1B3_HUMAN Gene/Protein Processing [8]
Solute carrier organic anion transporter family member 2B1 (SLCO2B1) OTERJ4VQ SO2B1_HUMAN Gene/Protein Processing [8]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Phosphodiesterase 5A (PDE5A) DTT PDE5A 1.60E-01 -0.25 -0.99
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Potent inhibition of human phosphodiesterase-5 by icariin derivatives. J Nat Prod. 2008 Sep;71(9):1513-7.
2 [Effects of Epimedium pubescens icariine on proliferation and differentiation of human osteoblasts]. Zhongguo Zhong Yao Za Zhi. 2005 Feb;30(4):289-91.
3 Icariin inhibits gastric cancer cell growth by regulating the hsa_circ_0003159/miR-223-3p/NLRP3 signaling axis. Hum Exp Toxicol. 2022 Jan-Dec;41:9603271221097363. doi: 10.1177/09603271221097363.
4 Potent inhibition of human phosphodiesterase-5 by icariin derivatives. J Nat Prod. 2008 Sep;71(9):1513-7.
5 Icariin protects against intestinal ischemia-reperfusion injury. J Surg Res. 2015 Mar;194(1):127-38. doi: 10.1016/j.jss.2014.10.004. Epub 2014 Oct 8.
6 Icariin enhances endothelial nitric-oxide synthase expression on human endothelial cells in vitro. Vascul Pharmacol. 2007 Jul;47(1):18-24.
7 Proliferation-stimulating effects of icaritin and desmethylicaritin in MCF-7 cells. Eur J Pharmacol. 2004 Nov 19;504(3):147-53. doi: 10.1016/j.ejphar.2004.10.002.
8 Interaction of the bioactive flavonol, icariin, with the essential human solute carrier transporters. J Biochem Mol Toxicol. 2014 Feb;28(2):91-7. doi: 10.1002/jbt.21540. Epub 2013 Nov 21.