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
• #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
  UNII: VNM47R2QSQ
  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 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

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.