Details of the Drug

General Information of Drug (ID: DM3DB8X)

• Drug Name: Icariside II
• Synonyms: Baohuoside I; 113558-15-9; Icariside II; CHEBI:82619; Icarlin II; Baohuoside-I; Baohuoside I;; Icarisid II;; AC1NUQWY; 3,5,7-Trihydroxy-4'-methoxyl-8-prenylflavone-3-O-rhamnopyranoside; SCHEMBL4229321; CHEMBL560116; DTXSID40150457; 2h44; MolPort-020-006-007; HY-N0011; ZINC70455423; C27H30O10; CS-3673; 4H-1-Benzopyran-4-one, 3-((6-deoxy-alpha-L-mannopyranosyl)oxy)-5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-butenyl)-; AK169968; anhydroicaritin-3-O-alpha-L-rhamnopyranoside; N2538; Y0106; FT-0686579; Q-100071

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]

• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 1:
  Molecular Weight (mw); 514.5
  Logarithm of the Partition Coefficient (xlogp); 3.5
  Rotatable Bond Count (rotbonds); 6
  Hydrogen Bond Donor Count (hbonddonor); 5
  Hydrogen Bond Acceptor Count (hbondacc); 10
• Chemical Identifiers:
  Formula: C27H30O10
  IUPAC Name: 5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-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(C(=CC(=C3C2=O)O)O)CC=C(C)C)C4=CC=C(C=C4)OC)O)O)O
  InChI: InChI=1S/C27H30O10/c1-12(2)5-10-16-17(28)11-18(29)19-21(31)26(37-27-23(33)22(32)20(30)13(3)35-27)24(36-25(16)19)14-6-8-15(34-4)9-7-14/h5-9,11,13,20,22-23,27-30,32-33H,10H2,1-4H3/t13-,20-,22+,23+,27-/m0/s1
  InChIKey: NGMYNFJANBHLKA-LVKFHIPRSA-N
• Cross-matching ID:
  PubChem CID: 5488822
  ChEBI ID: CHEBI:82619
  CAS Number: 113558-15-9
  TTD ID: D06TLQ

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
3-phosphoinositide-dependent protein kinase 1 (PDPK1)	OTT09ZVP	PDPK1_HUMAN	Post-Translational Modifications	[2]
Alanine aminotransferase 1 (GPT)	OTOXOA0Q	ALAT1_HUMAN	Protein Interaction/Cellular Processes	[3]
Apoptosis regulator BAX (BAX)	OTAW0V4V	BAX_HUMAN	Gene/Protein Processing	[4]
Apoptosis regulator Bcl-2 (BCL2)	OT9DVHC0	BCL2_HUMAN	Gene/Protein Processing	[4]
Aspartate aminotransferase, cytoplasmic (GOT1)	OTZLM5UB	AATC_HUMAN	Protein Interaction/Cellular Processes	[3]
ATP-binding cassette sub-family C member 2 (ABCC2)	OTJSIGV5	MRP2_HUMAN	Gene/Protein Processing	[3]
Bile acid receptor (NR1H4)	OTWZLPTB	NR1H4_HUMAN	Gene/Protein Processing	[3]
Bile salt export pump (ABCB11)	OTRU7THO	ABCBB_HUMAN	Gene/Protein Processing	[3]
Caspase-3 (CASP3)	OTIJRBE7	CASP3_HUMAN	Gene/Protein Processing	[5]
Caspase-8 (CASP8)	OTA8TVI8	CASP8_HUMAN	Gene/Protein Processing	[5]

Molecular Expression Atlas of This Drug

• The Studied Disease: Discovery agent
• ICD Disease Classification: N.A.

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] Blockade of epidermal growth factor receptor/mammalian target of rapamycin pathway by Icariside II results in reduced cell proliferation of osteosarcoma cells. Food Chem Toxicol. 2014 Nov;73:7-16. doi: 10.1016/j.fct.2014.08.002. Epub 2014 Aug 10.
• [3] Baohuoside I inhibits FXR signaling pathway to interfere with bile acid homeostasis via targeting ER degradation. Cell Biol Toxicol. 2023 Aug;39(4):1215-1235. doi: 10.1007/s10565-022-09737-x. Epub 2022 Jul 8.
• [4] Reactive oxygen species-mediated mitochondrial pathway is involved in Baohuoside I-induced apoptosis in human non-small cell lung cancer. Chem Biol Interact. 2012 Jul 30;199(1):9-17. doi: 10.1016/j.cbi.2012.05.005. Epub 2012 Jun 9.
• [5] Cyclooxygenase-2/prostaglandin E2 pathway mediates icariside II induced apoptosis in human PC-3 prostate cancer cells. Cancer Lett. 2009 Jul 18;280(1):93-100.