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
Structure
3D MOL 2D MOL
#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
CHEMBL560116
CAS Number
113558-15-9
TTD ID
D06TLQ
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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
Bile acid receptor (NR1H4) OTWZLPTB NR1H4_HUMAN Gene/Protein Processing [2]
Bile salt export pump (ABCB11) OTRU7THO ABCBB_HUMAN Gene/Protein Processing [2]
Mitogen-activated protein kinase 1 (MAPK1) OTH85PI5 MK01_HUMAN Post-Translational Modifications [3]
Mitogen-activated protein kinase 3 (MAPK3) OTCYKGKO MK03_HUMAN Post-Translational Modifications [3]
Nuclear receptor subfamily 0 group B member 2 (NR0B2) OT7UVICX NR0B2_HUMAN Gene/Protein Processing [2]
Poly polymerase 1 (PARP1) OT310QSG PARP1_HUMAN Protein Interaction/Cellular Processes [4]
Proline-rich AKT1 substrate 1 (AKT1S1) OT4JHN4Y AKTS1_HUMAN Post-Translational Modifications [3]
Vascular endothelial growth factor A, long form OTIM9MZ3 VEGFA_HUMAN Gene/Protein Processing [4]
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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
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 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.
3 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.
4 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.