Details of the Drug

General Information of Drug (ID: DM0B7NO)

Drug Name
Isoarnebin 4
Synonyms Shikonin; NSC 252844; Shikonin S; Shikonin,(S); Tokyo Violet
Indication
Disease Entry ICD 11 Status REF
Coronavirus Disease 2019 (COVID-19) 1D6Y Investigative [1]
Therapeutic Class
Antiviral Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 288.29
Logarithm of the Partition Coefficient (xlogp) 3
Rotatable Bond Count (rotbonds) 3
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 5
Chemical Identifiers
Formula
C16H16O5
IUPAC Name
5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-enyl]naphthalene-1,4-dione
Canonical SMILES
CC(=CC[C@H](C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O)O)C
InChI
InChI=1S/C16H16O5/c1-8(2)3-4-10(17)9-7-13(20)14-11(18)5-6-12(19)15(14)16(9)21/h3,5-7,10,17-19H,4H2,1-2H3/t10-/m1/s1
InChIKey
NEZONWMXZKDMKF-SNVBAGLBSA-N
Cross-matching ID
PubChem CID
479503
ChEBI ID
CHEBI:81068
CAS Number
517-89-5
TTD ID
D0QM4U

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
COVID-19 papain-like proteinase (PL-PRO) TTNHMO8 R1AB_SARS2 (819-2763) Inhibitor [1]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
72 kDa type IV collagenase (MMP2) OT5NIWA2 MMP2_HUMAN Gene/Protein Processing [2]
Actin, aortic smooth muscle (ACTA2) OTEDLG8E ACTA_HUMAN Gene/Protein Processing [3]
Amphiregulin (AREG) OTJFOR67 AREG_HUMAN Gene/Protein Processing [2]
Apoptosis regulator Bcl-2 (BCL2) OT9DVHC0 BCL2_HUMAN Gene/Protein Processing [3]
Cadherin-1 (CDH1) OTFJMXPM CADH1_HUMAN Gene/Protein Processing [2]
Cadherin-2 (CDH2) OTH0Y56P CADH2_HUMAN Gene/Protein Processing [2]
Caspase-3 (CASP3) OTIJRBE7 CASP3_HUMAN Protein Interaction/Cellular Processes [3]
Cellular tumor antigen p53 (TP53) OTIE1VH3 P53_HUMAN Gene/Protein Processing [4]
Collagen alpha-1(I) chain (COL1A1) OTI31178 CO1A1_HUMAN Gene/Protein Processing [3]
Collagen alpha-1(III) chain (COL3A1) OTT1EMLM CO3A1_HUMAN Gene/Protein Processing [3]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Structure of Mpro from COVID-19 virus and discovery of its inhibitors. Nature. 2020 Apr 9.
2 Shikonin suppresses small cell lung cancer growth via inducing ATF3-mediated ferroptosis to promote ROS accumulation. Chem Biol Interact. 2023 Sep 1;382:110588. doi: 10.1016/j.cbi.2023.110588. Epub 2023 Jun 1.
3 Functional and mechanistic investigation of Shikonin in scarring. Chem Biol Interact. 2015 Feb 25;228:18-27. doi: 10.1016/j.cbi.2014.12.037. Epub 2015 Jan 12.
4 Shikonin suppresses proliferation and induces cell cycle arrest through the inhibition of hypoxia-inducible factor-1 signaling. Chem Biol Interact. 2017 Aug 25;274:58-67. doi: 10.1016/j.cbi.2017.06.029. Epub 2017 Jul 3.